5+ Bedroom Vacation Rentals In Anna Maria, FL

$1380.1

Back To Blue: Amazing Bean Point Location, Resort Style Backyard with Pool by Anna Maria Life

Anna Maria, Florida, United States

Back to Blue by Anna Maria Life Vacation Rentalsbr850 North Shore Drive, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation, Location, Location – Coveted AMI North End, just a 5-minute walk to Bean Point and directly across the street from the BaybrRoom for Everyone – 5 bedrooms / 5 bathrooms, five king beds plus a queen sofa sleeperbrPrivate Casita – Separate guest house with its own entrance, king bed, full bath & kitchen — perfect for grandparents, new parents with a baby, or couples wanting extra privacybrEvery Bedroom Has Its Own Bath – No sharing or waiting; each bedroom has its own dedicated bathroombrResort-Style Heated Pool & Spa – Private pool with spa and in-pool lounge chairsbrMultiple Outdoor Living Spaces – Upper deck with dining, covered poolside lounge, breezeway seating, and shady hangout areas to spread outbrPoolside Bar & Game Room – Garage level opens to the pool and doubles as a fun indoor/outdoor bar & game area with TVbrPing Pong, Cornhole & Games – Plenty of ways to play, rain or shinebrOutdoor Showers & Foot Wash Stations – Rinse off the sand after days at the beach or baybrGrill & Dine Outside – Gas grill, picnic table and outdoor patio diningbrBeach-Ready – Beach towels, beach chairs and a beach wagon providedbrEasy Parking – Driveway parking for up to four carsbrbrDetails:brTucked away on the treasured North End of Anna Maria Island, Back To Blue is a spacious, light-filled retreat designed for families and groups who want room to truly relax. With the Bay just across the street and the sugar-white sands of Bean Point a short stroll away, you'll enjoy the best of both the bay and the Gulf in one of the most sought-after neighborhoods on the island.brInside, you'll find five bedrooms and five bathrooms, all with king beds and their own dedicated bathrooms, so every guest has a comfortable, private place to unwind. The home is ideal for multi-generational trips, extended families, or couples traveling together, offering a great balance of together time and personal space.brA standout feature is the separate guest house (casita) with its own entrance. This studio-style space includes a king bed, full bathroom, and fully equipped kitchen — perfect for grandparents who like quiet evenings, parents with a napping baby, or anyone who wants a little extra retreat within the retreat.brThe primary suite includes a king bed, en-suite bathroom, and a private upper-level deck with seating to take in tranquil water views. A spiral staircase from this deck leads directly down to the backyard and pool, making it easy to slip out for a morning coffee by the water or an evening soak in the spa.brAcross the main house, you'll find additional king bedrooms, each with access to its own bathroom and thoughtful touches like smart TVs and cozy linens from a professional linen service. Complimentary Wi-Fi and in-home laundry keep your stay as convenient as it is relaxing.brbrOutdoor Living & FunbrBack To Blue really shines with its abundance of outdoor living space.brThe private heated pool and spa are the heart of the backyard, complete with in-pool lounge chairs on the sun shelf for lazy afternoons in the water. After the beach, rinse off in the outdoor shower or use the foot wash stations before heading inside.brbrAt the pool level, the covered lounge and game area creates an ideal indoor/outdoor hangout zone. The garage opens into this space and is set up as a poolside bar and game room with seating and a TV, so everyone can cool off in the shade without leaving the action. There's ping pong, cornhole, puzzles, games and books, giving all ages plenty to do from morning to night.brOn the second level, a deck with patio dining for six is perfect for breakfast al fresco or sunset dinners. The ground level offers even more outdoor seating, a picnic table, and a gas grill for easy cookouts after a day at the beach.brBeach days are a breeze with beach towels, chairs, and a beach wagon provided — just load up and head to Bean Point or stroll across to the bay.brbrWalkable North-End LocationbrFrom Back To Blue, you're within easy walking distance of shops, restaurants, and the island's free trolley, which runs the full 7 miles of Anna Maria Island. Park the car, hop on and off at your leisure, and explore the beaches, piers, Pine Avenue, and local favorites without worrying about parking.brThis is truly a “park once and relax” kind of vacation home.brbrBedroom 1 - King Bed, Ensuite Bathroom, 55 inch Smart TV - Floor 1brBedroom 2 - King Bed, Ensuite Bathroom, 55 inch TV Smart TV - Floor 1brBedroom 3 - King Bed, Ensuite Bathroom, Backyard & Pool Access, 55 inch Smart TV - Floor 2brBedroom 4 - King Bed, TV - Floor 2brBedroom 5 - King Bed EnSuite Bath, 55 Inch SmartTV - Floor 2 (Located in Guest House)brLiving Room - Queen Sofa BedbrbrPlease note:brPets are not allowed in this home.brThe garage is configured as a poolside bar & game room and not available for vehicle parking.brAmenities, furnishings and decor are subject to change from time to time.brDriveway parking is available for a maximum of 4 cars. Parking for additional vehicles is not available. brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night so everyone can enjoy the quiet North End atmosphere.brbrVR22-000012brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

Bed

Bath

Sleeps

$898.81

/ Nightly

Private Vacation Home

Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach

Anna Maria, Florida, United States

Montego Bay by AMI Locals brVPR16-000472brbrEscape to Montego Bay, an Anna Maria Island vacation home with a private pool, rooftop deck with Gulf views, and multiple balconies designed to give you the ultimate experience! This spacious five-bedroom, four-bath home is just one and a half blocks from the north end of the beaches and Pine Avenue’s shops and restaurants, allowing you to indulge in the best of Anna Maria Island with your own personal, luxurious touch. Surrounded by tropical breezes and scenic water vistas, this home is perfect for creating lifelong memories whether relaxing on the balcony, dining in the backyard, or exploring the island!brbrHighlights br• 4 minutes / 1.5 blocks to Anna Maria Beachbr• 5 Bedroom / 4 Bathbr• 4 King beds, 2 twin/twin bunksbr• Private pool with sun shelf and hot tubbr• Rooftop deck with Gulf viewsbr• Outdoor living spacebr• Outdoor TV and dining table br• 4-minute walk to Pine Avenue’s boutique shops and waterfront restaurants br• Washer and dryerbr• 4 Parking spacesbrbrRelax outdoors in your tropical backyard oasis, lounge poolside on the sun shelf, enjoy a family cookout at the BBQ grill, or unwind on the balcony with a good book or evening cocktail. The spacious covered lounge offers a TV and outdoor seating, while the rooftop deck provides breathtaking tropical views and spectacular sunsets.brbrInside, the home features a bright, open-concept main living area with coastal decor, comfortable seating, and large windows framing water views. The fully equipped kitchen with stainless steel appliances, ample counter space, and a large island is perfect for island-inspired cooking or casual snacks. The dining area seats eight and overlooks the backyard and pool, ideal for meals and socializing in style.brbrRetreat to the primary bedroom on the second floor, complete with a king bed, ensuite with dual vanity sinks, walk-in shower, and balcony access to enjoy peaceful Gulf vistas. The second bedroom, also on the second floor, boasts a king bed, ensuite bathroom with walk-in shower, and balcony views. The third bedroom provides a king bed and balcony access, while the fourth bedroom has a king bed, both sharing hall bathrooms with walk-in showers. The fifth bedroom, perfect for kids or additional guests, features two twin bunk beds, with a hall bathroom containing a combined shower and tub, all with premium linens and TVs for restful nights.brbrRoom Details br• Primary Bedroom (2nd floor): King bed, ensuite bathroom with walk-in shower, dual vanities, balconybr• Second Bedroom (2nd floor): King bed, ensuite with walk-in shower, balconybr• Third Bedroom (2nd floor): King bed, balcony access br• Fourth Bedroom (3rd floor): King bed br• Fifth Bedroom (3rd floor): Two twin bunk bedsbrbrTake a leisurely stroll to nearby beaches, shops, and waterfront dining, or hop on the free trolley to explore all seven miles of Anna Maria Island, from secluded Bean Point to Coquina Beach.brbrBook Montego Bay today and enjoy a luxurious escape in the heart of Anna Maria Island. With stunning Gulf views, outdoor amenities, and proximity to beaches and shops, this estate offers everything you need for a memorable, relaxing vacation. Reserve your dates now and create lifelong beach memories!brbrbr-brThere are no pets allowed in this home.brbr4 cars maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by AMI Locals, an Anna Maria Island property management company.brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.brbrPlease see our AMI Locals Rental Policies for full details.brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$2359.86

/ Nightly

Private Vacation Home

Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All!

Anna Maria, Florida, United States

The Big Yellow House on Pine by Anna Maria Vacations brHome in Anna Maria, FL brbrWelcome to The Big Yellow House on Pine by Anna Maria Vacations, a beachfront five-bedroom, four-bath home that captures the relaxed spirit of Anna Maria Island. Perfectly positioned along the Gulf, this charming coastal retreat offers spectacular beach views, a private pool and in-ground spa, and spacious living areas designed for family gatherings. Located right on Pine Avenue, guests are just steps away from local boutiques, coffee shops, and waterfront dining; making this the perfect home base for a classic Old Florida beach vacation. brbrHighlights br• Beachfront home with direct Gulf access br• 5 Bedrooms / 4 Bathrooms br• 2 King beds, 1 Queen bed, 4 Twin beds br• Private pool and in-ground spa br• Ping pong table and BBQ grill br• Recently updated first floor br• Washer and dryer br• Multiple living spaces and dining areas br• Steps from Pine Avenue shops and restaurants br• 5 Parking spots brbrEnjoy the ultimate island lifestyle at this family-friendly beachfront home. The covered patio and pool area overlooks the turquoise waters of the Gulf, creating an ideal space for morning swims, sunbathing, and sunset dinners. Fire up the BBQ grill, challenge the family to a ping pong match, or simply unwind in the bubbling spa as you listen to the waves roll in. With direct beach access, you can walk from your patio straight onto the soft white sand of Anna Maria Beach, making this one of the most desirable vacation rentals on Anna Maria Island. brbrInside, guests will find two spacious living areas, one on each floor; each featuring cozy seating, TVs, and dining tables perfect for shared meals. The main kitchen on the ground floor is fully equipped for home-cooked meals, while the second-floor kitchenette adds extra convenience for larger groups. Step out onto the upper balcony to take in uninterrupted Gulf views, the perfect spot for your morning coffee or an evening glass of wine. brbrEach bedroom has been thoughtfully designed for comfort and relaxation, offering soft linens, ample storage, and serene coastal touches. The home features two primary suites, each with a king bed and an ensuite bathroom with a walk-in shower. On the main floor, there are two additional bedrooms; one with a queen bed and one with two twin beds, sharing a hall bath with a shower and tub combination. Upstairs, a twin bedroom offers an ensuite bath with a walk-in shower, providing the ideal retreat for younger guests or friends traveling together. brbrRoom Details br-Primary Bedroom (1st floor): King bed, ensuite bath with walk-in shower br-Second Bedroom (2nd floor): King bed, ensuite bath with walk-in shower br-Third Bedroom (1st floor): Queen bed br-Fourth Bedroom (1st floor): Two Twin beds br-Fifth Bedroom (2nd floor): Two Twin beds, ensuite bath with walk-in shower brbrBeyond the beach, explore the best of Anna Maria Island right from your doorstep. Stroll along Pine Avenue to find local shops, bakeries, and restaurants, or spend your days exploring the island by bike or trolley. The home also features a washer and dryer, making it easy to keep beachwear fresh throughout your stay. brbrFrom its beachfront location to its private pool and spa, The Big Yellow House on Pine by Anna Maria Vacations offers a perfect mix of comfort, convenience, and coastal charm. Ideal for families and groups, this home captures the essence of island living with everything you need for a stress-free, sun-soaked getaway. brbrBook your stay today with Anna Maria Vacations and make unforgettable memories at The Big Yellow House on Pine! brbr- brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.

Bed

Bath

Sleeps

$685.52

/ Nightly

Private Vacation Home

Antigua Bay! Rooftop Views and Private Pool!

Anna Maria, Florida, United States

Antigua Bay by Anna Maria Vacations brHome in Anna Maria, FL brVR16-000450 brbrWelcome to Antigua Bay, a stunning five-bedroom, four-bath luxury vacation home located on the prestigious north end of Anna Maria Island, just steps from the Gulf. Perfect for large families and groups, this dog-friendly retreat offers premium amenities including a rooftop deck with panoramic island views, a private pool and in-ground spa, and fun family entertainment with both a pool table and foosball table. With Pine Avenue’s charming shops and restaurants just around the corner. brbrHighlights br-3-minute walk to Anna Maria beach br-5 Bedrooms / 4 Bathrooms br-4 King beds, 2 Twin-over-Twin bunks br-Rooftop deck br-Private heated pool and in-ground spa br-Covered patio with foosball, pool table, and bar area br-Outdoor dining and BBQ grill br-Near Pine Avenue restaurants and shops br-Dog-friendly br-6 Parking spots brbrFrom sunrise coffee on the rooftop deck to sunset swims in the private pool, Antigua Bay is designed for memorable island living. Spend the day exploring Anna Maria’s pristine beaches, then return to tropical landscaping, lounge chairs for sunbathing, and a shaded entertainment area with a pool table, foosball, and bar. An outdoor dining space and BBQ grill to make breezy meals. brbrThe open living area welcomes you with plenty of natural light, plush seating, and a large TV. The fully equipped kitchen features stainless steel appliances, cookware essentials, and an island with seating, ideal for casual breakfasts or evening appetizers. A dining table provides ample room for family meals, while multiple balconies invite you to sip morning coffee with gentle Gulf breezes. brbrAntigua Bay offers two luxurious primary suites, one on each living floor, each featuring a king bed, furnished balcony, and ensuite bathroom with double vanities and walk-in showers. Two additional guest bedrooms also feature king beds, and the fifth bedroom is perfect for kids with two twin-over-twin bunk beds. Bathrooms are stylishly appointed, with walk-in showers and a shower-tub combination for added convenience. brbrRoom Details br-Primary Bedroom 1: King bed, balcony, ensuite bathroom with double vanity and walk-in shower br-Bedroom 2: King bed, balcony, ensuite bathroom with double vanity and walk-in shower br-Bedroom 3: King bed, balcony access br-Bedroom 4: King bed br-Bedroom 5: Two twin-over-twin bunk beds brbrThis property participates in Anna Maria Vacations’ Professional Linen Program, providing guests with premium-quality bedding, bath towels, and beach towels, all freshly laundered and ready for your stay. Other amenities include Wi-Fi, washer and dryer, and multiple entertainment options indoors and out. brbrSpend your days exploring nearby Pine Avenue with its boutiques, ice cream shops, and waterfront dining, or hop on the island trolley to discover the rest of the island. brbrAntigua Bay offers the perfect blend of luxury, location, and entertainment. Book your dream Anna Maria Island getaway today! br br- brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details. brbrThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.

Bed

Bath

Sleeps

$685.1

/ Nightly

Private Vacation Home

Absolute Paradise - Private Pool, Spa, and Game Room! Short walk to Beach

Anna Maria, Florida, United States

Absolute Paradise by Anna Maria Vacations brVR16-000465 brbrWelcome to Absolute Paradise, a beautifully updated five-bedroom, four-bath beach home just a short stroll from the white sand shores of Anna Maria Island. Perfectly located near Pine Avenue’s shops and restaurants, this home combines coastal charm and modern comfort with fantastic outdoor spaces. Featuring a rooftop deck, private pool with in-ground spa, and covered patio for dining and lounging. Enjoy the relaxed island lifestyle where everything you love about Anna Maria Island is just steps away. brbrHighlights br• 4-minute walk to the beach br• 5 Bedrooms / 4 Bathrooms br• 4 King beds, 1 Twin-over-Full bunk bed, 1 Sleeper Sofa br• Rooftop deck with island views br• Private pool and in-ground spa br• Outdoor dining area and BBQ grill br• Ping pong table and cornhole br• Near restaurants and shops on Pine Avenue br• Professional Linen Program br• 3 Parking spots brbrSpend your days relaxing by the private pool and spa, soaking up the sun, or enjoying a family BBQ in the covered patio area with plenty of seating and a dining table. Challenge your friends to a game of ping pong or cornhole, then head up to the rooftop deck for breathtaking views and sunset cocktails. Whether you’re swimming, grilling, or stargazing, every moment at Absolute Paradise is made for easygoing island fun. brbrStep inside to discover bright, updated interiors filled with beachy hues and comfortable furnishings. The main living area includes a plush sofa, cozy chairs, and TV for relaxing after a day in the sun. The fully equipped kitchen has everything you need to prepare meals, including cookware, stainless steel appliances, and a spacious dining table where everyone can gather together. Large sliding glass doors lead out to the balcony, letting in natural light and fresh Gulf breezes. brbrThis home features two primary suites, each with king beds, ensuite bathrooms, and private balconies for quiet mornings or late-night stargazing. The guest bedrooms offer king beds with luxury linens, while the bunk room is perfect for kids, featuring a twin over full setup. A den on the third floor with a sleeper sofa and TV provides additional space for guests. Bathrooms are equipped with walk-in showers or shower/tub combinations, and all linens are provided through our Professional Linen Program for added comfort. brbrRoom Details br-Primary Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with double vanity and walk-in shower br-Second Primary Bedroom (3rd Floor): King bed, balcony, walk-in closet, ensuite bathroom with double vanity and walk-in shower br-Third Bedroom (2nd Floor): King bed, balcony access br-Fourth Bedroom (3rd Floor): King bed br-Fifth Bedroom (2nd Floor): Twin-over-Full bunk bed br-Den (3rd Floor): Sleeper sofa brbrGuests will love the home’s walkable location, just minutes from Pine Avenue’s local cafes and boutiques. Explore the island on foot, by bike, or on the island trolley, which makes it easy to reach beaches, parks, and family attractions. Whether kayaking the bay, shopping for souvenirs, or dining under the stars, Absolute Paradise places you at the heart of everything Anna Maria Island has to offer. brbrPerfect for families, couples, and groups, Absolute Paradise by Anna Maria Vacations offers the ideal mix of modern comfort and laid-back island living. Enjoy a private pool, rooftop views, and an unbeatable location just steps from the beach and local favorites on Pine Avenue. brbrBook your stay at Absolute Paradise by Anna Maria Vacations today and experience the relaxed coastal charm of Anna Maria Island! brbr- brNo pets are allowed in this home. brbrThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. brbrThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. Please see our Anna Maria Vacations Rental Policies for full details. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$1036.26

/ Nightly

Private Vacation Home

Large Private Beach Home! Private Pool, Spa and Outdoor Lighting

Anna Maria, Florida, United States

Southern Exposure by Anna Maria Vacations brHome in Anna Maria, FL brVRC16-000065 brbrWelcome to Southern Exposure by Anna Maria Vacations, a five bedroom, four and a half bath luxury home perfectly located on the prestigious north end of Anna Maria Island. A 7-minute walk from the beach, this retreat combines coastal elegance with laid-back island comfort. Enjoy a private heated pool and hot tub, elevator access, and multiple balconies where you can unwind with your morning coffee or evening cocktail. Just one block from Pine Avenue’s shops and restaurants, Southern Exposure offers the perfect blend of relaxation and convenience for your next Anna Maria Island getaway. brbrHighlights br• 7-minute walk to the beach br• 5 Bedrooms / 4 Bathrooms br• 3 King beds, 1 Queen bed, 1 Twin-over-Twin bunk, 1 Queen sleeper sofa br• Private heated pool and hot tub br• Ping pong table and outdoor lounge area br• Elevator and multiple balconies br• One block from Pine Avenue’s shops and restaurants br• Washer and dryer br• Professional Linen Program included br• 4 Parking spots brbrDiscover outdoor living at its finest. The tropical pool area invites you to soak up the Florida sunshine or relax beneath the covered patio while the kids splash in the pool. The built-in bistro table is perfect for snacks and refreshments, and the hot tub offers the ideal way to unwind after a day on the sand. Challenge friends to a ping pong match or gather on the outdoor sectional for a family movie night under the island breeze. Every detail at Southern Exposure was designed to make guests feel at home in paradise. brbrStep inside and be greeted by a bright, open floor plan that flows seamlessly from the living room to the dining area and kitchen. The coastal decor and natural light set the perfect tone for a relaxing stay. The living room features plush seating, TV, and a wet bar with a wine fridge, creating an inviting space to unwind after exploring the island. The chef’s kitchen is fully equipped with stainless steel appliances, ample counter space, and barstool seating for casual dining. A colorful dining area and covered pool deck provide additional spots to enjoy meals together. brbrThe primary suite is a tranquil retreat featuring a king bed, balcony access, and a spa-inspired ensuite with a soaking tub, double vanity, and walk-in shower. Two additional king bedrooms and a queen bedroom each include ensuite bathrooms with walk-in showers, ensuring comfort and privacy for all guests. The fifth bedroom includes twin-over-twin bunk beds and a queen sleeper sofa, making it ideal as a playroom or flexible family space. brbrRoom Details br-Primary Bedroom: King bed, ensuite with soaking tub and walk-in shower br-Second Bedroom: King bed, ensuite with walk-in shower br-Third Bedroom: King bed, ensuite with walk-in shower br-Fourth Bedroom: Queen bed, ensuite with walk-in shower br-Fifth Bedroom: Twin-over-Twin bunk beds and Queen sleeper sofa brbrLocated between the Gulf and Bay, Southern Exposure offers easy access to both calm bay waters and the white sand beaches of Anna Maria Island. Spend your mornings beachcombing, afternoons paddleboarding, and evenings dining along Pine Avenue, just a short stroll away. For guests wanting to explore further, hop on the island trolley or rent a golf cart to experience all seven miles of island beauty. brbrWith its heated pool and spa, elevator, and prime location near the beach and Pine Avenue, Southern Exposure by Anna Maria Vacations is the ideal home for families and groups seeking the perfect balance of comfort and coastal charm. Book your stay today with Anna Maria Vacations and experience the best of Anna Maria Island living at Southern Exposure! brbr- brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.

Bed

Bath

Sleeps

$957.58

/ Nightly

Private Vacation Home

One block off Pine Ave w/ Amazing Rooftop Views! - AMI Memories

Anna Maria, Florida, United States

AMI Memories by AMI Locals brVR20-000052 brbrWelcome to AMI Memories, a stunning five bedroom, three and a half-bath Anna Maria Island vacation home that offers luxury coastal living across three levels. Perfectly located just a four-minute walk to the Gulf beaches and close to local restaurants and boutiques, this elegant retreat features a private pool, rooftop deck with 360° Gulf and Bay views, and a spacious layout designed for families and groups to relax and make unforgettable island memories. brbrHighlights br• 4-minute walk to the beach br• 5 Bedrooms / 3.5 Bathrooms br• Private Pool br• Rooftop Deck with Gulf and Bay Views br• Elevator br• BBQ Grill br• Outdoor Dining br• Covered Patio with Lounge Seating br• Screened-in Balcony Dining Area br• 4 Parking Spaces br• No Pets Allowed brbrThe backyard is a private tropical paradise with a sparkling pool surrounded by lush landscaping, perfect for soaking up the Florida sunshine. Relax in the comfortable wicker seating under the covered patio, enjoy evening cookouts on the BBQ grill, or dine at the outdoor table. Rinse off in the outdoor shower after a beach day, then head up to the rooftop deck to watch the sunset paint the sky over the Gulf. brbrInside, you’ll find bright, coastal inspired decor and elegant finishes throughout. The open concept main living area features a comfortable living room with plush seating, a large TV, and direct access to the screened-in patio with a dining table overlooking the backyard. The gourmet kitchen is fully equipped with high-end appliances, including a Wolf six-burner gas range, wine refrigerator, and separate ice maker. Enjoy meals together at the modern dining table or breakfast at the spacious island before heading out to explore the island. An elevator provides easy access to every floor, ensuring convenience for all guests. brbrEach bedroom is designed for relaxation and privacy. The primary suite features a king bed, private screened lanai, and a spa-like ensuite bathroom with a double vanity and walk-in shower. Upstairs, the second bedroom also offers a king bed, while the third bedroom features a cozy queen bed. The fourth bedroom includes a twin-over-full bunk with a twin trundle, and the fifth bedroom has a twin daybed with trundle, perfect for kids or teens. These two rooms share a Jack-and-Jill bathroom with a shower and tub combination, and an additional hallway bathroom ensures comfort for all. brbrRoom Details br-Primary Bedroom, 2nd Floor: King bed, ensuite bathroom with walk-in shower br-Second Bedroom, 3rd Floor: King bed br-Third Bedroom, 3rd Floor: Queen bed br-Fourth Bedroom, 3rd Floor: Twin-over-Full bunk with Twin trundle, shares Jack-and-Jill bathroom br-Fifth Bedroom, 3rd Floor: Twin daybed with Twin trundle, shares Jack-and-Jill bathroom brbrGuests can enjoy Pine Avenue boutique shops, restaurants, and cafes. The Anna Maria Island trolley is nearby, making it easy to explore Holmes Beach, Bradenton Beach, and local attractions. Whether you’re enjoying coffee on the screened patio, lounging by the pool, or catching sunsets from the rooftop deck, AMI Memories delivers a luxurious island experience from sunrise to sunset. brbrWith its rooftop deck views, private pool, and beautifully designed living spaces, AMI Memories by AMI Locals is the perfect home base for your next Anna Maria Island getaway. Ideal for families and groups; this coastal retreat promises comfort, style, and plenty of unforgettable memories. brBook your stay today with AMI Locals and start making your own island memories at AMI Memories! brbr- br4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by AMI Locals, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrThis property does not allow pets. brbrPlease see our AMI Locals Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$709.03

/ Nightly

Private Vacation Home

Coastal Retreat with Beach Views, Pool and Serene Outdoor

Anna Maria, Florida, United States

Ocean Sunset by Anna Maria Vacations brHome in Anna Maria, FL brVR17-000051 brbrExperience laid-back luxury just steps from the beach at Ocean Sunset, a beautiful five bedroom, three bathroom vacation retreat located just three houses from the shoreline in the heart of Anna Maria. This island escape offers breathtaking Gulf views from multiple balconies, a private backyard oasis with a pool, and stylish coastal interiors, ideal for families or groups seeking serenity and proximity to all the best island attractions. brbrHighlights br-2-Minute Walk to the Beach br-5 Bedroom / 3 Bathrooms br-1 King, 3 Queens, 1 Twin over Full Bunk br-Private Pool with Outdoor Lounge Area br-Balcony with Beach Views and Outdoor Dining br-Professional Linen Service Included br-Close to Pine Avenue and Gulf Dr Dining br-Washer and Dryer br-6 Parking Spaces brbrStep outside to your serene backyard oasis, featuring a private pool, a covered patio with plush seating, and a BBQ grill for casual island cookouts. Multiple balconies provide Gulf views and the perfect spots to enjoy morning coffee, evening cocktails, or simply watch the colorful sunsets Anna Maria is known for. brbrStep inside the main living area where natural light and coastal decor invite you to relax. The welcoming living room offers plush seating and a TV, perfect for post-beach movie nights. The fully equipped kitchen features generous counter space and a complete appliance package, while the formal dining table seats six for group meals and celebrations. Open the doors to the balcony for al fresco dining with sunset views and a fresh sea breeze. brbrOutside, enjoy your private backyard with a sparkling pool, shaded patio seating, and BBQ grill. Whether you're enjoying your morning coffee on the deck, gathering for a casual poolside lunch, or relaxing after a beach day, Ocean Sunset makes outdoor living feel effortless. brbrRoom Details br-Primary Bedroom, 3rd Floor: King bed, balcony access, two closets, and ensuite bathroom with walk-in shower and soaking tub br-Second Bedroom, 3rd Floor: Queen bed br-Third Bedroom, 2nd Floor: Queen bed br-Fourth Bedroom, 2nd Floor: Queen bed br-Fifth Bedroom, 3rd Floor: Twin over Full bunk bed brbrLocated in a quiet neighborhood just two minutes from Palmetto Ave Beach, Ocean Sunset is perfectly positioned for beach days, sunset strolls, and exploring the best of Anna Maria Island. Walk or bike to Gulf Drive’s top restaurants and shops or hop on the island trolley to discover Pine Avenue’s boutiques, Bridge Street, and more. brbrBook Ocean Sunset today and enjoy premium comfort, a prime location, and the peaceful rhythm of coastal island life! br br- brThis property does not allow pets of any kind. brbrThis home has a Ring Camera that faces the street. brbr6 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our Anna Maria Vacations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$999.86

/ Nightly

Private Vacation Home

Charming Duplex Getaway with Pool, Steps from the Beach

Anna Maria, Florida, United States

Sugar Plum Beach by Anna Maria Vacations brDuplex in Anna Maria, FL brVRC18-000058 brbrWelcome to Sugar Plum Beach, your perfect family and friends retreat just five houses from the sugar-white sands of Anna Maria Island’s Gulf beaches. This colorful 6-bedroom, 4-bathroom vacation duplex offers two fully furnished living spaces, making it ideal for large groups who want to stay close but still enjoy a bit of extra privacy. Lounge around the sparkling pool, fire up the grill under the pergola, and unwind in this tropical backyard oasis after days at the beach or exploring nearby Pine Avenue. brbrHighlights br• 2-Minute walk to the Beach br• 6 Bedrooms / 4 Bathrooms br• 4 King Beds, 4 Twin Beds br• Private Pool + Large Pergola with Grill br• Outdoor Dining br• BBQ grill br• One Block from Anna Maria Island Trolley Stop br• Walk to Pine Avenue Shops and Restaurants br• 3 Car parking br• Pet friendly with host approvalbr• Rent Together or Separately as Sugar Plum Beach West and East brbrThe shared backyard is the heart of Sugar Plum Beach, offering a serene spot to gather, swim, and dine. The pool area includes loungers and shaded seating, while the large pergola provides cover for the BBQ grill and outdoor dining table. You’ll also find ample parking, easy beach access, and quick proximity to the free Anna Maria Island trolley stop, which gives you a car-free ticket to explore everything from Pine Avenue to Bridge Street. brbrInside each unit, you’ll find coastal-inspired living rooms featuring stylish sofas, beachy decor, and TVs. The fully stocked kitchens come with cookware, utensils, and breakfast bars for quick morning bites, while the concrete dining tables in the dining areas invite family-style dinners or late-night board games. Both sides of the duplex mirror each other in layout and comfort, offering a harmonious vacation experience. brbrEach unit includes three beautifully appointed bedrooms and two full bathrooms, making Sugar Plum Beach ideal for up to twelve guests. The primary bedrooms feature king beds, floral accents, and ensuite bathrooms with elegant, purple-tiled walk-in showers. Additional king bedrooms and twin bedrooms in each unit provide space and flexibility for families, couples, or kids, while the updated hall bathrooms offer shower and tub combos for added convenience. brbrRoom Details brSugar Plum Beach West: br• Primary Bedroom: King bed, ensuite bathroom with walk-in shower br• Second Bedroom: King bed br• Third Bedroom: Two Twin beds brbrSugar Plum Beach East: br• Primary Bedroom: King bed, ensuite bathroom with walk-in shower br• Second Bedroom: King bed br• Third Bedroom: Two Twin beds brbrWhether you’re planning a family reunion, group getaway Sugar Plum Beach by Anna Maria Vacations gives you the best of island living, just steps from the beach and walking distance to Anna Maria’s favorite attractions. Rent together or individually, under Sugar Plum Beach East or West, for smaller groups to enjoy paradise. brbrBook today and start making unforgettable island memories! brbr- brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. Weight limit of 50lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. See our Anna Maria Vacations Policies for full details. brbr3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. brbrThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.

Bed

Bath

Sleeps

$924.65

/ Nightly

Private Vacation Home

Playing Hooky: On Canal, Dock, Pool & Spa, Game Room by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Playing Hooky by Anna Maria Life Vacation Rentalsbr513 Loquat Drive, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! North End Canal Home! 1 Block to Bay!br6 Bedrooms / 3 Full Bathrooms & Two Half Bathroomsbr2 Kings, 3 Queens, 2 Sets of Twin over Twin BunkbedsbrPrivate Heated Pool & SpabrPool Loungers & UmbrellabrPoolside Covered Lounge with Patio SeatingbrOutdoor ShowerbrGas GrillbrSummer Kitchen with Mini Fridge & Outdoor Bar with Seating for SixbrOutdoor Patio Dining for 10brGame Room Lounge with TV, Foosball, Ping Pong, Arcade Game, Shuffleboard GamebrKeurig & Drip Coffee MakerbrIce MachinebrDock Access (on Canal)brBoat Dock (Up to 50 ft) * lift unavailable for guest use *brProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrDog Friendly (with fee - see notes below)brBeach Towels, Beach Chairs & Beach WagonbrParking for 5 CarsbrbrDetails:brbrIt's time to Play Hooky! Our six bedroom vacation home is located on the north end of Anna Maria a block from Tampa Bay! Enjoy the dock overlooking the canal while living the island life.brbrThe main living level on the second floor features gorgeous canal views and includes the kitchen, living and dining area. A table for 10 and counter and bar seating ensures everyone has a seat at the table. Step outside through the patio doors from the living room and dine al fresco. With seating for 20 at the table and bar, relax and enjoy the view of boats and sea birds.brbrTwo of the six bedrooms are on the main living level and include a master with king bed and en-suite bathroom and a queen bedroom. The third floor features a second king master with en-suite bathrooms, two queen bedrooms, one which includes an en-suite half bathroom and the final guest room with two sets of twin over twin bunkbeds. Each bedroom includes a TV, and crisp linens and plush towels from our professional linen company.brbrYour guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a full-sized washer and dryer.brbrA sparkling, heated pool is one of the highlights of backyard and is complete with pool loungers, umbrella, outdoor shower and grill. A patio dining set features room for 6. The poolside lounge area offers covered seating to enjoy some time out of the sun.brbrSpend the day in the sun and enjoy the outstanding water views. Playing Hooky is located on one of Anna Maria's canals which lead to Tampa Bay. The dock is available for your boat.brbrStep into the game room and enjoy ping pong, foosball, shuffleboard and an arcade game. Relax in the lounge furniture and enjoy the large screen TV.brbrPlaying Hooky is dog friendly with a pet fee of $150 plus tax per dog. If you have added a pet to your reservation, the fee including tax ($168) has been included in your total.brbrPlaying Hooky is easy walking distance to many shops and restaurants. Catch the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The maximum occupancy is 14.brbrBedroom 1: King bed with ensuite bathroom and TV on Floor 2brBedroom 2: Queen bed with TV on Floor 2brBedroom 3: King bed with ensuite bathroom and TV on Floor 3brBedroom 4: Queen Bed with ensuite half bathroom on Floor 3brBedroom 5: Queen Bed with TV on Floor 3brBedroom 6: Two sets of Twin over Twin Bunk Beds with TV on Floor 3brbrPlease note:brThe boat lift is not available for guest use.brAmenities are subject to change.brbrDISCLAIMER: Depth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.brbrVR22-000037brbrGolf Cart DEAL ALERT!!! brReserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.brFUN way to explore the island for the entire family.brMention Anna Maria Life Vacation Rentals and receive this VIP deal!brwww.FunAndMoreRentals.combr941-462-2719brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

Bed

Bath

Sleeps

$1299.48

/ Nightly

Private Vacation Home

A Wave From It All! 5BR Luxury Home with Pool, Spa, Game Room and Walk to Beach

Anna Maria, Florida, United States

A Wave From It All by Anna Maria Island Accommodations brHome in Anna Maria, FloridabrVR19-000058 / DWE5105449 brbrWelcome to A Wave From It All, a luxurious five-bedroom, six-and-a-half-bath vacation rental in the heart of Anna Maria Island. Just a short seven-minute walk to the island’s white-sand beaches and steps from the boutiques and eateries along Pine Avenue, this family-friendly retreat is ideal for large families and groups seeking comfort, fun, and relaxation. With a private heated pool, hot tub, and game room, this coastal-chic home is designed to make every Gulf Coast getaway unforgettable. brbrHighlights br-7-minute walk to Anna Maria Island beaches br-5 Bedrooms / 6.5 Bathrooms br-4 King beds, 2 Twin beds, Full-over-Full bunk beds br-Private heated pool and hot tub br-Game room with foosball and ping pong br-Outdoor grill and multiple dining areas br-Dog friendly with approval and fee br-Washer and dryer br-Parking for 4 vehicles brbrYour private backyard oasis awaits with a sparkling pool, bubbling hot tub, and plenty of lounge seating for soaking up the Florida sunshine. Challenge family and friends to a round of foosball or ping pong or gather for cookouts around the BBQ grill and outdoor dining table. Multiple balconies and covered seating areas provide plenty of spaces to relax with coastal breezes and Gulf sunsets. brbrThe main level features an inviting open concept layout with a coastal-inspired living room, plush seating, and a large TV for family movie nights. The fully equipped gourmet kitchen includes stainless steel appliances, abundant counter space, and a spacious island that makes meal prep easy. An elegant dining table seats eight, while casual meals can be enjoyed on the outdoor balcony. Upstairs, a second den provides an additional lounge space with a large TV and cozy seating. brbrEach bedroom is designed for rest and privacy, with plush bedding, TVs, and ensuite bathrooms. The primary suite is a serene escape with a king bed, private balcony, and ensuite bath featuring dual vanities and a walk-in shower. Three additional king bedrooms each offer ensuite bathrooms with walk-in showers. The fifth bedroom includes two twin beds and its own ensuite, while the upstairs den features a built-in full-over-full bunk bed and a bathroom with a shower/tub combo—perfect for kids or extra guests. brbrRoom Details br-Primary Bedroom, 2nd Floor: King bed, private balcony, ensuite bath with dual vanity and walk-in shower br-Second Bedroom, 2nd Floor: King bed, ensuite bath with walk-in shower br-Third Bedroom, 2nd Floor: King bed, ensuite bath with walk-in shower br-Fourth Bedroom, 3rd Floor: King bed, ensuite bath with walk-in shower br-Fifth Bedroom, 3rd Floor: Two Twin beds, ensuite bath with walk-in shower br-Den, 3rd Floor: Full-over-Full built-in bunk beds, ensuite bath with shower/tub combo brbrThis home includes Wi-Fi, a washer and dryer, and parking for up to four vehicles. Dog-friendly accommodations are available with host approval and an additional fee. Located just steps from local restaurants, boutique shopping, and the Anna Maria Island trolley, guests can enjoy both convenience and relaxation. brbrWith its spacious design, private pool and spa, game room, and unbeatable location near Anna Maria’s beaches, A Wave From It All is the perfect vacation rental for large families and groups. Book your stay with Anna Maria Island Accommodations today and experience the best of Florida’s Gulf Coast in style and comfort! brbr br- br br*Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Island Accommodations Rental Policies for full details. brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. brWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brPlease Remember: brYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$1039.48

/ Nightly

Private Vacation Home

Kingfish House: Luxury Canal Home, Boat Dock, Pool, Spa by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Kingfish House by Anna Maria Life Vacation Rentalsbr233 Oak Ave, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! 1.5 Blocks to the Beach! Canal Front!br5 Bedrooms / 5.5 Bathroomsbr1 King, 3 Queens, 2 Sets of Twin of Twin BunkbedsbrPrivate Heated Pool & SpabrPool LoungersbrPoolside Covered Lounge AreabrBoat Dock (Boat Lift is Not Available for Guest Use)brElevator to all FloorsbrGas GrillbrCovered Patio Dining for 8brMultiple VerandahsbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrParking for 4 CarsbrbrDetails:brWelcome to Kingfish House, a dream getaway on Anna Maria Island just 1.5 blocks from the sugar sand beach. Framed by swaying palms and sunlit skies, this stunning elevated home offers sunlit verandahs, breezy gathering spaces, and a private pool and spa overlooking a canal.brbrThe luxury kitchen is designed for effortless gathering, featuring a spacious island with seating for four, high‑end appliances, and warm coastal finishes. Just beyond the island, a bright window‑wrapped dining nook offers a cozy spot for morning coffee, family meals, or game nights. With built‑in seating, and views of swaying palms, it becomes a natural extension of the kitchen and a favorite place to unwind during your stay.brbrThe main living and dining area offers a bright, open space designed for gathering and relaxation. A comfortable sectional anchors the living room, complemented by stylish seating and a large TV for movie nights or quiet evenings in. Just beside it, the dining area provides a welcoming place to share meals, with plenty of room for everyone to come together. The entire space is filled with natural light and finished with coastal‑inspired details, creating a warm, inviting atmosphere at the heart of the home.brbrThe home features five beautifully appointed bedrooms, each with its own ensuite bathroom to ensure privacy and comfort for every guest. On the top floor, the king suite offers a serene retreat with its own balcony and TV, joined by a charming bunk room perfect for kids or groups, as well as a queen suite with another private balcony. The second floor includes two additional queen suites, one with its own balcony, giving guests plenty of space to unwind.brbrThe home also offers several inviting verandahs that extend the living space outdoors. These covered retreats provide comfortable spots to relax in the shade, enjoy the island breeze, or take in the surrounding tropical views. Whether you're unwinding with a book, sharing a quiet conversation, or simply soaking up the island atmosphere, these outdoor spaces add yet another layer of relaxation to your stay.brbrStep outside to a true resort‑style oasis. The covered poolside lounge offers a spacious sectional, ceiling fan, and plenty of shade for relaxing between swims. Just steps away a built‑in grill makes al fresco cooking effortless. An adjacent patio dining area overlooks the pool and tropical landscaping, creating an easy flow for outdoor meals and gatherings.brbrThe sparkling pool and spa sit at the center of it all, surrounded by lush greenery and ample sun loungers, with an outdoor shower for quick rinses after the beach or pool. Along the canal, a private dock provides a peaceful spot for fishing, launching kayaks, or docking your boat — giving you direct access to the water whenever you're ready for adventure.brbrAn elevator services all levels of the home, making access effortless from floor to floor. Throughout your stay, you'll enjoy complimentary Wi‑Fi, professional linen service, and the convenience of a washer and dryer. Beach days are made easy with provided towels, chairs, and a wagon, and there's parking for up to four cars, ensuring a seamless arrival and stay.brbrKingfish House sits in an ideal spot for guests who want to be close to everything. It's an easy stroll to Gulf Drive, where you'll find local restaurants, shops, and access to the free island trolley that runs the full seven miles of Anna Maria IslandbrbrBedroom 1 - King Bed, Ensuite Bathroom, Balcony, TV - Floor 3brBedroom 2 - 2 Sets of Twin over Twin Bunkbeds, Ensuite Bathroom, - Floor 3brBedroom 3 - Queen Bed, Ensuite Bathroom, Balcony, TV - Floor 3brBedroom 4 - Queen Bed, Ensuite Bathroom, Balcony, TV - Floor 2brBedroom 5 - Queen Bed, Ensuite Bathroom, TV - Floor 2brbrPlease note:brThis home is not pet friendly.brAmenities are subject to change.brDriveway parking is available for 4 cars. Parking for additional vehicles is not available.brBoat Dock (Boat life is Not Available for Guest Use)brbrDISCLAIMER:brDepth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The minimum requirement for this home is no less than seven nights. The maximum occupancy is eight.brbrVR26-000006brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

5

Bed

5

Bath

8

Sleeps

$1429.71

/ Nightly

Private Vacation Home

Summer Paradise-Rooftop deck and private heated pool/spa

Anna Maria, Florida, United States

Summer Paradise 244 Willow Ave, Anna Maria, FL 34216 What you will love about this property: • Less than 8-minute walk to the beach • Luxury home with luxury finishes • Canal front property with private dock • Private balconies and roof top deck with stunning views • Private pool and spa with swim up bar/Tiki • Private Elevator • Outdoor living and dining space with grill • Open-concept kitchen and living areas • Professional Linen program • 3 Full size washer and dryer • Close to shops, restaurants and free trolley access • In the heart of Anna Maria Property details: Welcome to Summer Paradise. Your dream getaway on Anna Maria Island! This stunning brand-new, canal-front luxury home in the heart of Anna Maria Island offers the perfect blend of luxury and coastal charm, featuring 6 spacious bedrooms and 6.5 elegantly designed bathrooms, making it ideal for family vacations or group retreats. With a private dock, a resort style pool with a swim up bar, and a rooftop deck showcasing stunning island views, this vacation rental is designed for unforgettable gatherings with family and friends. Just a short walk from the beautiful beaches of Anna Maria and Pine Avenue’s boutique shops and waterfront dining, Summer Paradise offers the perfect blend of relaxation and island adventure. Step inside to discover a beautifully decorated interior that exudes a relaxed yet sophisticated vibe. The open-concept living area is bathed in natural light, showcasing high-end finishes and stylish furnishings. The gourmet kitchen is a chef’s paradise, equipped with top-of-the-line appliances and ample counter space, perfect for preparing meals for your loved ones. Outside, unwind in your private oasis. The sparkling pool overlooks the serene canal, providing a tranquil spot for sunbathing or a refreshing dip. The spa invites you to relax under the stars, while the outdoor kitchen is ready for barbecues and gatherings. The highlight of your outdoor space is the charming tiki hut, complete with swings for lazy afternoons. With direct canal access you can easily head out for a peaceful morning paddle toward the bay. End each day watching the sunset from the rooftop deck, where panoramic island and water views make every moment unforgettable. For those seeking a panoramic view, the rooftop deck offers breathtaking views of the island and the sunset, making it the perfect spot for evening cocktails. With its prime location just steps from the beach, this vacation rental ensures that you have everything you need for an unforgettable stay on Anna Maria Island. Get everyone together in comfort and style at Summer Paradise. Book with us today. Bedrooms & Bathrooms • Primary Bedroom: King bed, ensuite bathroom with double vanity and walk-in shower and freestanding tub • Second Bedroom: King bed, ensuite bathroom with walk-in shower • Third Bedroom: King bed, ensuite bathroom with walk-in shower • Fourth Bedroom: King bed, ensuite bathroom with walk-in shower • Fifth Bedroom: King bed, ensuite bathroom with walk-in shower • Sixth Bedroom: full over full bunk bed with en-suite bathroom with walk-in shower This property participates in our Professional Linen Program. In Beach House Real Estate's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high quality linens; including bedding, bath towels, wash cloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. Exciting news Golf carts offer a delightful, cost-effective, and hassle-free means of transportation on Anna Maria Island throughout your visit. Live life at a slower pace while on vacation. Cruise around in the Florida sunshine feeling the Gulf Coast breeze. Rent a six-seater electric golf cart for only $750 a week. Please contact us to reserve your golf cart today! Are you bringing the kiddos We have pack & plays and highchairs too! Your item(s) will be at your rental property for your arrival, and we will pick them up at your departure. We rent by the week: Pack & Play - $50.00 Highchair - $40.00 Please contact us to reserve your baby equipment. Friendly reminders No pets are allowed in this home. This home is managed by Beach House Real Estate, an Anna Maria Island property management company. Please remember you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. Please note that homes with elevators do not have living accommodation on the first floor. If you have members in your party that struggle with the use of stairs, we strongly recommend that you reserve a property on the ground floor. Beach House Real Estate cannot be held accountable for any malfunctions of the elevator and does not offer compensation. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please note: 6 cars maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

6

Bed

6

Bath

12

Sleeps

$1881.49

/ Nightly

Private Vacation Home

Happy Ours – NEW LISTING, Direct Beachfront Home On Magnolia

Anna Maria, Florida, United States

Welcome to Happy Ours!brOn Anna Maria Island (Anna Maria, FL)brbrExperience Happy Ours — a rare direct beachfront retreat tucked along Magnolia Avenue on Anna Maria Island's coveted north end.brbrPositioned on one of the most desirable beachfront stretches of the island, this home sits directly on the sand with uninterrupted Gulf views and the soothing rhythm of the waves just beyond your porch. Here, mornings begin with coffee overlooking the water, afternoons are spent drifting between beach and balcony, and evenings gather around the firepit under a sky full of stars.brbrPerfect for: families, multi-generational groups, writers, creatives, and anyone seeking an authentic beachfront escape with space to gather and breathe.brbrHighlightsbr- Direct Gulf-front home on Magnolia Avenue — one of Anna Maria Island's most sought-after beachfront streetsbr- Private beach path directly from the home to the sandbr- 5 Bedrooms | 2 Bathrooms across two spacious living levelsbr- Expansive wraparound covered porch with panoramic Gulf viewsbr- Adirondack chairs and firepit for sunset gatheringsbr- Outdoor shower for sandy beach daysbr- Two indoor living rooms for relaxing and gatheringbr- Walkable to shops and restaurants on Pine Avenuebr- Parking for 2–3 vehiclesbrbrInterior SpacesbrHappy Ours welcomes guests into a bright, open living space designed to capture the beauty of the Gulf from nearly every angle. The upstairs living room features comfortable seating, large windows, and coastal textures that reflect the natural surroundings.brbrNatural light pours through the windows while the expansive Gulf views provide a constant reminder of how close you are to the shoreline.brbrA spiral staircase connects the main living level to the lower level, creating two separate gathering spaces ideal for larger families or groups traveling together.brbrDownstairs, a relaxed second living room opens directly toward the dunes and beach access. With its finished concrete floors and laid-back coastal feel, it perfectly embraces the spirit of beachfront living where sandy feet and salty air are simply part of the experience.brbrKitchen & DiningbrThe spacious kitchen is designed for gathering, cooking, and sharing meals together.brbrFeatures include:br- Premium Wolf wall ovenbr- Stovetop cooking surfacebr- Microwavebr- Two dishwashers for easy cleanupbr- Two large kitchen islands for prep and conversationbr- Bar areabr- Coffee stationbr- Large dining table for group mealsbr- Additional desk workspacebrbrWhether you're preparing breakfast before a beach walk or hosting a sunset dinner, the open layout makes it easy for everyone to stay connected.brbrSliding doors open to the covered wraparound porch, where dining, reading, and ocean watching quickly become daily rituals.brbrOutdoor LivingbrLife at Happy Ours is centered around the water.brbrStep outside onto the wraparound covered porch where Adirondack chairs and breezy seating areas invite you to linger with a book or a glass of wine while the Gulf stretches endlessly before you.brbrA private beach path leads directly from the property through the dunes and onto the sand.brbrAfter long beach days, rinse off in the outdoor shower, gather around the firepit, or relax in the Adirondack chairs as the sun dips into the Gulf.brbrFew places on Anna Maria Island offer this kind of immediate connection to the beach and the natural beauty of the north end.brbrBedrooms & LayoutbrUpper LevelbrPrimary King Suitebr- King bedbr- En-suite bathroom with walk-in showerbr- Gulf views and natural lightbr- Bunk Roombr- Twin-over-full bunkbr- Twin-over-twin bunkbr- Hall bathroom with walk-in showerbr- Smart TVbr(Both upstairs bedrooms include TVs but do not have closets.)brbrLower LevelbrThe lower level offers a relaxed coastal vibe with direct access to the beach path and outdoor areas.brbrQueen Bedroom #1br- Queen bedbr- Comfortable and quiet space for restful nightsbrbrQueen Bedroom #2br- Queen bedbr- Light-filled and welcomingbrbrBunk Roombr- Two twin-over-twin bunk bedsbr- Two additional twin bedsbr- A shared hall bathroom with walk-in shower serves the downstairs bedrooms.brbrThis level also includes a second living room, perfect for movie nights, kids' space, or relaxing after long days on the beach.brbrAdditional Amenitiesbr- High-speed Wi-Fibr- Smart TVs throughout the homebr- Washer and dryerbr- Professionally laundered linens and towelsbr- Beach towels providedbr- Outdoor showerbr- Firepit and Adirondack seatingbr- Private beach access pathbrbrParkingbr- Driveway parking for 2–3 vehiclesbrbrThe LocationbrMagnolia Avenue is widely considered one of the most special beachfront streets on Anna Maria Island. Tucked away on the island's peaceful north end, the area offers a quiet residential feel while still being just minutes from Pine Avenue's restaurants, boutiques, and island charm.brbrFrom this location you can walk the beach toward Bean Point, explore the shops on Pine Avenue, or simply stay close to home and let the rhythm of the Gulf set the pace for your days.brbrWrite Your Vacation StorybrHappy Ours is the kind of place that invites you to slow down. Morning coffee with Gulf views. Long afternoons on the sand. Evenings gathered on the porch listening to the waves.brbrHere, the beach isn't just nearby.brIt's part of the home.brbrCome experience direct Gulf-front living on Anna Maria Island and write your vacation story at Happy Ours.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO PETS. NO SMOKING.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrCity of Anna Maria Vacation Rental License: VR22-000002brMax Occupancy: 12 Guests | Max Vehicles: 2-3brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.

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Bath

Sleeps

$1297.6

/ Nightly

Private Vacation Home

Once Upon a Tiki: Canal, Dock, Backyard Paradise, Games, Pool by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

211 Chilson Ave, Anna Maria, FL 34216brWhat You'll Love About This Home:brbrLocation! One Block to the Beach! On a Canal!br5 Bedrooms / 3 Bathroomsbr3 King Beds, 2 Sets of Twin over Twin Bunk Beds, Full over Queen Bunk BedbrGround Level Canal HomebrPrivate Heated PoolbrIn Pool LoungersbrOutdoor ShowerbrBoat & Fishing DockbrOne of the Largest Backyards on the IslandbrPool Table, Ping Pong, Giant Jenga Game & Cornhole brHammocksbrGas GrillbrPoolside Tiki Hut with Lounge Furniture & Patio DiningbrProfessional Linen Service & Washer & DryerbrComplimentary WIFIbrSonos Sound System Indoors & Outdoors (Blue Tooth Enabled)brCommercial Large Capacity Ice Maker (in garage for easy cooler fill ups)brBeach Towels, Beach Chairs & Beach WagonbrParking for 5 CarsbrbrDetails:brUp your vacation game and take relaxation to the next level at Once Upon A Tiki. Our five bedroom, single level home has everything you need for the beach vacation of your dreams.brbrThe open design and beachy decor of the living room is the perfect gathering place while the chef in the family creates a meal in the fully equipped kitchen. With counter seating at the center island for five and a dining table for eight, everyone will have a place to dine. Patio doors on each side of the home provide natural light throughout the home with access to the outdoor spaces.brbrThe master bedroom features a king size bed, en-suite bathroom and access to the backyard and pool through patio doors. Two of the additional guestrooms also have king sized beds and one has an ensuite bathroom. The kids in the family will love the bunk rooms, one with two sets of twin over twin bunk beds and the other with a set of full over queen bunk beds. Each bedroom has a TV and includes crisp linens and plush towels from our professional linen company. Your guests will stay connected with complimentary WFI and enjoy all of the comforts of home, including a washer and dryer.brbrStep outside and take in one of the largest backyards in Anna Maria! With a sparkling pool with in-pool lounge chairs, large sun deck, covered tiki hut with hammocks, patio lounge furniture and patio dining and back lanai with lounge furniture and TV. The outdoor fun never ends! A pool table, ping pong table, and cornhole set will provide endless fun for your family.brbrOnce Upon a Tiki is located on one of Anna Maria's beautiful canals. With a dock for fishing and Adirondack chairs for watching the world go by, you may even be lucky enough to see manatee and some of the beautiful wild birds that call the island home.brbrOnce Upon a Tiki is easy walking distance to many shops and restaurants, and less than a block to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrBedroom 1: King, Ensuite Bath, TV brBedroom 2: King, Ensuite Bath, TVbrBedroom 3: King, TVbrBedroom 4: 2 Sets of Twin Bunks, TVbrBedroom 5: Full over Queen Bunk, TVbrbrPlease note:brPets are not allowed in this home.brAmenities are subject to change.brDock measures 25'.brbrDISCLAIMER: Depth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrVR16-000452brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

Bed

Bath

Sleeps

$1776.49

/ Nightly

Private Vacation Home

Precious Memories: North End! Quick Walk to Beach! Elevator,Pool,Ping Pong & Pool by Anna Maria Life

Anna Maria, Florida, United States

Precious Memories by Anna Maria Life Vacation Rentalsbr753 Jacaranda, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! AMI North End! Quick Walk to Beach!br5 Bedrooms / 4 Bathroomsbr4 King Beds, 3 Sets of Twin over Twin Bunk Beds brSleeps 12!brElevator (to all floors)brPrivate Heated Pool & SpabrSun Deck with Pool LoungersbrPool Level Entertainment & Lounge with TVbrCovered Bar with SeatingbrPool Table & Ping Pong TablebrGas GrillbrPatio Dining off Kitchen (Overlooks Pool)brMultiple Verandahs & DecksbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrParking for 4 CarsbrbrDetails:brLocated on the North End of Anna Maria, Precious Memories welcomes you to make vacation memories to last a lifetime. Bring the whole family! This home sleeps 12 guests! With the shimmering waters and sugar sand beaches of the Gulf of Mexico less than a block away, your beach retreat awaits.brbrNatural light from the oversized windows and patio doors fills the living and dining rooms. The gorgeous outdoor deck overlooking the tropical backyard is easily accessed from the kitchen and living room. Prepare a meal in the full kitchen and dine al fresco on the deck with patio dining. If you prefer to share your meals inside, the dining table seats eight with additional counter bar seating for four.brbrTwo of the king bedrooms are on the main living area on the 2nd floor. The master king room features an en-suite bathroom and a sliding door to a private patio. The second King room is near the full bathroom on this level which features a sink and toilet across the hall from a separate tub and shower.brbrThe two other king rooms are located on the third floor and share a jack n jill bathroom outfitted with a shared shower but with each bedroom having its own private vanity and toilet. The kids will love the bunk bedroom with a set of twin over twin bunkbeds. The 3rd floor common area has a full guest bathroom and two sets of built-in twin over twin bunk beds. Each bedroom has a TV and includes crisp linens and plush towels from our professional linen company. Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrTake a dip in the pool and relax in the hot tub while enjoying the lush landscape backyard. The poolside level features a covered, outdoor lounge with a pool table, patio furniture, TV, bar with bar seating, and gas grill. The ping pong table is steps away in the garage.brbrPrecious Memories is easy walking distance to many shops and restaurants the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrBedroom 1: King with TV and Ensuite Bath - Floor 2brBedroom 2: King with TV and Jack & Jill Bath - Floor 3brBedroom 3: King with TV and Jack & Jill Bath- Floor 3brBedroom 4: King with TV - Floor 2brBedroom 5: Twin over Twin Bunk - Floor 3br3rd Floor Common Area: 2 Sets of Twin over Twin Bunk Beds brbrPlease note:brPets are not allowed in this home.brAmenities are subject to change.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrVR21-000027brbrGolf Cart DEAL ALERT!!! brReserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.brFUN way to explore the island for the entire family.brMention Anna Maria Life Vacation Rentals and receive this VIP deal!brwww.FunAndMoreRentals.combr941-462-2719brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

Bed

Bath

Sleeps

$1208.18

/ Nightly

Private Vacation Home

Beach à la Mode | Waterfront with Heated Pool, Canal Views, Steps to Anna Maria Beaches

Anna Maria, Florida, United States

Beach à la Mode | Waterfront Beach Escape with Heated Pool, Canal Views, Steps to Bayfront Park & Anna Maria Beachesbrbr Why You'll Love This HomebrWake up to shimmering canal views from your private luxury sanctuary on Anna Maria Island. Relax by the heated pool and spa, dine al fresco under the stars, or take in wide water vistas from the rooftop lookout — all just a short stroll to soft sandy beaches and local dining. This is effortless Florida living with a sophisticated coastal vibe.brbr ‍ ‍ Perfect ForbrUpscale families, friend groups, and beach lovers seeking luxury waterfront comfort and easy access to Anna Maria Island's iconic shores.brbr ️ Imagine ThisbrImagine a sunrise coffee on your private balcony, water shimmering as boats drift past your canal-front view. Days melt into lazy lounge sessions by your own heated pool and spa, while evenings find you sipping chilled wine on the rooftop, the sky splashed with sunset hues. Walk just under 0.3 miles to Bayfront Park for a beach day, or wander to local eateries and island shops. Here, every moment feels like pure seaside serenity.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, Main Floor, TV, Private Balconybr• Bedroom 2: King Bed, Ensuite Bath, Main Floor, TVbr• Bedroom 3: Queen Bed, Ensuite Bath, Upper Floor, TVbr• Bedroom 4: Queen Bed, Ensuite Bath, Upper Floor, TVbr• Bedroom 5: Four Twin Beds, Shared Bath, Upper Floor, TVbrbr Explore the Areabr• 0.3 miles to Bayfront Park – Family-Friendly Beach, Calm Water, Picnic Areasbr• 0.5 miles to Anna Maria City Pier – Historic Pier with Dining and Water Viewsbr• 0.6 miles to Pine Avenue – Boutiques, Cafés, Galleries and Island Shopsbr• 0.8 miles to Anna Maria Beach – Wide White-Sand Shoreline for Swimming and Shellingbr• 1.0 mile to Bean Point Beach – Quiet, Scenic Beach with Stunning Sunset Viewsbr• 2.8 miles to Bridge Street – Dining, Nightlife, Shopping and Waterfront Boardwalkbr• Easy access to the Free Island Trolley – Quick Trips to Beaches, Shops and Restaurantsbrbr⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean program, featuring a 6-hour deep clean and 35-point inspection to ensure your stay starts beautifully.brbr PLEASE NOTE: The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. This home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.

Bed

Bath

Sleeps

$2200.66

/ Nightly

Private Vacation Home

Seaside Magnolia~1 Block to Pine Ave, Heated Pool!

Anna Maria, Florida, United States

Summary:brbrSeaside Magnolia is a luxury island retreat just 3 blocks from the beach and steps to Pine Ave ️. Enjoy a private heated pool & spa, putting green, ping pong, cornhole, and a spacious backyard perfect for family fun ☀️⛳. This dog-friendly home offers 7 beautifully styled bedrooms, beach gear, and elegant coastal interiors—your perfect Anna Maria Island getaway awaits! ✨brbrbrbrThe Space:brbr Seaside Magnolia ~ 1 Block to Pine Ave, Heated Pool & Spa brbrbrbrWelcome to Seaside Magnolia, a stunning luxury island retreat designed with timeless coastal elegance and five-star comfort. Just 3 short blocks from the beach ️ and steps from Pine Avenue’s shops and dining, this spacious home is perfect for large families and group getaways.brbrbrbrThe main living area on the second floor features an open, airy layout with a designer kitchen, oversized island, and seamless flow into the dining and living spaces—perfect for gathering ️✨ Glass doors open to your private backyard oasis, where a heated pool with sun shelf, spa, putting green, ping pong table, cornhole, and covered patio bar await endless fun .brbrbrbrEach bedroom is thoughtfully styled with plush bedding and coastal charm. The primary suite is a true retreat, complete with a private balcony, massive walk-in closet, and spa-like bathroom . Add in beach gear, a large yard, and dog-friendly accommodations, and you have the ultimate Anna Maria Island escape.brbrbrbr✨ Highlights ✨brbrbrbr• ‍♂️ Private heated pool & spabrbr• ⛳ Putting green, ping pong & cornholebrbr• Spacious backyard for family gatheringsbrbr• ️ 3-block walk to AMI beachesbrbr• Beach chairs & beach cart providedbrbr• Dog friendlybrbr• Washer & dryerbrbr• Community center across the street (gym & tennis day passes available)brbr• ⭐ Owner managedbrbrbrbr ️ Bedroom Layout ️brbrbrbr3rd Floorbrbr• Primary Suite: King bed, private balcony, ensuite bath with soaking tub & walk-in showerbrbr• Bedroom 2: King bed, shared hallway bathbrbr• Bedroom 3: Twin-over-Full bunk with Twin trundle, shared hallway bathbrbrbrbr2nd Floorbrbr• Bedroom 4: King bed, balcony, ensuite bath with walk-in showerbrbr• Bedroom 5: King bed, shared hallway bathbrbr• Bedroom 6: King bed, shared hallway bathbrbr• Bedroom 7: Two Twin-over-Twin bunk beds, shared hallway bathbrbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space. ☀️brbrbrbrOther Things to Note:brbrTo make your stay effortless, the home is fully stocked with 10 beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 4 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨

Bed

Bath

Sleeps

$1120.28

/ Nightly

Private Vacation Home

Luxury Beach Home | Steps From AMI Beachs | Heated Pool

Anna Maria, Florida, United States

Luxury Beach Home • Gulf Views • Heated Pool • Steps to Beach • Sleeps 10brbrWelcome to Sunset Paradise, a stunning Anna Maria Island vacation home located just three houses from the Gulf and steps from the beach. With breathtaking Gulf views, a private heated pool, and multiple balconies designed for sunset watching, this five-bedroom coastal retreat offers the perfect setting for unforgettable island getaways with family and friends — and it’s now pet friendly so your four-legged family members can join the vacation too.brbrLocation. Views. Walkability.brbrThe Space:brStep inside to bright coastal interiors filled with natural light and vibrant island charm. The open-concept living area is designed for gathering after long beach days, with comfortable seating, colorful coastal décor, and large windows that frame beautiful Gulf views.brbrTwo dining tables provide plenty of space for shared meals, board games, and conversation, while the spacious layout allows everyone to relax and unwind.brbrThe fully equipped kitchen features:br• Stainless steel appliancesbr• Spacious countertops and barstool seatingbr• All cookware and essentials for preparing mealsbr• Open flow into the living and dining areasbrPerfect for family vacations, group trips, and beach getaways.brbrOutdoor Living:brStep outside to your private tropical retreat where you can relax, dine, and soak up the island sunshine.br• Private heated pool & spa surrounded by palm treesbr• Spacious patio with lounge chairsbr• Covered outdoor dining areabr• BBQ grill for cookoutsbr• Multiple furnished balconies with Gulf viewsbrbrWhether you’re enjoying morning coffee on the balcony or returning from the beach for an evening swim, the outdoor spaces are designed for true island relaxation.brbrSleeping Arrangements (Sleeps 10):brPrimary King Suite (3rd Floor) – Balcony access, ensuite bath with soaking tub, walk-in shower, and dual vanitybrSecond King Bedroom (3rd Floor)brThird Bedroom (3rd Floor) – Queen bedbrFourth Bedroom (2nd Floor) – Queen bed with balcony access and ensuitebrFifth Bedroom (2nd Floor) – Twin-over-Twin bunk bedbrSixth Bedroom - Full Daybed with Full Size TrundlebrbrPerfect for families, multiple couples, and group vacations!!!!brbrPrime Anna Maria Island Location:br✔ 1-minute walk to Anna Maria Beachbr✔ Steps to Pine Avenue shops, restaurants & boutiquesbr✔ Walk to the Sandbar Restaurantbr✔ Near Bayfront Parkbr✔ Easy access to the free Anna Maria Island trolleybrYou can truly park and explore the island on foot.brbrGuest Access:br• Full private access to the home and pool/spabr• Beach access just steps awaybr• Outdoor grill and dining areabr• Washer and dryer available for guest usebr• Self check-inbrbrImportant Details:br• Maximum occupancy: 10 guestsbr• Maximum 6 vehicles allowed (no overnight street parking)br• Rooftop deck is not available for guest use.br• Pet friendly: Up to 2 pets maximum allowed. $125 per pet non-refundable fee applies and can be requested through our guest portal after booking.br• Pool heating at this location is complimentary.br• Professionally managed.

Bed

Bath

Sleeps

$1771.77

/ Nightly

Private Vacation Home

Dream Luxury Vacation Home with a Guest House, Private Pool, and Bay Views!

Anna Maria, Florida, United States

Blue Bay by Anna Maria Island Accommodations brVPR16-000138brbrExperience the ultimate coastal retreat at Blue Bay, a luxurious and expansive vacation estate offering eight bedrooms and six bathrooms! Located just across the street from the pristine Tampa Bay, this home embodies beachside elegance with breathtaking water views, a private pool, and a sprawling backyard. Take a short stroll and explore Pine Avenue’s local shops, top rated restaurants, and island attractions. Blue Bay combines comfort, luxury, and seamless bay and beach access for the ultimate island escape!brbrHighlights br• Across the street from Bay Beachesbr• 13-minute walk to Gulf beachesbr• 8 Bedroom / 6 Bathbr• 7 King beds, 1 Full-over-full Bunk with trundlebr• Private pool and spa br• Outdoor dining and BBQ grillbr• Ping pong table br• 2-minute walk to Pine Avenue’s shops, boutiques, restaurants, and water activitiesbr• Pet Friendly br• Washer and dryer br• 4 Parking SpacesbrbrThe lush backyard is a true haven for families and groups, featuring a sparkling heated swimming pool complete with an in-pool tiki table, a soothing spa, and plenty of lounge chairs. Whether you're planning a lively family BBQ feast, playing a game of ping pong, or enjoying panoramic views from several balconies, this backyard oasis provides everything you need to make lasting memories together!brbrInside the main residence, you'll find a spacious, elegant living area perfect for gatherings. The chic, comfortable seating invites relaxation for movie nights or casual chats. The formal dining table offers plenty of space for family dinners, while the fully equipped kitchen, with deluxe appliances and a large island with additional bar seating, an area where everyone can come together.brbrThe main home boasts a spacious primary suite on the third floor, featuring a plush king bed, private balcony with stunning bay views, and an ensuite with a walk-in shower, double vanity, and soaking tub, an ideal sanctuary. This home is perfect for accommodating large groups with three additional king bedrooms, each with their own en-suite bathrooms with walk-in showers. A fun bunk room consists of a full-over-full bunk with a trundle, a cozy area for kids or extra guests.brbrAcross the backyard, the guest house adds flexibility, featuring two king bedrooms that share an ensuite, Jack-and-Jill style, bathroom with a walk-in shower, modern, coastal decor, TVs for entertainment, and generous storage. brbrMain House, Room Details br• Primary Bedroom (3rd floor): King bed, ensuite with walk-in showerbr• Second Bedroom (3rd floor): King bed, Shared hallway full bathbr• Third Bedroom (3rd floor): King bed, shared hallway full bathbr• Fourth Bedroom (3rd floor): King bed, ensuite with walk-in showerbr• Fifth Bedroom (2nd floor): King bed, ensuite with walk-in showerbr• Sixth Bedroom (2nd floor) Full-over-full bunk and twin trundle brbrGuest House, Room Detailsbr• Seventh Bedroom: King bed, Jack-and-Jill style bathroombr• Eighth Bedroom: King bed, Jack-and-Jill style bathroombrbrBook Blue Bay today and enjoy a luxurious, Bayfront escape perfect for large groups or family reunions. With stunning water views, outdoor paradise amenities, and easy access to beaches, shops, and waterfront dining, this estate offers everything you need for an unforgettable Anna Maria Island vacation! Reserve now and create lifelong memories in this premier coastal retreat!brbrbr-brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company.brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Island Accommodations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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