Vacation Home Rentals By Owner In Anna Maria, FL

This unique, beautifully appointed Boutique Spanish Style Villa on the North End of Anna Maria Island is a perfect getaway nestled in a quiet neighborhood. Come relax in this 2 bedroom, 2 bathroom, 2 flex rooms that sleep 2 people each, just a short walk to the white sand beach, clear turquoise gulf waters, or relax and enjoy all that Anna Maria has to offer.brbrThe master bedroom boasts a king bed with his and hers closets and an en-suite renovated bathroom. The washer and dryer sits in this large bathroom as well. The guest bedroom includes a king size bed and built in shelves to hold all your vacation goodies. Each bedroom has its own smart TV. The renovated guest full bathroom is located in the hallway across from the guest bedroom.brbrThe main living area is open to the dining room and kitchen with multiple comfy sitting areas. The queen sleeper sofa allows for 2 additional guests to sleep comfortably. The dining room has a built in buffet with all the vintage and Spanish charm ready for your getaway. The kitchen is fully stocked and includes a gas/propane grill right outside the sliding doors. brbrThe Surfboard room is a fun hangout for any age. The room is off the front and includes 2 daybeds and unique furnishings. It has it's own AC system to keep it cool in the heat of the summer.brbrThe Boutique Spanish Style Villa has outdoor dining, cooking and lounging. 2 bikes are included for your use to travel to Pine Ave, local shops and restaurants, The city pier, which is also home to a remote research center for Mote Marine, parks, Bean Pointe, and so much more that the North End has to offer.brbrbr**We also rent out the property next door and can rent out both for large parties, if the Villa is booked take a look at this property! brhttps://www.homeaway.com/vacation-rental/p2019100vb uni_id=2583617brbr

*NEWLY RENOVATED* Boutique Spanish-Style Villa - perfect for family & friends

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1743.49

Dolce Vita by Anna Maria Life Vacation Rentalsbr848 N Shore Drive, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! North End! Gorgeous Bay Views!br5 Bedrooms / 5 Bathroomsbr4 Kings, Queen over Queen BunkbedbrPrivate Heated Pool & SpabrPool LoungersbrElevator (all floors)brMini Golf Putting Green, CornholebrPropane FirepitbrCovered Poolside Lounge Area with Sofas & Dining TablebrPool, Ping Pong & Foosball TablesbrGas GrillbrMultiple Verandahs with Seating including a Swing LoungerbrRooftop Deck Experience with Lounge Cabana & Privacy Sun ShadebrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels. Beach Chairs & Beach WagonbrParking for 4 Cars in Driveway & 2 Cars in GaragebrbrDetails:brLocated on the desirable North End of Anna Maria Island, Dolce Vita is a stunning vacation home offering the ultimate getaway experience. With panoramic views of the sparkling bay, it's the ideal destination for those seeking relaxation, luxury, and adventure. This spacious 5-bedroom, 5-bathroom home comfortably accommodates up to 8 guests with 4 king-sized beds and a queen-over-queen bunk bed.brbrFour of the of the bedrooms feature a King Bed and ensuite bathroom. The final bedrooms includes a queen over queen bunk bed. Each bedroom includes crisp linens and plush towels in the bathrooms from our professional linen service. With an elevator for easy access to all floors and a washer and dryer, every comfort has been thoughtfully considered. Additional amenities include complimentary Wi-Fi, beach towels for your convenience, and ample parking space for 4 cars in the driveway and 2 in the garage.brbrEnjoy outdoor living at its finest with a private heated pool and spa, pool loungers, and a propane firepit for cozy evenings under the stars. The expansive outdoor space also features multiple verandahs with plenty of seating, including a swing lounger perfect for unwinding with a view.brbrFor fun-filled activities, this home includes a mini golf putting green, cornhole, and an assortment of games like pool, ping pong, and foosball. For added convenience, a gas grill is available for those who love cooking outdoors.brbrThe rooftop deck is a luxurious experience with ample seating and a lounge cabana with a privacy sunshade, offering a serene escape with breathtaking views. brbrWhether you're relaxing by the pool, enjoying the games, or soaking in the views from the rooftop, Dolce Vita promises a memorable and rejuvenating stay on one of Florida's most beautiful islands.brbrDolce Vita is easy walking distance to Pine Ave, restaurants, and 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!brVR25-000008brbrBedroom 1 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 2 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 3 - King Bed, Ensuite Bathroom, Balcony, TV - Floor 2brBedroom 4 - King Bed, Ensuite Bathroom, Balcony, TV - Floor 2brBedroom 5 - Queen over Queen Bunk Bed, TV - Floor 2brbrPlease note:brThis home is not pet friendly.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. The minimum requirement for this home is no less than seven nights. The maximum occupancy is eight.brbrGolf 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.combr941-462-2719 brbrIMPORTANT 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.

Dolce Vita: Amazing Rooftop Experience, Views, Pool, Spa by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$4463.83

Nestled in Anna Maria, this delightful house offers guests a tranquil and peaceful retreat. With 8 bedrooms including 7 king beds and 1 bunk bed, and 9 bathrooms equipped with all the essentials, this adorable property is perfect for large groups or families looking for a relaxing getaway. Kickback, relax, and enjoy everything Anna Maria and our house has to offer. Float around the lazy river pool, unwind in the spa, or challenge friends and family to a game on the putting green!brbrWe have three children, so please let us know if there's anything we can provide in order to make your travel experience easier! brbrBedroom details: brbr-Primary Bedroom, 3rd floor: King bed, balcony, and ensuite bathroom with walk-in shower and soaking tubbr-Second Bedroom: King bed and ensuite bathroom with walk-in shower and soaking tubbr-Third Bedroom: King bed and ensuite bathroom with walk-in showerbr-Fourth Bedroom: King bed and ensuite bathroom with walk-in showerbr-Fifth Bedroom: King bed and ensuite bathroom with walk-in showerbr-Sixth Bedroom: King bed and ensuite bathroom with walk-in showerbr-Seventh Bedroom: King bed and ensuite bathroom with walk-in showerbr-Eighth Bedroom: Twin over Twin bunk bed and ensuite bathroom with walk-in showerbrbrPack n plays / slumberpods / toddler air mattresses are all available to borrow!

Lazy River! Mini Golf! Sleeps 16 Anna Maria Island - Nautical Situation

Anna Maria, Florida, United States

Bed

Bath

16

Sleeps

$735.7

Tucked away on the coveted north end of Anna Maria Island, this stunning 4-bedroom, 4.5-bathroom pool home on Pine Avenue offers the perfect blend of luxury, privacy, and coastal charm.brbrDesigned for both relaxation and entertaining, the home features a spacious open-concept layout with beautifully appointed interiors, high-end finishes, and plenty of natural light throughout. The main living areas flow seamlessly into the outdoor oasis, where you’ll find a private pool surrounded by lush tropical landscaping—ideal for soaking up the Florida sunshine.brbrOne of the standout features is the detached bedroom suite, offering added privacy for guests or extended family. Just steps from the pool, a separate TV room provides the perfect spot to unwind after a day at the beach, making it an ideal hangout space for kids or a cozy retreat for movie nights.brbrHead upstairs to the rooftop balcony, where you can enjoy peaceful mornings with coffee or take in breathtaking sunset views over the island—an unforgettable way to end each day.brbrLocated just a short stroll from the beach, boutique shops, and local dining along Pine Avenue, this home combines convenience with a serene island setting. Whether you're planning a family getaway or a trip with friends, this exceptional property delivers the ultimate Anna Maria Island experience.brbrBEACH DISCLAIMER: Please be aware that the beach and sand may differ from the photos due to natural processes like tides, weather, and erosion. The beach environment is dynamic and constantly changing, and we appreciate your understanding. Enjoy the beauty of our beachfront properties!brbrPETS: Please note this property does NOT allow pets. brbrPARKING: 3 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.brbrNOTE: For security and insurance purposes, there are exterior-only video cameras on the premises.brbr***OVERCROWDING CONSEQUENCES***: Maximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.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.br*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Prana Sanctuary: Luxury 4 Bedroom Home in Heart of Anna Maria

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$745.9

Photos updated April 2025!brbrWelcome to Castle Azul, a stunning canal-front vacation home on Anna Maria Island! Just one block from the Bay, a short walk to the Gulf of Mexico, and two blocks from Pine Street and the Anna Maria City Pier, this home offers the perfect island retreat.brbrWith four bedrooms and four and a half bathrooms, there's ample space for everyone. The open living area features large windows with beautiful canal views. The fully equipped kitchen boasts stainless steel appliances, a wine fridge, and a spacious island, perfect for quick snacks or coffee on the balcony. Enjoy meals indoors or dine al fresco with fresh seafood on the outdoor grill.brbrThe primary bedroom radiates luxury with a private balcony and an ensuite bathroom with dual sinks and a walk-in shower. Each additional bedroom offers comfort, including a bunk room ideal for younger guests.brbrOutside, the backyard oasis awaits. Lounge by the pool and hot tub, practice on the putting green, or relax on the dock. Try your luck fishing, paddleboarding, or kayaking, and keep an eye out for manatees! For indoor fun, play ping pong or catch a movie in the lounge. brbrExplore all seven miles of the island with the free trolley or book a local adventure like a fishing charter, dolphin tour, or bike rental. Castle Azul is your luxury island getaway!brbrOF NOTE:br-The elevator is not in service.br-The fireplace in the living room is not operational.br-For security and insurance purposes, there are exterior-only video cameras on the premises. Three cameras have a view of the driveway, pool equipment (side of house), and dock.brbrPETS: A dog is allowed with prior approval. Must be well trained and less than 40lbs. 1 dog max. A $150 non-refundable pet fee applies per pet.brbrPARKING: 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.brbrDOCK/BOATS: Dock can accommodate a boat approximately 20ft and has a ladder. **Please note that the boat lift and any motorized watercraft are not available for guest use**brbr--DISCLAIMER: 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.brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.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.brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Castle Azul: Luxury canal front w/pool, hot tub, putting green, and ping pong

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1118.11

Dragonfly Harbor by Anna Maria Life Vacation Rentalsbr511 Loquat Dr, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! North End Canal Home! 2 Blocks to Bay!br4 Bedrooms / 4.5 Bathroomsbr3 King Beds, 1 Twin Bed & 1 Set of Twin BunkbedsbrPrivate Heated Pool & SpabrIn Pool LoungersbrOutdoor ShowerbrDock Access (on Canal)brBoat Dock (Up to 50 ft) * lift unavailable for guest use *brCorn HolebrFoosball Table & Ping Pong TablebrPutting GreenbrGas GrillbrMultiple Decks with Outdoor SeatingbrRooftop Deck with Patio Dining Set & 360 ViewsbrProfessional Linen Service & Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs & Beach WagonbrParking for 4 CarsbrDetails:brDragonfly Harbor has it all; location, views, games for family fun, boat dock, sparkling pool and gorgeous outdoor spaces. Welcome to your ultimate AMI beach vacation!brbrSitutated on one of Anna Maria's famed canals, you will enjoy the quaint water views while relaxing dockside.brbrWith three levels of decks, including a roof top deck with views of Tampa Bay and the Sunshine Skyway, Dragonfly Harbour delights in sunsets and sunrises. The many glass doors and windows soak the living room in natural light while providing a relaxing vista to watch boats sail by.brbrThe well appointed kitchen will please the chef in the family. Dine inside at the table for six or take a step outside the patio doors and enjoy the island breezes with your meal at the patio dining table for eight.brbrGuests will have the choice of three king bedrooms or a bedroom with a twin bed and a set of twin bunkbeds. Each bedroom features an en-suite bathroom, a Smart TV, and includes crisp linens and plush towels from our professional linen company.brbrThe huge sundeck overlooks the canal and features an oversized pool with in pool loungers with an umbrella and hot tub. The outdoor shower and many deck chairs complete the poolside vibe. Poolside dining is complete with a patio dining table for four and gas grill. Adirondack chairs on the dock are the perfect place to thrown in a fishing line or read a good book. The 100 ft dock can support a boat up to 50 ft.brbrChallenge your family to ping pong, foos ball or a game of corn hole and don't forget about the putting green. With so much to enjoy, Dragonfly Harbour will become your favorite island home.brbrYour guests will stay connected with complimentary WFI and enjoy all of the comforts of home, including a washer and dryer.brbrOur home is easy walking distance to many shops and restaurants, and the free island trolley stops a few blocks way and 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 on Floor 3brBedroom 2: King with TV and Ensuite Bath on Floor 3brBedroom 3: 1 Twin Bed and a set of Twin Bunkbeds with TV and Ensuite Bath on Floor 3brBedroom 4: King with TV and Ensuite Bath (shared with hall) on Floor 2brbrPlease note:brThis home does not allow petsbrThe boat lift and any onsite motorized watercraft are not available for guest usebrThe golf cart is not available for guest use**brThe fireplace is not operablebrAmenities are subject to change.brDock can accommodate boat up to 50'. 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.brbrIMPORTANT 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.brVR18-000011

Dragonfly Harbour: Spectacular Canal Front Home, Pool, Hot Tub Rooftop Deck by Anna Maria Life

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1380.1

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.

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

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$468.19

Welcome to Beach N Bay 206! br Pool COOLING for hot summer days!br A honeymooners delight or a couple's retreat! Enjoy a romantic getaway! Don't miss your chance to stay at the North end of Anna Maria Island in the highly desirable village of Anna Maria, one of Coastal Living Magazine's Top 10 Happiest Seaside Towns! Located right in the middle of all that happiness, Beach N Bay is the island vacation cottage duplex that's so tropical and fun, you'll swear you can hear steel drums!br Ideally situated at the corner of Spring and Crescent Avenues, it's right in the middle of everything the village of Anna Maria has to offer. br br HIGHLIGHTSbr br Private pool/spa (21x12 ft)br Pool COOLING for hot summer days!br 832 sq ft. br 171 sq ft. of screened in patiobr Centrally located near Pine Avenuebr 0.3 miles from bay access br 0.3 miles from beach accessbr br BEDROOMSbr br Sleeps 4br Primary Bedroom: King br Second Bedroom: Two Twinsbr br BATHROOMbr br Primary Bathroom: Walk-in Showerbr br EXTERIORbr br The 21' x 12' pool is private for this side of the duplex. It is being heated and cooled to the perfect temperature all year round at a cost of $150.00 per week. Please no smoking inside, in the lanai, or by the pool area. This is a smoke free property! There is a designated smoking area by the fire pit in front of the house. If you like hanging out under the sun and stars when you're in Florida, Beach N Bay will be the perfect place to call home! Be sure to pack your mini drink umbrellas because you'll want to jump right in the pool, tropical drink in hand, and soak up the Anna Maria sunshine! This fantastic, private saltwater pool isn't just heated for wintertime enjoyment, it's one of only a handful of pools on the Island that are cooled for those hot summer months! At one end you'll find a tanning ledge, designed for sunbathing with your toes in the water - also a great place to supervise little ones. On the other end you'll find a swim-up bar table and stools, as well as a spa. Lovely bronze herons serve as deck jets, shooting water into the pool. Your outdoor amenities are rounded out with a big grill that offers options for smoking, as well as cooking with gas or with charcoal. There's also a drink cooler, a firepit surrounded by Adirondack chairs, an outdoor shower, and a screened porch with flat panel TV. br br The weekly pool heat/cool fee is $150.00. Pool heaters in private homes are locked for your safety and controls must not be tampered with as they are monitored by the pool company. 86 F is the highest heat temperature setting which might not be always reached. Please note if cold days and nights occur, water temperatures will drop and may stay cooler longer. Pool heaters will not operate and will automatically shut down if outside temperatures get too cold. While we take every precaution to ensure that pools are heated as specified, weather conditions may affect the temperature of the pool. Nothing can be done about this issue. Outdoor spas are not hot tubs and require heat at the additional cost. The temperature of a spa is typically set at the same temperature as the pool. In the event of pool equipment malfunction during your stay, Duncan Real Estate will expedite repairs as quickly as possible. It may be necessary to close swimming pools for maintenance purposes. No refund or rent adjustment will be made for circumstances beyond our control, malfunctions, or loss of use of equipment or amenities.br br PET POLICYbr br Beach N Bay 206 is a pet friendly property for a maximum of 2 dogs up to 50 lbs. The non-refundable pet fee is $150.00 per pet and will be charged for each week. Short stays are not prorated. The pet fee does not cover any damage caused by the pet. br Due to property insurance policies and liability concerns, the following breeds or crossbreeds are not permitted:br Pit Bullbr Akitabr Rottweilerbr German Shepherdbr Siberian Huskybr Malamutebr Doberman Pinscherbr Chowsbr Any Wolf-dog hybridbr Any dog with biting historybr br br Rent the other side of this duplex to accommodate up to 8 people under one roof! Call for occupancy details.br br Beach N Bay 206 has two parking spots reserved for guests.br br Please keep in mind that 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.br Amenities Include:br - Bedroom 1 Kingbr - Bedroom 2 Twinsbr - Bathroom 1 Walk-in Showerbr - Hot Waterbr - Ground Level Ybr - Central A Cbr - Cental Heatbr - Sqft under a c 832br - Free Parkingbr - Parking Spots 2br - Dogs up to 50 lbs Ybr - Self Check Inbr - Keyless Entrybr - Bath Towelsbr - Beach Towelsbr - Quality Linensbr - Hair Dryerbr - Hangersbr - Refrigeratorbr - Stovebr - Cookwarebr - Toasterbr - Blenderbr - Keurigbr - Drip Coffee makerbr - Dishwasherbr - Microwavebr - Dining Tablebr - High Speed WIFIbr - TV 4br - Cable Channelsbr - Washerbr - Dryerbr - Ironbr - Ironing Boardbr - Cleaning Kitbr - First Aid Kitbr - Fire Extinguisherbr - Smoke Alarmbr - Carbon Monoxide Alarmbr - Private Pool Ybr - Pool Dimensions 21'x12'br - Spa Ybr - Pool Alarmsbr - Sun Loungersbr - Screened Lanaibr - Patiobr - Outdoor Diningbr - Propane Grillbr - Charcoal Grillbr - Fire Pitbr - Beach Amenitiesbr - Exterior Outletbr - Duncan Emerald Club

Beach N Bay 206 by Duncan Real Estate

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$327.05

Welcome to Beach N Bay 204! A honeymooners delight or a couple's retreat! Enjoy a romantic getaway! Don't miss your chance to stay at the North end of Anna Maria Island in the highly desirable village of Anna Maria, one of Coastal Living Magazine's Top 10 Happiest Seaside Towns! Located right in the middle of all that happiness, Beach N Bay is the island vacation cottage duplex that's so tropical and fun, you'll swear you can hear steel drums!br Ideally situated at the corner of Spring and Crescent Avenues, it's right in the middle of everything the village of Anna Maria has to offer. br br HIGHLIGHTSbr br 832 sq ft. br 171 sq ft. of screened in patiobr Dog friendly up to 50 lbsbr Centrally located near Pine Avenuebr 0.3 miles from bay access br 0.3 miles from beach accessbr br BEDROOMSbr br Sleeps 4br Primary Bedroom: King br Second Bedroom: Two Twinsbr br BATHROOMbr br Primary Bathroom: Walk-in Showerbr br EXTERIORbr br If you like hanging out under the sun and stars when you're in Florida, Beach N Bay will be the perfect place to call home! Be sure to pack your mini drink umbrellas because you'll will have a tropical drink in hand, and soak up the Anna Maria sunshine! Your outdoor amenities are rounded out with a big grill cooking with gas. There's also a drink cooler, a firepit surrounded by patio chairs, an outdoor shower, and a screened porch with flat panel TV.br br Rent the other side of this duplex with the pool with heating and cooling capabilities to accommodate up to 8 people under one roof! Call for occupancy details.br br Beach N Bay 204 has two parking spots reserved for guests.br br Beach N Bay 204 allows dogs up to 50 lbs. The non-refundable pet fee is $150.00 per pet and will be charged for each week. Short stays are not prorated. The pet fee does not cover any damage caused by the pet. br br Please keep in mind that 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.br Amenities Include:br - Bedroom 1 Kingbr - Bedroom 2 Twinsbr - Bathroom 1 Walk-in Showerbr - Hot Waterbr - Ground Level Ybr - Central A Cbr - Cental Heatbr - Sqft under a c 832br - Free Parkingbr - Parking Spots 2br - Dogs up to 50 lbs Ybr - Self Check Inbr - Keyless Entrybr - Bath Towelsbr - Beach Towelsbr - Quality Linensbr - Hair Dryerbr - Hangersbr - Refrigeratorbr - Stovebr - Cookwarebr - Toasterbr - Blenderbr - Keurigbr - Drip Coffee makerbr - Dishwasherbr - Microwavebr - Dining Tablebr - High Speed WIFIbr - TV 4br - Cable Channelsbr - Washerbr - Dryerbr - Ironbr - Ironing Boardbr - Cleaning Kitbr - First Aid Kitbr - Fire Extinguisherbr - Smoke Alarmbr - Carbon Monoxide Alarmbr - Screened Lanaibr - Patiobr - Propane Grillbr - Fire Pitbr - Exterior Outletbr - Duncan Emerald Club

Beach N Bay 204 by Duncan Real Estate

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1572.4

Summary:brbr Palmetto Sunset is a stunning multi-level luxury retreat featuring 4 ensuite bedrooms, open-concept living, and upscale finishes throughout. Enjoy a chef’s kitchen, 75” TV with fireplace, private balconies, elevator access, and a rooftop deck with Gulf views . Relax in your heated pool and spa, grill outdoors, and unwind in spacious comfort just moments from the beach. ✨ ️brbrbrbrThe Space:brbr ✨ Welcome to Palmetto Sunset – Your Private Coastal Retreat ✨ brbrStep into elevated island living at Palmetto Paradise, a stunning multi-level luxury home designed for unforgettable beach getaways. From the moment you arrive and enter through the spacious two-car garage, convenience meets sophistication. Choose the elevator or staircase to ascend to the heart of the home — where comfort, style, and space blend beautifully.brbrbrbr First Main Living Level – Open & ElegantbrbrThe expansive open floor plan invites gathering and relaxation.brbr ️ Dining Area – Large table with seating for eight, perfect for family dinners and celebration meals.brbr ️ Living Room – Sink into plush seating while enjoying the 75-inch TV and cozy electric fireplace — the perfect ambiance for movie nights.brbrbrbr ‍ Chef’s Kitchen – Fully equipped with:brbrGas stovebrbrDouble ovenbrbrFour bar stools at the islandbrbrWalk-in pantry with microwavebrbrBar fridge with built-in ice makerbrbrSeparate laundry room with two front-loader washers & dryersbrbrStep outside to the private balcony with comfortable seating and a gated staircase providing direct access down to the pool area.brbrbrbr ️ Main Level Bedroomsbrbr✨ King Ensuite #1brbrWalk-in showerbrbrPrivate balconybrbrCustom walk-in closetbrbr✨ King Ensuite #2brbrWalk-in showerbrbrSpacious layoutbrbrbrbr Half bath conveniently located in hallway.brbrbrbr Third Level – Private RetreatsbrbrUpstairs, privacy and comfort continue.brbrbrbr ️ Bunk SuitebrbrTwin-over-twin bunkbrbrWorkspace/desk areabrbrEnsuite with walk-in shower & single vanitybrbrbrbr ️ King Ensuite #3 (Premier Suite)brbrCustom walk-in closetbrbrPrivate balconybrbrLarge bathroom with tub/shower combobrbrDouble vanitybrbrAdditional hallway storage closet for convenience.brbrbrbr Rooftop EscapebrbrAscend one more flight and discover the showstopper — a breathtaking rooftop deck offering sparkling Gulf views. The perfect place for sunset cocktails and stargazing evenings. brbrbrbr Backyard OasisbrbrYour private resort-style paradise awaits:brbr Heated pool & spabrbr Propane grillbrbr ️ Outdoor dining table with seating for fourbrbr ️ Outdoor couch & accent chairs for loungingbrbrbrbrWhether you're sunbathing poolside, grilling dinner, or soaking in the spa after a beach day, this outdoor space was designed for relaxation.brbrbrbr✨ Palmetto Sunset offers luxury at every level — spacious living, private ensuite bedrooms, multiple balconies, rooftop Gulf views, and a stunning pool retreat.brbrYour perfect beach getaway begins here. brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with 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! ✨

Palmetto Sunset -Heat Pool/Spa, Steps to Beach!

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$2337.14

Summary:brbr Palmetto Paradise is a stunning multi-level luxury retreat featuring 4 ensuite bedrooms, open-concept living, and upscale finishes throughout. Enjoy a chef’s kitchen, 75” TV with fireplace, private balconies, elevator access, and a rooftop deck with Gulf views . Relax in your heated pool and spa, grill outdoors, and unwind in spacious comfort just moments from the beach. ✨ ️brbrbrbrThe Space:brbr ✨ Welcome to Palmetto Paradise – Your Private Coastal Retreat ✨ brbrStep into elevated island living at Palmetto Paradise, a stunning multi-level luxury home designed for unforgettable beach getaways. From the moment you arrive and enter through the spacious two-car garage, convenience meets sophistication. Choose the elevator or staircase to ascend to the heart of the home — where comfort, style, and space blend beautifully.brbrbrbr First Main Living Level – Open & ElegantbrbrThe expansive open floor plan invites gathering and relaxation.brbr ️ Dining Area – Large table with seating for eight, perfect for family dinners and celebration meals.brbr ️ Living Room – Sink into plush seating while enjoying the 75-inch TV and cozy electric fireplace — the perfect ambiance for movie nights.brbrbrbr ‍ Chef’s Kitchen – Fully equipped with:brbrGas stovebrbrDouble ovenbrbrFour bar stools at the islandbrbrWalk-in pantry with microwavebrbrBar fridge with built-in ice makerbrbrSeparate laundry room with two front-loader washers & dryersbrbrStep outside to the private balcony with comfortable seating and a gated staircase providing direct access down to the pool area.brbrbrbr ️ Main Level Bedroomsbrbr✨ King Ensuite #1brbrWalk-in showerbrbrPrivate balconybrbrCustom walk-in closetbrbr✨ King Ensuite #2brbrWalk-in showerbrbrSpacious layoutbrbrbrbr Half bath conveniently located in hallway.brbrbrbr Third Level – Private RetreatsbrbrUpstairs, privacy and comfort continue.brbrbrbr ️ Bunk SuitebrbrTwin-over-twin bunkbrbrWorkspace/desk areabrbrEnsuite with walk-in shower & single vanitybrbrbrbr ️ King Ensuite #3 (Premier Suite)brbrCustom walk-in closetbrbrPrivate balconybrbrLarge bathroom with tub/shower combobrbrDouble vanitybrbrAdditional hallway storage closet for convenience.brbrbrbr Rooftop EscapebrbrAscend one more flight and discover the showstopper — a breathtaking rooftop deck offering sparkling Gulf views. The perfect place for sunset cocktails and stargazing evenings. brbrbrbr Backyard OasisbrbrYour private resort-style paradise awaits:brbr Heated pool & spabrbr Propane grillbrbr ️ Outdoor dining table with seating for fourbrbr ️ Outdoor couch & accent chairs for loungingbrbrbrbrWhether you're sunbathing poolside, grilling dinner, or soaking in the spa after a beach day, this outdoor space was designed for relaxation.brbrbrbr✨ Palmetto Paradise offers luxury at every level — spacious living, private ensuite bedrooms, multiple balconies, rooftop Gulf views, and a stunning pool retreat.brbrYour perfect beach getaway begins here. brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with 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! ✨

Palmetto Paradise~Heated Pool/Spa, Steps to the Beach!

Anna Maria, Florida, United States

4

Bed

5

Bath

Sleeps

$522.48

WELCOME to Paradise on Pine a stylish island retreat perfectly situated in the heart of Anna Maria! This charming 3-bedroom, 2-bath vacation home is nestled right on Pine Avenue just 1.5 blocks to the stunning Gulf beaches and only a few blocks from the bay, City Pier, and all the boutique shops, eateries, and island favorites Anna Maria is known for. No need for a car you're just a flip-flop stroll to it all!br br br Paradise on Pine is an elevated home that sits above a quiet retail shop and offers a private backyard oasis complete with a heated pool, lush tropical landscaping, lounge seating, and a gas grill your own serene escape after a day of sun and sand.br br Step inside to a breezy, open-concept living space featuring recycled distressed wood floors and cozy coastal furnishings. The living area is open and inviting, featuring beachy distressed wood floors, comfortable coastal furnishings, a queen sleeper sofa, and a brand new smart flat screen TV. A Sonos speaker is available for streaming your favorite music or shows. Two sets of French doors in the dining area open to the spacious back porch that overlooks the pool the ideal spot to relax or entertain.br br The fully stocked kitchen includes granite countertops, stainless steel appliances, and all the essentials for cooking and dining. The breakfast bar seats 6, and the dining table accommodates up to 8 guests.br br The primary suite features a king bed, flat screen TV, porch access, and a spa-inspired ensuite bath with a large walk-in shower, clawfoot tub, dual vanities, and private water closet. The second bedroom has a queen bed and the third bedroom offers two twin beds both with flat screen TVs and private access to a porch. The shared hallway bathroom is thoughtfully designed with a split layout to help everyone get ready with ease. For added privacy, a hallway curtain can separate the guest bedrooms from the main living space.br br You'll also find luxury linens, high thread-count sheets, plush bath towels, and six oversized beach towels for your use. Other thoughtful extras include a high-capacity washer/dryer, Roku devices on every TV, and beach gear like chairs, a cart, and umbrella.br br Additional perks include:br br 1 assigned parking spacebr br 1 designated golf cart parking spacebr br Free island trolley stop just steps awaybr br Whether you're sipping morning coffee on the porch, lounging poolside, or catching a Pine Ave sunset, Paradise on Pine delivers the island lifestyle you came for.br br We're so excited to welcome you to Salty Mermaid Vacation Rentals!br br Disclaimers: br br *There is 1 assigned parking space for this unit, and 1 additional golf cart space. Please note you cannot charge electric golf carts in this space, we recommend renting a gas golf cart. *br br *Florida Law requires an audible alarm to be installed on doors and windows that open to a pool area. The purpose of these alarms is to alert an adult if a child walks out to a pool area unattended. These alarms typically have a bypass button that allows the door to be opened for 7 seconds before the alarm goes off. These alarms must not be removed or tampered with in any way. Any evidence of tampering or damage to pool alarms will be billed to the credit card on file for the reservation. * br br *This home has a 4-night minimum stay requirement* br br *Reservations that are 30 nights or longer will require a mid-stay clean, one of our rental agents will provide more information at the time of booking. br br *Please note this is not a party or large gathering house. Noise complaints may result in eviction* br br *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you! * br br *Check-in time is 4 pm on the day of your arrival, check out time is 10 am on the day of your departure. No early access or late departure is allowed unless special arrangements are made with our office, our cleaning and Inspection team need time to ensure the rental is clean and safe for your stay* br br *A starter kit of paper towels, toilet paper, trash bags, laundry detergent, and coffee & tea. Full sized luxury hand soap, shampoo, conditioner, and body wash are provided at check-in. Also available if requested, while supplies last, is a toothbrush and sewing kit. Any additional items that you may need during your stay can be purchased at one of the local grocery stores. * br br *Pools are heated from approximately Thanksgiving to Easter only and are set no higher than 80 degrees. During colder weather, we cannot guarantee that the pool can be maintained to that degree. No refunds, credits, or discounts will be offered if the pool temperature cannot be maintained due to unusually cold weather*

Paradise on Pine

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$898.81

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.

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

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$815.66

Escape to your private waterfront oasis on Anna Maria Island at Paradise Pointe.brbr*Features include* brbr* Canal front with private dock br* 3 bedrooms, 2 full bathrooms plus denbr* Master bedroom with ensuite bathbr* Private saltwater pool and spabr* Indoor and outdoor dining br* Laundry room and office spacebr* Basketball pool gamebr* Sun loungersbr* Gas grill br* Beach chairs, umbrella and cartbr* Walk to Bean Point brbrTucked away on the tranquil North End of Anna Maria Island, this three-bedroom retreat offers the ultimate blend of coastal charm and modern comfort. With a private dock on the canal, a sparkling outdoor pool, and an unbeatable location just blocks from Bean Point Beach, Paradise Pointe is your gateway to island living at its finest.brbrInside, the thoughtfully designed layout ensures both comfort and privacy. The primary suite features a plush king bed, an ensuite bathroom with a double vanity, and a walk-in shower. The second bedroom offers two twin beds and shares a Jack-and-Jill bathroom, which also has convenient hallway access. The third bedroom offers another king bed and all bedrooms feature cable TV.brbrGather for meals in the spacious dining room, where large windows overlook the shimmering pool, creating the perfect backdrop for family dinners. The open-concept living area includes a separate sitting space, offering plenty of room to unwind. For those seeking a quiet escape, a small den with chaise provides the ideal spot to curl up with a book and relax.brbrSituated directly on a picturesque canal, Paradise Pointe offers endless entertainment as mullets leap from the water, providing a free show. Cast a fishing line from the private dock or simply soak in the tranquil waterfront views. And when you're ready for sun and sand, the coveted shores of Bean Point Beach are just a short walk away.brbrWith its seamless blend of indoor comfort and outdoor beauty, Paradise Pointe is designed for effortless island living. Book your stay today and experience the best of Anna Maria Island!brbrPET POLICY: brbrWe are small DOG FRIENDLY! A fee of $150 + tax is required in advance. brbr1 pet maximum unless granted an exception. Weight limit of 20 lbs maximum per pet. brbrDue to property insurance policies and liability concerns NO dangerous breeds or aggressive animals are allowed. The following breeds (purebred or crossbred) are not permitted: brbrPit Bull, Akita, Rottweiler, German Shepherd, Siberian Husky, Malamute, Doberman Pinscher, Chows, Any Wolf-dog hybrid, Any other dog that has been known to have bitten anyonebrbrADDITIONAL INFORMATION brbrWe generally require a minimum stay during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you! brbrHousekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay. brbrOur cleaning fee includes a professional linen service. When you stay with us you can rest assured that you will have high quality linens such as those at a fine hotel. We also provide plenty of luxury bath and beach towels. brbrAnna Maria Island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors. brbrThis home provides off-street parking for up to 4 vehicles.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.

Paradise Pointe by Beach Boutique Rentals

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$2757.79

Welcome to Lap of Luxury!This home is new as of 2022 and has been meticulously built and designed to create a space for full relaxation. Lap of Luxury is only 150 steps from the white sand beaches of the Gulf of Mexico with beautiful views from every floor. It features 4 bedrooms and 5 and a half baths and is just a short stroll away from the historic shopping area along Pine Ave and the famous Bean Point beach area.Step through the zen inspired courtyard area to the main entrance. Main House: Take the elevator to the first floor living area. This main area has an open plan living room with electric fireplace and a dining area with a large dining table with seating for 8. There is a spacious open deck for al fresco dining and a conversation area for 4 while you take in the beautiful vistas and nightly sunsets. The kitchen is equipped with top of line appliances such as an AGA Range and Sub-Zero Refrigerator and has a large island complete with 4 barstools and topped with a beautiful, custom, wood inlay countertop. Light starter provisions provided: Coffee, Water, Condiments, Spices, Butter, Olive Oil, Soda, Welcome Wine and Beer and Paper Products.The laundry area and half bathroom are off the kitchen.There is also the luxurious primary bedroom with a large ensuite bathroom featuring a huge walk-in shower and soaking tub.On the upper floor is the second living area which features a large flat screen tv, wet bar with beverage fridge, and sofa with large expansive balcony and outdoor seating. Relax on 2 sun loungers or read a book enjoying the breezes of the Gulf of Mexico sitting in one of the four Adirondack chairs. You will find two bedrooms both with ensuite bathrooms and a third hall bathroom.Guest Suite:Across the breeze way by the kitchen back door from the main house is an exquisite private guest suite featuring a large bedroom with king size bed and flat screen TV and a balcony with seating for morning coffee. There is also the ensuite bathroom with walk in shower and soaking tub to enjoy those romantic evenings.HIGHLIGHTS 3924 sq. ft. 150 Steps from the beach Private 60X14 ft. lap pool and hot tub Plenty of outdoor seating and loungers Sub Zero Refrigerator Aga Gas Stove Elevator Washer/dryer in main house Separate Guest SuiteBEDROOMS Sleeps 8 Primary Bedroom: King Ensuite Second Bedroom: King Ensuite Third Bedroom: Twins - X Long Ensuite Forth Bedroom: King (Guest Suite) EnsuiteBATHROOMS Ensuite Bathroom: Walk-in Shower and Soaking Tub Second Ensuite Bathroom: Walk-in Shower Third Ensuite Bathroom: Walk-in Shower Fourth Bathroom: Walk-in Shower Fifth Ensuite Bathroom: Walk-in Shower and Soaking Tub (Guest Suite) Half BathroomEXTERIORThe living room opens to the large balcony with outdoor dining which over looks the pool area and expansive views of the Gulf of Mexico and guest suite. There is plenty of seating and loungers in the covered and outdoor areas under both the main house, guest house and around the 60X14 ft. pool. Other features include an outdoor shower, gas grill and beach equipment.There are 4 parking spaces designated for this property. The garage is not available to guests.Pool heaters in private homes are locked for your safety and controls must not be tampered with as they are monitored by the pool company. 86 F is the highest heat temperature setting which might not be always reached. Please note if cold days and nights occur, water temperatures will drop and may stay cooler longer. Pool heaters will not operate and will automatically shut down if outside temperatures get too cold. While we take every precaution to ensure that pools are heated as specified, weather conditions may affect the temperature of the pool. Nothing can be done about this issue. Outdoor spas are not hot tubs and require heat at the additional cost. The temperature of a spa is typically set at the same temperature as the pool. In the event of pool equipment malfunction during your stay, Duncan Real Estate will expedite repairs as quickly as possible. It may be necessary to close swimming pools for maintenance purposes. No refund or rent adjustment will be made for circumstances beyond our control, malfunctions, or loss of use of equipment or amenities. Please keep in mind that 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. VR22-000093brbrAmenities Include:brbr- Bedroom 1 Kingbrbr- Bedroom 2 Kingbrbr- Bedroom 3 Twinsbrbr- Bedroom 4 Kingbrbr- Work Space Ybrbr- Bathroom 1 Soaking Tub/Walk in Showerbrbr- Bathroom 2 Walk in Showerbrbr- Bathroom 3 Walk in Showerbrbr- Bathroom 4 Walk in Showerbrbr- Bathroom 5 Soaking Tub/Walk in Showerbrbr- Half Bathbrbr- Hot Waterbrbr- Beach Viewbrbr- Water Viewbrbr- Beach Access 150 stepsbrbr- Elevatedbrbr- Elevator Ybrbr- Central A Cbrbr- Cental Heatbrbr- Sqft under a c 3924brbr- Free Parkingbrbr- Parking Spots 4brbr- Front Security Camerabrbr- Self Check Inbrbr- Keyless Entrybrbr- Bath Towelsbrbr- Beach Towelsbrbr- Quality Linensbrbr- Hair Dryerbrbr- Hangersbrbr- Refrigeratorbrbr- Ice Makerbrbr- Wine Fridgebrbr- Stovebrbr- Cookwarebrbr- Toasterbrbr- Blenderbrbr- Keurigbrbr- Drip Coffee makerbrbr- Butler's Pantrybrbr- Dishwasherbrbr- Microwavebrbr- Garbage Disposalbrbr- Dining Tablebrbr- Breakfast Barbrbr- High Speed WIFIbrbr- TV 4brbr- TV Streaming Onlybrbr- Washerbrbr- Dryerbrbr- Ironbrbr- Ironing Boardbrbr- Cleaning Kitbrbr- First Aid Kitbrbr- Fire Extinguisherbrbr- Smoke Alarmbrbr- Carbon Monoxide Alarmbrbr- Private Pool Ybrbr- Pool Dimensions 60X6, 60X14brbr- Spa Ybrbr- Pool Alarmsbrbr- Sun Loungersbrbr- Balcony 3brbr- Outdoor Diningbrbr- Outdoor Showerbrbr- Propane Grillbrbr- Beach Amenitiesbrbr- Board Gamesbrbr- Exterior Outletbrbr

Lap of Luxury by Duncan Real Estate

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$771.99

AM I Dreaming by AMI LocalsbrVR19-000055 brbrWelcome to AM I Dreaming, a luxurious three bedroom, three and a half bath canal-front home offering the best of Anna Maria Island vacation living. Perfectly located across from Bayfront Park and a 15-minute walk to the Gulf beaches, this stunning retreat combines tranquil waterfront views with high end amenities. From the private saltwater pool and spa to the rooftop deck with panoramic island views, every detail creates a modern coastal escape designed for relaxation and style. brbrHighlights br• Canal Front br• Private Pool with In-Ground Spa br• Rooftop Deck with Bay Views br• 15-Minute Walk to Gulf Beach br• 3 Bedrooms / 3.5 Bathrooms br• 3 Kings, and Full Murphy bed br• 2 Hideaway bed available br• Pet-Friendly with host approval br• Across the street from Bayfront Park and near Pine Avenue Shops br• Kayak and Paddleboard Launch - 2 kayaks for guest usage br• Dedicated workspacebr• 2 Parking Spaces brbrStep outside to your private resort-style oasis. Lounge beside the heated saltwater pool, soak in the in-ground spa, or share meals in the covered outdoor dining area. With direct canal access, guests can easily launch kayaks or paddleboards for a peaceful morning adventure on the bay. End each day watching the sunset from the rooftop deck, where panoramic island and water views make every moment unforgettable. brbrInside, the open concept living area creates a warm and inviting atmosphere. Plush sofas surround a TV, while large windows fill the space with natural light and water views. The fully equipped kitchen features stainless steel appliances, ample counter space, and a large island ideal for family gatherings. Enjoy meals together at the six-seat dining table or sip coffee on the balcony’s bistro set as you take in the coastal breeze. A convenient laundry room is located just off the kitchen. brbrThe third-floor primary suite offers a serene retreat complete with a king bed, two private balconies, and an ensuite bathroom with dual vanities, a walk-in shower, and a soaking tub. On the second floor, the two guest bedrooms continue the coastal theme: both with king beds and each featuring a TV and private ensuite bath with walk-in shower. A bonus murphy bed area is perfect for children or teens and is located across from the hallway bathroom. brbrRoom Details br-Primary Bedroom (3rd Floor): King bed, balcony, ensuite bath with dual vanities, soaking tub, 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-Bonus Area (2nd Floor): Murphy bed full size brbrEnjoy easy access to Bayfront Park, and Pine Avenue, home to charming boutiques, local restaurants, and ice cream shops. Beach wagons are provided for effortless trips to the white-sand Gulf beaches. brbrEmbrace island luxury at AM I Dreaming by AMI Locals, where modern design meets Old Florida charm. From the canal-front setting and rooftop deck to the private pool and spa, every detail is crafted for an exceptional Anna Maria Island getaway. Book your stay today and experience the best in luxury beach homes! brbr- brThe garage, boat lift, and elevator are not available for guest use. brbr2 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. 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 AMI Locals Rental Policies for full details. brbrThese premises are monitored by video surveillance in select exterior areas. 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 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.

Luxe AMI Stay! Saltwater Pool and Rooftop Views

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$417.5

29 PalmsbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience the ultimate island retreat at this luxurious getaway on Spring Avenue, ideally situated in the heart of the vibrant village of Anna Maria. Just one block from the bustling charm of Pine Avenue, two blocks from the tranquil bay, and a short three-block stroll to the pristine beach, this sunlit sanctuary places you close to everything yet feels like a peaceful escape. Nestled on Anna Maria Island, this exceptional home offers easy access to local treasures such as Bean Point’s breathtaking views, the iconic Anna Maria City Pier, Manatee Beach, historic sites, art galleries, and an array of activities from snorkeling and diving to dolphin-watching tours. brStep inside to discover a bright, spacious open-concept layout with stylish furnishings, a cozy seating area, a large smart TV, and a collection of classic board games for relaxed evenings in. The sleek chef’s kitchen is fully outfitted with stainless steel appliances and a charming coffee station featuring a 2-in-1 Instant Pot K-cup brewer—perfect for morning lattes on the patio. Enjoy al fresco dining, swaying palm views, and warm sea breezes from your private outdoor space, complete with a grill. High-speed WiFi, central air conditioning, and a convenient washer/dryer complete this carefully curated oasis where comfort meets coastal elegance.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Sunny home near the water with patio, streaming, washer/dryer, grill, fast WiFi

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$1326.28

Sentimental Sunset by Anna Maria Life Vacation Rentalsbr755 Jacaranda Rd, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! North End! Quick Walk to Bean Point & Pine Ave!br4 Bedrooms / 4.5 Bathroomsbr3 King Beds, One set of Twin/Twin XL Bunkbeds, XL Twin Bed, XL Twin Trundle BedbrPrivate Heated Pool & SpabrOutdoor ShowerbrPoolside Covered Lounge AreabrElevator (to all floors)brMultiple BalconiesbrCovered Verandah with Lounge Furniture & Gulf ViewsbrSundeck with Patio Loungers & Gulf ViewsbrOutdoor Covered Dining AreabrGas GrillbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrParking for 4 CarsbrbrDetails:brLocated on the coveted North End of Anna Maria, Sentimental Sunset is a quick walk to famous Bean Point and the shops and restaurants of Pine Ave. This one-of-a-kind home is what vacation dreams are made of.brbrThe main level on the 2nd floor is bathed in natural light and features the kitchen, dining, and living rooms. Oversized patio sliders provide access to one of the verandahs overlooking the tropical landscaped backyard and pool. The top level of the home features a large verandah with lounge furniture and a sundeck with cushioned chaise loungers and fantastic views of the shimmery blue waters of the Gulf of Mexico.brbrTwo of the king bedrooms are on the main living area with the other king bedroom on the third level. The final guest room is also on this floor and includes a set of XL twin over twin bunk beds, an additional XL twin bed and a twin trundle bed. Each bedroom includes an ensuite bathroom, 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 washer and dryer.brbrA sparkling, heated pool and spa, pool loungers, and an outdoor shower are highlights of the backyard. Additional outdoor amenities include a gas grill and outdoor patio dining.brbrSentimental Sunset is easy walking distance to many shops and restaurants, and 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 vacationbrbrBedroom 1 - King Bed, Ensuite Bathroom, TV on Floor 2brBedroom 2 - King Bed, Ensuite Bathroom, TV on Floor 2brBedroom 3 - King Bed, Ensuite Bathroom, TV on Floor 3brBedroom 4 - One set of Twin/Twin XL Bunkbeds, XL Twin Bed, XL Twin Trundle Bed, Ensuite Bathroom, TV on Floor 3brbrPlease 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. brbrVR21-000053brbrGolf 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.

Sentimental Sunset: Pool & Spa, Near Bean Point & Pine! by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Bed

Bath

Sleeps

$507.52

Camp Campoamor 11107 Gulf Drive, Anna Maria, FL 34216 What you will love about this property: • Brand new renovations!! • Less than one minute walk to the beach • 3 properties from the beach • Beach items and fishing gear • Outdoor showers • Close to shopping and restaurants • In the heart of Anna Maria • Professional Linen program • Close to Pine Avenue shops, restaurants, and free trolley access • Full size washer and dryer Property details: Welcome to Casa Campoamor. This home is the definition of a what a charming beachside cottage vacation is on Anna Maria Island! This 4-bedroom, 2 full bathrooms and 2 half bathroom home cozily accommodates 8 people. This clean and quaint is perfect for a small family, couple(s), or group of friends looking to stay in the heart of downtown Anna Maria within walking distance of everything you need... shops, piers, and beaches! this home is easily within walking distance of the Pine Avenue, shops, and restaurants, as well as the beautiful white sand beaches alongside the Gulf of Mexico! The home is also very close to the community center which is perfect for those looking for a fitness center, tennis courts, and even playground to use throughout their stay! Get everyone together in comfort and style at Casa Campoamor. Book with us today. Bedrooms & Bathrooms - Primary Bedroom- Queen bed with master bathroom with walk in shower - Second Bedroom- King bed with access to the hallway bathroom with shower and bathtub combination - Third Bedroom- Queen bed - Forth bedroom- Bunk bedroom with twin bunk beds - Two half bathrooms - Livingroom has pull out sofa 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 at 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. 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: 3 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.

Casa Campoamor- 4 bedrooms and steps from beach

Anna Maria, Florida, United States

4

Bed

3

Bath