Home Vacation Home Rentals By Owner In Anna Maria, FL

Showing 380 Of 689 Vacation Rentals
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Exceptional(32)

$1303.05

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Private Vacation Home

Bikini Bottom: 5 Hole Mini Golft, Games,3 Blocks to Beach, Dog Friendly, Pool, by Anna Maria Life

Anna Maria, Florida, United States

Bikini Bottom by Anna Maria Life Vacation Rentalsbr302 Spring Ave, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! 5 Min Walk to Gulf! 5 Min Walk to Bay!br4 Bedrooms / 4.5 BathroomsbrHeated Pool & SpabrPool LoungersbrOutdoor ShowerbrPoolside Lounge Area with Swings & FurniturebrPool Level Indoor Living Room & Game Room with Foos Ball & Ping Pong TablebrCornholebr5 Hole Mini Golf CoursebrOutdoor Patio Dining (4 Top)brGas GrillbrFurnished Roof Top Deck with Amazing Views of Gulf & Bay!brKeurig & Drip Coffee MakersbrDog Friendly (with fee - see notes below)brFenced YardbrBeach Towels, Beach Chairs & Beach WagonbrDriveway Parking for 4 CarsbrbrDetails:brWelcome to Bikini Bottom, your dream vacation retreat in the heart of Anna Maria Island! Perfectly situated just a block from Pine Avenue, you'll enjoy being close to shops, dining, and the beach. A quick stroll down Spring Avenue brings you to the sparkling waters of the Gulf of Mexico — paradise is just steps away.brbrOur three-level beach retreat provides guests with lovely gathering places inside and out. The main living level on floor two consists of the spacious kitchen with island bar seating for six, dining room with a table for eight and living room. Oversized windows allow the sunshine to flood the living space and patio doors provide access to a furnished deck.brbrThe second floor is also home to two bedrooms, one with a king bed and the other with two sets of twin over queen bunkbeds. Each of these rooms have an ensuite bathroom. Two additional king bedrooms with ensuite bathrooms are on level three. Each bedroom has a TV and includes 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.brbrEnd your day on the furnished rooftop deck, the ideal spot to take in a breathtaking Anna Maria Island sunset while gazing out at the Gulf and Bay.brbrThe fun continues downstairs with an indoor game room featuring foosball, ping pong, and a cozy seating area with a TV. Step outside to the heated pool and spa, surrounded by lounge chairs, a shaded lounge area with swings, and a gas grill for easy outdoor dining. Challenge your group to a friendly round of cornhole or try out the private 5-hole mini golf course — perfect for guests of all ages!brbrBikini Bottom 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.brbrBikini Bottom 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 Bathroom, TV on Floor 2brBedroom 2: Twin over Queen Bunkbeds (2 Sets), Ensuite Bathroom, TV on Floor 2brBedroom 3: King, Ensuite Bathroom, TV on Floor 3brBedroom 4: King, Ensuite Bathroom, TV on Floor 3brQueen Sofa Bed in 3rd Floor LoftbrbrPlease note:brAmenities are subject to change.brDriveway parking is available for a maximum of four 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. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. brbrVR20-000056brbrIMPORTANT 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.brbrVRC20-000139 br brGolf 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
Bed 4

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Bath 4

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Sleep 8

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Exceptional(11)

$484.54

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Private Vacation Home

Beach Cottage! Pool, Porch and 2-Min Walk to Gulf!

Anna Maria, Florida, United States

Gulf Shore Cottage by Anna Maria Island AccommodationsbrVR16-000101 brbrYour dream beach vacation begins at Gulf Shore Cottage, a newly renovated four-bedroom, two-bathroom coastal retreat located just six houses from the pristine sands of the Gulf. With a private pool, foosball table, and pet-friendly policy, this charming cottage blends Old Florida character with modern updates, making it the perfect getaway for families and friends looking to enjoy Anna Maria Island’s laid-back lifestyle. brbrHighlights br-2-minute walk to the beach br-4 Bedrooms / 2 Bathrooms br-2 King beds, 1 Twin-over-Full bunk, 2 Twin beds br-Private pool, foosball table, and corn hole br-Screened-in front porch br-Across the street from Anna Maria Island trolley stop br-BBQ grill and outdoor shower br-Dog friendly with host approval br-Washer and dryer br-4 Parking Spaces brbrThe fenced backyard is your private oasis, featuring a sparkling pool surrounded by lounge chairs and corn hole for endless fun. After a day at the beach, rinse off in the outdoor shower, fire up the BBQ grill, and enjoy meals together at the high-top covered patio. The screened-in front porch adds another relaxing spot, perfect for sipping morning coffee. brbrInside, Gulf Shore Cottage offers an open and inviting layout with coastal-chic décor. The living room includes two plush sofas and a TV, while the dining area has ample space for group meals. The modern kitchen features new appliances, plenty of cabinet storage, and a spacious island with stool seating, making meal prep a breeze. brbrThe primary bedroom is designed for comfort, with a king bed, nightstands, ambient lighting, and a spa-like ensuite bathroom featuring a double vanity and walk-in shower. The second and third bedrooms are connected by a Jack and Jill bathroom with a walk-in shower; the third bedroom even includes a foosball table for extra fun. The fourth bedroom has two twin beds, perfect for kids or additional guests. brbrRoom Details br-Primary Bedroom: King bed, ensuite bathroom with double vanity and walk-in shower br-Second Bedroom: King bed, shares Jack-and-Jill bathroom with walk-in shower br-Third Bedroom: Twin-over-Full bunk, shares Jack-and-Jill bathroom with walk-in shower br-Fourth Bedroom: Two Twin beds brbrThis home also includes a washer and dryer, Wi-Fi, and a pet-friendly policy with host approval. With a trolley stop across the street, you can easily explore Anna Maria’s shops, waterfront dining, historic sites, and best Gulf Coast attractions without needing a car. brbrGulf Shore Cottage is the ideal vacation rental for creating lasting memories. Whether you’re swimming in the pool, strolling to the beach, or hopping on the trolley to explore, this cottage offers the perfect balance of relaxation and adventure. brbrBook your stay today and experience the charm of Anna Maria Island at Gulf Shore Cottage! br br- br*Please note: 4 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. 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. brbrThis home is managed by Anna Maria Island Accommodations, 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 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.
Bed 4

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Bath 2

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Sleep 8

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Exceptional(4)

$2381.19

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Private Vacation Home

NEW! Meet Me At Sunset! 3 Homes from the Beach!

Anna Maria, Florida, United States

Summary:brbr Meet Me at Sunset is a 4BR/4.5BA beach-boho villa just 3 homes from the Gulf . Enjoy a heated pool & spa, private balconies, ping pong , outdoor grill ️, and dog-friendly stays . Walk to Pine Avenue shops & dining ️, hop on the AMI trolley , or bike the island . Beach chairs & cart provided ️. Perfect for families or friends seeking the ultimate Anna Maria Island getaway ☀️ .brbrbrbrThe Space:brbr Welcome to Meet Me at Sunset brbr109 Palmetto Ave | Anna Maria Island, FLbrbrbrbrEscape to Meet Me at Sunset, a stunning 4BR / 4.5BA beach-boho villa just three homes from the Gulf—no busy roads to cross! Enjoy private balconies, a heated pool with spa, ping pong, and outdoor grilling, plus dog-friendly stays with prior approval . Walk to Pine Avenue’s shops and dining, hop on the free AMI trolley, or explore the island by bike .brbrbrbr✨ Highlightsbrbr• Just 3 homes from the beach brbr• Private heated pool & spa brbr• Ping pong table for family fun brbr• Outdoor grill & covered dining area ️brbr• Dog-friendly with approval and fee brbr• Walk to Pine Avenue shops & restaurants ️ brbr• Beach chairs and cart provided ️brbrbrbr Island Comfort & StylebrbrStep inside to airy, light-filled interiors featuring a chef’s kitchen with quartz countertops and high-end appliances, open living and dining areas, and seamless indoor-outdoor flow . Relax on the balcony, enjoy movie nights, or gather for family meals .brbrbrbr ️ Bedrooms & Bathsbrbr• Primary Suite (3rd Floor): King bed, smart TV, ensuite with soaking tub + shower brbr• 2nd & 3rd Bedrooms: King beds with ensuite walk-in showersbrbr• 4th Bedroom: Full-over-full bunk with ensuite bath—perfect for kidsbrbrbrbr Outdoor OasisbrbrSoak up the sun in your resort-style heated pool and spa, dine alfresco under the covered patio, or play ping pong with family and friends . Beach chairs and a cart make trips to the Gulf easy.brbrbrbr The Island ExperiencebrbrFrom fishing at Historic City Pier, kayaking in the bay, birdwatching, or sunset cruises, Anna Maria Island offers endless activities. With calm Gulf waters, tropical breezes, and a prime location, Meet Me at Sunset is your ultimate island getaway ☀️ ️.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.brbrbrbrThe Neighborhood:brbrMeet Me at Sunset is nestled in a peaceful, quiet neighborhood jbrbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with 6 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 here to help! You can call or text me directly on my cell. I’m available 24/7 to answer questions, offer local tips, or assist with anything that comes up. Your comfort is my priority!
Bed 4

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Bath 4

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Sleep 8

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Exceptional(4)

$2171.08

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Private Vacation Home

Gorgeous canal front home on Anna Maria!

Anna Maria, Florida, United States

Shell We Dance is a charming coastal retreat located on Anna Maria Island, perfect for those seeking a relaxing getaway. This beautifully designed home features an inviting open-concept living area, adorned with coastal decor that creates a warm and welcoming atmosphere. Large windows allow natural light to fill the space, offering stunning views of the surrounding landscape.brbr224 Chilson Ave, Anna Maria, FloridabrbrExperience the pinnacle of luxury on Anna Maria Island at Shell We Dance, a brand-new, canal-front estate boasting six lavish bedrooms and six and a half bathrooms! This stunning home features a private pool, spa, rooftop deck with sweeping water views, and an outdoor bar, perfect for sophisticated gatherings, family reunions, or friends’ escapes. Located minutes from Pine Avenue shops and restaurants, Palmetto Avenue Beach, and the Anna Maria City Pier. Shell We Dance offers the perfect blend of elegance, outdoor fun, and island adventure!brbrHighlightsbr-Canal front Homebr-6-minute walk to Anna Maria Beachbr-6 Bedroom / 6.5 Bathbr-5 King beds, 1 twin-over-full bunkbr-Private saltwater pool and spa br-Rooftop deckbr-Outdoor entertainment area br-Located near Pine Avenue’s shops, waterfront dining, parks, and local attractions brbrExclusive Amenitiesbr• Luxury Beach Chairs and a Beach Cart for Guest Usebr• Upgraded Bed and Bath Linens and Toiletriesbr• Portable Pack and PlaybrbrInside, the home exudes sophistication with a luxurious seating area adorned with high-end sofas, side chairs, and a large TV, ideal for relaxing or game nights. The fully equipped kitchen is designed to impress the chef, with premium appliances, an expansive island with bar stools, and a formal dining table for memorable island dinners. Sliding doors lead from the living area to the covered balcony and outdoor lounge, seamlessly blending indoor comfort with outdoor island vibes.brbrEach of the six bedrooms is styled for relaxation and comfort, with luxurious bedding, TVs, and some with private balconies. The primary bedroom offers a king bed, a large walk-in closet, and an ensuite bathroom with a walk-in shower and a spacious standalone tub, perfect for unwinding after a day of adventure. The other four king bedrooms each come with modern decor and ensuite walk-in showers. The bunk room, designed with kid or guests in mind, features a twin-over-full bunk bed and an ensuite bathroom with a shower/tub combo. For added ease, there is a washer and dryer included.brbrRoom Detailsbr-Primary Bedroom: King bed, ensuite with walk-in shower and tub br-Second Bedroom: King bed, ensuite bathroombr-Third Bedroom: King bed, ensuite bathroombr-Fourth Bedroom: King bed, ensuite bathroombr-Fifth Bedroom: King bed, ensuite bathroombr-Sixth Room: Twin-over-full bunk bed, ensuite with shower/tub combobrbrRelax outdoors in your tropical backyard oasis, featuring a private saltwater pool with a swim-up bar and spa. The large patio offers a BBQ grill, outdoor TV, and plenty of lounge chairs, perfect for sunset cocktails, outdoor dinners, or peaceful daytime relaxation. Stroll in just a few minutes to the beach and use the provided beach gear, chairs, and portable pack and play or explore Pine Avenue’s shops and restaurants, or rent kayaks, paddle boards, and enjoy fun water adventures right in your backyard. Plus, the rooftop deck provides breathtaking water views ideal for finishing your day with spectacular sunsets.brbrEnjoy your beach days with ease. We supply beach towels, beach chairs, and a wagon to make your trips to the shore effortless.brbrBook Shell We Dance today and immerse yourself in a luxurious, fun-filled island retreat. With stunning water vistas, outdoor amenities, and a prime location near beaches, shops, and dining, this estate provides everything for an unforgettable Anna Maria Island experience. Reserve now and start creating lifelong memories in paradise!brbr-brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will applybrbrThe modern kitchen is fully equipped, making it ideal for preparing delightful meals, while the spacious dining area is perfect for gathering with family and friends. Each bedroom is thoughtfully appointed, ensuring comfort and tranquility for a restful night's sleep.brbrStep outside to discover a private outdoor space that includes a refreshing pool, ideal for soaking up the sun or enjoying a dip after a day at the beach. The home is just a short walk from the white sandy shores and turquoise waters, allowing guests to easily immerse themselves in the island's natural beauty.brbrWith its perfect blend of comfort and style, Shell We Dance is the ultimate destination for a memorable vacation on Anna Maria Island.brbrPool Heating DisclaimerbrbrPlease note that pool heaters are weather-dependent. When outdoor air temperatures drop below 55°F, electric pool heaters will not operate, and pool water will remain cold. Even when temperatures rise slightly above 55°F but stay in the low 60s, the heater may produce minimal heat and may not significantly warm the pool.brbrThe only way to guarantee a consistently warm pool during colder months is with a gas pool heater, which can operate in very low temperatures but requires substantial gas usage to maintain warmth.brbrBy booking during cooler months, guests acknowledge that pool temperature and heater performance are directly affected by weather conditions, which are beyond the control of the property owner or management. We strongly recommend reviewing and acknowledging this information prior to booking to ensure clear expectations regarding pool heating during your stay.brbrImportant Note:brWhen you stay at our vacation rental homes, we want to ensure your experience is comfortable and convenient right from the start. Each home comes with a thoughtfully prepared starter pack to help you settle in seamlessly. This pack includes:brbr- *Laundry Detergent*: Enough for your initial laundry needs.br- *Dish Soap*: For easy clean-up after meals.br- *Dish Sponge*: Essential for washing dishes.br- *Dishwasher Pods*: A few pods to kickstart your dishwashing.br- *Toilet Paper*: Two rolls per bathroom to get you started.br- *Paper Towels*: One roll for quick clean-ups.br- *Extra Trash Bags*: To accommodate your waste disposal needs.brbrPlease note that we do not provide used kitchen items like oil, spices, or butter, ensuring a fresh start for your cooking adventures. Additionally, all homes are equipped with drip coffee makers, but remember to bring your own coffee filters to enjoy your morning brew.brbrWith these amenities, you can focus on enjoying your vacation without the worry of running out of essential supplies.brbrEarly Check In & Late Check Out:brFrom February through August, we regret to inform our guests that early check-ins and late check-outs will not be available. This decision is due to a high volume of reservations during these peak months, which unfortunately limits our ability to accommodate flexible check-in and check-out requests. We appreciate your understanding and encourage you to plan your arrival and departure times accordingly. Thank you for your cooperation!
Bed 6

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Bath 6

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Sleep 12

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Exceptional(49)

$385.26

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Private Vacation Home

Hav'Anna Holiday: 2 Blocks to Beach! North End! Private Pool by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Hav'Anna Holiday by Anna Maria Life Vacation Rentalsbr211 Periwinkle, Anna Maria, FL 34217brbrWhat You'll Love About This Home:brLocation! 1.5 Blocks to the Beach!br3 Bedrooms / 2 Bathroomsbr2 King Beds, 3 Twin BedsbrPrivate, Heated PoolbrHuge Tropical Landscaped BackyardbrGas Grill - Flat Cooktop (Griddle)brSunny Florida RoombrSingle Level Ranch Style HomebrProfessional Linen Service, Complimentary WIFI, Washer & DryerbrBeach Towels. Beach Chairs & Beach WagonbrDriveway Parking for 4 CarsbrbrDetails:brHav'Anna Holiday is ready for your vacation! Located on the North End of Anna Maria and 1.5 blocks to the beach, you couldn't ask for a more delightful area to call home.brbrOur one-story home features 2 king bedrooms and a bedroom with three twin beds. Each bedroom includes a TV and crisp linens and plush towels in the bathrooms from our professional linen service. Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrTake relaxation to the next level in the tropical backyard with the sparkling pool as the centerpiece. Surrounded by pool loungers, deck chairs and patio dining options, you won't want to leave! But when the sugary sand of the beach calls, you are a four-minute walk to the shimmering water of the Gulf of Mexico. Beach chairs and beach towels are provided.brbrHav'Anna Holiday is close to everything the island has to offer. The free trolley stops nearby 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.brbrBedroom 1: King with TVbrBedroom 2: King with TVbrBedroom 3: Three Twins, Ensuite Bathroom, TVbrbrPlease 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.br​​​​​​​brVR16-000404brbrGolf 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 3

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Sleep 7

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Exceptional(49)

$1241.75

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Private Vacation Home

Vitamin Sea managed by Beach Retreats FL Anna Maria Island

Anna Maria, Florida, United States

☀️ Vitamin Sea by Beach Retreats Vacation Rentalsbr 146 Crescent Dr, Anna Maria, FL 34216brbrWelcome to Vitamin Sea, a stunning 5-bedroom, 5-bath luxury retreat located on the coveted north end of Anna Maria Island, just a 10-minute stroll to Bean Point Beach. With a private dock, heated saltwater pool and spa, elevator, and multiple balconies, this home has everything you need for the ultimate coastal getaway.brbrPerfect for families and groups of up to 12 guests, Vitamin Sea combines modern comforts with laid-back island charm. Whether you're relaxing by the pool, biking through the island, or watching the sunset at Bean Point, this home delivers the perfect blend of relaxation and adventure.brbr Highlightsbrbr 10-minute walk to Bean Point Beachbrbr Private heated saltwater pool + spa + sun shelfbrbr Semi-Private boat dock + 2 kayaks includedbrbr 2 adult cruiser bikesbrbr Huge outdoor living area with dining, lounge seating & big-screen outdoor TVbrbr 5 bedrooms, 5 bathrooms — sleeps 12 comfortablybrbr Elevator for easy access to all levelsbrbr Family-friendly: pack & play, highchair, toys, and beach gear providedbrbr Inside Your Retreatbrbr Backyard Tiki bar + propane BBQ grillbrbr Outdoor dining deck with island breezesbrbr Pet-friendly (max 2 pups, $250 fee each)brbr Parking for 4 vehiclesbrbr Free high-speed Wi-FibrbrThe professionally decorated interiors are bright, spacious, and welcoming. The open concept living area is perfect for gathering, with plush seating, Smart TVs, and direct access to the deck overlooking the pool and tropical backyard.brbrThe chef's kitchen boasts top-of-the-line appliances, a 36” gas stove, Keurig + drip coffeemakers, an ice machine, blender, crockpot, and all the cookware you'll need. A large dining table and bar seating make it easy to share meals together.brbr Room DetailsbrbrPrimary Suite: King bed, ensuite w/ shower & vanity, balcony, Smart TVbrbrBedroom 2: King bed, ensuite w/ double vanity & shower, balcony, Smart TVbrbrBedroom 3: King bed, ensuite w/ shower & vanity, Smart TVbrbrBedroom 4: King bed, ensuite w/ shower & vanity, Smart TVbrbrBedroom 5: Two bunk beds (4 twins), Smart TV, access to full bath with shower/tub combobrbrEach bedroom is designed for comfort and privacy, featuring luxury linens and fresh coastal décor.brbr Outdoor LivingbrbrStep into your private backyard oasis complete with a heated pool, spa, sun shelf, outdoor dining, propane grill, lounge seating, and a large covered area for shade. Enjoy watching the game on the big-screen outdoor TV or sip cocktails under the stars.brbrWith a private boat dock, kayaks, and bikes, adventure is always at your doorstep.brbr Location & Things to Dobrbr Hop on the free Anna Maria Island trolley for island exploringbrbr Walk or bike to favorites like Chateau Anna Maria, Beach Bistro, and Skinny'sbrbr Stroll to Bean Point Beach for breathtaking sunsetsbrbr Nearby shops, markets, and island essentials (Publix, CVS, Walgreens)brbrFrom paddleboarding and fishing to fine dining and casual beach bites, Vitamin Sea puts you close to everything.brbr✅ Important InfobrbrMax occupancy: 12 guestsbrbrParking: -2car garage (one side is owner occupied + driveway parking for 3 vehiclesbrbrPool heating included (85° Oct–May)brbrLinens & towels provided (premium linen service)brbrGuests must be 25+ to book (or accompanied by parent/guardian)brbrCancellation Policy:brbrNo cancellation fees!brbrCancel 60+ days before arrival → Full refundbrbrCancel within 60 days → No refundbrbrExtended stays & large bookings → Payment due 90 days prior, non-refundablebrbr$500 deposit due at booking; balance due 60 days before arrivalbrbrFor reservations 21+ nights or $20,000+ → 10% deposit due at time of booking. brbr​​​​​​​Third party travel insurance cost is due at time of purchase brbrGuests must be 25+ to book (or accompanied by a parent/guardian)brbr2 parking spaces available; no overnight street parkingbrbrPet Friendly: Max 2 dogs allowed, $250 non-refundable fee per petbrbrRentals typically run Saturday–Saturday; inquire for alternative staysbrbrQuiet hours apply 10pm - 8 am— please respect the neighborhoodbrbr Book your stay at Vitamin Sea today and experience the best of Anna Maria Island living — luxury amenities, unbeatable location, and endless opportunities for relaxation and fun.brbrTraveling with a large group Ask us about renting the home next door: Casa Amiga— a 4-bedroom, 4.5-bath retreat that sleeps 10. 1293349
Bed 5

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Bath 5

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Sleep 12

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Exceptional(1)

$1038.61

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Private Vacation Home

Mermaid’s Purse~Private Pool! 40 steps to beach!

Anna Maria, Florida, United States

Summary:brbr ‍♀️ Mermaid’s Purse is a charming 2BR/2BA north-end retreat just 40 steps from Palmetto Beach—no roads to cross . Enjoy a private heated pool, dog-friendly comfort, and a prime location less than a 5-minute walk to Pine Avenue’s shops and dining. With a fully equipped kitchen, cozy living space, and free island trolley nearby, this home is perfect for a relaxing Anna Maria Island getaway ☀️ ️ brbrbrbrThe Space:brbr ‍♀️ Mermaid’s Purse – Private Pool | Just Steps to the Beach! brbrOnly 40 steps to the sand with no roads to cross!brbrbrbrWelcome to Mermaid’s Purse, a charming north-end island retreat perfectly located just two homes from Palmetto Beach and less than a 5-minute walk to Pine Avenue’s shops and restaurants ️ . This owner-managed, dog-friendly vacation home features 2 bedrooms, 2 bathrooms, and a private heated pool—everything you need for a relaxing Anna Maria Island escape.brbrbrbr✨ Island Comfort & Easy LivingbrbrGather with family and friends in the cozy living area to plan your island adventures or relax with your favorite shows . The fully equipped kitchen offers ample counter space and everything needed to prepare delicious island-inspired meals ️. Enjoy quick bites at the kitchen island, morning coffee on the balcony ☕, or al fresco BBQ dinners under the covered patio .brbrbrbr ️ Restful Sleeping Spacesbrbr• Primary Bedroom: King bed & TV—bright, colorful, and relaxing brbr• Second Bedroom: Two twin beds & TV with ensuite bathbrbr• Living Area: Queen sleeper sofa for additional guestsbrbrbrbrAfter sun-filled beach days, refresh in the modern bathrooms featuring walk-in showers .brbrbrbr Outdoor Fun & Prime LocationbrbrSpend your days lounging by the sparkling private pool, or take a short stroll to the sugar-white sands of the Gulf to enjoy warm turquoise waters and unforgettable sunsets . Walk to Pine Avenue for shopping, dining, ice cream, bike rentals, and hop on the free island trolley to explore the island with ease .brbrbrbr Make It an AdventurebrbrBook fishing charters, dolphin and manatee tours, kayaking, boating, biking, or golfing—all just minutes away!brbrbrbr Pack your bags and complete your dream island getaway at Mermaid’s Purse!brbrbrbrGuest 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:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with 4 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 2 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 here to help! You can call or text me directly on my cell. I’m available 24/7 to answer questions, offer local tips, or assist with anything that comes up. Your comfort is my priority!
Bed 2

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Bath 2

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Sleep 6

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$530.78

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Private Vacation Home

Canal Front, Bay Breeze Bungalow by SeaBreeze Vacation

Anna Maria, Florida, United States

A few things that make Bay Breeze Bungalow special:br- North end of Anna Maria - private home on cul-de-sacbr- Pool (not heated)br- Canal front with 15 ft dock (6 ft clearance)br- Enclosed screened-in patiobr- Grill (propane included)br- Professional Linen Servicesbr- Complimentary WiFibr- Beach chairs, beach wagon, & beach umbrellabrbrTucked away on a quiet cul-de-sac at the desirable north end of Anna Maria, Bay Breeze Bungalow is a charming two-story canal-front home offering the perfect blend of comfort, space, and coastal living. Featuring 3 bedrooms and 2 bathrooms, the layout is ideal for families or small groups. The spacious primary suite includes a king bed and a private ensuite bathroom. Bedrooms two and three, each with a queen bed and a shared Jack-and-Jill bathroom.brbrThe updated kitchen is fully equipped for preparing meals at home, while the open living area flows seamlessly onto a screened-in balcony, perfect for enjoying morning coffee or evening breezes without the bugs. Downstairs, an additional screened-in lounge area with a TV provides a relaxed space to unwind after a day in the sun.brbrStep outside to enjoy canal views and direct water access, complete with a 15-foot boat dock—great for kayaking, fishing, or simply soaking in the waterfront setting. Please note: canal access includes low bridges, and clearance may be as low as approximately 6 feet depending on tide levels.brbrThe private pool offers a refreshing escape (note: it is not heated), and there is parking for up to 3 vehicles. The peaceful, low-traffic location enhances the home's laid-back island appeal. Whether you're looking to relax poolside, explore the waterways, or enjoy the tranquility of Anna Maria's north end, Bay Breeze Bungalow is a comfortable and inviting home for your stay.brbrProperty Cancellation Policy - SeaBreeze Vacation has spent a great deal of time and effort into formulating a cancellation policy for you. SeaBreeze Vacation has the most flexible cancellation policy on the Island. You are allowed to cancel your reservation up to 14 days prior to check-in to receive a refund. Additional terms and conditions apply. brbrSeaBreeze Linen & Amenity Packs - With all SeaBreeze Vacation properties, we think of the little things to make your vacation special. Included to get you started are the following: brPer Guest: 1 Bath Towel, 1 Hand Towel, 1 Washcloth, 1 Pool/Beach TowelbrPer Full Bathroom: 2 Rolls of Toilet Paper, Hand Soap, Shower Products Set (including trial size shampoo, conditioner, shower gel, and body lotion), Cosmetic Cloth, Bath MatbrPer Kitchen: 2 Rolls of Paper Towels, Hand Soap, Dish Soap, Sponge, Dishwasher Pods (x4), Laundry Detergent Pods (x4), All-Purpose Disinfectant, Microfiber Cloth, 2 Kitchen Towels 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.brbrCity of Anna MariabrMax Occupancy: 6 Guests | Max Vehicles: 3brQuiet Hours: 10 p.m. - 7 a.m. - please respect our island communitybrMin stay requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.
Bed 3

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Bath 2

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Exceptional(1)

$1565.8

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Private Vacation Home

Coastal Elegance! Pool, Putting Green, Movie Room, and More!

Anna Maria, Florida, United States

Periwinkle Place by Exclusive Vacations brVR25-000004 brbrIndulge in the ultimate luxury beach home at Periwinkle Place, part of our Exclusive Collection. This stunning estate in the heart of Anna Maria offers six spacious bedrooms and six and a half bathrooms. Just a five-minute walk from the pristine shoreline and steps from the shops and dining on Pine Avenue, Periwinkle Place combines coastal style with upscale amenities, including a pool with hot tub, private dock, golf cart, a private movie room and more, for an unforgettable beach vacation! Perfect for large families, retreats, or multi-generational gatherings, this home combines sophistication, comfort, and endless outdoor entertainment for your perfect stand getaway. brbrHighlights br• 5-minute walk to Anna Maria Beach br• 6 Bedrooms / 6.5 Bathrooms br• 5 Kings, 2 Twins/ Queen bunks br• Private Dock br• Private Pool with hot tubbr• Outdoor Kitchen br• Private Movie Room br• Putting Green br• Elevator access to all floors br• Short walk to Pine Avenue shops and dining br• Pet-friendly with approvalbrbrExclusive Amenities br• 6 Seat Club Car Cru Golf Cart for Guest Use br• Luxury Beach Bikes for Guest Use br• Beach Chairs and a Beach Cart for Guest Use br• Upgraded Bed and Bath Linens and Toiletries br• Portable Pack and Play br brExperience outdoor luxury with a private pool with hot tub, putting green, and lush tropical landscaping creating your own backyard paradise. The outdoor kitchen and BBQ grill make outdoor entertaining easy, while scenic balconies and a rooftop deck offer breathtaking views of the Gulf and surrounding water. Explore local water sports, fish from your private dock, or return after a day at the beach for a relaxing dip or sunset drinks. brbrStep inside this modern estate and be greeted by a seamless open-concept design. The elegant living room invites relaxation with plush seating, a large TV, and stylish decor, perfect for movie nights or unwinding in style. The gourmet kitchen boasts premium appliances, expansive countertops, and plenty of space for culinary creations, ideal for entertaining. The sophisticated dining area, seating eight comfortably, makes every meal a memorable occasion. br brRetreat to one of six luxurious bedrooms, each offering a tranquil sanctuary. The primary suite features a lavish king bed, a walk-in closet, and an ensuite with a double vanity, spacious walk-in shower, and a spa-like soaking tub. The remaining five bedrooms, all with plush decor, feature four king beds and one bunk room with two twins-over-a queen bed, each with ensuite bathrooms and walk-in showers to ensure privacy and comfort for everyone. The home also includes a half bath and an additional washer and dryer for convenience. brbrRoom Details br• Primary Bedroom: King bed, ensuite with walk-in shower and double vanity  br• Second Bedroom: King bed, ensuite with walk-in shower  br• Third Bedroom: Two Twins-over-a Queen bunk bed and ensuite bathroom br• Fourth Bedroom: King bed, ensuite with walk-in shower  br• Fifth Bedroom: King bed, ensuite with walk-in shower  br• Sixth Bedroom: King bed, ensuite with walk-in shower  br brBook Periwinkle Place today and enjoy an escape filled with water views, outdoor entertainment, and luxurious comforts. Perfect for family reunions, groups, or those seeking a stylish retreat, this home blends island charm with modern luxury. Reserve your dates now and start creating lifelong memories on Anna Maria Island! br brbr- brThis home is managed by AMI Locals, an Anna Maria Island property management company. 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 Rental Policies for full details. 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. brbrUse of the provided golf cart requires the driver to maintain a current U.S. automobile insurance. Proof of insurance is required upon request.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. Please 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 7

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Bath 6

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$728.93

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Private Vacation Home

Chilli Fish by Duncan Real Estate

Anna Maria, Florida, United States

Chilli Fish offers the best of island living on the North end of Anna Maria Island. This gorgeous home features 4 bedrooms, 3 baths with a private pool and is just a short stroll to the white sandy beaches. There is plenty of room to host 8 guests. brbrEnter the home and get greeted by wonderful beachy decor and wide plank flooring and beautiful area rugs. brbrThis Island home offers a comfortable living area with plenty of seating, a dining area and a stunning renovated open kitchen area. There is also a full laundry room inside the house. Get to know the Island and explore its little side streets or take the easily accessible free Island trolley!brbrThe ground level floor plan makes it easy to take advantage of the backyard. The pool area is very inviting with the sun on it throughout the day and provides total privacy with mature palm trees. brbrHIGHLIGHTSbrbr1,900 sq. ft. brbrPool deck spacebrbrPrivate poolbrbrLuxury Rental brbr0.2 miles from bay access brbr0.4 miles from beach accessbrbrBEDROOMSbrbrSleeps 8brbrPrimary Bedroom: King EnsuitebrbrSecond Bedroom: King Ensuite brbrThird Bedroom: Queen Ensuite brbrFourth Bedroom: 2 x FullbrbrBATHROOMSbrbrPrimary Bathroom: Walk-in ShowerbrbrSecond Bathroom: Walk-in ShowerbrbrThird Bathroom: Shower/Tub Combo brbrEXTERIORbrbrRelax in the pool after your day at the beach. Enjoy evening cocktails in the covered patio area with the outdoor big screen TV for watching your favorite games or cook up fresh seafood on the grill and dine alfresco. This is Island style living at its best.brbrThe pool heat is $150.00 a week. 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. brbrThere are four designated parking spaces in the driveway for this property. brbrPlease 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.brbrAmenities Include:brbr- Bedroom 1 Kingbrbr- Bedroom 2 Kingbrbr- Bedroom 3 Queenbrbr- Bedroom 4 2 Fullbrbr- Hot Waterbrbr- Beach Access 0.4 milesbrbr- Bay Access 0.2 milesbrbr- Ground Levelbrbr- Central A Cbrbr- Cental Heatbrbr- Sqft under a c 1650brbr- Parking Spots 4brbr- Front Security Camerabrbr- Keyless Entrybrbr- Bath Towelsbrbr- Beach Towelsbrbr- Quality Linensbrbr- Hair Dryerbrbr- Hangersbrbr- Refrigeratorbrbr- Ice Makerbrbr- Stovebrbr- Ovenbrbr- Cookwarebrbr- Toasterbrbr- Blenderbrbr- Keurigbrbr- Drip Coffee makerbrbr- Dishwasherbrbr- Microwavebrbr- Garbage Disposalbrbr- Dining Tablebrbr- High Speed WIFIbrbr- TV Streaming Onlybrbr- Washerbrbr- Dryerbrbr- Ironbrbr- Ironing Boardbrbr- Cleaning Kitbrbr- Fire Extinguisherbrbr- Smoke Alarmbrbr- Carbon Monoxide Alarmbrbr- Private Pool Ybrbr- Pool Alarmsbrbr- Sun Loungersbrbr- Patiobrbr- Propane Grillbrbr- Beach Amenitiesbrbr- Board Gamesbrbr- Duncan Emerald Clubbrbr
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Exceptional(1)

$522.66

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Private Vacation Home

Chardonnay Shores - Beautiful 2 Bedroom Home

Anna Maria, Fl, United States

Chardonnay Shores by Anna Maria Island AccommodationsbrbrWelcome to Chardonnay Shores, a beautifully refreshed three-bedroom, two-bath Anna Maria Island vacation rental located in the heart of Anna Maria City, just a short stroll from the sugar-white sands of Anna Maria City Beach and the charming shops and restaurants of Pine Avenue. This stunning home has undergone a major renovation and now feels like an entirely new coastal retreat. Designed for families and groups looking for the perfect island getaway, Chardonnay Shores combines stylish interiors, fun-filled outdoor spaces, and a fantastic location close to everything that makes Anna Maria Island unforgettable.brbrHighlightsbr• Recently renovated upscale home br• 3 Bedrooms / 2 Bathrooms br• 2 Kings, 1 Twin over Full Bunk, 1 Queen Sleeper Sofa br• Private heated pool br• Converted garage game room br• Movie screen, ping pong, shuffleboard, and Connect 4 br• Newly turfed backyard with putting green br• Two outdoor showers br• Family friendly island retreat br• Convenient location near Pine Avenue shopping and dining br• 4 parking spaces brbrStep outside and discover your own private island escape designed for both relaxation and fun. The newly turfed backyard creates a fresh, clean outdoor space perfect for gathering with family and friends after a beach day. Practice your short game on the private putting green, rinse off the sand with two convenient outdoor showers, or unwind under the Florida sunshine with plenty of room to lounge and play. brbrThe converted garage game room is one of Chardonnay Shores’ standout features, offering endless entertainment for guests of all ages. Challenge the family to ping pong, shuffleboard, or Connect 4, then settle in for a movie night with the large projector screen for the ultimate vacation hangout space. Whether you're enjoying sunny afternoons outside or game nights indoors, this home is built for making memories. Inside, Chardonnay Shores offers a bright and welcoming open layout with fresh coastal finishes and comfortable spaces designed for easy vacation living. The living room features plush seating and a queen sleeper sofa, creating the perfect place to gather for movie nights, morning coffee, or planning your next beach adventure. Large windows bring in natural light and add to the airy island feel throughout the home.brbrThe kitchen is beautifully updated and fully equipped with everything needed for preparing family meals, from quick breakfasts before the beach to evening dinners after sunset walks on the shore. Ample counter space, modern appliances, and a nearby dining area make entertaining effortless while keeping everyone connected.brThe primary bedroom is a peaceful retreat featuring a king bed, soft linens, and a private ensuite bathroom with a walk-in shower. This relaxing space is designed to help guests unwind after long days spent exploring Anna Maria Island, with plenty of room for luggage and a calm coastal atmosphere.brbrThe second bedroom also offers a king bed, making it ideal for another couple or additional guests seeking comfort and privacy. The third bedroom is perfect for kids or flexible group sleeping arrangements, featuring a twin over full bunk bed that adds both function and fun to the space. These guest rooms share a conveniently located hallway bathroom with a shower and tub combination, ideal for families returning from beach days and outdoor adventures.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroom with walk-in shower br• Second Bedroom: King bed br• Third Bedroom: Twin over Full Bunk br• Hall Bathroom: Shower and tub combination br• Bonus: Queen Sleeper Sofa in living room brbrChardonnay Shores includes thoughtful extras that make your stay even more convenient, including a washer and dryer, outdoor showers for rinsing off after the beach, and a spacious layout that allows everyone to spread out comfortably. Its prime Anna Maria location places you just minutes from local boutiques, waterfront dining, and the beloved Pine Avenue district, where guests can enjoy shopping, ice cream stops, and sunset strolls.brbrChardonnay Shores by Anna Maria Island Accommodations is the perfect blend of comfort, style, and location for your next Anna Maria Island vacation. With a beautifully renovated interior, exciting game room, private putting green, and close proximity to the beach and Pine Avenue, this home offers everything you need for an unforgettable stay. Book your getaway today and start making memories in paradise.brbr-brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company.brbrThis property does not allow pets of any kind. brbrThis property has an active Ring doorbell at the entrance. 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. Please 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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Bath 2

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Exceptional(13)

$3445.6

/ Nightly
Private Vacation Home

Luxury Beachfront on the Sand of Gulf of Mexico

Anna Maria, Florida, United States

Photos Updated January 2025!brbrSunnyside Escape is a newly built luxury home situated on the famous white sand gulf beaches of Anna Maria Island. The property is filled with top-of-the-line appliances and finishes throughout the home. Take in the view while lounging in the main living room, cooking, or enjoying a meal in the dining room. Large floor-to-ceiling windows allow spectacular views throughout the home. brbrThe large back deck has a space for everyone. Whether you are looking to soak in the sun in the gorgeous infinity pool, cookout your favorite meal in the outdoor kitchen, or lounge in the shade, Sunnyside Escape will provide! Take a quick stroll down to the water's edge with exclusive access to the gulf beaches. After a long day in the sun, the media room is the perfect refuge to watch a movie on the oversized sectional. Missing your Peloton rides while you are on vacation We have you covered with a Peloton bike in the upstairs gym. All you need to bring is your shoes and access to your account! brbrFloor 2 (main living level): brBedroom 1: King with TV and ensuite bathroom with walk-in showerbrMedia Room with large sectional with extra-large TVbrHalf bath in hallbrLaundry room with second half bath and direct access to pool patiobr(Please note that the fireplace in the living room and on balcony have been disabled and are not available for guest use.)brbrFloor 3:brBedroom 2: King master with TV, ensuite bathroom with walk-in shower, and Gulf ViewsbrBedroom 3: Queen Bed with ensuite bathroom with walk-in shower brBedroom 4: Queen Bed with ensuite bathroom with walk-in shower brExercise room with Peloton. brbrNOTE: For security and insurance purposes, there are exterior-only video cameras on the premises.brbr**PETS: Please note this property is NOT pet friendly. **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. *Note that the garage is owner-use only and is not available for parking.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.
Bed 4

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Bath 5

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Exceptional(2)

$801.62

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Private Vacation Home

Sandy Beach Retreat - 3 bedroom on the beach with amazing views and private pool

Anna Maria, Florida, United States

Welcome to Sandy Beach Retreat! You will fall in love with the beautiful beaches of Anna Maria Island as your backyard in this luxury vacation home! Spend your days lounging by the private heated pool or simply cross over to dip your toes in the Gulf waters. A one-of-a-kind, luxurious home located along the Gulf waters of Anna Maria! This multilevel 3-bedroom, 2.5 bathrooms home has all the best amenities featuring panoramic views, a private pool and an elevator to make bringing in your gear or groceries a breeze. Create your perfect beach getaway with family and friends as the home can comfortably sleep 6 guests! Literally just a couple steps from the sugary white sandy beach, close to incredible restaurants and shopping where you can find unique take-home treasures. Lazy beach days ahead!! Quiet spaces, large gathering spaces- this place literally has it all! When your day is done on the beach, then take a dip in the refreshing pool. Fire up the grill and take in the glowing sunsets nightly, straight from the comforts of your own beach house! In the evening, have your camera and cocktails ready! Sandy Beach Retreat will give your VIP sunset views from the privacy of your own home with open air decks. Great location and steps from the sand. Don’t feel like driving Then take a ride on the free Island trolley to other popular areas of Anna Maria Island where you can discover all the natural beauty this area has to offer. Grab your beach bags and escape from it all here at Sandy Beach Retreat! Home Layout: Bedroom #1: King Bedroom #2: King Bedroom #3:Twin
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Exceptional(4)

$902.09

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Private Vacation Home

Luxury North End Escape | 3 king beds + pool/spa

Anna Maria, Florida, United States

⭐️Super host Property + Verified for Cleanliness + Communication⭐br 228 Gladiolus Street - `Castaway Cove`br Castaway Cove | North End AMI | Pool + Spa + Walk to EverythingbrbrStay in the heart of the north end of Anna Maria Island at Castaway Cove, just steps from top restaurants, boutiques, Bay beaches, Gulf beaches, and the famous Anna Maria City Pier.brbr✨ Highlights:brbr• Private pool + hot tubbr• 3 King bedroomsbr• 2 full bathroomsbr• Sleeper sofa for extra guestsbr• Prime walkable locationbrbr Sleeping Setup:brbr• Primary: King bed, TV, ensuite with walk-in showerbr• Bedroom 2: King bed, TVbr• Bedroom 3: King bed, TVbr• Living Room: Sleeper sofabrbrEnjoy mornings at the beach, afternoons by the pool, and evenings dining just steps away — no car needed!brbrGood to Know:br• Entry code sent day of arrival after inspectionbr• Welcome book with WiFi + local tips providedbr• Rental agreement required prior to check-inbrbrCastaway Cove is the perfect island retreat for couples, families, or friends looking for location, comfort, and coastal charm all in one.brbrPlease note a starter set of supplies are left for your arrival. Anything beyond what is left renters are responsible for providing. Starter set includes. 2 rolls of toilet paper per bathroom, small hand soap, 1 roll of paper towels, 2 garbage bags, small dish soap and 2 pods for dishwasher.brbrPools are heated October - April at no additional costs. Full disclosure if temperate drop below 60 heaters do not work at full capacity fighting the ambient temp. Below 60 the heaters do not come on until temperatures risebrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level. Noise ordinance is in effect 10pm to 7am. Excessive and unreasonable noise can result in disciplinary actions including fines and/or termination of your rental agreement without refund.brQuiet hours between 10pm - 6ambrNo partiesbrNo smoking
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Bath 2

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$812.8

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Private Vacation Home

North end AMI, 5* luxury home in one of the prettiest towns on gulf coast!

Anna Maria, Florida, United States

Welcome to Castaway Cove, this beautiful residence is a Bean Point gem, a stunning 4 bedroom property and 2.5 bathroom on the exclusive Northern end of Anna Maria Island! Hide away from the world, relax and soak up the sun in the private backyard with heated pool and lush tropical landscaping.brbrWalk to Pine Ave & City Pier from this designer 4BR/4.5BA home on Anna Maria’s coveted north end. Enjoy a private heated pool & spa, three suite bedrooms, a kids’ bunk room, and the convenience of an elevator — just a 5-minute stroll to the sugar-sand beach. brbrThe downstairs game room provides an excellent 8ft Pool Table and Air Hockey table, perfect for adults and kids, or enjoy either of the 2 Smart HD TV's (internet only). Want to work on your beach body during your stay Make use of the Bow-flex weights & treadmill in the Castaway Cove gym or stretch out your back on the inversion table! Have a refreshing outdoor hot or cold outdoor shower after the workout.brbrWe have 2 Adult Bikes, 2 Kids Bikes + one small Bike, all for you to use around the island at your leisure.brbrGet the best of both worlds in a gorgeous home with fantastic amenities and a great location with the pristine white sandy beaches of Bean Point just a short 2 minute walk away! Three houses to the beach. Other fantastic local spots to visit are the renowned Rod and Reel Pier and Restaurant located just a brief 4 minute walk away, or the beautiful, newly renovated Anna Maria Pier and the popular Pine Avenue showcasing local boutiques and restaurants and so much more!brbrThe sleeping arrangements include a King-sized bed in the Master bedroom, 2 Queen sized beds on the upper floor and a set of bunk beds-comfortably accommodating a group of 8.brbrEnjoy the fully equipped kitchen, with new appliances in 2023, ideal for making a home cooked meal with the fresh catch of the day or simply indulge in the local cuisine, there are many fantastic restaurants or home delivery to choose from! Our Bull Outdoor Kitchen is down by the pool to make the best BBQ in town, recently added our new pool bar with refrigerator to keep all those drinks ice cold!brbrFor your convenience, Wi-Fi internet, a stereo, DVD player and a TV in each bedroom is provided-although you will probably spend most of your time pool-side or catching the sun on the beach-the choice is up to you, you are on vacation after all!brbr**Please keep in mind if the elevator becomes inoperable due to any reason, the stairs will be the only form of transportation to and from your unit**brbrBaby care facilities include a high chair, a stair gate, 2 pack 'n' plays and a sun tent for the beach. There is also a large trunk of toys by the pool.
Bed 4

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Exceptional(20)

$729.93

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Private Vacation Home

Hop, Skip and a Beach - 4Bed Pool Home in Anna Maria City - By Island Real Estat

Anna Maria, Florida, United States

Oh so close to the beach all it takes is a Hop, Skip and a Jump to get to the Beach! This newer 4 bedroom private pool home is west of Gulf Drive in beautiful Anna Maria City. This home has everything you and your family will need, and is less than 2 minutes to the flour soft sand beaches of the Gulf of Mexico. Hop, Skip and a Beach is an elevated home that boasts a private heated pool with spa(hot tub) and many other covered areas poolside ideal for lounging after a busy day of exploring Anna Maria Island. Enjoy an outdoor meal under the covered lanai or the island tiki overlooking the spacious pool. There is also a brand new game room with bar, large TV, electronic dart board, and vintage fridge! Also take in a game of corn hole with custom boards offered by the owner.brbrThere are so many outdoor decks you will need to extend your stay in order to enjoy them all, and get yourself enough of the fresh sea air everyone talks about. The great room area is open to the fully stocked gourmet kitchen, living area and dining area. Just at the top of the stairs is a washer and dryer on the third floor for guest convenience. Three of the four bedrooms are located upstairs on the third floor including the Master suite. This private West of Gulf Drive home comfortably accommodates a group of 8 with a King sized bed in the master bedroom, a second master with King bed, a Queen bed in the fourth guest bedroom off the living area and a full over queen bunkbed in the third bedroom perfect for kids or adults.brbrHop, Skip and a Beach is located on the North end of Anna Maria Island in Anna Maria City. The elevated home is just a short trolley ride, bike ride or walk away from some of the great local shops and restaurants. Walk the beach for 15 minutes to the famed Sandbar restaurant for a beachside cocktail.brbrPlease note: this property books Saturday to Saturday. We may sometimes gladly accept non Saturday to Saturday stays from middle of August to middle of December or for short stays. Please ask a reservation specialist for more details.brbrDon’t see availability for your exact dates, give our office a call 941-778-6066.brbrTo be eligible for a refund, less our $250 cancellation fee, guests must cancel in writing outside 60 days from arrival.brbrIMPORTANT INFORMATION:brbrYour booking is with Island Real Estate Vacations. We will send you check-in instructions 30 days prior to your arrival date. Please review the cancellation policy prior to booking. Island Real Estate Vacations will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.brbrPayment of reservation deposit is considered acceptance of all terms regardless of signature status of contract. Guest is responsible for adhering to the rental terms and dates. Any error on Guest’s part is not the responsibility of the agent. Sub-leasing of your vacation rental is strictly prohibited. A mid-stay clean and charge equal to the standard cleaning fee are required for all stays 21 nights or longer. By providing your phone number, you agree to receive text messages from our company. Message and data rates may apply. Message frequency varies.brbrYour final balance is due 60 days prior to your arrival date. Please note unless alternative arrangements are made, the bank account or credit card on file will be charged your remaining balance automatically at 60 days. If you do not wish to pay with the bank account or credit card on file, please reach out to pay several days in advance of 60 days prior to your arrival. If you initially paid with an eCheck and received the booking incentive, please remember future payments must also be made with an eCheck. Thank you for choosing eCheck to help reduce the cost of business. Please note the eCheck payment option cannot be used within 14 days of arrival. Any refunds on checks and echecks will be delayed at least 14 days after deposit or until funds are verified.brbrAll our properties provide luxury linens for you to enjoy during your stay.brbrbrVR17-000012brbrMax Vehicles Allowed:4 Max Day Guests Allowed:2brbrPlease be sure to obey all traffic laws and be sure you are parking in a permitted area if parking on the streets. If you park in a non-parking zone or against traffic, you will be ticketed.brbrAnna Maria Island’s noise ordinance aims to ensure citizens can enjoy a peaceful environment. The ordinance applies to all areas of the city, including public and private property, and places of business. It defines noise as any sound that annoys or disturbs a reasonable person of ordinary sensibilities or causes or tends to cause an adverse physical or psychological effect on such reasonable person. The noise ordinance limits the maximum permissible noise levels to: br7 AM–10 PM: 65 decibels: (Consistently shouting in the pool exceeds 65 decibels)br10 PM–7 AM: 50 decibels: (An audible conversation from 50’ or 15 meters away exceeds 50 decibels)brThe ordinance also prohibits plainly audible noise, which refers to any sound that can be clearly heard by a person using their normal hearing faculties. This means that a person can still be in violation if the noise can be easily heard by responding officers from a distance of 100 feet from the property line. Fines for excessive noise can range from $100 to $1,000.
Bed 4

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Exceptional(2)

$489.87

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Private Vacation Home

Dock of the Bay by Duncan Real Estate

Anna Maria, Florida, United States

Welcome to Dock of the Bay!br br Located on the North end of Anna Maria, Dock of the Bay is a newly remodeled two- bedroom, three-bathroom vacation home directly on a canal with a private pool. This property has boat access to the intercoastal passing 2 low clearance bridges. br br Dock of the Bay is a direct walk to Bean Point which is one of the most picturesque parts of Anna Maria Island.br br br HIGHLIGHTSbr br 2228 sq. ft. br Private Pool 35x20'br Boat dock br Canal accessbr Screened lanai br br Dog friendly up to 25 lbs.br br BEDROOMSbr br Sleeps 4br Primary Bedroom: King Ensuitebr Second Bedroom: Queen and bunk bedsbr br BATHROOMSbr br Primary Bathroom: Walk-in Showerbr Second Bathroom: Walk-in Showerbr Third Bathroom: Walk-in Shower br br EXTERIORbr br Relax on the large-screened lanai after a day at the beach and look out for mullets jumping in the canal. Take a dip in the lagoon shaped pool with shallow wading area. Dock of the Bay is located on quiet Gladiolus St and just a short walk away from the Bay side and Pine Avenue shopping area. Here you can try out the delicious local cuisines, browse through shops and much more! If you are looking to unwind, Dock of the Bay is your perfect location! Come experience for yourself all the best that Anna Maria Island has to offer!br br There are three parking spaces designated for this property in the driveway and garage.br br The weekly pool heat 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. 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 pools for maintenance purposes. No refund or rent adjustment except for pool heat fees will be made for circumstances beyond our control, malfunctions, or loss of use of equipment or amenities.br br br This property welcomes any day arrival for the months mid-August to January except holiday weeks. Please contact us for approval.br Amenities Include:br - Bedroom 1 Kingbr - Bedroom 2 Queen and bunk bedsbr - Bathroom 1 Walk-in Showerbr - Bathroom 2 Walk-in Showerbr - Bathroom 3 Walk-in Showerbr - Water View Ybr - Canal Viewbr - Canal Accessbr - Beach Access 0.3 milesbr - Ground Level Ybr - Central A Cbr - Cental Heatbr - Sqft under a c 2228 sqftbr - Parking Spotsbr - Garagebr - Dogs up to 25 lbs Ybr - Self Check Inbr - Keyless Entrybr - Bath Towelsbr - Beach Towelsbr - Quality Linensbr - Hair Dryerbr - Hangersbr - Refrigeratorbr - Ice Makerbr - Stovebr - Cookwarebr - Toasterbr - Blenderbr - Drip Coffee makerbr - Dishwasherbr - Microwavebr - Garbage disposalbr - Breakfast Barbr - High Speed WIFIbr - TV 3br - TV Streaming Onlybr - Washerbr - Dryerbr - Ironbr - Ironing Boardbr - Cleaning Kitbr - First Aid Kitbr - Fire Extinguisherbr - Smoke Alarmbr - Carbon Monoxide Alarmbr - Private Pool Ybr - Pool Dimensions 35x20'br - Spa Ybr - Pool Alarmsbr - Sun Loungersbr - Screened Lanaibr - Outdoor Diningbr - Boat Dockbr - Fishing Dockbr - Propane Grillbr - Beach Amenitiesbr - Board Gamesbr - Exterior Outletbr - Duncan Emerald Club
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Exceptional(2)

$766.89

/ Nightly
Private Vacation Home

Blue Mermaid Beach Bungalow

Anna Maria, Florida, United States

Highlightsbr- 2 minute walk to the Beach of Anna Maria Islandbr- 5 minute walk to Pine Ave.br• Private Poolbr• Outdoor Showerbr• Beach gear (chairs, umbrella, towel, kid's toys)brbrBlue Mermaid by Reel Coastal Propertiesbr111 Sycamore AvebrAnna Maria, FL 34216brbrWelcome to Blue Mermaid, where you are just one house away from the beach! Take a quick walk to the warm white sands and relax to the sound of ocean waves. The backyard features a private pool surrounded by lush landscaping, lounge chairs, and a screened-in patio where you can retreat for deep relaxation and even watch your favorite movies on tv. This vacation home is situated two blocks from Anna Maria Island’s famous Pine Avenue, so there will be no shortage of flavorsome local treats or boutiques.brbrThe Blue Mermaid is an enchanting three-bedroom, a two-bathroom beach vacation home. The living area’s coastal décor provides a welcoming atmosphere where conversations and relaxation are encouraged. Open the sliding glass doors to the patio where your guests enjoy early morning coffee or late-night drinks while taking in the ocean view. The fully equipped kitchen has festive Caribbean hues, broad kitchen countertops that make meal preparation a breeze, and plenty of cabinet space to store your goodies and ingredients for an excellent best island meal.brbrThe primary bedroom’s vibrant tropical colors are sure to brighten up your vacation, and the ensuite bathroom features a shower/tub combo. The second bedroom has beautiful island décor and the opportunity to open the shuttered windows to gaze upon the lush landscaping and to bring in the Anna Maria sun. The third bedroom is perfect for younger guests and has a tv for late-night show watching. The second and third bedrooms share a hallway bathroom that has a shower/tub combo.brAfter a beautiful day at the beach, retreat to your backyard, where you can lounge by the pool and take a shower at the outdoor shower located on the backside of the house. Cook up some of your family favorites on the charcoal BBQ grill to enjoy at the outdoor dining table. Explore Anna Maria Island on your own or check out the local tour guides to show you some local treasures on the land and at sea! Blue Mermaid is so close to the delicious restaurants and locally owned boutiques that it is sure to have something for everyone in your group.brbrRoom Detailsbr- Primary Bedroom, 2nd floor: King bed, tv, and ensuite bathroombr- Second Bedroom, 2nd floor: King bed and tv.br- Third Bedroom, 2nd floor: Twin beds and tv.brbrThere are no pets allowed in this home.brbr*Please note: 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.brbrPlease 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.br*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
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Exceptional(33)

$875.43

/ Nightly
Private Vacation Home

Canalfront Island Gem with Private Heated Pool, Dock, Ping-Pong, & Putting Green

Anna Maria, Florida, United States

Mermaid ManorbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThe island lifestyle will be hard to leave once you indulge in a stay at this gorgeous retreat in the heart of Anna Maria. Boasting a bright interior, driftwood-inspired floors, and shiplap walls, this will be just the place to spoil even the most design-oriented of guests. Start each morning with a warm cup of coffee on the furnished balcony as you look out to the canal system and plan a full day of fun. When days heat up, everyone can head out to the private pool (can also be heated upon request!) and lounge in bliss while the kids play in the refreshing water. Whipping up poolside snacks and gourmet meals will be easy in the fully equipped kitchen and everyone will love eating al fresco on the covered deck! After watching the sunset from your favorite spot, head inside and you will have the option to gather for a movie night on one of the flatscreen TVs or let your competitive side out with a ping-pong tournament! Additional entertainment can be achieved thanks to the professional-grade 4 hole putting green - the putters and balls will be provided to you, so there's no need to worry!brbrHeading to bed each night will be a treat in itself, as each bedroom is immaculately furnished and decorated. Starting from the entrance of the home, the first three bedrooms can be found by following the hall directly to the right at the top of the stairs. On the right side of the hall is a bedroom with a twin/double bunk bed. The next bedroom offers a queen bed. Plus, a full bathroom is located at the need of the hall. On the left is a master suite with a king bed and a beautiful en suite bathroom. Make your way to the other end of the home and you will find the last bedroom located off of the living area that is complete with a queen bed and easy access to another full bathroom across the hall. brbrThere will be no lack of excitement on this vacation, as Anna Maria is packed with fun for the whole family to enjoy. With access to Bimini Bay via the unique canal system, taking your boat out for a day on the emerald water of Tampa Bay will be a breeze. Sugar-white sand can be found just blocks away, or you can make your way to Bean Point Beach for room to spread out and watch the waves just over a mile from your front door. When the group works up an appetite, amazing restaurants like The Waterfront Restaurant, Rod and Reel Pier, and The Sandbar Restaurant will be just the ticket for a plate of fresh seafood. brbrTHINGS TO KNOWbrPool heat is included and maintained at 80°F. Additional pool heat to 85°F is available upon request for $32 per day plus tax. A 48 hour notice is required. Heat may not be available if temperatures drop below 65 degrees. We will not be accepting payments for pool heat for the months of May through OctoberbrThe golf cart is not for guest use.brbrParking notes: There is free parking available for 2 vehicles.brbrDock details: 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.
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Exceptional(32)

$769.67

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Private Vacation Home

Beach Bay Serenity: Pine Ave canal front pool home

Anna Maria, Florida, United States

Welcome to Beach Bay Serenity!brbrThis gorgeous 4 bedroom 3.5 bath waterfront home located on Pine Avenue is the perfect place to enjoy your next vacation!brbrBeach Bay Serenity is an immaculate home with updated features throughout. This home offers open living space, canal views, spacious kitchen with built in dining area, solid wood cabinets, granite countertops, elevator, large master suite with separate tub and shower, private deck off the master, walk-in closets, 2nd master suite, Guest bedroom, Bunk bedroom, and garage. Beach Bay Serenity offers direct access to Tampa Bay and The Gulf of Mexico. Relax and entertain outdoors by the heated pool! Conveniently located on Pine Avenue you have many restaurants and boutiques right at your door step! Bring your boat and dock directly in your backyard or enjoy fishing off the dock. Leave the car at home with the free Anna Maria Trolley passing right by your front door, travelling throughout the island very convenient!brbr**Please note that boat lift is not available for guest use.brbr*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.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.
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