Home Vacation Rentals By Owner In Anna Maria, FL

Showing 420 Of 792 Vacation Rentals
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Exceptional(1)

$1321.88

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Private Vacation Home

Bayfront Luxury | Rooftop Spa, Resort Pool + Golf Cart

Anna Maria, Florida, United States

Deckadence by Exclusive Vacations brBayfront Luxury | Rooftop Spa, Resort Pool + Golf Cart brVR25-000002 brbrWelcome to Deckadence by Exclusive Vacations, a luxury coastal retreat ideally located across the street from the bay and just a short walk to the Gulf beaches on Anna Maria Island. This four-bedroom, four-and-a-half-bath home features a rooftop deck with spa and fire pit, heated private pool, and outdoor kitchen, offering the perfect balance of water views, walkability, and resort-style amenities. Designed for families and groups, Deckadence delivers a private island experience with both sunrise bay views and easy access to Gulf sunsets - a rare combination on the island. brbrHighlights br• Across the street from bay beaches (water views and easy access) br• 5-minute walk to Gulf beaches br• Rooftop deck with massive spa, fire pit and bay views br• Private heated pool br• Outdoor kitchen, dining and lounge areas br• 4 Bedrooms | 4.5 Bathrooms br• 3 King suites + bunk room (4 twins) br• 6-seat Club Car Cru golf cart included br• Luxury beach bikes, chairs and beach cart br• Dog friendly with host approval br• 4 on-site parking spaces br• Close to Pine Avenue shopping and dining brbrDeckadence is a bright, modern coastal home designed for relaxed island living. Natural light fills the open-concept interior, while warm finishes and comfortable furnishings create an inviting space to gather after a day at the beach. The main living area offers ample seating and a seamless flow into the dining and kitchen spaces. The fully equipped kitchen features a large island for casual dining, premium appliances, and generous workspace - ideal for preparing meals, hosting, or enjoying time together. brbrOutdoor spaces define the Deckadence experience. The heated private pool and surrounding lounge areas create a relaxing backyard retreat, while the outdoor kitchen and dining space make entertaining effortless. Above it all, the rooftop deck offers a unique vantage point of the bay, complete with a massive spa and fire pit—perfect for morning coffee, sunset cocktails, or unwinding under the stars. Guests can also enjoy outdoor games and gathering spaces designed for both relaxation and fun. brbrRoom Details brEach bedroom is designed for comfort and privacy, with ensuite bathrooms throughout: br• Primary Bedroom: King bed, ensuite bathroom with walk-in shower br• Bedroom 2: King bed, ensuite bathroom with walk-in shower br• Bedroom 3: King bed, ensuite bathroom with walk-in shower br• Bedroom 4: Two twin-over-twin bunk beds (sleeps 4), ensuite bathroom br• Half Bathroom: Main living level brbrExclusive Vacations Amenities brEvery stay includes premium amenities designed for a seamless experience: br•6-Seat Club Car Cru golf cart br• Luxury beach bikes br• Luxury beach chairs, umbrellas and beach cart br• Kayaks for fun in the bay br• Upgraded bed and bath linens and premium toiletries br• Fully stocked house supplies br• Portable Pack and Play brbrDeckadence offers a unique location just steps from the bay and a short walk to the Gulf beaches, giving guests access to both sides of Anna Maria Island. Enjoy peaceful bay views, easy beach days, and quick access to Pine Avenue’s shops, restaurants, and local favorites. brWith its massive rooftop spa and bay views, private pool, and dual water access location, Deckadence by Exclusive Vacations delivers a well-rounded Anna Maria Island experience - perfect for families and groups seeking both relaxation and convenience. brReserve your stay and enjoy the best rooftop experience on the island! 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. brbrUse of the provided golf cart requires the driver to maintain a current U.S. automobile insurance. Proof of insurance is required upon request.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 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 4

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Bath 4

Bath

Sleep 8

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$724.76

/ Nightly
Private Vacation Home

Private Pool / Spa Home - Steps to Anna Maria Island Beach

Anna Maria, Florida, United States

Charming Pool Home Just Steps to Anna Maria Island Beachesbrbr Welcome to Sea Shack, a cozy and stylish 2BR/2BA ground-level home with a private pool, perfectly located just a short stroll to the white-sand beaches of Anna Maria Island and only minutes from the boutiques and restaurants on Pine Avenue. Relax with island vibes, comfortable furnishings, and everything you need for a stress-free coastal getaway. brbrWhat You’ll Lovebrbr 5-minute walk to the beach and Pine Avenue shopsbrbrPrivate heated pool with shaded lounging areabrbrCozy, open-concept living with beachy décorbrbrFully equipped kitchen with plenty of storagebrbrSmart TVs and free high-speed WiFibrbrSleeps up to 6 guests comfortablybrbrOptional baby gear rental: Snoo, pack & play, high chairbrbr Relaxing Coastal Interiorsbrbr Sea Shack features a bright, open living area with comfortable seating and curated coastal accents. The fully equipped kitchen offers ample counter space, cookware, and all essentials for easy meals at home. The two bedrooms provide soft linens and restful escapes after long days in the sun. brbrOutdoor Living & Poolside Comfortbrbr Step outside to your private backyard oasis with a refreshing pool, outdoor seating, and shaded lounge area perfect for morning coffee, afternoon swims, or grilling after a day at the beach. brbrPerfect AMI Locationbrbr Quick walk to Gulf beachesbrbrEasy access to bike paths and bayfront parksbrbrClose to Pine Avenue’s boutiques, cafés, and popular restaurantsbrbrNear trolley stops for car-free island exploringbrbr Family-Friendly Amenitiesbrbr Families love Sea Shack’s welcoming layout and optional baby gear rentals including a Snoo, pack & play, and high chair. The convenient ground-level floor plan makes this home ideal for guests of all ages. brbrBook Direct & Savebrbr Experience the charm of Anna Maria Island with comfort, convenience, and coastal style. When you book direct with Island Time AMI Rentals, you get the best rates and exceptional local service. Your island escape starts here—reserve Sea Shack today! brbr Note About Our Island CommunitybrbrAt Sea Shack on Spruce, we want to make sure you have the most relaxed and carefree stay possible. As our beautiful island continues to rebuild and renew itself after recent hurricanes, you may notice occasional construction or restoration projects happening in the surrounding neighborhood.brbrOur community is working hard to bring everything back better than ever, and while the island’s easygoing charm remains, there may be moments of daytime noise or activity nearby.brbrThank you for your understanding as we all do our part to restore the magic of Anna Maria Island. We’re grateful to have you here and are always just a message away if you need anything during your stay.brbrIsland Time vibes only
Bed 2

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Bath 2

Bath

Sleep 6

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$1238.76

/ Nightly
Private Vacation Home

Poolest House on the Island by Duncan Real Estate

Anna Maria, Florida, United States

Welcome to Poolest House on the Island! This beautiful, North-end 5-bedroom, 4 1/2-bathroom pool home has 3270 sqare feet under A/C of elevated living space and offers the best of Island vacationing. Up to twelve guests will be accommodated very comfortably inside and out. From the quality quilts and linens on the beds, spacious interior and several fantastic outdoor areas nothing has been spared to provide a perfect beach getaway. With the very short flip flop walk to beautiful, white beaches, you will catch the salty sea breeze and never miss a sunset! Family entertainment is provided with ping pong and foos ball in the game room and with 10 TVs throughout the house. HIGHLIGHTS 3270 sq. ft. Game room Private heated pool and hot tub Ping Pong Table Foos Ball Table North end location on the Island 0.1 miles from beach access BEDROOMS Sleeps 12 Primary Bedroom: King Ensuite Second Bedroom: King Ensuite Third Bedroom: King Ensuite Fourth Bedroom: Queen Five Bedroom: twins x 2 bunks; full x 2 bunksBATHROOMS Primary Bathroom: Walk-in-Shower and soaking Tub Second Bathroom: Walk-in-Shower Third Bathroom: Walk-in-Shower Fourth Bathroom: Shower/Tub - Jack N Jill Half BathroomEXTERIOREnjoy the outdoors on the various porches and the fantastic back yard area. From the living room porch, a staircase leads to your own private Island oasis. Plenty of seating and sun loungers surround the large 32' x 13' size pool so you can bask in the Florida sunshine. Rinse off after the beach in the outdoor shower and splash away! Have a cocktail after your day at the beach or prepare the catch of the day on the outdoor grill by the pool. The perfect way to end your day is a late-night swim.Optional pool heat, up to 86 F, is available from November to April at $150/week. Weather conditions may affect the temperature of the pool. Spa heat only is available in the summer months for $15/night where applicable. Pool alarms are mandated per city licensing ordinance and cannot be disarmed. Pools are professionally serviced weekly and debris due to tropical climate might occur in between service days. Duncan Real Estate will expedite repairs of reported malfunctions, but no refund will be made for circumstances beyond our control. Minimum stay: 3 nights and Maximum occupancy: 12 peopleThere are five parking spaces in the driveway.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.brbrAmenities Include:brbr- Bedroom 1 Kingbrbr- Bedroom 2 Kingbrbr- Bedroom 3 Kingbrbr- Bedroom 4 Queenbrbr- Bedroom 5 Full x 2, Twin x 2brbr- Denbrbr- Work Space Ybrbr- Bathroom 1 Soaking Tub/ Walk-in-Showerbrbr- Bathroom 2 Walk-in-Showerbrbr- Bathroom 3 Shower/Tubbrbr- Bathroom 4 Walk-in-Showerbrbr- Half Bathbrbr- Hot Waterbrbr- Beach Access 0.1 milesbrbr- Elevatedbrbr- Elevator Ybrbr- Central A Cbrbr- Cental Heatbrbr- Ceiling Fan Living Areabrbr- Sqft under a c 3270 Sqftbrbr- Free Parkingbrbr- Self Check Inbrbr- Keyless Entrybrbr- Bath Towelsbrbr- Beach Towelsbrbr- Quality Linensbrbr- Hair Dryerbrbr- Hangersbrbr- Refrigeratorbrbr- Ice Makerbrbr- Wine Fridgebrbr- Stovebrbr- Ovenbrbr- Cookwarebrbr- Toasterbrbr- Blenderbrbr- Keurigbrbr- Drip Coffee makerbrbr- Dishwasherbrbr- Microwavebrbr- Garbage Disposalbrbr- Dining Tablebrbr- Breakfast Barbrbr- High Speed WIFIbrbr- TV 10brbr- Cable Channelsbrbr- Washerbrbr- Dryerbrbr- Ironbrbr- Ironing Boardbrbr- Cleaning Kitbrbr- Fire Extinguisherbrbr- Smoke Alarmbrbr- Carbon Monoxide Alarmbrbr- Private Pool Ybrbr- Pool Dimensions 32' x 13'brbr- Spa Ybrbr- Pool Alarmsbrbr- Sun Loungersbrbr- Balcony 3brbr- Deckbrbr- Outdoor Showerbrbr- Propane Grillbrbr- Beach Amenitiesbrbr- Game Roombrbr- Board Gamesbrbr- Ping Pongbrbr- Foosballbrbr
Bed 5

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Bath 5

Bath

Sleep 12

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Exceptional(30)

$991.16

/ Nightly
Private Vacation Home

Beach Escape! Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach

Anna Maria, Florida, United States

Beach Escape by AMI Locals brVR18-000090 brbrWelcome to Beach Escape, a stunning five-bedroom, four-bath luxury home just one street from the powdery white sands of Anna Maria Island. Ideally located on the peaceful north end near Bean Point Beach, this coastal retreat combines upscale comfort with endless outdoor fun. Spend your days lounging by the private pool and spa, practicing your swing on the backyard putting green, or challenging friends to a game of ping pong. With beach chairs, a wagon, and plenty of space to gather and unwind, Beach Escape offers the perfect blend of family-friendly relaxation and island luxury for your next unforgettable getaway. brbrHighlights br-3-minute walk to Bean Point Beach br-5 Bedrooms / 4 Bathrooms br-4 King beds, Twin-over-Full bunk with trundle br-Private pool and hot tub br-Putting green, ping pong table, and cornhole br-Rooftop deck with sunset views br-Beach chairs and wagon br-Dog friendly with host approval br-Parking for 4 vehicles br-Washer and dryer brbrThe lush backyard is designed for both play and relaxation. Take a dip in the sparkling pool, soak in the spa, or enjoy a game of miniature golf, ping pong, or cornhole. Fire up the BBQ grill for a cookout, dine outdoors under the palms, or head up to the rooftop deck to watch the stunning Anna Maria Island sunsets. With beach gear included your trips to the shoreline are effortless. brbrStep inside to coastal-inspired living spaces filled with natural light. The open living room features comfortable seating and TV, while the fully equipped kitchen includes stainless steel appliances, ample storage, and everything you need for preparing group meals. Gather around the indoor dining table for eight or enjoy island breezes while dining al fresco on the balcony or poolside patio. brbrThe primary suite is a relaxing retreat with balcony access, a king bed, and a spa-like ensuite bathroom with dual vanities and a walk-in shower. Two additional king bedrooms feature ensuite bathrooms with walk-in showers, while a fourth king bedroom and a cheerful bunk room provide flexible sleeping arrangements. The bunk room, with its twin-over-full bunk and trundle, is perfect for kids or teens. brbrRoom Details br-Primary Bedroom: King bed, ensuite bathroom with walk-in shower, balcony access br-Second Bedroom: King bed, ensuite bathroom with walk-in shower br-Third Bedroom: King bed, ensuite bathroom with walk-in shower br-Fourth Bedroom: King bed br-Fifth Bedroom: Twin-over-Full bunk with trundle brbrThis home includes a washer and dryer, Wi-Fi, and multiple balconies with seating. Guests can easily explore Anna Maria Island’s shops, restaurants, and attractions by bike or trolley. brbrWith its private pool, rooftop deck, and fun family amenities, Beach Escape is the perfect blend of luxury and play. Whether you’re lounging poolside, biking to Bean Point, or enjoying sunset views from the rooftop, this home delivers the ultimate Gulf Coast experience. brbrBook your stay at Beach Escape today and create unforgettable memories on Anna Maria Island! br br- br4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by AMI Locals, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. 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. 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 5

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Bath 4

Bath

Sleep 12

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Exceptional(97)

$441.83

/ Nightly
Condo

3 bedroom on Pine in Anna Maria Island, private pool and PET friendly!

Anna Maria, Florida, United States

Seashell is 3 bedroom 2 bath second story condo that is set up like a single family home. It features wood floors, a king size bed in the master bedroom, one queen bed in the second bedroom as well as two twin beds in the third bedroom. The master bedroom ensuite has a shower, bath tub, granite vanity top with double sinks. Each bedroom has its own flat screen television. brbrThe living area has a open floor concept with a breakfast bar. The kitchen entails granite counter tops which features a full range of stainless steel appliances. The fully stocked kitchen includes all your household items that make you feel like you are at home. brbrFrom the living room area you have access to the front and back porch. Indulge in the large flat screen TV in the living room that offers sports package and all local channels. Relax, as natural light will illuminate the whole living space. If you are hosting guests, the dining room table seat up to 8 people. brbrThe front porch faces south toward Pine Avenue. The back porch faces north overlooking the private fenced pool . Outdoor furniture and a gas grill complete the private pool oasis. Beach wagon and beach items are also available. One assigned parking. Bus stop of the free Island trolley is just in front of the house. At this location you could completely forget your car!brDogs are welcome. Pet fee is $200 per pet plus taxes, maximum of 2 pets unless otherwise approved by FDR. brbrFree Wi-Fi, linens & towels, etc. + beach equipment provided.brbrAccommodates up to 6 people. Minimum Stay Required: 1 Week. brMax. parking: 1brbrYou 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* Cancellation more than 90 days prior to arrival will receive a deposit refund less a $250 cancellation fee. Cancellation less than 90 days prior to arrival will forfeit all deposit received. Cancellation less than 60 days prior to arrival will forfeit all monies on account. Cancellations must be confirmed in writing.
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(8)

$488.45

/ Nightly
Private Vacation Home

Private Pool - Island Dream

Anna Maria, Florida, United States

Island Dream is your perfect coastal escape. This spacious 4-bedroom, 4-bathroom coastal retreat with a fully equipped kitchen and a stunning backyard perfect for outdoor entertaining. Ideally located near the beach, shops and restaurants, it offers the perfect blend of comfort, convenience and relaxation.brbrStep into the light and airy interior where coastal charm meets modern convenience. The fully-equipped kitchen is a dream for any home chef, featuring granite countertops, stainless steel appliances, and everything you need to prepare meals with ease. Outside, you'll find an amazing backyard oasis made for entertaining and unwinding. There's plenty of comfortable seating, a portable grill, prep area, and even a refrigerator - perfect for alfresco dinners or lazy afternoons in the sun. Please note that the built-in grill is not to be used.brbrLocated in a prime spot just minutes from the beach, Island Dream also puts you close to great shops and restaurants. Enjoy your mornings or evenings on one of the home's inviting balconies, the perfect place to sip coffee or a cocktail and soak in the coastal breeze. brbrWhere you're here for adventure or relaxation, Island Dream has everything you need for an unforgettable stay. brbrCancellation 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. brbrThe property participates in our Professional Linen Program. SeaBreeze Vacation strives to bring only the best quality experience to our guests. To do so, we provide a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you high-quality linens that are in place and ready for your use upon your arrival. Our high-quality linens are laundered in a commercial setting that uses only hypoallergenic, perfume & dye-free soaps assuring all of our guests a comfortable stay.brbrWith all SeaBreeze Vacation properties, we think of the little things to make your vacation special. Included to get you started are the following: brbrPer 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 TowelsbrbrWe also offer a range of supplemental services including pre-stock grocery shopping and babysitting. Need a pack and play or high chair, etc. These are available for a small additional fee and will be waiting in the home on your arrival.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.
Bed 4

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Bath 4

Bath

Sleep 8

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Exceptional(10)

$630.92

/ Nightly
Private Vacation Home

La Cocolia located north end of AMI, Lagoon Pool

Anna Maria, Florida, United States

Need a GREAT AMI GETAWAY Just steps from the bayfront park in the City of Anna Maria is a charming island beach house called La Cocolia lovingly translated as the little crab. This property is ready to host you and your family as you enjoy this newly renovated and decorated 2 bedrooms, 2 bath island beach house. La Cocolia offers privacy, comfort, luxury, and relaxation. Its location is ideal on a quiet street, north of Pine Ave and just a few flip flop steps away from the ...Bayfront Park and the Rod and Reel Pier. Anna Maria Bayfront Park offers white sand beaches, a shaded area for children to play, amazing views of the Skyway Bridge, and the boats traveling back and forth on Anna Maria Island. La Cocolia greets you with a modern yet cozy living room with easy access to both bedrooms and galley kitchen. Just off the dining room is a newly updated laundry room. The dining room features views of the backyard Oasis. Your family will enjoy get-togethers with all the outdoor space and shaded area under the Jasmin trellis. Leave your car parked (2 spots provided) the town is very walkable, and our island's free trolley is only 2 short blocks away at the City Pier. La Cocolia offers all the goodies to make sure your vacation doesn't skip a beat. As always, we make sure you have the ability to stay connected on our free high-speed wireless internet! Kick back relax turn on the Flat screen and catch that flick you always wanted to see or that must-see sports game. We are so excited you chose to stay with us!brbrDisclaimers: brbr*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.* brbr*Dogs are welcome, A $250+Tax Pet fee is required per pet and is non-refundable. This is a separate fee paid directly to Salty Mermaid Real Estate after booking. Pets that are not disclosed to our office will result in additional cleaning charges to your reservation. We do have pet restrictions such as no more than 25 lbs unless it's approved by the owner and is subject to a possible price increase.brbr*Check in time is 4pm on the day of your arrival, Check out time is 10am 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*brbr*A starter kit of paper towels, toilet paper, trash bags, laundry detergent, coffee & tea, 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.*brbr*Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian*brbr*This home has a 4 night minimum stay requirement* brbr*Security camera on exterior of property*brbr*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.brbr*Parking for up to 2 Vehicles in the Driveway.*brbr*Please note this is not a party or large gathering house. Noise complaints will result in eviction*brbr*Pools are heated from approximately Thanksgiving to Easter only and are set no higher than 80 degrees. Spa temperatures default to the pool temperature when not in use and can reach 100 Degrees under normal weather circumstances. During colder weather, we cannot guarantee that the pool/spa can be maintained to that degree. No refunds, credits, or discounts will be offered if the pool/spa temperature cannot be maintained due to unusually cold weather*
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(9)

$1,370

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Private Vacation Home

Luxury Beach House with Bay Views and Pool

Anna Maria, Florida, United States

Welcome to The Glass House by the Beach, a luxurious modern vacation retreat on Anna Maria Island, designed to immerse you in breathtaking views and ultimate comfort. With its striking floor-to-ceiling atrium windows, this home bathes the spacious main living area in natural light, creating a serene oasis that seamlessly blends indoor and outdoor living.brbrThis elegant getaway features three beautifully appointed bedrooms, each with its own ensuite bathroom, plus a versatile loft with a queen murphy bed, comfortably accommodating up to eight guests. Whether you're relaxing in the rooftop spa or taking in the panoramic views of Tampa Bay, the Anna Maria City Pier, and the iconic Sunshine Skyway Bridge from the rooftop deck, every moment here is crafted for relaxation and awe.brbrStep outside to discover a heated pool with a unique pool window, adding a touch of fun and sophistication to your swim. The ground-level dining and lounge area, complete with a cozy fire table, is the perfect spot for evening gatherings and making memories under the stars.brbrNestled in a central location, The Glass House by the Beach is just a short stroll from Pine Avenue's charming shops, delightful restaurants, and vibrant local attractions. Experience the best of Anna Maria Island in style—book your stay today!brbrDISCLOSURES:brFor security and insurance purposes, there are exterior-only video cameras on the premises.brThe living room fireplace is non-functional.brThe rooftop kitchen is disabled for safety. Note there is a functional outdoor kitchen off the dining room.brbrPETS: This property is NOT pet friendly. brbrPARKING: 4 cars* maximum are able to park at this home and the driveway is shared with two other homes. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. The shared driveway may not be blocked at any time for any reason.brbr*Garage bays are narrow - large/oversize vehicles will not fit. There is one open area to the left of the garage bays to park larger 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.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

Bed

Bath 3

Bath

Sleep 8

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Exceptional(31)

$756.75

/ Nightly
Private Vacation Home

1 block to the beach! Adorable bungalow with Pool and Spa, great for families!

Anna Maria, Florida, United States

Beach Breeze by AMI Locals brVR16-000510 brbrWelcome to Beach Breeze by AMI Locals, a vibrant four bedroom, three bath coastal retreat perfectly situated in the heart of Anna Maria Island. Just a two-minute walk to the beach and two minutes from Pine Avenue’s charming shops and restaurants, this home combines island style with modern comfort. Featuring a private heated pool and in-ground spa, lush tropical landscaping, and pet-friendly accommodations, this inviting getaway is ideal for families and groups looking to relax and reconnect in paradise. brbrHighlights br• 2-minute walk to Anna Maria Island Beach br• 4 Bedrooms / 3 Bathrooms br• 3 Kings, 2 Twin Bunks and Trundle, Queen sleeper sofabr• Pet-friendly with host approval br• 2-minute walk to Pine Avenue shopping and dining br• Private pool and spa br• Ground-level layout for easy access br• Outdoor BBQ and dining area br• 4 parking spaces brbrStep outside to your own tropical oasis, where the heated pool and spa are surrounded by lush greenery and plenty of sunshine. Enjoy poolside lounging during the day and evening dips under the stars. The outdoor patio includes a BBQ grill and dining table, making it perfect for family meals and casual get-togethers after a day on the sand. brbrInside, guests are welcomed by a bright and cheerful open living area featuring comfortable seating and plenty of natural light. The modern kitchen is fully equipped with stainless steel appliances, quartz countertops, and a breakfast island that seats three. The dining area offers seating for six and opens onto the patio, allowing guests to easily transition between indoor and outdoor living. brbrThe primary bedroom features a king bed, ensuite bathroom with dual sinks, and doors that open directly to the pool area. Two additional bedrooms inside the main home offer cozy spaces with beach-inspired decor, including a king bedroom and a bunk room with two twin bunks and a pull-out trundle; perfect for kids or friends. The fourth bedroom, located in a private poolside suite, includes a king bed and ensuite bathroom, making it an ideal retreat for couples or guests seeking added privacy. brbrRoom Details br-Primary Bedroom: King bed, ensuite bath with dual vanities, pool access br-Second Bedroom: King bed, hallway bathroom access br-Third Bedroom: Two twin bunk beds with trundle, shared hallway bath with tub/shower combo br-Fourth Bedroom: King bed, ensuite bath in separate poolside suite br-Livingroom: Queen sleeper sofa brbrLocated in a quiet neighborhood just steps from the Gulf beaches and Pine Avenue, Beach Breeze gives you easy access to local boutiques, ice cream shops, and waterfront dining. Pack your beach gear, enjoy sunny afternoons by the sea, and return home to unwind in your private spa. This home allows dogs with prior approval and an additional fee. brbrEnjoy the best of Anna Maria Island living at Beach Breeze by AMI Locals, where coastal comfort meets tropical luxury. With a private pool and spa, unbeatable location near the beach, and easy island charm, this home is the perfect setting for your next getaway. Book your stay today and start making unforgettable memories at Beach Breeze! brbr- br*Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by AMI Locals, an Anna Maria Island property management company. 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. 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. 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 3

Bath

Sleep 10

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Exceptional(13)

$764.49

/ Nightly
Private Vacation Home

Golf Cart - Beach Escape by SeaBreeze Vacation

Anna Maria, Florida, United States

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS!brAll Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance. The golf cart $25 fee is per golf cart, not per driver. This cost covers the extra insurance required. brbrWelcome to Beach Escape! As you drive up the private driveway, you'll be enveloped by lush native plants, providing the seclusion and privacy you desire. This charming 3-bedroom, 2.5-bathroom home comfortably accommodates up to 8 guests. Just a short distance from the stunning beaches of Anna Maria, along with nearby restaurants and shops, Beach Escape offers the perfect retreat to help you slip into true vacation mode.brbrPlease note: The third bedroom is located on the ground floor and is accessed via the carport. There's also a convenient half-bathroom with private outdoor shower on this level, perfect for when you're enjoying the pool. The other two bedrooms and bathrooms are located on the main floor, down the hallway from the kitchen, living room, and dining area. The living room has a queen sleeper sofa. This property is also equipped with an Xbox Series X, complete with a selection of games in the entertainment console, perfect for anyone looking to enjoy some gaming during their stay.brbrOutside, you'll find yourself in a tropical oasis, with lush plants surrounding the property to ensure total privacy. Relax by the pool, rinse off in the private outdoor shower after a day at the beach, or unwind in the cozy outdoor seating area while watching television—whatever your mood, there's a perfect spot for you to enjoy. There's a screened-in balcony off the primary bedroom that wraps around the home, offering a serene space to relax and enjoy the outdoors in the evening. It's the perfect spot to unwind with a breeze and take in the peaceful surroundings.br​​​​​​​brPrimary Bedroom - King-size bed with ensuite bathroombrBedroom 2 - 2 Full-size beds with hallway bathroombrBedroom 3 - King-size bed with half bathroom (ground floor - private door off carport)brThis property offers parking space for up to 4 carsbrbrCancellation 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. brbrThe property participates in our Professional Linen Program. SeaBreeze Vacation strives to bring only the best quality experience to our guests. To do so, we provide a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you high-quality linens that are in place and ready for your use upon your arrival. Our high-quality linens are laundered in a commercial setting that uses only hypoallergenic, perfume & dye-free soaps assuring all of our guests a comfortable stay.brbrWith 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 TowelsbrbrWe also offer a range of supplemental services including pre-stock grocery shopping and babysitting. Need a pack and play or high chair, etc. These are available for a small additional fee and will be waiting in the home on your arrival.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.
Bed 3

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Bath 2

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Exceptional(120)

$447.21

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Private Vacation Home

Bay Breeze Cottages #3

Anna Maria, Florida, United States

Summary:brBay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.brbrThe Space:brEach Cottage has a fully renovated kitchen, two renovated bathrooms, and living area. Each cottage has a full kitchen with brand new stainless steel appliances including: full sink, faucet, garbage disposal, cook tops, ovens, microwaves, dishwasher, and refrigerator. Exquisite granite counter tops with custom hand carved wood shelves and built in wooden cutting boards are standard. Each renovated bathroom has a new toilet, vanity, custom deluxe shower head, and vanity tiles. The bedrooms includes brand new Beauty Rest Queen beds and high quality Queen pull out sofa, new 32 inch flat screen HD tv's, custom wood floors and wood ceilings throughout.brbrGuest Access:brUpon booking one of our cottages, you will receive a welcome email with the access code for the electronic key lock on the entry door plus a secondary code for the lock box which contains the physical keys as a back up.brbrThe Neighborhood:brThe North end of Anna Maria Island is the most desirable location on the entire island. PARADISE would best describe the surrounding areas of Bay Breeze Cottages. White Sandy Beaches, Two Piers, Aquatic Life such as Dolphins, Manatees, and Pelicans can be seen daily. The North end of Anna Maria has the best restaurants, shops, bars, and other tourist attractions.brbrGetting Around:brIncluded in your stay are street legal golf carts & beach cruiser bicycles which allow you to venture out to the entire island with convenience & ease. Public parking is plentiful throughout the island at all local establishments and attractions.brbrOther Things to Note:brLocation! Location! Location! Bay Breeze Cottages is located on the highly desirable North end of Anna Maria Island. We are just steps from the famous Rod & Reel Pier, Anna Maria City Pier, White Sandy Beaches, Shops, Restaurants, Bars, and other local attractions. Our included amenity package will save guests an average of $1,000 to $1,500 based on one week's stay.brbrInteraction with Guests:brWe are always here to answer any questions you may have during your stay and we are always accessible to our guests.
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Bath 2

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Sleep 7

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Exceptional(175)

$361.01

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Private Vacation Home

2nd House from the Beach with No Roads to Cross

Anna Maria, Florida, United States

The Seaside Sanctuary is the upper level unit of a beachfront duplex. It is the 2nd house from the beach with no roads to cross. The front yard is literally thirty steps from one of the most pristine beaches on the Gulf of Mexico. If you open the windows at night, you can hear the rolling surf and smell the salt air. The house is located on a quiet residential street near the north tip of the island. There is no public parking in this area so you pretty much have the beach to yourself. The front deck features a breathtaking gulf view and is a great place to watch the sunset. The house is clean, comfortable and well appointed. The back yard has a shed with some beach gear, a BBQ grill, picnic table and a sun sail shade. We welcome well behaved dogs and have a fully fenced yard for your pup to play. brbrThe house is light and bright with a multitude of windows showcasing fantastic views. Everything is decorated in a fun and classy seaside style. We believe in a good night's sleep so we invested in high quality memory foam mattresses, crisp, clean linens and plenty of pillows. For the chef in the family, there is a fully stocked kitchen with everything needed to cook and serve most meals. Nothing is more annoying than going to a vacation home that has only one pot and 3 plates! The house has high def smart TVs, bluetooth sound bar for streaming your favorite music and lightning fast wifi throughout. We are neat freaks so you can expect the house to be immaculately clean. In fact, we do a full deep cleaning after each guest. We tried to think of everything so you have all the comforts of home. brbrThe Village of Anna Maria, on the north tip of Anna Maria, is the best part of the island. It is known for beautiful beaches, breathtaking sunsets and a bunch of really nice people. Not surprisingly, our number one recommendation is to set up an umbrella, plop down on a beach chair and watch the waves roll in. If being a beach bum is not your thing, you can stay busy by hunting for seashells, building a sandcastle or trying your hand at surf fishing. Either way, we provide all the equipment and recommendations to make your day at the beach relaxing and enjoyable.
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$618.39

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Cottage

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Anna Maria, Florida, United States

CAST AWAY your stress and worries at this adorable piece of old Florida near BEAN POINT. Charming vintage cottage with LUSH TROPICAL HEATED POOL & SPA area. brbrTwo bedrooms with queen beds, well equipped kitchen, flat screen TVs mounted in each room, full sized washer & dryer, and large front porch with mini fridge all combine as your home base in paradise. Enjoy relaxing moments poolside, beachfront, or exploring the whimsical boutiques in the SUNNY QUAINT VILLAGES on Anna Maria Island. brbrEverything you need to enjoy your days on the island is at the cottage - just add food & drink + swimsuit & flip flops. We provide a STREET LEGAL GOLF CART (4 seats), beach chairs, beach umbrellas, Wheeleez beach wagon, bicycles, four stand up paddle boards, two-seat kayak, private outdoor shower/changing room with hot & cold water, two gas grills, coolers, and more! After a day at the beach or sightseeing, the private pool/spa awaits - chilled or heated - any time of the year. A 55 inch Smart TV is set up for you to watch your favorite team (or whatever!) while chilling in the pool! Ledge Lounger ice bucket/table in pool splash pad for your drinks.brbrDon't bring beach towels, paper towels, or toilet paper! We have all the basics (and more) supplied in the kitchen and bathroom. Pack n Play, high chair, booster seat & stroller are in the hall closet for the small ones. Pet dishes in place for your OTHER small ones! brbrSpices, chocolates, wine, water at each bedside, coffee, and tea complete the arrival necessities. Coffee grinder is also provided.brbrLocated a short leisurely stroll down a charming sandy pathway from Gulf beaches with sparkling crystal clear water and gorgeous white sand, the cottage locale also provides access to delicious island eateries or come home and grill your own freshly caught fish and DINE AROUND THE POOL. Don’t miss the blackened grouper or scallops at the nearby Waterfront, a classic Philly cheesesteak at Slim's, or a cheeseburger in paradise at Duffy's Tavern! brbrSunshine, seashells, sand, surf, and saltwater ☀ - all of the sublime ingredients needed to change your clock to ISLAND TIME!brbrOur cottage offers all that you will need to relax and unwind in the twinkling of a mermaid's eye.
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Bath 1

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Sleep 4

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Exceptional(25)

$1162.07

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Private Vacation Home

Pool*Hot Tub*Tiki Bar*Pickleball Court*Dock

Anna Maria, Florida, United States

Modern southern style and comfort await you at Conch Shell: A resort-like property on Bimini Bay. Meandering walkways take you to a well-placed hammock between two curvy coconut palms, to the salt water pool and spa, and to the tiki bar and game area. Rent a kayak or paddle board to explore the mangroves. Relax and catch some fish from our private dock. You can even play pickleball on the newly installed court! Just put up the net across the driveway for some competitive play... and you haven’t even been inside! But before heading in, pick a fresh lemon from our lemon tree to add to your cocktail. brbrThe exterior of the home truly tells you what to expect on the inside: Charming and warm with a trendy boho beach vibe. The large expanse of the open family room and conversation area invites your entire family. A chef-approved kitchen means you can leave your knives at home. Open the French doors to your guest wing the first floor bedrooms are spacious and super comfy. An ensuite king with private desk for remote work, another king bedroom with door to bath, and a two twin bed haven.brbrUpstairs and private, the romantic and luminous master bedroom suite is just so sweet! Walk-in closet, master bath with shower and tub, and French doors leading you to your private deck and outdoor shower with views of Tampa Bay. The last surprise is the crow's nest, which includes a 360-degree view of Tampa Bay, Bimini Bay, and Anna Maria Island perfect for your sunset viewing pleasure.brbr*Pickleball is at your own risk*brbrPETS: Please note this property is NOT pet friendly. brbrDOCK/BOATS;  New dock will accommodate a boat up to 18ftbrbr*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. *Note that the garage is owner-use only and is not available for parking.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.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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$564.96

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Apartment

Your Pine Ave Getaway | Walk to Beaches, Boutiques & Dining

Anna Maria, Florida, United States

Base House on Pine Ave Anna Maria Island | Walk to Beach, Shops & DiningbrWake up in the heart of Anna Maria Island, where mornings start with a short walk to grab coffee on Pine Avenue and evenings end with sunsets over the Gulf just minutes away. At Base House on Pine Ave, you're not just visiting the island, you're living it.brbrPerfectly positioned in Anna Maria City on Pine Avenue, this private 2-bedroom retreat places you steps from charming boutiques, local restaurants, and some of the most beautiful beaches on Florida's Gulf Coast. Whether you're biking to Bean Point, strolling to dinner, or simply soaking in the laid-back island atmosphere, this location delivers an experience that's hard to match.brbr⚓ Prime Pine Ave location, walk to beach, shops & diningbr⚓ Private entrance + fully separate living spacebr⚓ Bright, updated kitchen and modern interiorbr⚓ Private outdoor deck for relaxingbr⚓ Beach chairs, wagon, and a cooler availablebr⚓ High-speed Wi-Fi, Smart lock for Self-Check-in, Luxurious Linens and Towels Provided.brbrWho This Property Is Perfect For:br⚓Couples looking for a walkable island staybr⚓Small families wanting easy beach accessbr⚓Guests who want to be in the center of Pine Avenuebr⚓Travelers who value location, convenience, and comfortbrbrThe Property & ExperiencebrBase House on Pine Ave is a thoughtfully designed 2-bedroom apartment located within a mixed-use building. The front portion of the building includes a quiet office space, with interior storage units positioned between the office and the rental.brThe apartment itself occupies the entire rear portion of the building and features its own private entrance, providing a fully separate and comfortable space for your stay.brInside, you'll find a bright and modern coastal interior with an open-concept layout. The updated kitchen offers ample counter space and modern appliances, making it easy to prepare meals or enjoy a quick bite before heading out to explore.brThe living area is designed for relaxation, with clean finishes, natural light, and a comfortable setup perfect for unwinding after a day at the beach.brbrStep outside to your private back deck, a great space for:br⚓Morning coffee before heading to the beachbr⚓Casual outdoor diningbr⚓Relaxing in a quiet, private settingbrbrBedroom 1: Queen Bed, Ensuite Bathroom, Smart TV brBedroom 2: Queen Bed, Smart TV brbrPrime Location – Pine Avenue, Anna MariabrThis is where Base House truly stands out.brLocated directly on Pine Avenue, you are within walking distance of everything that makes Anna Maria Island special:br⚓Walk to restaurants, coffee shops, and local boutiquesbr⚓Short walk or bike ride to the Gulf beachesbr⚓Minutes to Bean Point and Bayfront Parkbr⚓Close to bike rentals and island activitiesbrThis location allows you to park your car and fully enjoy the island lifestyle.brbrParking is available for 1 vehicle and 1 golf cartbrbrA full-size washer and dryer are tucked into the utility closet off the kitchen. four beach chairs are provided so you can travel light. Every detail in this house was chosen deliberately, from the rattan textures to the brass fixtures to the linen upholstery. It photographs beautifully. But it lives even better.brbr*No Pets Allowed br *Located within a mixed-use buildingbrbrDamage Waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee (“Management”), plus tax if applicable (the “Damage Waiver”). brThe Damage Waiver covers you for up to $1,500 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.
Bed 2

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Bath 2

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Sleep 4

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