Home Vacation Home Rentals By Owner In Anna Maria, FL

Showing 520 Of 689 Vacation Rentals
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Exceptional(20)

$1299.48

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Private Vacation Home

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

Anna Maria, Florida, United States

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

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Bath 6

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Sleep 14

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Exceptional(26)

$471.19

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Private Vacation Home

Wave n Sea - Close to the Beach with Pool - Anna Maria Island - By Island Real E

Anna Maria, Florida, United States

“Wave N’Sea” is a premiere vacation home located in the city of Anna Maria on Anna Maria Island. Here you’ll find a perfect mixture of casual calm, and comfort. A 3 bed two bath home, “Wave N’Sea” has both the space and the amenities to accommodate up to 8 guests. With its spacious layout, a king, a queen, and two queen beds set up as bunks, sleeping 8 is easy for this Anna Maria rental. The kitchen is well equipped with the appliances you’ll need to prepare and enjoy your meals, and the living area is great for relaxing in after a great day at the nearby beaches. Kick your feet up and watch some of your favorite shows on the TV or surf the web using the free wireless internet. Other amenities for this home included to grand oversized yard, with tropical landscaping, and a heated pool. There’s even a propane grill!brbrIn addition to island style comfort “Wave N’Sea” boasts a fantastic location, placing you near fantastic sites and views. From the home’s pergola style roof porch, you can catch views of Sunshine Skyway, Tampa Bay, and the Gulf of Mexico. As well as the crystal sands of Bean Pointe beach. The famous Bean Pointe Beach is within walking distance of this paradise home.brbrTake a trip to Pine Avenue, where you’ll find great island shopping, food, and even art galleries. Once you’ve finished there hop aboard the free island trolley, which runs all seven miles of the island. Taking it south you’ll find the city of Bradenton Beach, where you can enjoy island nightlife, as well as more great local dining. brbrThis home offers parking for two vehicles with the added convenience of a washer and dryer to make your stay a breeze.brbrVR22-000046brbrMax Vehicles Allowed: 2 Max Day Guests Allowed: 2brbrIMPORTANT 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.brbr• Dog Friendly - fee of $250 plus tax per dog.brbrAll our properties provide luxury linens for you to enjoy during your stay.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 3

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Bath 2

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Sleep 6

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$693.45

/ Nightly
Private Vacation Home

Beach Baby/ 4 Min Walk to The Bean Point Beach/Private Heated Pool/HotTub

Anna Maria, Florida, United States

Slip into island time at Beach Baby, a bright and breezy two-bedroom retreat just a short stroll (only six houses!) from the sparkling Gulf waters. Tucked along a quiet street on the north end of Anna Maria Island, this coastal hideaway is all about easy days, salty air, and unforgettable sunsets.brbrWake up and wander down to Bean Point Beach in just 4 minutes, or cruise over to Pine Avenue for local shops, beachy boutiques, and fresh island dining.brbr Highlights You’ll Lovebrbr4-minute walk to the beachbrPrivate heated pool + hot tubbrOutdoor game room with TV & foosball brCovered outdoor lounge perfect for sunset hangsbrTwo hammocks for ultimate relaxationbrBBQ grill for poolside cookoutsbrSpacious parking (up to 5 cars)brbr Outdoor Living, Island Stylebrbr- Your private backyard feels like your own mini island retreatbr- Lounge by the pool, soak in the hot tub, or relax in a hammock with a drink in handbr- Fire up the grill and enjoy easy dinners by the pool in the coastal breezebr- Covered deck with comfy seating—perfect for morning coffee or evening cocktails after the beachbrbr Bright, Breezy Living Spacesbrbr- Open-concept living area designed for relaxing and spending time togetherbr- Fully equipped kitchen with stainless steel appliances and beautiful granite countertopsbr- Perfect for everything from morning pancakes to fresh seafood dinnersbr- Cozy living room ideal for movie nightsbr- Large glass deck, bringing in fresh island breezesbrbr Sweet Dreams After Sunsetsbrbr- Primary Suite: King bed, TV, ensuite bathbr- Second Bedroom: Twin-over-twin bunk bedbr- Living Room: Queen sleeper sofa brbr Explore Like a LocalbrbrFrom this peaceful north-end spot, you’re within walking distance to Bean Point and nearby parks. Hop on the free island trolley and explore everything Anna Maria has to offer—from North End to South end Coquina Beach —with plenty of stops for waterfront dining and shopping along the way.brbr Good to KnowbrbrNO PETS allowedbrMaximum 4 vehiclesbrPrimary renter must be 25+brLocated in a quiet residential area (please be respectful of neighbors)brbrWhether you're here for beach days, poolside lounging, or sunset strolls, Beach Baby is your perfect slice of island life.brbr Book your stay and start soaking up the Anna Maria Island vibe!
Bed 2

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Bath 2

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Sleep 6

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Exceptional(20)

$490.89

/ Nightly
Private Vacation Home

Stunning 3Bed/3 Bath, Heated Pool, FREE WiFi, Close to Beach, On Canal to Dock your Boat

Anna Maria, Florida, United States

**ASK ABOUT LAST MINUTE DEALS!brbrWelcome to paradise at Pelican Point! This stunning 3 bedroom/3 bath home has everything you need to enjoy a wonderful vacation on beautiful Anna Maria Island.brbrLocated right on a canal, you can enjoy the amazing views of the water and pool from your screened-in porch off the living room area. The inviting pool has plenty of space to relax and enjoy the spectacular Florida weather including plenty of seating, a poolside beach with sand, a TV, a fire pit ...and a shaded area to relax and enjoy. Right on the canal is a dock where you can fish or launch your kayaks. It is located close to open waters and the beaches of Anna Maria are only a few blocks away. Bringing a Boat There are 2 humpback bridges to cross under with 6' to 7' height restrictions at low tide. Launch at Holmes Beach Boat ramp at 6398 Marina Way, Holmes Beach, FL 34217. Contact the office for trailer parking info. brbrInside, this home has so much to offer! In the main area, the living room has plenty of comfortable seating with beautiful furnishings in coastal decor as well as a flat-screen TV. The dining area seats 8 and is conveniently located right off the spacious kitchen with stainless steel appliances. Also on the main level is a full-size bathroom with a tub/shower combination. brbrUpstairs, the first bedroom has a walk-out balcony, king bed, TV and en suite bath. This updated bath has a tiled walk-in shower. The second bedroom has a queen bed and the third has a full/twin trundle bed and both have TVs. The third full bath is located in the hall with a tub/shower combo.brbrIf you ever decide to venture from your perfect vacation home, Anna Maria Island has lots of great shopping, dining and activities to tempt you - not to mention the most beautiful beaches on the Gulf! There is even a free trolley that will take you anywhere on the Island.brbrCome enjoy a memorable and relaxing vacation at Pelican Point.brbrFor your information the owner has chosen to have outdoor security cameras that overlook the pool and the canal for safety purposes. brbrA NOTE ABOUT POOL HEAT: If you book online, your reservation will automatically populate with a pool heat charge for one week. If your reservation is for a longer period, someone on our staff will adjust the pool heat rate to reflect the longer stay. We recommend pool heat at this property, regardless of the time of year, as pools near shady trees stay cooler, even in the summer.brbrWhile we know you love your furry friends, this property is not pet friendly. Please make other arrangements for your pets.brbrOur Cancellation Policy: In order to protect our owners from loss of income, ALL MONIES PAID TOWARDS YOUR RESERVATION MAY BE NON-REFUNDABLE AFTER A CERTAIN DATE! FULL AND PARTIAL REFUNDS MAY BE GIVEN UNDER CERTAIN CONDITIONS. Ask our office for details, or check your rental agreement.
Bed 3

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Bath 3

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Sleep 6

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$622.65

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Private Vacation Home

The Fish House: Canal Front, Dock, Pool Spa by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

The Fish House by Anna Maria Life Vacation Rentalsbr231 Oak Ave, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! 1.5 Blocks to the Beach! Canal Front!br3 Bedrooms / 3 Bathroomsbr1 King, 1 Queen, 2 Sets of Twin over Twin BunkbedsbrPrivate Heated Pool & SpabrPool LoungersbrPoolside Lounge SeatingbrBoat Dock (Boat Lift is Not Available for Guest Use)brOutside Patio DiningbrGas GrillbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrDriveway Parking for 3 CarsbrbrDetails:brWelcome to The Fish House, your perfect island retreat on Anna Maria Island, ideally located just 1.5 blocks from the beach and directly on a peaceful canal. This beautifully appointed 3-bedroom, 3-bathroom home offers the best of both worlds—easy access to the sugar-sand shoreline and your own private boat dock right in the backyard.brbrStep inside to a bright, open-concept living space designed for comfort and connection. The spacious living room features a large sectional sofa and a stunning stone fireplace, creating a cozy focal point for relaxing evenings. Natural light pours in through multiple windows and glass doors, offering views of the lush backyard and pool area. The living space flows seamlessly into the fully equipped kitchen, complete with a large island and plenty of room for gathering. Exposed ceiling beams and recessed lighting add to the home's airy coastal feel, making it ideal for entertaining family and friends.brbrOutside, your private heated pool and spa invite you to unwind after a day at the beach. Lounge in the sun on poolside loungers, relax in the lounge seating area, or enjoy meals together at the outdoor patio dining table. Surrounded by tropical landscaping, the backyard feels like a secluded oasis. The canal-front setting includes a private boat dock, perfect for bringing your boat or launching a paddleboard or kayak. A gas grill makes outdoor cooking easy, whether you're preparing fresh local seafood or a casual family dinner.brbrThe home comfortably accommodates guests across three thoughtfully designed bedrooms. The primary suite features a king bed, ensuite bathroom, and TV for added privacy and relaxation. The second bedroom offers a queen bed and an ensuite bathroom. The third bedroom is perfect for kids or larger groups, featuring two sets of twin-over-twin bunk beds. Professional linen service is provided, and a washer and dryer add extra convenience during your stay.brbrAdditional amenities include complimentary WIFI, beach towels, beach chairs, and a beach wagon to make your short stroll to the sand effortless. With driveway parking for three cars, there's plenty of space for your group to come and go with ease.brbrWhether you're spending your days boating from the dock, lounging by the pool, or walking to the beach for sunset, this canal-front Anna Maria Island getaway offers everything you need for a relaxing and memorable coastal vacation.brbrThe Fish House is easy walking distance to Gulf Ave, restaurants, and the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrBedroom 1 - King Bed, Ensuite Bathroom, TVbrBedroom 2 - Queen Bed, Ensuite BathroombrBedroom 3 - Two Sets of Twin over Twin Bunk BedsbrbrPlease note:brThis home is not pet friendly.brAmenities are subject to change.brDriveway parking is available for 3 cars. Parking for additional cars is not available. br​​​​​​​The boat life is not available for guest use.brbrDISCLAIMER: brDepth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The minimum requirement for this home is no less than seven nights. The maximum occupancy is eight.brbrVR19-000056 brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.
Bed 3

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Bath 3

Bath

Sleep 8

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Exceptional(1)

$1039.48

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Private Vacation Home

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

Anna Maria, Florida, United States

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

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Bath 5

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Sleep 8

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$693.21

/ Nightly
Private Vacation Home

AMI Beach Hideaway by Beach Boutique Rentals

Anna Maria, Florida, United States

Welcome to your new favorite Anna Maria Island retreat. With its unbeatable location and fresh coastal updates, AMI Beach Hideaway offers the perfect blend of island charm and vacation-ready comfort.brbr*Features Include*brbr* Prime location West of Gulf Drivebr* Private tropical backyardbr* L-shape heated pool with sun ledgebr* Elevated home with open-concept layoutbr* Fully equipped kitchen with modern finishesbr* 2 bedrooms, 2 full bathroomsbr* Sleeper sofa br* Washer and dryerbr* Gas grillbr* Beach chairs, umbrella, and cartbr* Walkable to restaurants and Pine Avenue shopsbrbrAMI Beach Hideaway is ideally situated on quiet Beach Avenue in Anna Maria - just steps to the pristine Gulf shore with no busy streets to cross. You'll also love being close to island favorites like the Sandbar Restaurant, Ginny & Jane E’s and Pine Avenue shops.brbrInside, this elevated home has been completely remodeled with fresh, coastal style and comfortable furnishings. The open-concept living area includes a cozy sleeper sofa, stylish decor, and a flat-screen TV - perfect for unwinding after a day in the sun. The updated kitchen features stainless appliances, stone countertops, and everything you need for meals at home. Gather in the dining area for a relaxed breakfast or dinner with the family.brbrThe home offers two spacious bedrooms: a king master with ensuite bath, and a second bedroom with two full-sized beds - perfect for families or friends traveling together. AMI Beach Hideaway offers two full bathrooms, one with a walk-in shower and the second with a shower/tub combo. Both bathrooms have been fully remodeled with fresh, modern finishes.brbrThe true highlight of AMI Beach Hideaway is the private backyard oasis. The large heated pool features a ledge for sunbathers or little ones, and is surrounded by lush tropical landscaping and chaise lounges for soaking up the Florida sunshine. The covered outdoor dining table seats six, and the shaded lounge space with cushioned seating and TV makes it easy to relax, dine, and entertain outdoors all day long. Whether you're enjoying a quiet morning coffee or gathering for an evening barbecue, this outdoor retreat is made for island living.brbrWith its prime location, stylish updates, and easy beach access, AMI Beach Hideaway is everything you need for an unforgettable island vacation. Book your stay today and start making memories on Anna Maria Island!brbrADDITIONAL INFORMATION brbrWe generally require a minimum stay during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you!brbrHousekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay.brbrOur cleaning fee includes a professional linen service. When you stay with us you can rest assured that you will have high quality linens such as those at a fine hotel. We also provide plenty of luxury bath and beach towels. brbrAnna Maria Island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors. brbrThis home provides off-street parking for up to 3 vehicles in the driveway only. No parking in the garage.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.
Bed 2

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Bath 2

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Sleep 6

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Exceptional(24)

$3238.52

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Private Vacation Home

Beaches and Dreams: Ultimate Luxury Beachfront Paradise

Anna Maria, Florida, United States

Welcome to the Ultimate Beach Front Paradise on Anna Maria Island at Beaches & Dreams, where stunning panoramic bay views and top-tier amenities await you. This 4-bedroom, 5-bathroom home offers endless entertainment for you and your guests.brbrBeaches & Dreams features an outdoor bar with a fridge and ice machine, a swinging outdoor bed, a large heated pool with waterfalls, a spa, see-through kayaks, paddleboards, a game room, a gym, a putting green, an elevator, an outdoor grill, and much more!brbrLocated directly on the beach in the desirable north end of Anna Maria Island, it's steps away from the Rod & Reel Pier and Bayfront Park. Enjoy dolphin and manatee sightings right from the home. The popular Bean Point and Pine Street are just a short walk away.brbrNew as of late 2020, the home spans over 3,000 square feet and has been professionally designed with a coastal elegant theme, featuring shiplap and local art. Each bedroom includes an ensuite bathroom and captures the spirit of Anna Maria Island. Two king bedrooms are beachfront with balcony access, and the fourth bedroom includes a ship-themed bunk bed system and a multi-cade system with over 60 games.brbrThe Shark's Den game room, top-of-the-line kitchen, spacious family room, and incredible pool and patio area with a commercial-grade bar, putting green, and private beach access complete this luxurious retreat. The 2-car garage is stocked with bikes, beach gear, and various toys and games for your perfect vacation.brbrGOLF CART: For an additional fee of $550, the owner is offering the enjoyment and convenience of a 6-seat electric golf cart to explore the island. Instructions for payment and necessary paperwork will be available in the unit. brbrSORRY, DUE TO FAMILY ALLERGIES, WE CANNOT ALLOW ANIMALS OF ANY KIND IN OUR HOME.brTHERE IS ABSOLUTELY NO SMOKING OR VAPING OF ANY KIND IN OR ON OUR PREMISES AND NO PARTIES/EVENTS. BREAKING OF ANY HOUSE RULES WILL RESULT IN IMMEDIATE EVICTION AND LOSS OF ALL PAYMENTS AND DEPOSITS. MINIMUM AGE OF PRIMARY RENTER: 25 YEARS OLD.brbrBEACH DISCLAIMERbrPlease be aware that the beach and sand may differ from the photos due to natural processes like tides, weather, and erosion. The beach environment is dynamic and constantly changing, and we appreciate your understanding. Enjoy the beauty of our beachfront properties!brbrNOTE: For security purposes there are exterior only video cameras on premises.brbrAmenities Include:br- Beach Frontbr- View Tampa Baybr- Bed Size 1st Master King w/ ensuitebr- Bed Size 2nd Rm King w/ ensuitebr- Bed Size 3rd Rm King w/ ensuitebr- Bed Size 4th Rm 2 Twin-over-Queen bunk beds w/ ensuitebr- BBQ Grill Propanebr- 3 Balconiesbr- 10 4K TVsbrbr***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.
Bed 4

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Bath 4

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Sleep 12

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$1429.71

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Private Vacation Home

Summer Paradise-Rooftop deck and private heated pool/spa

Anna Maria, Florida, United States

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

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Bath 6

Bath

Sleep 12

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Exceptional(9)

$793.04

/ Nightly
Private Vacation Home

At Last: Ground-level, pool, hot tub, canalfront, dock

Anna Maria, Florida, United States

***Photos Updated May 2025***brCome slip away to this luxurious island retreat where all of your cares will drift away! This beautiful, professionally decorated, and newly remodeled home has every modern luxury you can think of. brbrThe two spacious king bedrooms are sure to provide you with a great night's sleep! The also spacious third bedroom offers a 2 queen sleeper sofas, along with a couch, providing a versatile space to watch movies, practice your putting, take part in a shuffleboard match, and get a good night's sleep! brbrSpend your days soaking up the Anna Maria sun in your private, canal-front backyard. The beautiful blue-bottomed pool is the perfect place to cool off! Enjoy cocktails at the swim-up table or take a dip in the hot tub! At Last's sunroom offers a picturesque, 180-degree view of the pool and canal! Looking for adventure At Last provides two bikes and two kayaks for its guests to enjoy during their stay! This home is perfectly located with beautiful gulf-front beaches just a 3-minute walk from your front door and bustling Pine Avenue a quick bike ride or golf cart trip away!brbrTESLA wall charger is available free of charge to At Last Guests. Non-Tesla vehicles must furnish their own NACS to CCS adapter. If possible, please charge between midnight and 7am.brbrPETS: Dogs considered, approval required. Must be well trained. A $150 non-refundable pet fee applies per pet.brbrDOCK/BOATS: Approximately 28 ft of open seawall is available to tie up a boat. Two widely spaced cleats available. **Please note that the boat lift and any motorized watercraft are not available for guest use**brbr--DISCLAIMER: Depth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.brbr*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. brTESLA wall charger is available free of charge to At Last Guests. Non-Tesla vehicles must furnish their own NACS to CCS adapter. If possible, please charge between midnight and 7am.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.
Bed 3

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Bath 3

Bath

Sleep 8

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Exceptional(15)

$839.56

/ Nightly
Private Vacation Home

Anna Maria Home with Pool and Rooftop Deck! 5-min Walk to Beach - Coconut Breeze

Anna Maria, Florida, United States

Coconut Breeze Estate by Anna Maria Island Accommodations brbrEscape to Coconut Breeze Estate, your ultimate four-bedroom, four-bathroom retreat on Anna Maria Island! Nestled on the highly desirable northern end, this stunning home is just a five-minute walk from the pristine beaches at Bean Point. Located near Pine Avenue’s charming shops and locally owned restaurants, this coastal estate offers the perfect setting for family gatherings, friends’ adventures, and memorable island experiences!brbrHighlights br• 5-minute walk to Bean Point Beachbr• 4 Bedroom / 4 Bathbr• 3 Kings, 2 Twin-over-twin Bunk Beds, 1 Queen Sleeper Sofabr• Saltwater poolbr• Rooftop deck br• Pool tablebr• Outdoor kitchen and dining br• Beach gear and cart providedbr• Close to Pine Avenue’s shops and diningbr• 4 Parking SpacesbrbrRelax outdoors in your private backyard paradise. Splash in the heated saltwater pool or head to the rooftop deck for spectacular sunset views over Anna Maria Bay. The full summer kitchen, outdoor dining table, lounge chairs, outdoor shower, and lush landscaping create the ideal setting for family barbecues, poolside cocktails, or simply soak up your tropical surroundings.brbrInside, the home boasts spacious, elegant interiors designed for comfort and gatherings. The large living room seamlessly connects to a modern kitchen featuring high-end appliances including a refrigerator, stove, oven, dishwasher, and microwave. The formal dining area comfortably seats over 10 guests, perfect for family dinners or special occasions. Large windows and sliding doors flood the space with natural light and open directly to the outdoor oasis.brbrRetreat into luxury with a primary bedroom offering a plush king-sized bed, a private ensuite bathroom, and serene water views. Each of the three additional bedrooms features ensuite bathrooms for premium convenience, two with king beds and a fourth with two twin-over-twin bunks, ideal for children or additional guests. A queen sleeper sofa adds extra sleeping space for larger groups, ensuring everyone enjoys restful nights in style.brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom br• Second Bedroom: King bed, ensuite bathroom br• Third Bedroom: King bed, ensuite bathroom br• Fourth Bedroom: 2 Twin-over-twin bunks, ensuite bathroom br• Bonus: Queen Sleeper SofabrbrBook Coconut Breeze Estate today and enjoy a luxurious escape on Anna Maria Island. Whether exploring nearby beaches, dining at Pine Avenue, or relaxing in your private outdoor oasis, this home provides everything you need for a memorable coastal getaway!brbrbr-brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. brbrThis property has an active Ring doorbell at the main entrance. brbrThis property does not allow pets of any kind.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.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 4

Bath

Sleep 12

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Exceptional(30)

$753.95

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Private Vacation Home

Luxury waterfront home with a heated pool and spa!

Anna Maria, Florida, United States

A beautifully furnished 4-bedroom, 3.5-bathroom home, this canal front property is in the heart of the Historic Anna Maria City.brbrIt sits right on an expansive waterway leading into Tampa Bay and has been lavishly decorated with all the creature comforts and more. Stunning water views from living room, dining room, kitchen and master bedroom. Full kitchen is equipped with all your needed items. Granite countertops, stainless steel appliances. Outdoor seating on decks off master bedroom upstairs and the living room which includes a 50 in flat screen TV. Lounge by the heated pool by the water or sit and unwind in the hot tub! Covered outdoor eating area on the ground level by the pool and gas grill.brbrWe offer four beach chairs and one umbrella for your visit!brbrBedroom Layout: #1 en suite main level King bed, 2# ensuite upper level King bed, with full sleeper sofa, #3 king bed, #4 2 twin beds. Sleeps 10brbr- Pool Policy: *Please note this property has a private heated pool - no charges apply.brbrPet Policy: **This property is NOT pet friendly. Please note: if we find an unauthorized pet in the home, we will ask for it to be removed immediately and charged an additional Non-Refundable fee of $500 and in some cases can be up to $1,000.brbrThe LoveRentals portfolio is comprised of curated, professionally managed vacation rental homes around the world. We only select professional property managers that meet our high standards. Book with peace of mind knowing that you will have the very best vacation.brbrLoveRentals - Find Your Bliss.
Bed 4

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Bath 3

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Sleep 10

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$1881.49

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Private Vacation Home

Happy Ours – NEW LISTING, Direct Beachfront Home On Magnolia

Anna Maria, Florida, United States

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

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Bath 3

Bath

Sleep 12

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Exceptional(60)

$364.18

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Private Vacation Home

Charming Beach home sits amongst huge Banyan Trees, walk to beach’s & Pine Ave.

Anna Maria, Florida, United States

Voted a Tropical paradise perched among native banyon trees.brWake to the sound of sea birds in this tropical paradise. Private fenced yard, fire pit, hammock and just steps to famous Pine ave’s shops and eateries. Walk 7-9 minutes to the beautiful calm Bayside beach & Anna Maria pier, then 4 minute beach walk south takes you to Rod and Reel fishing pier & restaurant pub where water life is seen daily, fishing rods and bait available . Walk further (4 minutes) to “ Bean Point Beach voted as one of the top ten most beautiful beaches in the world.brbrbrJust steps to historic Pine Ave. with quaint shops, restaurants, bike, kayak, and small motor vehicle rentals that is blocks to Annamaria gulf beach public access’s at the end of every street. Famous sandbar restaurant and bar on the beach. Also Bortells local sports bar for late night outings.brBeach gear is provided, however sometimes guests leave items out or at beach....br Small pets have a fenced yard to explore. Sprinklers do come on during the week early in the morning for a couple hours.br There is a laundry room in my Separate mother in law quarters downstairs for guests use staying more than 3 days. brbr** I live in Georgia but there are times that I stay in my separate quarters downstairs, It is a separate entrance and air system. If this is an issue, please let me know at the time of your request as I am always able to visit my family during your stay.brThere is a small WATER ACCESS dock steps down our road that leads out to the Anna Maria pier … launch your rental kayak, paddle board or park a jet ski or small boat overnight with prearranged permission . Outdoor fire bundle is available for the yard fire pit $ 10 if requested in advance. An extra bedroom may be available for elderly quests or pets for a additional fee and only upon availability and approval. Gas bbq. Regular coffee pot , blender . Smart tv and in master bedroom and family room .
Bed 2

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Bath 2

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Sleep 8

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Exceptional(6)

$471.4

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Private Vacation Home

Wade N' Sea: On Canal, North End, 1 Block to Pine by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Wade 'N Sea by Anna Maria Life Vacation Rentalsbr104 Gull Dr, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brRecently Renovated!brLocation! On a Canal, One Block to Pine!br3 Bedrooms / 2 Bathroomsbr2 Kings, 2 TwinsbrPrivate Heated PoolbrOutdoor Shower (Warm Water) with Privacy WallsbrPool Loungers & Adirondack Chairs on Pool DeckbrOutdoor Poolside Patio Dining for SixbrGas GrillbrPrivate Dock for Fishing and Launching Paddleboards, Kayaks, JetskisbrProfessional Linen Service, Complimentary WIFI, Washer & DryerbrBeach Towels, Beach Chairs, Beach WagonbrDriveway Parking for 3 CarsbrbrDetails:brNestled on the serene north end of Anna Maria Island, this charming 3-bedroom vacation home offers the perfect getaway for families or friends. Just a short stroll from the beach, Wade N Sea features an inviting private pool surrounded by lush landscaping, ensuring a peaceful and relaxing retreat.brbrInside, the home is beautifully furnished with coastal-inspired decor, offering a spacious open-plan living and dining area, a fully equipped kitchen, and large windows that let in natural light and offer views of the pool. With its prime location, you're just minutes from local shops, restaurants, and the stunning Gulf beaches, making this vacation home an ideal spot for a memorable Anna Maria Island escape.brbrEach bedroom is thoughtfully appointed for comfort with the master king bedroom featuring an en-suite bathroom. The guest rooms include a king-sized bed and a set of twin beds. Each bedroom includes a TV, crisp linens and plush towels in the bathrooms from our professional linen service.brbrYour guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrWhip up a meal on the grill and serve poolside while you enjoy the tropical Florida weather. With patio dining seating for six, enjoy the sunny days and island breezes. Ahhhh...vacation.brbrAfter a day at the beach, relax in the heated pool or poolside in a deck lounger. Beach towels and beach chairs are provided for you to take to the beach. Sunsets and shelling await!brbrThis stunning canal-front home offers the perfect setting for water enthusiasts and includes a private dock, allowing you to easily launch your paddleboards or jet skis for a day of adventure on the water. You may even be lucky enough to catch dolphins playing in the water!brbrWade 'N Sea 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. Hope on and off at your leisure and explore shopping, dining and the beaches.brbrBedroom 1: King, Ensuite Bathroom, TVbrBedroom 2: King, TVbrBedroom 3: Two Twin BedsbrbrPlease note:brThis home does not allow pets.brSmoking is not allowed in this home or on the premises.brAmenities are subject to changebrDriveway parking is available for a maximum of 3 cars. Parking for additional vehicles is not availablebrbr​​​​​​​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. Additionally, the entrance to the canal has a bridge that may have limited access during high tide. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The maximum occupancy is 6.brbrVR19-000002 brbrIMPORTANT INFORMATION:brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details.brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance.brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking.brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.
Bed 3

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Bath 2

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Sleep 6

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Exceptional(21)

$665.43

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Private Vacation Home

Luxury 4 bedroom, 3 bath private home with a heated pool in the heart of Anna Maria.

Anna Maria, Florida, United States

This luxury Key West style home has 4-bedrooms and 3-bathrooms and is situated in Anna Maria.brbrThe kitchen has lovely granite countertops and newer stainless-steel appliances. There is a full-sized refrigerator, dishwasher, stove, microwave and coffee maker. The small breakfast bar seats three and the formal dining area has room to seat six comfortably. With comfortable couches and plenty of seating options, the flat-screen TV can provide hours of entertainment. The extra-large master suite has a double shower, hot tub, toilet and sink and is fitted with a king-sized bed. The second bedroom has a queen-sized bed while the last 2 bedrooms has two twin beds. There is a two-car garage for ample parking and a laundry room comes complete with a full-sized washer and dryer.brbrWe offer four beach chairs and one umbrella for your visit!brbrBedroom Layout: #1 main floor queen size, #2 upper level ensuite king bed, #3 two twin beds, #4 two twin beds. Sleeps 8brbrThe pool has an expansive patio and sundeck area offering plenty of seating in the sun or the shade. There is an indoor sitting area just off the pool too.brbrThe home is walking distance to the Bayfront Park playground, Rod & Reel Pier, Anna Maria City Pier, trolley stop, and the Gulf beaches. Whether guests are looking for bike rides, fishing, boating, or kayaking, Anna Maria has it all.brbr**Please note this property offers an outdoor private pool.brbrThe LoveRentals portfolio is comprised of curated, professionally managed vacation rental homes around the world. We only select professional property managers that meet our high standards. Book with peace of mind knowing that you will have the very best vacation.brbrLoveRentals - Find Your Bliss.
Bed 4

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Bath 3

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Exceptional(43)

$551.14

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Private Vacation Home

Luxury bungalow with pool and spa! Canal front with dock!

Anna Maria, Florida, United States

Bamboo Bungalow by AMI Locals brVR19-000043 brbrWelcome to Bamboo Bungalow by AMI Locals, a beautiful three-bedroom, two-bathroom canal-front home tucked away in the peaceful north end of Anna Maria Island. This stylish retreat is perfectly situated just two blocks from Pine Avenue’s shops and restaurants and less than a 15-minute walk to the Gulf beaches, offering the ideal blend of relaxation and convenience. Featuring a private pool and hot tub, a lush bamboo garden, and a canal dock perfect for fishing or kayaking, this modern island escape is designed for effortless coastal living. brbrHighlights br• Canal-front with private dock br• Private pool and hot tub br• 15-minute walk to Gulf beaches br• 4-minute walk to Pine Avenue dining and shops br• 3 Bedrooms / 2 Bathrooms br• 2 Kings, 2 Doubles br• Outdoor dining area and lounge seating br• Updated kitchen and bathrooms br• 3 Parking spots brbrStep into your private tropical sanctuary, where the modern pool and hot tub invite you to unwind beneath swaying palms and bamboo. Enjoy sunny afternoons on the cushioned loungers or outdoora under the island breeze in the outdoor dining area. The private dock offers the perfect place to cast a line, sip your morning coffee, or launch a kayak or paddleboard for a tranquil canal tour. brbrInside, the open concept living area welcomes you with natural light and contemporary coastal decor. Relax on the large sofa for movie nights or enjoy the second sitting area overlooking the pool. The spacious, updated kitchen features modern appliances, ample counter space, and all the culinary essentials for easy vacation meals. Gather at the indoor dining table for a family-style dinner or step outside to savor meals in the fresh island air. brbrEach bedroom is designed with beach-inspired tones and modern comfort. The primary bedroom features a king bed, a cozy sitting area, and a private ensuite bathroom with a walk-in shower. The second bedroom, also with a king bed, provides easy access to the shared hallway bathroom with a shower/tub combo. The third bedroom includes two double beds and cheerful coral accents, creating the perfect space for families or friends. brbrRoom Details br-Primary Bedroom: King bed, sitting area, ensuite bathroom with walk-in shower br-Second Bedroom: King bed, shared hall bathroom with shower/tub combo br-Third Bedroom: Two double beds, shared hall bathroom with shower/tub combo brbrLocated just steps from Pine Avenue’s boutiques, ice cream shops, and local dining, Bamboo Bungalow puts you close to everything that makes Anna Maria Island special. Walk or bike to the Gulf beaches or explore Bayfront Park for classic waterfront views. brbrDiscover your slice of island paradise at Bamboo Bungalow by AMI Locals, where modern comfort meets laid-back coastal style. From lazy pool days to peaceful canal views, this home offers everything you need for a relaxing Anna Maria Island vacation. Book your getaway today and experience the charm of the island while living at Bamboo Bungalow! brbr- br*Please note: this home is strictly an animal-free zone due to severe allergies. Due to this homeowner allergy, we are unable to welcome any animals including service and/or emotional support animals. 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. 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 3

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Bath 2

Bath

Sleep 8

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Exceptional(20)

$589.22

/ Nightly
Private Vacation Home

Bella Vita: Canal front, pool, perfect location!

Anna Maria, Florida, United States

SECURITY CAMERAS IN USEbrbrLIFE IS BEAUTIFUL AND ALWAYS BETTER AT THE BEACH! BELLA VITA. YOUR NEW CORNER OF PARADISE!brbrTHIS GORGEOUS, TRULY UNIQUE 3 BEDROOM, 3 BATHROOM HOME IS FILLED WITH ISLAND CHARM AND CHARACTER. FROM LUSH, TROPICAL LANDSCAPING, TO A SPACIOUS KITCHEN AND OPEN TWO STORY LIVING ROOM, WITH LARGE WINDOWS, SHOWCASING THE PANORAMIC WATER VIEW OF THE CANAL. YOU CAN LOUNGE WITH A BOOK BY THE PRIVATE POOL.brbrTUCKED AWAY ON A PRIVATE STREET, ON THE LAST CANAL ON THE MUCH DESIRED NORTH END OF ANNA MARIA ISLAND ...IT'S LITERALLY STEPS AWAY FROM EVERYTHING! A SHORT STROLL TO THE SUGARY WHITE BEACHES OF TAMPA BAY AND THE GULF OF MEXICO, WHERE YOU CAN SCORE THE PERFECT TAN DURING THE DAY AND WATCH THE MOST AMAZING SUNRISE AND SUNSETS IN THE WORLD, WITHOUT EVER NEEDING A PARKING SPACE. brbrYOU'LL BE WALKING DISTANCE TO THE FAMOUS ROD AND REEL PIER, THE HISTORIC CITY PIER, SHOPPING ON DOWNTOWN PINE AVENUE, DINING AND MORE! WHETHER YOU'RE LOOKING TO PLAY A GAME OF POOL AT HOME OR HOP ON THE FREE TROLLEY AND HEAD OVER TO BRIDGE STREET FOR A NIGHT OUT, THE POSSIBILITIES ARE ENDLESS AND THE MEMORIES WILL LAST A LIFETIME. LIFE IS BEAUTIFUL AT BELLA VITA!brbrTHIS PROPERTY DOES NOT ALLOW PETSbrMAXIMUM OCCUPANY: 8brbrMINIMUM STAY REQUIREMENT: 2 NIGHTS (RESTRICTION MAY CHANGE DURING POPULAR WEEKS)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.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.
Bed 3

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Bath 3

Bath

Sleep 6

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Exceptional(23)

$1297.6

/ Nightly
Private Vacation Home

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

Anna Maria, Florida, United States

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

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Bath 3

Bath

Sleep 14

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