Vacation Rentals By Owner In Anna Maria, FL

$449.7

Spacious Island waterfront house w/ heated pool, steps to beach and dining

Anna Maria, Florida, United States

Spacious Waterfront Home w/Pool, Steps to BeachbrbrPerfect for families and groups, this coastal retreat offers a private pool, canal waterfront access, open living spaces, and a short walk to dining, shopping, and the beach.brbrWelcome to your Anna Maria island retreat! This bright and breezy 4 bedroom, 4 bathroom home is the perfect spot for family and friends to kick back, relax, and soak up the Florida sunshine, just steps from the world-famous Bean Point, white sands and turquoise waters of the Gulf of Mexico. Under new ownership as of August 2025, the home has been refreshed with updated furniture and decor for an even more comfortable stay.brbrThis spacious home offers a private pool surrounded by lush tropical landscaping and sits waterfront on Lake LaVista, with access to the Gulf, creating your own slice of paradise for kayaking or fishing.brbrInside, the open-concept living area is bright and inviting, with modern coastal décor, a fully equipped kitchen with single cup Keurig and Nespresso options, and plenty of space to gather. A complimentary starter pack of coffee, creamers and a bottle of wine greet each guest, ensuring your stay gets off to a great start. Each bedroom is thoughtfully appointed for comfort and privacy, all with en-suite bathrooms. The main floor bathrooms each have complimentary argan oil shampoo, conditioner and body wash to make your stay more like home.brbrEnjoy island living at its finest with multiple outdoor spaces, including a poolside lounge, covered patios, and balconies with outdoor dining, perfect for catching Anna Maria’s famous sunsets. A basketball hoop at the pool and ping pong table provide fun for the whole group.brbrWhether you’re strolling to the beach, dining at local island favorites, fishing on the private dock or exploring the boutique shops nearby, this home offers the perfect blend of waterfront privacy, convenience, and comfort.brbrWhat you’ll love:brbr• 4 bedrooms, 4 bathroomsbr• Private pool surrounded by lush palm treesbr• Private dock perfect for fishing and kayakingbr• A short walk to the beach, shops, and local diningbr• Spacious open living areas made for hanging out togetherbr• Multiple outdoor spaces for morning coffee or sunset cocktailsbrbrYour dream vacation on Anna Maria Island starts here!brbrPETS: Dogs are allowed with prior approval. Must be well trained and less than 40lbs. 2 dogs max. A $150 non-refundable pet fee applies per pet.brbrPARKING: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.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

Bath

Sleeps

$879.6

/ Nightly

Private Vacation Home

Canal Walk: Tiki Bar, Mini Golf, Pool & Spa On Canal by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Canal Walk by Anna Maria Life Vacation Rentalsbr223 Oak Ave, Anna Maria FL, 34216brbrWhat You'll Love About This Home:brLocation! 1.5 Blocks to Beach & On a Canal!br4 Bedrooms / 3 Bathroomsbr2 Kings, 1 Queen, 2 TwinsbrPrivate, Heated Pool & SpabrIn Pool Lounge Seating & UmbrellabrPool LoungersbrTiki Bar (Converted from Boat House) Overlooking Canal brOutdoor Kitchen with Built-In Gas Grill & FridgebrCovered Poolside Lounge Area with Firepit and Plush FurniturebrPing Pong Table, Corn Holebr3 Hole Mini Golf CoursebrKeurigbrLaundry Room with Washer & DryerbrProfessional Linen ServicebrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach Umbrella & Beach WagonbrParking for 5 CarsbrbrDetails:brLocated on one of Anna Maria's relaxing canals and 1.5 blocks to the sugar sand beach, Canal Walk is a vacation home paradise with abundant outdoor amenities.brbrA step inside our home reveals the bright and airy open living and dining rooms and centrally located kitchen. Oversized patio doors offer views to the tropically landscaped backyard.brbrThe master bedroom features a king-sized bed, ensuite bathroom, Smart TV, and oversized patio door access to outside. The additional two guest rooms have a king-sized bed and queen-sized bed with a Smart TV. The final guest room features a set of twin beds. Each bedroom includes crisp linens and plush towels from our professional linen company. Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrThe sparkling pool and spa are highlights of the lush backyard surrounded by pool loungers. The pool features in-pool loungers under the shade of a patio umbrella. Relax poolside in the covered entertainment area complete with a bar, built in gas grill and fire pit table.brbrThe converted boat house is now a Tiki Bar complete with bar seating, a fridge and large TV. Steps away, enjoy an afternoon in one of the Adirondack chairs overlooking the canal. Be prepared for visiting seabirds and possibly a manatee or dolphin while fishing from the dock. The family will also love the 3-hole mini-golf course.brbrCanal Walk is easy walking distance to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrBedroom 1 - King, Ensuite Bathroom, TVbrBedroom 2- King, TVbrBedroom 3 - Queen, TVbrBedroom 4 - 2 Twin Beds (no TV)brbrPlease note:brPets are not allowed in this home.brThe boat lift is not for guest use.brAmenities are subject to change.brDock is 30'. Seawall has docking pylons with boat cleats to tie off.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.brbrVR23-000042brbrGolf Cart DEAL ALERT!!! brReserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.brFUN way to explore the island for the entire family.brMention Anna Maria Life Vacation Rentals and receive this VIP deal!brwww.FunAndMoreRentals.combr941-462-2719brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

4

Bed

3

Bath

8

Sleeps

$497.11

/ Nightly

Private Vacation Home

Waterfront Home! Perfect for Large Groups or Families! – Dock of the Bay

Anna Maria, Florida, United States

Dock of the Bay by AMI Locals brVR16-000039 brbrWelcome to Dock of the Bay, a stunning waterfront duplex located on beautiful Bimini Bay in Anna Maria! Perfect for families and groups, this exclusive rental offers the entire duplex, Bay Cottage and Bay Haven, providing privacy and space for large gatherings. Enjoy breathtaking water views, outdoor seating, BBQ grill, and easy access to local attractions. Relax on the outdoor patio, take in the bay views, or explore nearby shops and restaurants. Dock of the Bay is your ideal Anna Maria Island retreat!brbr*Please note, the dock is temporarily unavailable*brbrHighlights br• Waterfront property br• 3 bedroom / 3 bathroombr• 3 kings, 1 sofa bedbr• Private dock (temporarily unavailable)br• 2 Screened-In Lanais, 2 Grillsbr• Whole duplex rental br• A mile to the beach and 0.8 miles to Bayfront Park br• Close to Pine Avenue shops and local dining spots br• Dog friendly br• Washer and dryers br• 6 Parking spacesbrbrStep out onto your two private outdoor lanais, perfect spots for sipping your morning coffee, enjoying laid-back meals fresh off the grill, or unwinding with a sunset view. Both units come with fantastic outdoor spaces, designed for hanging out with friends or family while taking in the scenic surroundings. From your backyard, you are just steps from the bay or, take a quick stroll or hop on the free trolley ride to hit the beach. Nearby water adventures are calling; fun and relaxation are always right around the corner! brbrBoth sides of the duplex feature fully equipped kitchens, inviting living rooms, and scenic water-view dining areas, creating a seamless indoor-outdoor flow. In Bay Haven, the primary bedroom offers a peaceful retreat with a TV and an ensuite walk-in shower. The second bedroom provides ample space and is close to the second bathroom, which features a shower/tub combo. Bay Cottage showcases a primary king bedroom with an ensuite, and a bonus queen sleeper sofa in the living area makes sleeping arrangements flexible for up to four guests in each unit.brbrIn Bay Haven, the primary bedroom features a king bed and an ensuite with a walk-in shower, while the second bedroom includes a king bed. Bay Cottage offers a primary king suite with an ensuite shower/tub combo. The living rooms in both units have sofa beds, accommodating additional guests comfortably and flexibly. With three bathrooms total across the duplex, your group’s comfort and privacy are fully catered to.brbrRoom Details br• Bay Havenbro Primary Bedroom: King with ensuitebro Second Bedroom: Kingbrbr• Bay Cottagebro Primary Bedroom: King bedroom with ensuitebro Bonus: Sofa bedbrbrKayaking, paddle-boarding, and sightseeing are available from the waterfront access nearby! Close proximity to local beaches, shops, and dining ensures your days are filled with adventure and relaxation alike.brbrBook Dock of the Bay today and make your dream coastal escape a reality. With scenic water views, comfortable accommodations for large groups, and access to Anna Maria’s beautiful beaches and vibrant local attractions, this duplex is your perfect home base for an unforgettable vacation filled with laughter and discovery. Reserve now and start creating lasting memories!brbrbr-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 AMI Locals Rental Policies for full details.brbr6 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. brbrPontoon boat and fire pit are for owner use only.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

Bath

Sleeps

$240.14

/ Nightly

Private Vacation Home

Bayfront Escape Dock and Dog-Friendly Charm

Anna Maria, Florida, United States

Bay Cottage by AMI Locals brVR25-000013brbrWelcome to Bay Cottage, a charming ground level waterfront duplex nestled along Bimini Bay in beautiful Anna Maria, Florida! This cozy one bedroom, one bath getaway is ideal for small groups, solo travelers, or couples seeking a peaceful escape from the water. Enjoy easy access to Bayfront Park and take a short walk to the quaint shops and dining along Pine Avenue. Bay Cottage sets the stage for a laid-back island vacation! brbr*Please note, the dock is temporarily unavailable* brbrHighlights br-Waterfront home on Bimini Bay br-1 Bedroom / 1 Bathroom br-1 King bed, 1 Queen sleeper sofa br-Private dock is temporarily unavailable br-Screened-In Lanai br-Dog friendly br-Grill br-1 mile to Anna Maria City Beach and 0.8 miles to Bayfront Park br-Walking distance to Pine Avenue shopping and dining br-Washer and dryer br-1 Parking Space brbrWake up to peaceful views and sip your morning coffee on the screened-in lanai with seating. Enjoy outdoor meals from the grill, sunset views on the bay, or head down to the private dock or nearby public dock to launch a kayak or paddleboard and explore Bimini Bay. brbrStep into the inviting living space, where coastal charm meets comfort. A plush sofa and smart TV create the perfect setting for a movie night or a quiet reading session. The open kitchen is equipped with everything you need, from appliances to cookware and utensils. Making it easy to whip up anything from beach snacks to a seafood dinner. brbrThe primary bedroom features a king-sized bed, soft linens, and calming décor to ensure restful nights after a day of adventure. The ensuite bathroom includes a convenient shower and tub combo. A queen sleeper sofa in the living room allows for flexible sleeping arrangements for up to four guests total. brbrRoom Details br-Primary Bedroom: King bed, ensuite bathroom with shower/tub combo br-Living Room: Queen sleeper sofa brbrThis dog-friendly retreat is perfectly located for those wanting to explore Bayfront Park, stroll Pine Avenue, or simply relax by the water. Enjoy dining at local favorites and boutique shopping, turning every day into an island adventure. brbrBook your stay at Bay Cottage with AMI Locals today! 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 AMI Locals Rental Policies for full details. brbr1 car maximum is 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. brbrPontoon boat and fire pit are for owner use only. 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

Bath

Sleeps

$1557.52

/ Nightly

Private Vacation Home

Paradise Blu by Beach Boutique Rentals

Anna Maria, Florida, United States

Welcome to Paradise Blu! Your luxury vacation awaits in this newly built 4 bedroom, 4.5 bath treasure. Perched in the most desired North End area of Anna Maria, Paradise Blu offers the privacy, space, and amenities of a modern island resort. brbr*Features include* brbr* Featured in 'Travel and Leisure' Magazinebr* Huge heated pool and spa br* Rooftop deck with sweeping water views br* 4 bedrooms, 4 ½ baths br* 3 king master suites with attached baths br* Indoor/outdoor living on all 3 levels br* Outdoor TV br* Patio dining for 6, plus lounge area br* Chaise loungers by the pool br* Air hockey, darts, cornhole and more br* 2 blocks to beautiful Bean Point beach! br* Beach chairs, umbrella, and cart brbrPure paradise from the moment you arrive, you will be wowed by the unpretentious style of this spectacular home. Paradise Blu lives large with its 20-foot ceilings in the great room and open-concept, indoor-outdoor living spaces. brbrOn the main living level you will find plenty of room for entertaining in the high end kitchen and dining room. The family chef will love the well-stocked kitchen with all the culinary essentials as well as gas range, beautiful quartz counters and an impressive island with enough seating along the breakfast bar to comfortably accommodate all your guests. Relax and unwind in the plush living room with extra large glass doors allowing you to enjoy the beautiful outdoors even when inside. Step out onto the spacious balcony and the gentle sea breeze will have you feeling refreshed in no time. brbrThe main level features one of three king master bedrooms, you will find this one complete with a zen spa bathroom that boasts double sinks, an oversized soaking tub and a huge walk-in shower. The second bedroom on this floor offers a great space for the kids with twin trundle beds as well as an attached bathroom with shower/tub combo. There is also the convenience of a half bathroom rounding out this level of the home. brbrUpstairs you will have your choice of two more king master suites. Each bedroom features a full bathroom with gorgeous walk-in tiled showers. There is an upper balcony perfect for relaxing with your morning coffee and listening to the peaceful sounds of this quiet neighborhood. On this floor you will even find a dedicated office space for when you absolutely must do a bit of work while away. brbrIt's all play and no work in the amazing backyard with its luxurious covered patio with indoor/outdoor seating, dining table for six and propane grill. Float your cares away in the huge pool or have a soak in the attached therapeutic spa tub. While in the spa you can enjoy a movie or sports game on the outdoor TV. You will find plenty of beach and pool supplies in the garage which also functions as a game room. Try your luck at the air hockey table, giant connect four, cornhole, darts and more. The entire family will be delighted to stay and play at Paradise Blu! brbrThis home allows parking for up to 4 vehicles in the driveway. Please do not park in the garage game room. 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 4 vehicles.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.

Bed

Bath

Sleeps

$1135.65

/ Nightly

Private Vacation Home

Dragonfly - Southern charm on the North end of Anna Maria Island

Anna Maria, Florida, United States

Dragonfly is a private retreat located right across the street from the sugary white sands of famous Bean Point Beach in Anna Maria, Florida. brbrGlimpse sparkling turquoise waters from upper floor bedrooms, frolic in the pool with spa and sundeck, and outdoor kitchen, or create culinary delights in the gourmet kitchen with dual-zone wine cooler and Thermador gas range. brbrWide open decks with retractable privacy and sun screens plus generously sized rooms enhance guest comfort and offer plenty of space for relaxing moments or celebratory events. brbrNOTICE: brThere is a motion activated video security camera above the garage. The area under surveillance is exposed to the street with no expectation of privacy in this area.brbrPLEASE NOTE: This property is offered exclusively through VRBO/Home Away and its affiliated entities. Fraudulent bookings through any other service or website are invalid and subject to immediate cancellation without return of deposit.brTHIS PROPERTY DOES NOT RENT ON OR THROUGH CRAIGSLIST.

5

Bed

3

Bath

8

Sleeps

$901.03

/ Nightly

Private Vacation Home

Waterfront -Canal, Tampa Bay, Large Heated Pool, Tiki Bar, Minutes to the Beach!

Anna Maria, Florida, United States

Newly renovated December 2024, with state of the art finishes! 5 King BR, 1 also has a Daybed + 2 King Sleeper Sofas, 1.5 Chaise Lounger, 5 BA Duplex with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! 3 King Bedrooms and 3 Bathrooms (1 ensuite) on the main level and 2 King Master Suites, 1 with extra daybed, and 2 Bathrooms (1 Ensuite) upstairs. No inside stairs connecting these levels, 2 sets of stairs on the outside. This is a Duplex property we only rent as one. Email owner about our other property that sleeps 6 for smaller groups listing vrbo 1309658 right on the Gulf! 1 or 2 6 passenger electric fully loaded and street legal golf carts are available for rent with this property, let us know and we will add them to your reservation as a property fee. It is optional but highly recommended. Inquire with owner for a quote.brbrThe back yard has a ladder for direct canal access for kayaking on the far left Night or Day! Oversized heated pool and your own private Tiki Bar! Brand new Pottery Barn furnishings, 5 New King Size Memory Foam cooling gel beds, 700 Ct Egyptian Cotton Sheets and Pillow cases on every bed! 9 brand new 4K Samsung TVs with Speaker bars in every bedroom, and great room, outside the LL and in Tiki bar. Fish on the famous Anna Maria Pier across the street! High Speed WIFI and Internet Streaming Amazon, Netflix, Apple, Disney +, sports and cable. Deck composite with Feeney steel cable LED lit railings, Tiki bar has freezer for ice, pizza oven and hotdog maker. Beach lawn chairs and uprights, rafts, cooler, umbrella, beach blanket, beach towels, beach toys, and more. Porch Swing Chair in front. Ceiling fans in most every room. 2 Office Desks upstairs. 2 Double Resort Style Chaise Lounge. New kitchen cabinets and LG appliances, all 5 bathrooms and 2 kitchens newly tiled and redesigned. brbrModular outdoor resort like furniture for cozy comfort and relaxing with 4 cushions, watch a movie from the pool! LED outdoor lighting in blue makes evenings tranquil and relaxing. brbrBluetooth speaker connects to your phone or iPad with ease in Tiki Bar. brbrThe main floor layout has 3 full-size bedrooms and 3 bathrooms. 2 face the pool and canal, one faces the bay side. The great room features a new modular xl sectional and sleeps 2 very comfortably. Extra bedding in media cabinet. A Maximum of 8 can sleep here on this level. brbrThere are steps up to the upper level from the outside front of the house and back by the pool. This has a larger layout with a bigger kitchen, 2 seating places on the porch to view the bay which accommodate 3, 5 and 4 people comfortably. Inside features a large living room with 55 tv and Bose speakers, 2 oversized suites, one accommodates an extra daybed for 2 along with a king bed and large closet. The other bedroom is large enough to easily fit a pack n play, or 3! That has a walk in bathroom with glass shower, and there's another bathroom in the hallway. The wrap around deck features a 6 person dining table and a double chaise lounge. The pool/bar area has 10 4 padded 4 chaise lounges, 8 bar stools, a 6 person dining set and a modular seating area for 6 under the home featuring a 55 4K Samsung TV sound bar and fan. brbrThis house is well stocked and designed for luxury and comfort!! Great location for family reunions, office get together, girls weekend, kid friendly, lower level handicap accessible. Please message owner if there's anything not listed that you'd want for your stay! Rent one level or both for large groups or multigenerational family gatherings! NO LOUD PARTIES ALLOWED, City Ordinance no noise after 10 PM. brbrIf your group is 6 or less please see our other listing 1309658! Luxury Beach home steps to the Gulf of Mexico!brPets are welcome with a photo of each sent to Carolyn Hodgson, the owner. The pet fee is $350 per pet.

Bed

Bath

Sleeps

$544.99

/ Nightly

Private Vacation Home

A Bay From It All: Private backyard oasis, steps to Bay, Bean Point

Anna Maria, Florida, United States

***Photos updated May 2025***brbrLeave the stress of everyday life and get A Bay From it All! This amazing 3 bedroom / 3 full bathroom home on the coveted north-end of Anna Maria Island is nothing short of spectacular. brbrEnjoy the charm and character of a roomy beach cottage with gorgeous modern updates, lovely furnishings, and captivating artwork throughout. The ambiance of this eye-popping property will have you feeling right at home from the moment you walk through the door. brbrThe fully furnished custom kitchen features stainless steel appliances, gorgeous granite countertops, and a fabulous cooktop island. Relax in one of the three different indoor living areas. brbrThe bedrooms include two King masters, each with an ensuite bath. Twin beds complete the third bedroom. The den opens to the pool deck and features a queen sleeper sofa. All bedrooms and the den include a TV. brbrOutside you'll find multiple outdoor spaces ideal for entertaining and enjoying the soothing island air. The large custom pool and hot tub form the centerpiece of an exquisite backyard that feels just like a botanical garden. brbrReady for a little time at the shore Easily walk less than a block to the Tampa Bay beach and Bayfront Park, or three blocks to popular Bean Point beach. Want to dine out The famous Rod and Reel Pier is one block away, and Pine Avenue with its fantastic shopping and restaurants is only three blocks away. This beauty at the beach comfortably sleeps 8!brbrBedroom 1: King with TV and ensuite bathroom with walk-in showerbrBedroom 2: King with TV and ensuite bathroom with shower/tub combobrBedroom 3: Twins with TVbrShared hall bathroom with shower/tub combobrQueen sleeper sofa in denbrbrPETS: Please note this property is NOT pet friendly. brbrPARKING: 3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.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

Bath

Sleeps

$896.27

/ Nightly

Private Vacation Home

Jungalow Bay by Beach Boutique Rentals

Anna Maria, Florida, United States

Welcome to Jungalow Bay. Your Anna Maria Island adventure awaits you in this unique, modern Bohemian and Polynesian paradise located on the North end of the island and surrounded by one of Anna Maria's most mature tropical landscapes! brbr*Features include* brbr* Private tropical heated pool br* Plenty of outdoor furniture including Ledge Loungers in the pool br* Outdoor living and dining spaces and tiki bar br* Poolside bar, TV and gas grill br* 3 bedrooms and 3 full bathrooms br* Amazing master bathroom with indoor/outdoor shower br* Spacious screened lanai br* Body boards and pool floats br* Beach chairs, umbrella and cart br* Walk to Bean Point brbrStep inside Jungalow Bay and you will immediately be embraced by island life through an enchanting, tropical space decorated with beautiful Mid-Century and Polynesian Pop-inspired art and modern coastal decor. This extravagant rental home offers treehouse-like views from every room and a spacious, open concept living and dining area connected to a screened-in patio that extends your living space and where you can relax and enjoy serene island breezes while gazing at the tropical palms and pool below. Enjoy your morning coffee in this lush and private jungle setting or sink into the cozy new sectional or Balinese accent chairs and relax while you take in the cheerful, eclectic vibe. brbrVenture down the back steps off the patio and your own private resort awaits! You will find the turquoise pool surrounded by a lush, tropical landscape that further inspires you to connect with nature. The spacious yard includes outdoor dining and pool-side lounging areas including your very own Tiki hut and outdoor bar, as well as a grilling area. Play some games or kick back and watch a movie in the additional large, ground floor family room. brbrRetreat upstairs to the uniquely designed bedrooms that include comfortable bedding and custom, chic decor. The master bedroom features a view of the palms outside as well as its own private deck with an outdoor shower. The gorgeous master bathroom features a large, glass-enclosed, dual shower surrounded by an outdoor garden and tropical palms. Two more bedrooms offer a King bed in one, and a Queen bed plus a Twin XL bed in the 3rd bedroom. Each bedroom also features cable television and streaming services as well as spacious closets.brbrJungalow Bay is located in a prime and highly desirable North end location on the island. Only a short walk to many of Anna Maria's most popular destinations such as Bayfront Park and beach, the shops and restaurants on Pine Avenue and the pristine Gulf waters and large white sand beaches at famous Bean Point. Take in the local Farmer's Market, watch for dolphins and manatees or try your hand at fishing. Or you can easily hop on the Free Trolley and explore the rest of the island! brbrPlease note, garages are not for guest use. brbrPET POLICY: brbrWe are DOG FRIENDLY! A fee of $150 + tax is required in advance for each dog you are bringing. brbr2 pets maximum unless granted an exception. Weight limit of 75 lbs total for 1 pet or 120 lbs for 2 pets. brbrDue to property insurance policies and liability concerns NO dangerous breeds or aggressive animals are allowed. The following breeds (purebred or crossbred) are not permitted: brbrPit Bull, Akita, Rottweiler, German Shepherd, Siberian Husky, Malamute, Doberman Pinscher, Chows, Any Wolf-dog hybrid, Any other dog that has been known to have bitten anyonebrbrADDITIONAL INFORMATION brbrWe generally require a minimum stay during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you!brbrHousekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay.brbrOur cleaning fee includes a professional linen service. When you stay with us you can rest assured that you will have high quality linens such as those at a fine hotel. We also provide plenty of luxury bath and beach towels. brbrAnna Maria Island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors. brbrThis home provides off-street parking for up to 3 vehicles.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.

Bed

Bath

Sleeps

$385.64

/ Nightly

Villa

MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street

Anna Maria, Florida, United States

Open for business in 2025! We are ready to host you and your family!!MI Oasis Getaway is a true oasis on both the outside and inside! When you step into our vacation rental, your eyes are immediately drawn to a one of a kind woven bamboo vaulted ceiling and then down to the beautiful Italian travertine tile. Your eye continues to follow the travertine tile to the outside patio. All from the front door!brbrWant to get around the Island like an Islander by Golf Cart Rent our Electric 6-passenger Club Car for $500 per week.brbrThe Italian travertine floor is found throughout the home as well as granite in both the kitchen and the bathroom. The kitchen is fully stocked with plenty of dishes, pots, and pans. A coffee maker with filters and Starbucks coffee provided for those tough mornings and a blender for those smoothies and margaritas. brbrThe dining table seats four with a beautiful view of the front landscaping.brbrThe master bedroom looks and feels like a luxurious hotel room with a King size mattress and soft, bamboo sheets. You also have an incredible view of the soothing rock wall water feature.brbrThe guest bedroom has two extra-long twin-size mattresses with soft, bamboo sheets. Lots of extra bedding is found in the closet.brbrThe master bedroom closet is packed with bathroom and beach towels.brbrThe outside oasis has beautiful mature palm trees and a lush, landscaped yard. We have plenty of games for all ages.brbrOur MI Oasis Getaway is just 200 steps from the white, sugar-sand beaches found on the Gulf side of Anna Maria. We are also located one block north of Pine Street, directly behind famous Poppo’s Taqueria. This location is ideal if you do not want to rent a car as everything is in walking distance, or via the free Island Trolley.br

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Sleeps

$1741.1

/ Nightly

Private Vacation Home

Jungalow Beach by Beach Boutique Rentals

Anna Maria, Florida, United States

Welcome to Jungalow Beach, a modern architectural gem perched close to the beach on Anna Maria’s North End where stunning, island-inspired contemporary design meets the indescribable beauty of the coastline. brbr*Features include* brbr* Oversized heated L-shaped pool with sun shelfbr* Two Polynesian-inspired lounges (indoor bar + 2-story palapa)br* Rooftop deck with sunset, island & water viewsbr* Putting greenbr* Outdoor kitchen, dining, pool bath & showerbr* 4 bedrooms | 6.5 bathrooms – all en-suitebr* Light-filled great room with gourmet kitchenbr* TV room opens to pool, Roku TVs throughoutbr* Sonos sound systembr* Tesla EV chargerbr* Elevator access to all floors^br* Steps to beach, Pine Ave & Bean Point brbrNestled in Anna Maria Island’s treasured North End, this sprawling, fully rebuilt beach retreat is more than just a vacation rental - it’s your private island-inspired paradise, complete with rooftop sunset views, lush jungle vibes, large living spaces and five-star amenities from top to tiki. Jungalow Beach thoughtfully blends organic modern elements with luxurious amenities, offering a vacation experience unlike any other.brbrInside, the open-concept living area is beautifully designed for both style and ease, with an open, light-filled gourmet kitchen featuring high-end appliances, a gas stove and large island. The great room and upstairs family room provide multiple distinct sitting areas with plenty of space to unwind, connect, or enjoy a quiet moment. A gorgeous dining table is perfect to gather and share meals and features multiple floor to ceiling glass accordion doors leading out to an oversized L-shaped veranda, further extending the space and bringing the outdoors in. brbrDiscover the home’s hidden gem: a secret tiki bar affectionately named The Forbidden Door, tucked away to transport you to the islands of Polynesia. A vintage, Hawaiian retreat complete with hard carved details and authentic Tiki decor is perfect for hosting intimate happy hours, a late night cocktail or simply relaxing island style. brbrOutside, the large, two story, poolside palapa is an entertainer’s dream, fully equipped with a second Tiki bar, and ample seating for gatherings day and night. Just steps away, a built-in grill, mini fridge, putting green, oversized heated L-shaped pool, a covered outdoor eating area and exotic, tropical landscape complete your private backyard oasis. brbrChoose from the home’s five fabulous verandas and balconies for morning coffee or a glass of wine, or settle into the unique, large ground floor family room with a big screen TV, plush seating and accordion doors that open to the pool - the perfect spot to unwind and enjoy the backyard after a day in the sun. For breathtaking sunsets, head to the rooftop deck to toast the day and take in sweeping views of the island, including the Gulf and glimpses of Tampa Bay. brbrAll four bedrooms are en-suite, each with its own stylish personality and luxe touches. The primary king suite offers a spa-like experience with its own private balcony, a floating double sink vanity, a luxe walk-in shower with dual shower heads and a deep soaking tub with a view of the sea. Two additional king suites, one with its own private balcony, provide elevated comfort and privacy for guests. The fourth bedroom features two extra long twin beds and two generously sized baths - including another easy access tub - perfect for kids or friends.brbrLocated just one block to the beach and steps to the shops and eateries on Pine Avenue, this North End gem delivers island living at its absolute finest. Jungalow Beach isn’t just a home, it’s a state of mind. Whether you’re drawn by the unique modern organic flair, the private resort-style tropical surroundings, or the unbeatable North End location, this stunning escape delivers a vacation experience like no other.brbrBook your stay and experience coastal luxury at its finest.brbr^Please keep in mind that residential elevators are advertised as a convenience only. If the elevator becomes inoperable for any reason, the stairs will be only way to access the living area of the home.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 4 vehicles.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.

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Bath

Sleeps

$579.63

/ Nightly

Private Vacation Home

4 bedroom, pet friendly, Anna Maria Island beach home, sleeps 8!

Anna Maria, Florida, United States

The flAMIngo house is a 4 bedroom, 2 bath Key West style beauty with all the comforts of home! Let's flamingo to the beach which is just a couple minute walk or to the famous Pine Ave! This home is tickled pink to host you.br brIts kitchen is thoughtfully stocked for making memorable dinners in and has loads of seating for a family meal around the table. All rooms are equipped with TV's and high speed internet and there are plenty of boards games, books and movies if you choose to stay indoors.brbr The house comfortably sleeps 8 people. The main bedroom has an ensuite bathroom and a king size bed. The guest room on the main floor has a queen size bed and a shelving unit with fun arts & crafts for the kiddos! The other two bedrooms upstairs both have a desk and chair, one room offers a queen bed and the other room has a set of twin beds.brbr Just wait until you set into the backyard, it steals the show with its outdoor waterfall shower, wishing well, game area, grilling kitchen and fire pit! To complete your evening, make yourself a drink and enjoy flocktail hour around the fire. The backyard also features corn hole and other outside entertainment. brbrA beach wagon, beach towels and beach chairs are provided for your convenience. At flAMIngo house dogs are welcome, so bring your fur babies along! Pet fee is $200 per pet plus taxes, maximum of 2 pets unless otherwise approved by FDR. brAccommodates up to 8 people. Minimum Stay Required: 3 nights Max. parking: 2; VRC #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* 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.

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Sleeps

$358.87

/ Nightly

Private Vacation Home

Cozy Barefoot Bungalow: Steps to Bayfront Park & Bean Point, Pet-Friendly!

Anna Maria, Florida, United States

Welcome to Barefoot Bungalow, a ground-level hideaway recently updated in early 2025. The open-concept living area welcomes you with plush seating and large windows that flood the space with natural light. The fully equipped kitchen features sleek countertops, stainless-steel appliances, and everything you need to whip up a casual breakfast before heading out. Two cozy bedrooms provide restful nights, and two full bathrooms (both accessible from the hallway) offer convenience for families or friends, while subtle beach-inspired décor keeps the vibe light and welcoming.brbrYou’re just a quick 5-minute stroll from Bayfront Park—where you can soak in pretty Tampa Bay views—and serene Bean Point Beach, known for its sugar-white sand and gentle waves. A 10-minute walk (or a breezy bike ride) brings you to the iconic Anna Maria City Pier and Pine Avenue, home to brunch spots, boutique shops, and ice-cream stands. From Pine Avenue, hopping on the free Island Trolley is a breeze, so you can explore the rest of Anna Maria Island without worrying about parking.brbrWhether you’re enjoying morning coffee inside or unwinding after a day of sun and surf, this casual retreat is the perfect home base. Pack your flip-flops and your sense of adventure—your Anna Maria escape starts here!brbrPETS: Dogs are allowed with prior approval. Must be well trained and less than 40lbs. 2 dogs max. A $150 non-refundable pet fee applies per pet.brbrPARKING: 2 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.

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Sleeps

$477.47

/ Nightly

Private Vacation Home

Canal-front Gem w/ Pool & Hot Tub in Anna Maria

Anna Maria, Florida, United States

Escape to the sandy shores of Anna Maria Island at ‘Easy Breezy’, a recently renovated canalfront vacation rental cottage only a short stroll from the beach! ‘Easy Breezy’ boasts a pristine coastal-themed interior, a stunning full kitchen, 2 beautiful bedrooms, 2 en-suite bathrooms, and a cozy sleeper sofa. Soak up the sun by the private pool and hot tub, fire up the grill for a summertime cookout, or enjoy the luxurious finishes of this exceptional Florida beach home.brbr-- THE PROPERTY --brbrLicense#: VR17-000046 | 1,285 Sq Ft | Family Friendly | Private Outdoor Entertainment | Modern Updates | Free WiFibrbrDesigned for couples and small families looking to experience Anna Maria in style, 'Easy Breezy' offers a pristine coastal interior with all the modern updates you need for a memorable coastal escape!brbrBedroom 1: King Bed | Bedroom 2: King Bed | Downstairs Living Room: Queen Sleeper SofabrbrSTEP OUTSIDE: Wraparound screened-in porch w/ outdoor dining space & patio furniture, lower-level patio w/ living room set, outdoor dining table, ceiling fans, gas grill, fenced-in yard w/ pool, hot tub & sun chairs, beautiful tropical landscaping, private dockbrINTERIOR LIVING: Beach-themed interior, dining table, 3 Smart TVs, ample natural sunlightbrKITCHEN: Fully equipped, stainless steel appliances, granite countertops, tile backsplash, ice maker, cooking basics, knife set, toaster, drip coffee makerbrGENERAL: Central A/C & heating, linens & towels provided, washer/dryer, beach chairs, towels & wagonbrFAQ: Stairs required for access, exterior security cameras (3 - front, side & back of home), optional nightly pool heat fee (paid pre-trip, applied to entire stay), no pool screenbrPARKING: Driveway (4 vehicles), garage (1 vehicle)brbr-- THE LOCATION --brbrSOAK UP THE SUN: Bayfront Park (0.3 miles), Anna Maria Public Beach Access (0.5 miles), Palmetto Ave Beach (0.7 miles), Bean Point Beach (0.8 miles), Manatee Public Beach (3.2 miles), Cortez Beach (6.0 miles), Coquina Beach (7.1 miles)brGOLF THE DAY AWAY: Bradenton Country Club (9.8 miles), Timber Creek Golf Course (11.2 miles), Pinebrook Ironwood Golf Course (12.0 miles), Manatee County Golf Course (12.1 miles), IMG Academy Golf Club (13.8 miles), Greens of Manatee Golf Course (14.9 miles), Longboat Key Golf Club (17.6 miles)brLOCAL ATTRACTIONS: Anna Maria Island Historical Society (0.2 miles), Neal Preserve (4.9 miles), Coastline Dolphin & Snorkeling Excursions (5.0 miles), Bradenton Beach Marina (5.9 miles), DeSoto National Memorial Park (10.0 miles), Bradenton Riverwalk (12.3 miles), Mote Marine Laboratory & Aquarium (18.0 miles), The John and Mable Ringling Museum of Art (19.4 miles)brAIRPORTS: Sarasota Bradenton International Airport (19.4 miles), St. Pete–Clearwater International Airport (47.3 miles), Tampa International Airport (55.5 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This home is not suitable for infants, as it does not have any baby gear, nor is it baby-proofedbr- NOTE: There is an optional pool heat fee of $30/night (+ fees & taxes, paid pre-trip, applied to entire stay)br- NOTE: The property does not have a pool screen so leaves will occasionally blow into the pool between the scheduled cleaningsbr- NOTE: Your safety matters. This property features 3 exterior security cameras, on the front, side and back of the house, all facing out. They do not look into any interior spaces

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Sleeps

$1181.16

/ Nightly

Private Vacation Home

Coastal home near the shopping district and Gulf beaches

Anna Maria, Florida, United States

Cloud Nine on Pine by Anna Maria Island Accommodations brbrWelcome to Cloud Nine on Pine, a six bedroom, six and a half bath luxury retreat in the heart of Anna Maria Island. This coastal home features three levels of stylish living space, a rooftop deck with 360° island views, and premium amenities that include a heated pool and spa, putting green, elevator, foosball, and ping pong. Just a four-minute walk to the Gulf’s white sand beaches and steps from Pine Avenue’s shops and dining, this vacation home is the perfect choice for families and groups looking for the ultimate Anna Maria Island getaway. brbrHighlights br• 4-minute walk to Anna Maria Beach br• 6 Bedrooms / 6.5 Bathrooms br• 5 King beds, 1 Full-over-Twin-over-Full bunk bed br• Rooftop deck with panoramic Gulf and Bay views br• Private heated pool and spa br• Elevator br• Putting green and cornhole br• Foosball, and ping pong table br• 4 parking spaces br• Steps from dining and shopping on Pine Avenue brbrSoak up the sun by the heated pool and spa, craft cocktails at the outdoor wet bar, or test your skills on the putting green. Kids and adults alike will love friendly competitions at the foosball and ping pong tables. When the day winds down, head to the rooftop deck for a front-row seat to Anna Maria’s breathtaking sunsets. With an elevator for easy access and plenty of space for everyone, this home truly has it all. brbrThe second-floor great room is designed for relaxation and entertainment, with comfortable sofas, a large TV, and private terrace views. The gourmet kitchen features upgraded appliances, quartz counters, and a spacious island with barstool seating, making it easy to prepare meals together. Dine around the large family table or enjoy a breezy meal outdoors. For added convenience, this level also includes a half bath and laundry room. brbrCloud Nine on Pine offers six beautifully appointed bedrooms, each with its own ensuite bathroom for added privacy and comfort. On the second floor, two king bedrooms and one triple bunk bedroom (full-over-twin-over-full) provide stylish accommodations, with the bunk room being a favorite for kids. Upstairs, the third floor features three additional king bedrooms, each with spa-inspired ensuite bathrooms, walk-in showers, and some with private balconies. In total, the home features five king bedrooms and one bunk room, making it perfect for large groups and families. brbrRoom Details brSecond Floor br-Primary Bedroom: King bed, ensuite walk-in shower br-Second Bedroom: Triple bunk (Full over Twin over Full), ensuite shower br-Third Bedroom: King bed, ensuite shower/tub combo brbrThird Floor br-Fourth Bedroom: King bed, ensuite shower br-Fifth Bedroom: King bed, ensuite shower br-Sixth Bedroom: King bed, ensuite shower brbrCloud Nine on Pine puts you right in the heart of Anna Maria Island. You’re within walking distance of Pine Avenue’s boutiques, ice cream shops, and restaurants, with quick access to the AMI Trolley for exploring Holmes Beach, Bradenton Beach, and beyond. Visit the Historic City Pier, enjoy local fishing, or take part in endless water adventures; everything is just minutes away. brbrWith luxurious amenities, a prime location, and plenty of room for families and groups, Cloud Nine on Pine by Anna Maria Island Accommodations is your dream vacation home. Whether you’re lounging poolside, watching sunsets from the rooftop deck, or discovering the charm of Anna Maria Island, this home makes every moment unforgettable. Book your island escape today! brbr- brThere are no pets allowed in this home. brbr *Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by AMI Accommodations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brPlease see our AMI Accommodations Rental Policies for full details. brbrPlease Remember: brYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

6

Bed

6

Bath

8

Sleeps

$412.45

/ Nightly

Private Vacation Home

Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-

Anna Maria, Florida, United States

Newly Renovated Boathouse Cottage is ready to welcome guests. New flooring, new beds, new furniture. Located on the west side of the duplex on the quiet street of Gladiolus on north end of Anna Maria. Removed from the condos, hotels, and crowds.brbrWe are one short block from sunrises on the bay, and the historic Rod and Reel Pier. Two short blocks to sunsets on the gulf, and the pristine beach of Bean Point-the perfect place for shelling, strolling, fishing, boating or just a quiet time.brbrThis 2 bedroom, one bath, duplex sleeps 4 and has ample living space with screened in porch, large private fenced in yard and heated pool. Many of you have stayed here in the past. As of 9/2020 under new ownership, both sides are available for rent, each side with private pool. The other side is called Angel Fish Cottages VRBO # 2053921.brbrOur patio is perfect for entertaining, outdoor barbeque's, and family relaxation. We provide beach and pool equipment.brbrFollow us on Instagram @ami-baypalms

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Sleeps

$1269.28

/ Nightly

Private Vacation Home

Sea Creatures Cottage: Steps to beach! Putting Green, Rooftop Deck, Pool by Anna Maria Life

Anna Maria, Florida, United States

Sea Creatures Cottage by Anna Maria Life Vacation Rentalsbr112 Mangrove Ave, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! Steps to the Beach! No Streets to Cross!br4 Bedrooms / 4.5 Bathroomsbr4 King Beds, Queen Sleeper Sofa in Living RoombrElevator (Service to Main Living Level from Ground Level)brPrivate Heated PoolbrOutdoor ShowerbrRoof Top Deck with Seating and Amazing Gulf ViewsbrOutdoor Verandahs with Seating on Floors 2 & 3brBuilt in Gas Grillbr3 Hole Putting GreenbrPool Table, Corn HolebrKeurig & Drip Coffee MakerbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs & Beach WagonbrDriveway Parking for 4 CarsbrbrDetails:brStep into paradise at Sea Creatures Cottage, where panoramic Gulf views, breezy balconies, and a stunning rooftop deck set the scene for your dream beach escape. Just steps from the sugar-soft sand with no streets to cross, this Anna Maria Island retreat puts you closer than ever to the Gulf of Mexico.brbrInside, beach-inspired designer details, custom mosaics, and vibrant local artwork create a laid-back yet luxurious vibe throughout the home. An elevator conveniently whisks you from the ground floor to the main living space, making it easy to unload luggage or groceries.brbrThe main floor features a bright, open-concept layout with a gourmet kitchen complete with an oversized island and seating for four. A spacious dining area with room for eight flows seamlessly into a cozy living room—perfect for relaxing after a day in the sun. Two of the four king bedrooms (each with an en-suite bath, TV, premium linens, and plush towels) are located on this level, with the other two tucked away upstairs for added privacy. A queen sleeper sofa in the living room offers extra accommodations.brbrStay connected with complimentary Wi-Fi, and enjoy all the comforts of home including a full-size washer and dryer.brbrOutside, your private backyard oasis awaits. The heated pool is surrounded by lush tropical landscaping and offers the ultimate relaxation zone with an outdoor shower, pool loungers, and a covered entertainment lounge featuring a gas grill, 3-hole putting green, pool table, shuffleboard, and Adirondack high-top seating.brbrHead up to the rooftop deck for unbeatable sunset views over the Gulf, or unwind on one of the furnished balconies on the second and third floors—perfect for morning coffee or evening cocktails with a sea breeze.brbrLocated in the heart of Anna Maria Island, Sea Creatures Cottage is just a short stroll to shops, restaurants, and the free island trolley that runs the full 7-mile stretch of this charming island. Whether you're here to explore or simply soak up the sun, this is beach vacationing at its best.brbrBedroom 1: King with En-suite Bathroom & TV - Floor 2brBedroom 2: King with En-suite Bathroom & TV - Floor 2brBedroom 3: King with En-suite Bathroom & TV - Floor 3brBedroom 4: King with En-suite Bathroom & TV - Floor 3brSofa Sleeper in Living RoombrbrPlease note:brThis home is not pet friendly.brAmenities are subject to change.brDriveway parking is available for a maximum of 4 cars. Parking for additional vehicles is not available.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

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$489.95

/ Nightly

Private Vacation Home

Canal Front, Dockside Paradise by SeaBreeze Vacation

Anna Maria, Florida, United States

Dockside Paradise is a beautifully updated two-bedroom, two-bathroom canal-front home designed for relaxed coastal living. Perfect for couples and small families, this inviting retreat features a private pool with a waterfall, a screened lanai, and a deep-water dock ideal for fishing and boating. Located on Bimini Bay, this home offers the perfect balance of convenience, comfort and island charm.brbrThe outdoor living space is your own private oasis, where you can swim in the sparkling pool, lounge in the screened lanai, or enjoy the sunshine while watching boats glide by along the canal. The private dock provides quick access to the bay for boating and fishing adventures, and after a day on the water, the poolside grill and outdoor shower make it easy to unwind and enjoy the breeze.brbrDockside Paradise, inside, features a bright beach-inspired interior with a modern, open layout. The living area offers comfortable seating and a TV, creating a welcoming space to relax after exploring Anna Maria Island. The fully equipped kitchen includes modern appliances and ample counter space, seamlessly connecting to the dining area and outdoor patio for effortless indoor-outdoor living.brbrThe primary bedroom is a peaceful retreat with a king bed, direct access to the pool, and a private ensuite bathroom with a walk-in shower. The second bedroom also features a king bed and easy access to a hallway bathroom with a walk-in shower. A den off the kitchen includes a twin daybed with a trundle, ideal for children or extra guests. Each space is thoughtfully styled with coastal décor and comfortable linens to ensure a restful stay.brbrGuests will enjoy the convenience of two parking spaces, a ten-minute walk to the Gulf beaches, and easy access to the Anna Maria Island trolley, which connects you to Bean Point, Holmes Beach, and Bradenton Beach. 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: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.brbrThe property comfortably accommodates a group of 6.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.

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Sleeps

$1372.7

/ Nightly

Private Vacation Home

A Shore Thing: On Canal! Pool Spa! Rooftop Deck by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

A Shore Thing by Anna Maria Life Vacation Rentalsbr108 Tern Dr, Anna Maria, FL 34216brbrWhat You'll Love About This Home:brLocation! On Canal! Near Bean Point & PIne Ave!br4 Bedrooms / 5.5 Bathroomsbr3 Kings, 1 Queen, 2 Sets of Twin over Twin Bunkbeds, Queen Sofa BedbrPrivate Heated Pool & SpabrPool LoungersbrOutdoor Showerbr20' Boat Dock with Ladder Access for Fishing and PaddleboardingbrGas GrillbrRooftop Deck with Panoramic Gulf & Bay ViewsbrVerandahs with SeatingbrElevator (not wheelchair accessible)brCovered Poolside Lounge AreabrPing Pong & Pool TablesbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrParking for 2 Cars in Driveway & 2 Cars in GaragebrbrDetails:brWelcome to A Shore Thing, a luxurious canal front retreat on the north end of Anna Maria Island featuring ultimate privacy, breathtaking Gulf & Bay views and effortless access to the pristine sands of Bean Point.brbrRelax in a stylish and spacious living area that effortlessly blends island charm with modern comfort. Featuring natural wood ceiling beams, a rich navy accent wall, and large windows that flood the room with natural light, this space invites you to unwind and relax with family and friends. A pool table adds an extra layer of entertainment, giving guests a fun spot to gather and enjoy a friendly game. Sliding glass doors open to a spacious verandah, create a seamless indoor-outdoor flow where you can enjoy lush tropical views, fresh air, and plenty of room for lounging or entertaining.brbrThe kitchen is designed for easy vacation living, featuring a large island with seating for six. Adjacent to the kitchen, a separate dining room offers an inviting setting for shared meals, complete with plenty of room for everyone to dine comfortably. Together, these spaces provide an ideal setup for guests looking to relax, cook, and enjoy time together during their stay.brbrEach of the four comfortable and well-appointed bedrooms are designed to give guests plenty of space and privacy. The second floor includes a spacious master suite with a king bed and ensuite bathroom and a TV. providing guests an ideal retreat for unwinding after a day of exploring or relaxing by the water. In addition to this bedroom, there is a queen bedroom with an ensuite bathroom on this level. brbrThe third floor offers three additional private bedroom suites, creating a comfortable retreat for families or groups. Two suites feature a king bed, an ensuite bathroom, and a TV, providing a quiet space tucked away from the main living areas. The third suite includes two sets of twin-over-twin bunkbeds, and an ensuite bathroom, - an ideal setup for kids or extra guests. With each room offering their own bathroom, this floor ensures everyone has space to relax and recharge.brbrYour guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrStep into a backyard that captures the island's laid-back rhythm. The heated pool and spa open to serene canal views, featuring in-pool seating and a shallow sun shelf perfect for effortless lounging. Around the water, you'll find plush loungers, a covered poolside lounge area with a TV, ping pong table, patio dining and a gas grill, making it easy to enjoy casual meals and unwind beneath the swaying palms. The outdoor shower provides the added convenience for rinsing off after a day at the beach.brbrThe rooftop deck offers a stunning, elevated vantage point perfect for taking in the surrounding beauty. From this spacious outdoor area, guests can enjoy sweeping views of the canal, lush greenery, and glimpses of the water beyond. Enjoy unobstructed sightlines in every direction, the rooftop deck adds a memorable highlight to the home's outdoor living experience.brbrThis peaceful waterfront dock offers an inviting spot for both relaxation and adventure. With calm, protected water right at your doorstep, it's an excellent place to cast a line and enjoy some quiet fishing surrounded by mangroves and natural scenery. It's also perfectly suited for launching paddleboards or kayaks, giving guests easy access to explore the winding waterways at their own pace.brbrOnly steps from the north-end beaches of Anna Maria Island and just minutes from the charming shops and cafés on Pine Avenue, A Shore Thing offers inviting spaces for everyone to gather and enjoy the stunning views.brbrBedroom 1 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 2 - Queen Bed, Ensuite Bathroom, TV - Floor 2brBedroom 3 - King Bed, Ensuite Bathroom, TV - Floor 3brBedroom 4 - King Bed, Ensuite Bathroom, TV - Floor 3brBedroom 5 -2 Sets of Twin over Twin Bunkbeds, Ensuite Bathroom - Floor 3brbrPlease note:brThe elevator is not wheelchair accessible.brThis home is not pet friendly.brAmenities are subject to change.brPaddleboards and fishing gear are not included.br20' Boat DockbrParking is available for 2 cars in the driveway and 2 cars in the garage. Parking for additional vehicles is not available.brbrDISCLAIMERbrDepth 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 ten.brbrVR18-000125 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

Bath

Sleeps

$584.59

/ Nightly

Private Vacation Home

Sunset Shores: Stunning sunset views over the beach!

Anna Maria, Florida, United States

Dreaming of the perfect beach vacation home Dreaming of sipping coffee on your choice of decks with views of the Gulf Stay for a week or a month at what is perhaps one of the most spacious beach view homes on the north end of Anna Maria Island, located at the end of a quiet beach street. Phenomenal views galore! Surround yourself in luxurious comfort - a cozy gas fireplace with a cushy living room, a large dining room table where the whole family can gather, unique bedrooms with floor to ceiling bookcases - the ample master bedroom includes a sitting area. You'll find an outdoor gas barbeque and speaking of outdoors - you are only sandy steps to one of the island's most pristine beach areas - perfect for snorkeling, shelling and sunset watching. You'll find all the amenities of home and some that are probably not in your home; such as an elevator and gleaming floor to ceiling windowsbrbr*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.

3

Bed

2

Bath

6

Sleeps

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