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Short Term Stays available Imagine waking up to a breathtaking panorama of the Gulf of Mexico,. This completely remodeled condo, the largest in the community, offers unobstructed, 8th-floor views that will take your breath away. Picture yourself stepping onto the expansive terrace and feeling the cool...
Distance to beach: 0.5 miles to Longboat
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Imagine waking up to dolphins playing just beyond your window. This exquisitely renovated Longboat Key luxury waterfront home offers breathtaking "Big Bayfront" views and unparalleled access to the Gulf of Mexico. Boater's Dream: • Direct access to the Gulf for fishing or cruising • Private...
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This fabulous, 2000-square-foot, fourth story, corner, direct beachfront, condominium features spectacular views of the gulf and bay. Hear the waves from the master suite and enjoy a dinner on the screened lanai while viewing one of Longboat's incredible sunsets. Sip a morning coffee on the back...
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Discover this newly rebuilt hurricane-resistant home at 701 Broadway St, Longboat Key, FL 34228 . Perfect for couples or small families seeking a serene vibe. Property Features 2 bedrooms, 2 bathrooms. 1 bedroom guest house above garage, just one flight up. Fully gated backyard with swimming...
Featured review
Absolutely loved our stay at this Longboat Key cottage! It’s perfect if you work from home — fast, reliable Wi-Fi and a dreamy window seat made it easy (and enjoyable) to stay productive. The location...
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Welcome to Cortez Cabana! Short drive to the World Class Beaches of Anna Maria Island Close proximity to Lakewood Ranch, Sarasota, and Tampa Private Heated Pool, Outdoor Seating with TV, BBQ Grill Private Boat Dock, Short Drive to Gulf High-speed Wi-Fi, Smart lock for Self Check-in, Luxurious Linens...
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Welcome to Dolphin Bay! Short Drive to the World Class Beaches of Anna Maria Island Bring your Boat or other Water Toys! Heated Pool, Sunset Views, Dolphin Activity Peloton Bike+ Fully stocked kitchen & BBQ Grill High-speed Wi-Fi, Smart lock for Self Check-in *Construction taking place...
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110 11th Street South - Bradenton Beach - FL 34217 No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60...
Featured review
The home was lovely. The pool and whirl pool were fabulous. Strong recommendations: TV by pool never worked. Multiple lightbulbs in lamps, etc. need to be replaced. Two blow dryers need to be replaced....
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Bay House Retreat by Beach Retreats Vacation Rentals Sarasota Bayfront – Near IMG Academy & Downtown Sarasota 5 Bedrooms | 4 Bathrooms | Sleeps 14 | Heated Saltwater Pool | 2 Private Docks Welcome to Bay House Retreat, a luxurious bayfront escape offering over 4,000 sq. ft. of comfort...
Featured review
Four siblings and their spouses enjoyed this spacious home for a week. Right at the water’s edge, with a great pool and spa, it was like a self-contained resort of its own. The views of sunrise and...
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The View at the Bradenton Beach Club offers panoramic views of the Gulf of Mexico and beautiful beaches from the living room, primary suite or private screened balcony. The condo is part of the Bradenton Beach Club that provides the very best in vacation accommodations. Amenities at the BBC include two...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
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NEW MANAGEMENT...Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex with 2 kitchens invites you to exhale and settle into vacation mode. With two fully private units under one roof, it's...
Featured review
Wonderful property and perfect for families with kids. The house was clean, well appointed with everything you could possibly need, and comfortable for everyone. The pool was always clean and well maintained....
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
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Welcome to Ocean Star! .01 Miles to Amazing Gulf Coast Beaches Private Heated Pool/Spa with Outdoor Seating & BBQ Beach Equipment Available for Use Every Bedroom Has a Private Bathroom Fully stocked kitchen for all of your favorite home-cooked meals High-speed Wi-Fi, Smart lock for Self Check-in...
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Welcome to Palma Sola Bay House your Water Front Oasis! Short drive to the World Class Beaches of Anna Maria Island Private Heated Pool/Spa, Game Room, Boat Dock, & more! Walk to the Palma Sola Causeway/ Jet Ski Rentals, Kayak rentals, and Horseback Riding! Close proximity to Lakewood Ranch,...
Featured review
We were a group of soccer moms (and one dad) there for a few days for a tournament. This house was everything we could have wanted! Clean, well appointed, excellent location, I can't say enough! Nights...
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Welcome to "The Plantation House"! Short drive to the World Class Beaches of Anna Maria Island Private Enclosed Heated Pool/Spa, Game Room, Boat Dock, & more! Walk to the Palma Sola Causeway/ Jet Ski Rentals, Kayak rentals, and Horseback Riding! Close proximity to Lakewood Ranch,...
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Welcome to Sweet Home Anna Maria! Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Private Heated Pool & Hot Tub with Plenty of Seating for the Whole Family! Game Room with Ping Pong, Dart Board, Extra Fridge & Bathroom Every Bedroom has an Ensuite Bathroom!...
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Are you dreaming of mornings by the pool and evenings watching sunsets on the sand? Are you travelling with little ones and need baby gear ready and waiting for you? Are you ready to trade your everyday routine for an unforgettable island escape? If this sounds like you, we’d love to welcome...
Featured review
Beautiful house and Celine is an excellent host. We stayed here a week for a family vacation and really enjoyed our time. House had everything we needed and more. Very clean and super close to the beach....
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Located in the heart of Holmes Beach on Anna Maria Island, this 4-bedroom, 5.5-bath coastal getaway is your dream vacation home — perfect for families, friends, or group trips. ️ Short walk to the beach Private mini putt-putt + game room Heated pool + spa oasis Close to bars, dining,...
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Breathtaking sunset views atop your own expansive and elevated deck await at this spacious single story home on gorgeous Anna Maria Island! This home features 4 large bedrooms, each with its own private en suite bathroom, a large kitchen, living room, additional sitting area plus two separate dining spaces....
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This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island! As you step through the front door, you enter a bright and...
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Welcome to 75 Palms! Short drive to the World Class Beaches of Anna Maria Island Private Gated Oasis: 2 Houses, 1 Lot, 8 Bedrooms Heated Pool, Hot Tub, Outdoor Kitchen, BBQ Grill Pickleball Court, 3 Hole Putting Green, Fire Pit & More! Game Room:98 in Smart TV, Billiards, Foosball, Arcade...
Featured review
75 Palms was amazing! We had a group of 21 people for a senior boys spring break trip, and it was perfect. The outdoor area is very big, and there’s a lot to do. The swimming pool is a great size, the...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
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What You'll Love About This Home: Location! 3 Blocks to the Beach! 4 Bedrooms / 4 Bathrooms 3 King Beds, Two Sets of Bunk Beds with Twin Bed over Full Bed Lagoon Style Heated Pool w/ sundeck & Spa In Pool Umbrellas Pool Deck Lounge Chairs Poolside Covered Lounge with Patio Furniture,...
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ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access! This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining...
Featured review
Our party of 10 has stayed at this wonderful property multiple times and plan to come back. The house is in wonderful shape and has all amenities you could want including heated pool and hot tub with slide,...
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Surf Side Beach House – Gulf Views Hosted by Beach Retreats Vacation Rentals 6605 Gulf Drive, Holmes Beach, FL 34217 VRC19-00290 Welcome to Surf Side Beach House, a stunning custom home located right across the street from the beach! ️ Enjoy beautiful Gulf views and an unbeatable island...
Featured review
The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally...
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Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this property is about 100 steps to the Gulf of Mexico and one of the best beaches on the West Coast of Florida. This ground level beach house offers 4 bedrooms, 3 bathrooms...
Featured review
This is a true retreat any time of the year. The backyard and pool area is well designed and an oh so private area that includes a hot tub, a pool, ping pong table, mini golf and hammocks for relaxing....
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Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach! Come enjoy a large family and friends gathering at this spacious luxury home just a few minutes stroll to the beach. One of the larger homes on the island, with 6 bedrooms and 4.5 bathrooms and 3400 sq. ft, this home has plenty of room for...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
Featured review
Wonderful house. Very clean and well stocked. The pool was clean and big. Very close to a very nice beach. Would stay here again.
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One of the highest rated vacation homes on Anna Maria Island with more than 160 five-star ratings from Airbnb/VRBO! Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated...
Featured review
We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met....
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Welcome to “Coastal Breeze” on beautiful Anna Maria Island. This vibrant four-bedroom, three-bathroom island retreat is your perfect vacation escape on AMI. The backyard is a true highlight, featuring a private heated pool with spa, cozy and colorful seating areas, and a one-of-a-kind tiki...
Distance to beach: 0.1 miles to Lido
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St. Armand's Canal-Front Pool Home steps to the beach! This gem, ranch style home estate has been completely rebuilt and remodeled in 2015 from the frame including all new finishes inside and out. With fresh, coastal Old-Florida decor, it is in one of the most desirable locations on the west...
Distance to beach: 0.1 miles to Lido
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Lovely remodeled and refurbished 5 bedroom 5.5 bath pool home on desirable St. Armand's Circle! This 3,000 s.f. home comfortably sleeps (8) in beds, and has T.V.'s in the family room and living room for when the family is not enjoying the caged pool and spa. Professionally decorated, quality...
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Very inviting home with pool, fenced yard and simple walk to St Armand's Circle. A Jewel on St. Armands Circle! The location makes this spacious 3BR+Casita/3BA with a private pool in a botanical setting a perfect month long vacation spot. This residence has it all for those who want to be right...
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Bring the whole family as this home features 3 bedrooms and 2 1/2 baths. This very spacious home is almost 2,600 square feet with plenty of room to relax. Huge open living area. You will love the fenced backyard featuring multiple seating areas and a pool to relax in. Portable putting green and safe ax...
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It's all about location on vacation, and Reef Romance does not disappoint! Sail away to this beautiful four-bedroom, four-and-a-half-bathroom custom-built home for a dose of luxury at the beach. Located on the prestigious north end of Anna Maria Island, you're just a few houses away from the...
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Beautifully renovated and immaculate home with pool and dock Near St Armand's and Lido Beach NEW PROPERTY Welcome to 440 Cleveland Drive, a stunning, fully renovated rental property on Lido Key where luxury meets coastal charm. Completed in March 2025, everything inside and outside this home...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
Featured review
A time much needed . We so enjoyed our stay at 2311 ave.c that we hope to return every year . We just felt like we were at home .
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! Welcome to your home-away-from-home! This 4-bedroom, 4 full bath, 2 half bath pet-friendly, canal-front retreat is made for making memories — whether you're here with family, friends, or your fishing crew. From sunrise to sunset, the views,...
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Immerse yourself in beachfront bliss at Lido Bliss: Imagine stepping off the elevator into your private sanctuary. Breathtaking panoramic views of the Gulf of Mexico greet you from your expansive balcony, setting the scene for an unforgettable stay. This meticulously kept, 4-bedroom 3.5 bath haven exudes...
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Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 12 people with the add-on of the sleeper sofas. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool, and an EV Charger. Upon entry in...
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Welcome to “Pineapple Cottage” – a beautifully updated ground-level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants, and fun on Pine Avenue. This charming cottage has been completely restored after hurricanes Helene and Milton. This...
Featured review
This house is in a great location, three blocks to the beach, restaurants, and three blocks to the pier, and many other amenities. It is beautiful, spacious and has everything you need to make your stay...
Distance to beach: 0.1 miles to 30 seconds to your left
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This newly redesigned elevated pet friendly 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state of the art quartzite counter tops, stainless steel appliances and driftwood style hardwood floors and ceilings. Relax on the covered porch with direct views of the Gulf of Mexico and...
Distance to beach: 0.1 miles to Bayside Beach
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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 can sleep 14 total 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...
Featured review
Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was...
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Beachfront paradise awaits you at the TripleTail. Located in a prime location - just one block from Pine Avenue and the City Pier, the 4 bed/4 bath bayfront home offers everything you need for the perfect vacation. On the ground floor, you’ll find a beachfront king bedroom, along with a...
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NO CANCELLATION FEES: Effective for reservations made on or after August 13, 2025) $500 deposit due at time of booking; balance due 30 days prior to arrival Cancel 30+ days before arrival → Full refund (no fees). Cancel within 30 days of arrival → No refund. Cancellations must be made in writing...
Featured review
This house was incredible! Absolutely beautiful, well stocked, an amazing pool and outdoor setup, and so conveniently located! While it's not beach-front, it's just a house or two away from the beach entrance...
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Indulge in the ultimate beach escape to “Oceans Blue” located on the *premier corner* of Coconut & Los Cedros in Anna Maria. Oceans Blue is a very short walk (only 0.15 miles) to the gorgeous, white sandy beaches of Anna Maria Island, just north of Pine Ave. This *ultimate beach house*...
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Create unforgettable memories at “Mia Bella” located on Hammock Road, just north of Pine Avenue, in a *premier deep water canal location* in Anna Maria. Mia Bella is a short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *very spacious beach house* has been fully renovated...
Featured review
Salty Mermaid Vacation Rental in Anna Maria Island- Even before arriving to Mia Bella, the communication with both Bella and David was incredible. They both go above and beyond to make you feel comfortable...
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Welcome to Hammock Hideaway! .02 Miles to Pine Ave. Shopping, Restaurants, and more! .03 Miles to AMI Beaches Private Heated Pool, BBQ Grill, Sun Loungers Beach chairs, wagon, and a cooler available Family friendly with pack'n'play and highchair High-speed Wi-Fi, Smart lock for Self-Check-in,...
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Escape to paradise at our stunning vacation rental, located at 230 Lakeview on beautiful Anna Maria Island. This exquisite property offers the ultimate coastal getaway, boasting a brand-new pool and spa where you can unwind and soak up the Florida sun in style. For those seeking outdoor fun, our rental...
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Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 City of Anna Maria | 4 Bedrooms | 4.5 Bathrooms | Sleeps 10 | Heated Pool + Jacuzzi | Rooftop Deck | Shared Dock Luxury Island Living Near Bean Point Welcome to Casa Amiga, a beautifully designed 4-bedroom, 4.5-bath...
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