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Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

Heated Pool - Just 1 mile to Beach! Updated/Fun!

Fun for the whole family!! Only 1 mile to the Beach! This newly updated home comes fully furnished with 4 bedrooms and 3 bathrooms. With a total of 6 beds, the home sleeps 10 comfortably. The Heated Pool is perfect for swimming, and being only 1 mile to the world famous Siesta Key Beach Access 12, this home also makes beach going easy and convenient. Inside, the home is clean, spacious and newly updated and equipped with smart tvs, air hockey table, pool table foose-ball, Pac-Man - fun for all

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Private 30’ Pool &Boat Dock & Only Steps to Beach

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

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Walk to Beach! Waterfront Lux Retreat w/Kayaks

As seen on the Emmy award-winning show, Staycation. Experience the serene beauty of a waterfront Indian Rocks Beach Home. Wake up to breathtaking views of the water, right from your window. Enjoy the luxury of kayaking or fishing off your private boat dock. Spend evenings gathered around the fire pit or showcase your culinary skills with our grill. Just a 7-minute walk and you'll find yourself on the pristine white sands of Indian Rocks Beach. Kayaks and boat lift available.

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

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Your private Waterfront Pool home!

Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422

2/2 Beach House Apt. on Siesta Key. Heated Pool

Siesta Key waterfront apartment that sleeps 6. This split-plan, 2-bedroom, 2-bath “Beach House” features a full kitchen and recent updates. Bedroom 1 has a king bed, bedroom 2 has a queen, and the living room offers a sleeper sofa. Enjoy a 75” smart TV in the living room and a private screened lanai with canal views to Sarasota Bay. Located in a charming, quaint resort with a heated swimming pool, and guests enjoy free use of kayaks!

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New Pool Tropical Waterfront Dock & Optional Boat

Located on a highly desirable street, the house is perched high above Curry Creek offering spectacular water views from every room. The property includes a boat ramp to avoid the public launch. Three kayaks (two tandems and one single). Two miles from Nokomis Beach and only half a mile from The Legacy Bike Trail. You can do so many fun things, or just have a drink on the dock and watch the manatees. Pet Friendly

Renovated Beach Paradise. Ground Floor unit 64

Completely renovated. Everything is new. Amazing location. This condo has patio. Condo management will help you with your accommodation. The unit offers everything you may want and need!!! Escape to our Tropical Paradise with beautiful beach, heated pool and awesome sunsets. Beach side condo located on the first floor, just a short walk from your door to the beach and pool. No crossing the streets.

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Waterfront Pool Home Steps to Beach

Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!