Vacation rentals with a kayak in Bradenton Beach

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

Limited Availably w/ Private Boat Dock & 30' Pool

✨ 4.95★ GUEST FAVORITE! Canal Front & 1/2 Block to Beach Experience the ultimate AMI getaway! This 4.95-star tropical oasis features a wide canal with a 30' boat/fishing dock, a massive 16'x30' private pool, and is just a 1/2 block to the beach. Walk to everything:• 3-min walk to Bay Beach, 15 to Bean Point• Steps to Pine Ave shopping & City Pier• Stroll to Waterfront Restaurant & Two Scoops. Bring your boat, lounge poolside, or hit the sand. Perfect island living with 200+ rave reviews!

Near Anna Maria Island Beach-Studio on Wares Creek

This place delivers ample living space,latest amenities, and quick,easy access to Coastal Water,Anna Maria Island Beaches,and city Down Town. Spacious,bright,and tastefully furnished,with great screened porch,cozy gazebo,sparkling heated swimming pool . We supply 2 kayaks and everything that you might need to spend a day at the beach or on the water.We also supply fishing rods(adults and kids) and bait bucket. We can take you on a coastal trip in our boat if you wish (extra charges will apply )

Heated saltwater pool home - turf putting green

Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Cozy AF Tiny-House Oasis

Awarded a *Unique Stay* by Airbnb, welcome to the **Cozy AF Tiny-House Oasis**, a rustic tiny home that started its journey as a world-traveling storage container. Now transformed into a charming cottage, it’s filled with unique and fun details waiting to be discovered. Enjoy the entire backyard, complete with a hot tub, koi pond, fire pit, hammocks, greenhouse, and even a bunny garden! Our goal is not just to offer you a place to stay but an experience you’ll cherish forever

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.

NEW Canal Family Home - Pool, Kayaks, Game Room

Just minutes from Anna Maria Island's turquoise water and powder-white beaches, Sandpiper Retreat is your home base for the ultimate Gulf Coast getaway. Wake up to canal views, paddle out to Robinson Preserve at sunrise, then dive in your private heated pool and spa when you come home. A dedicated game room with pool table, foosball, and ping-pong keeps everyone happy once the sun finally sets.

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!

“Topside” luxury home in Cortez Village

Upscale 2BR/2BA condo in historic Cortez Fishing Village!** Walk to 4 waterfront restaurants or take a 5-min drive (15-min walk) to Anna Maria Island. Enjoy a fully renovated space with a screened in pool, modern kitchen, private balcony, Relax in coastal comfort with easy access to beaches, dining, and local charm. Book your stay today!

AMI Sunset Beach - Gulf View Retreat w/ Pool+Decks

AMI's Sunset Beach part of 7 miles of white sand beaches! • 200+ five-star ratings over all sites! • Gulf-views inside home. • Decks with views of Beach + Gulf + Pool. • Heated Pool with sun shelf. • Paddleboard + Kayak + Firepit + Patio + Grill. • High-speed WiFi. • Top floor of duplex. • Central location next to Sunset Beach.