Holiday rentals with a kayak near Anna Maria Island

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

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

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.

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

Pergola Oasis | Walk to Beach + Outdoor Living

Welcome to Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to the white sandy beaches of Anna Maria Island, this home features a private covered pergola with outdoor lounge seating and dining, creating the perfect space to relax day or night. Steps from shops and eateries, with nearby bike and golf cart rentals, plus access to community amenities including a boat ramp, kayak launch, fishing dock, and tennis & pickleball courts.

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.

4-Bed Coastal Retreat w/Ht Pool, Private, Near AMI

Welcome to Las Tres Palmeras in Bradenton, FL! A single-level home less than 7 miles from Holmes Beach/Anna Maria Island and 24 miles from Siesta Key. A small private beach is just a 15-minute walk (2-minute drive)! Relax in a high-end, quiet neighborhood on a large private lot surrounded by tall fences, palms, and tropical foliage. Fully stocked with family-friendly amenities—everything you need for a comfortable and unforgettable stay.

Limited Availably w/ Private Boat Dock & 30' Pool

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

“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.

Backyard Bliss Anna Maria Island

Welcome to Backyard Bliss, where resort-style living meets premier location! With the powdered sands of the Gulf of Mexico only 500 steps away and a retreat that offers endless amenities, a stay at Backyard Bliss will guarantee a smile on your face when you’re here, and a frown when you have to leave.