Vacation rentals with a kayak near Bean Point Beach

4.98 out of 5 average rating, 114 reviews

A bright and airy living area features large windows allowing natural light to fill the space. Comfortable seating is arranged around a woven coffee table, with art pieces adorning the walls. A door leads to outdoor views, enhancing the inviting atmosphere.

Home in Terra Ceia

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.

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.96 out of 5 average rating, 112 reviews

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

Superhost

The outdoor area showcases a heated saltwater pool surrounded by lounge chairs and a covered seating area. A manicured artificial turf putting green is prominently featured, providing a playful touch to the spacious backyard, which is framed by lush landscaping and bright skies.

4.79 out of 5 average rating, 368 reviews

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.

5 out of 5 average rating, 108 reviews

A plunge pool features a vibrant blue tiled interior, flanked by a wooden frame. Two pink flamingo floaties rest on the water's surface. A greenery wall in the background is adorned with a softly illuminated sign reading 'Tiny Oasis.'

Guest suite in Largo

Tiny Oasis | Pool | Stocked Stay Near Indian Rocks

Welcome to The Tiny Oasis! A cozy boutique style retreat in Largo, FL, near Indian Rocks and Clearwater Beach that’s packed with luxury. Lounge by the plunge pool, fire up the Blackstone or enjoy an outdoor movie night. Unique touches and a 5-star experience prove that small spaces make big memories! Tap ‘Show More’ below! What’s There To Look Forward to? 👙Plunge Pool 🚿Outdoor Shower 🔴 Corn Hole ⛱️ Beach Gear 🍔Grill 🅿️ Private Parking 🍳Cook at Home 🧺 Your own private Washer/Dryer

5 out of 5 average rating, 15 reviews

Home in Holmes Beach

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.

5 out of 5 average rating, 7 reviews

Home in St. Petersburg

Mid-century cottage on Coffee Pot Bayou in Old NE

Water views of Coffee Pot Bayou and private dock! Due to owner's severe allergies NO SERVICE ANIMALS OR GUIDE DOGS. This beautiful home is located in the Old Historic Northeast neighborhood with relaxing water views of Coffee Pot Bayou. This lovely residence is perfect for anyone looking to enjoy the best of Saint Petersburg. Enjoy a cup of coffee from the seating at the dock or take a walk down to north shore park! Please let me know if you have any questions!

A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

4.95 out of 5 average rating, 190 reviews

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.

An aerial view of a beachside home is presented, featuring a large porch facing the sandy shore. Colorful kayaks and a stand-up paddleboard are placed on the sand, while numerous lounge chairs are positioned along the beach, surrounded by clear turquoise waters.

4.96 out of 5 average rating, 99 reviews

ami skyview

When you open your door and step out, you will enjoy your own private white sandy beach, with sparkling blue/green, Gulf/Bay water. The location and view are incredible, only a blocks walk, to the famous Anna Maria City Pier, Pine Avenue, restaurants boutiques and shops. Enjoy kayaks, paddle boards and bicycles, all FREE, for our guests. Come and enjoy paradise! There is only one camera located at the front entrance (street side).

Guest favorite

4.89 out of 5 average rating, 76 reviews

Serendipity |Hot Tub | Golf Cart | Elevator | Pet

Welcome to Serendipity, a luxury 4-bedroom beachfront home on the North End of Anna Maria Island, steps from Bean Point Beach. Enjoy direct beach access, a beachfront hot tub, elevator to all floors, and an included 6-passenger golf cart. King beds in every bedroom, pet-friendly (pre-approval required), plus bikes, paddleboards & kayak included. Perfect for unforgettable island sunsets and relaxed coastal living.

A screened enclosure surrounds a private swimming pool, providing a sunny outdoor space. Comfortable seating is visible alongside a dining area with a table and chairs. Lush greenery and palm trees can be seen in the background, enhancing the tropical atmosphere.

5 out of 5 average rating, 24 reviews

“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!

A spacious outdoor area features a sparkling pool surrounded by lounge chairs and palm trees. A tiki hut provides shade, alongside a putting green. In the background, a rock waterslide is visible, creating an inviting atmosphere for relaxation and recreation.

5 out of 5 average rating, 30 reviews

Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT

Tortuga Bay is a canalfront 5BR/3BA escape just a 2-minute walk to the beach 🏖️! Enjoy a private pool with spa & waterslide 💦, tiki hut, BBQ, new putting green ⛳, private dock for a 30ft boat ⚓, and 2 kayaks 🛶. Walk to Pine Ave dining and shops, relax in stylish coastal interiors, and experience nonstop island fun! 🌞