Holiday rentals with a pool in Palmetto

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

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

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 )

Ellenton Getaway

Central, cozy & convenient. Your FL getaway awaits! Relax in this cozy 508 sq ft mobile home in a friendly RV community in Ellenton, FL. Sleeps 3 with a king bed, queen sofa sleeper, and full bath. Just 1 mile from I-75, you’re perfectly located for a beach and shopping getaway. Spend your days exploring nearby Bradenton, Sarasota, St. Pete, or Tampa—offering white-sand beaches, dining, local boutiques, and top shopping spots. A laid-back retreat close to Florida’s best coastal experiences.

Coastal Paradise w/private heated pool

Your comfortable home away from home. Centrally located to anything you want. Feel the Florida tropical feel here in your private resort style pool patio area. Nestled in palm trees you will feel relaxed. Enter your personal entrance to the stairway to your private upstairs retreat with 1300 sq ft of private Florida living. We take pride in being Superhosts and giving you the service you deserve. Please read more about our cozy home to see if it's a good destination for you and your group.

Summer Breeze 3B2BA Pool/Theater

This cozy abode offers a generous layout with a comfy sectional sofa in the main living area. The kitchen is fully equipped with appliances and all the essentials for preparing tasty meals while you're here. Step outside to the furnished, screened sunroom and savor a meal outdoors in the crisp air. Movie buffs will love the home theater with a popcorn machine for movie nights. Take a dip in the private pool and kick back for ultimate relaxation. The fenced backyard is great for family fun.

Island Home 5 min to Park, 25 min to Beach, Pool

Soak up the Florida sunshine from this inviting 1969 home on Snead Island! Whether it's the oceanside air, or the beachy design of this impeccably clean vacation rental, guests find themselves relaxing as soon as they arrive. Our light-filled interior includes a fully equipped kitchen and all the comforts of home. Spend time by the pool & hot tub, then head to the shores of lovely Anna Maria Island (14 miles away) for a beach picnic just in time for sunset! (Message me about multiple pets)

*Memorable Vacation* Heated pool-Playroom & more

This is our dream vacation home, every detail in this house was made with a lot of love and care. Our house is fully equipped. We tried to create a happy and calm environment so we can run away from the daily stress of our lives and we proudly accomplished that because every time we spend days here it's like a recharge. If you're looking for a place to recharge and enjoy yourself or with your family and friends our house is the place for you. We will be very pleased and happy to host you.

Bradenton Gem - BRAND NEW POOL!

** NEW POOL! ** You’re going to love this! The house is central to everything. World-Famous beaches 15 minutes away. Explore up-and-down the coast... Anna Maria Island, Holmes Beach, Coquina, Longboat, Lido, Siesta, etc. Downtown Bradenton (incl Bishop Museum, RiverWalk and Pier 22 Restaurant) is only 1 mile away. Tampa and Sarasota attractions, including the Ringling Museum, Sarasota Jungle Gardens, Busch Gardens, St. Pete's Pier, wildlife Preserves all around… fun for the whole family!

Waterfront Retreat•Pool•PingPong•Near AMI Beaches

Relax at this cozy waterfront cottage with a private pool, & a short drive to Anna Maria Island’s white-sand beaches. 2BR/2BA with two living areas include a bright Florida room overlooking the canal. Enjoy ping pong and a putting green ⛳. Start your mornings with coffee on the dock, watching fish jump out of the water. Fast WiFi, workspace, beach gear, and a kitchen with cooking essentials. Perfect for beach days, family getaways, or a relaxing coastal escape.

Heated Pool Riverfront / Ferry to Beach /Game Room

Elevated Hospitality, Thoughtfully Delivered Experience true white-glove hospitality. Our dedicated team responds within minutes, with hands-on management and a quality inspector ensuring every detail is thoughtfully prepared before you arrive. Throughout your stay, we remain available and attentive to any need—so you can relax and enjoy a seamless, comfortable experience. With warm days, fresh air, and beautiful river views, spring here is simply unforgettable.

Designer 2BR Retreat w/ Private *Heated* Pool!

Step into a thoughtfully designed retreat where comfort meets style. The primary suite offers a king bed, plush mattress, built-in desk, walk-in closet, and private en-suite. Vaulted ceilings and an open layout create an airy feel, while the split-bedroom plan adds privacy. Outside, a screened-in patio with a bar, TV, wine fridge, and ice maker sets the scene for relaxing evenings, along with a private pool and cozy fire pit—your own slice of Florida paradise.