
Vacation rentals with a pool in Sarasota County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sarasota County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Living The Dream: Heated Pool + Mini Golf +Swings
BNB Breeze Presents: Living The Dream! From the swings at the dining room table and the neon sign, to the moss wall and the private putt-putt course, Living the Dream is fully loaded and is the ultimate luxury vacation home! Located just 15 minutes away from BOTH Lido Key and Siesta Key Beach, this incredible stay includes: ✔ Backyard Putt-Putt Course ✔ Private Heated Saltwater Pool w/ Lounge Chairs ✔ Covered Patio w/ String Lights ✔ Jura Espresso Machine ✔ 65" Frame TV w/ Youtube TV Included!

Luxury Heated Pool Family House-Siesta Beach/DT
Embrace the height of comfort and convenience at your home away from home! Step into this meticulously renovated pool home, where spaciousness and brightness create an atmosphere of sheer luxury. Tucked away on a serene street, it offers a serene setting while keeping you close to Sarasota's prime attractions. Experience the allure of Siesta Key Beach, the vibrant downtown ambiance, and the renowned Fresh Fish Waltz Market—all just moments away. Enjoy easy access to I-75, Nathan Park, and UTC.

ROYS PLACE private, tropical, romantic paradise.
NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

Pool house by the bay
Come stay in our beautiful, Mid-Century Modern, light drenched home just one block from the bay with a private pool. The private yard is surrounded by lush landscaping & the pool is the perfect place to cool off on hot afternoons. The house is spacious & minimally decorated with finds from our world travels. We've recently replaced the bed and the neighborhood is quiet and easy to explore on foot. Note: this is our home, so please expect a warm lived in feel in the space, not that of a hotel.

Your private retreat near Siesta Key Beach.
Welcome to your private Retreat! Nestled at the end of a quiet dead-end street. This distinguished property guarantees a relaxing Florida vacation for everyone! Completely remodeled with Coastal-Modern Decor. 3 bedroom, 2 bath, amazing heated pool home and private back yard is located in the Gulf Gate Estate neighborhood. A short drive (less than 2 miles) to the white coastal sands of Siesta Key Beach, Gulf Gate shopping mall, grocery store, restaurants, cafes. Must be at least 25 years old

The Cottage At Central Park
There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

Tropical Oasis Heated Pool Hot Tub Near Siesta Key
Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

Pool Courtyard, patio w/ fire pit, 2 mls downtown
Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

Tropical Luxury Villa: Pool, Game Room, Near Beach
Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. Bedrooms: 4 private suites, plush linens and blackout shades ensure restful nights. Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. Heated pool & sun loungers Arcade-style game room Fast Wi-Fi & 5-star cleanliness Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today!

Oasis by Siesta Key Beach and Downtown SRQ w/pool
Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

Maggie's Hideaway
This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

Sunshine house +6 min. from Siesta +heated pool
★ "Second floor 1 bedroom 1 bathroom apartment" 🌴 Stylish Retreat Near Siesta Key & Heated Pool! Welcome to your perfect Sarasota getaway! This is pet-friendly home offers a heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.
Popular amenities for Sarasota County rentals with a pool
House rentals with a pool

Deja Blue Villa Salt Water Heated Pool & Spa

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Morning Side

Coastal Home in Sarasota-8min from Siesta Key

Lake Front House with a Pool

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

Siesta Key private pool house/ beach!

The Blessing House- Htd Pool/Spa, Close to Beaches
Condo rentals with a pool

Gateway to Siesta Key - 1/2 Mile to the Beach

Cozy 1BR Beach Condo on Siesta Key!

On the Beach; Siesta Key SunBum Studio

LIDO KEY 1 BR/1Bath Heated Pool 16

Sunset and beach view from your balcony Unit 403

Siesta Key Ground Floor Condo 2BR On Trolley Line

Oceanview on LBK: Open Tomm & Wed, $140/nt + Fees!

Siesta Key Beach Front Condo
Other vacation rentals with a pool

2 BR condo in Siesta Key w/ Private beach access

Retreat by the Bay-Heated Saltwater Pool

Modern coastal downtown home w/saltwater pool

Homey Downtown Studio Apartment

Heated Pool-Siesta Key 10 min-King Adjustable bd

Walk to Lido Beach &St. Armands -grill/HEATED POOL

Cozy Condo in Siesta key with boat dock

Siesta Key Modern Retreat with Heated Pool & Spa
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- John's Pass
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Cortez Beach
- Anna Maria Public Beach
- Lido Key Beach
- Vinoy Park
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- North Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- Englewood Beach
- North Beach At Fort DeSoto Park
- Point Of Rocks
- Don CeSar Hotel
- Lakewood National Golf Club
- Marie Selby Botanical Gardens
- Things to do Sarasota County
- Nature and outdoors Sarasota County
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