
Vacation rentals with a pool in Sarasota
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sarasota
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!

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.

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.

Beautifully Remodeled Home with Pool Near Siesta
It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

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!

Oceanview: Open Wed & Thurs, $225/nt + Fees!
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

The Wisteria Oasis W/swings, heated pool & hot tub
So much fun to be had and memories to be made at this charming cottage! Revitalize and rejuvenate at our serene 3 bedroom cottage. Perfect for families looking for a peaceful and relaxing vacation, our home boasts a private fenced-in backyard with a heated saltwater pool, hot tub, hammock, and swings for your ultimate comfort. The added bonus of a fire pit allows for perfect evenings spent making s'mores and enjoying quality time with your loved ones.

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!

Family Retreat w/Pool&HotTub 5 min to Siesta Key!
Family-Friendly 3BR Home w/ Private Heated Pool, Hot Tub & Backyard– Near Siesta Key! Located just minutes from world-famous beaches, and a wide variety of dining, shopping, and entertainment options, this home is the perfect base for your Sarasota vacation. Whether you’re planning a family trip, a couples’ retreat, or a friends’ getaway, you’ll love the blend of comfort, convenience, and fun!
Popular amenities for Sarasota rentals with a pool
House rentals with a pool

The Oasis

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

Beautifully Remodeled Heated Pool Home in Sarasota

Salt Water Heated Pool|Arcade Games|Game Room

Luxe Oasis Mins to Beach & Downtown w/Heated Pool

The Blessing House- Htd Pool/Spa, Close to Beaches

Sunshine House, close to Downtown

Private Siesta Beach House Oasis with Heated Pool.
Condo rentals with a pool

Sunshine house +6 min. from Siesta +heated pool

Cozy 1BR Beach Condo on Siesta Key!

On the Beach; Siesta Key SunBum Studio

LIDO KEY 1 BR/1Bath Heated Pool 16

Luxury 3/3 Margaritaville Resort

Sunset and beach view from your balcony Unit 403

Siesta Key Beach Front Condo

Near beach. Daily rentals. Pool. king bed
Other vacation rentals with a pool

Chic Oasis | Private Heated Pool| Legacy Trail

Toes In The Sand | Private Pool, Walk to Beach!

Sarasota Sunshine House with Heated pool & E-bikes

Cabana/Guest house w/spa/pool 5min to Siesta key.

Coastal Home in Sarasota-8min from Siesta Key

Pool house with outdoor shower, 10 minutes from SK

Turtle Bay - minutes to Boca Grande!

Private Oasis: Mini Golf and firepit. 2 king beds.
Quick stats about vacation rentals with a pool in Sarasota
Total rentals
1K properties
Nightly prices starting at
€ 9 before taxes and fees
Total number of reviews
31K reviews
Family-friendly rentals
820 properties are a good fit for families
Pet-friendly rentals
400 properties allow pets
Rentals with dedicated workspaces
630 properties have a dedicated workspace
Destinations to explore
- Seminole Vacation rentals
- Miami Vacation rentals
- Central Florida Vacation rentals
- Orlando Vacation rentals
- Saint Johns River Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Panama City Beach Vacation rentals
- House rentals Sarasota
- Rentals with a fire pit Sarasota
- Condo rentals Sarasota
- Guesthouse rentals Sarasota
- Family-friendly rentals Sarasota
- Rentals with beach access Sarasota
- Beach condo rentals Sarasota
- Rentals with a patio Sarasota
- Rentals with a hot tub Sarasota
- Rentals with a kayak Sarasota
- Tiny house rentals Sarasota
- Bungalow rentals Sarasota
- Beachfront rentals Sarasota
- Rentals with lake access Sarasota
- Villa rentals Sarasota
- Rentals with a washer and dryer Sarasota
- Boutique hotel rentals Sarasota
- Townhouse rentals Sarasota
- Luxury rentals Sarasota
- Rentals with breakfast Sarasota
- Rentals with an EV charger Sarasota
- Private suite rentals Sarasota
- Cottage rentals Sarasota
- Smoking-friendly rentals Sarasota
- Fitness-friendly rentals Sarasota
- Rentals with a fireplace Sarasota
- Waterfront rentals Sarasota
- Beach house rentals Sarasota
- Pet-friendly rentals Sarasota
- Apartment rentals Sarasota
- Rentals with outdoor seating Sarasota
- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Lido Key Beach
- Anna Maria Public Beach
- Cortez Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Streamsong Resort
- Gulfport Beach Recreation Area
- Jannus Live
- Manasota Key Beach
- ZooTampa at Lowry Park
- North Beach
- Adventure Island
- River Strand Golf and Country Club
- Splash Harbour Water Park
- Things to do Sarasota
- Nature and outdoors Sarasota
- Things to do Sarasota County
- Nature and outdoors Sarasota County
- Things to do Florida
- Sightseeing Florida
- Wellness Florida
- Tours Florida
- Art and culture Florida
- Nature and outdoors Florida
- Entertainment Florida
- Food and drink Florida
- Sports activities Florida
- Things to do United States
- Sightseeing United States
- Entertainment United States
- Wellness United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Sports activities United States
- Nature and outdoors United States