Vacation rentals with a pool in Sarasota Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sarasota Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.

Home in Sarasota

4.88 out of 5 average rating, 159 reviews

5 minutes to private Siesta Key Beach + 2 pools

Escape to this luxurious 1st-floor condo on Siesta Key, just 5 minutes from the award-winning Siesta Key Beach. Enjoy private access to its soft, white sand and turquoise waters. Perfect for families, the condo offers two heated pools, lighted tennis and pickleball courts, a fishing pier, gym, and sauna for endless fun and relaxation. Nestled in a tropical setting, it’s the ideal spot for your beach vacation, staycation, or a peaceful getaway. Everything you need for an unforgettable experience!

Guest favorite

A private pool area is framed by lush tropical landscaping, featuring palm trees and vibrant plants. Comfortable lounge chairs are positioned beside the inviting blue water. A boat dock can be seen in the background, offering scenic views of the bay.

Home in Sarasota

4.96 out of 5 average rating, 71 reviews

True Island Living House/beach/water views

Charming Bayfront Home in heart of Siesta Key. 3 bdrm/3.5 bath, full water views, spectacular sun rises, private, gas heated pool, boat dock/ lift, outdoor sitting area /lush tropical landscape. Open floor plan, contemporary decor, gas fireplace, hardwood floors throughout, updated kitchen, stainless steel appliances, granite counters and a full walk-in pantry. 2 Master Suites upstairs and one guest bdrm on main floor. Washer and dryer inside, 3 TV’s. Outdoor shower. Fishing. Parking for 2 cars.

Guest favorite

A spacious swimming pool is surrounded by palm trees and lounge chairs, reflecting clear blue skies. The pool area is well-maintained, and the building's balcony overlooks the pool, providing a serene atmosphere for relaxation.

Condo in Siesta Key

4.9 out of 5 average rating, 120 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

Top guest favorite

An elegant home exterior is shown, featuring a landscaped yard with manicured grass and palm trees. A private heated pool is centered on the patio, surrounded by lounge chairs. Large windows offer a view of the modern design, enhancing the spacious outdoor area.

Home in Sarasota

5 out of 5 average rating, 19 reviews

Sarasota Escape | Minutes to Beaches + Downtown

HEATED POOL. NONTOXIC + ECO FRIENDLY. Relax with the whole family or bring that group chat trip to life at this peaceful retreat in the heart of Sarasota. Boasting a spacious and nature-inspired design, this home is a short drive to several world class beaches, the downtown Sarasota arts district, 5 star dining, shopping and more. The home is also located within walking distance of a park complete with playground, public pool, tennis + basketball courts, workout area and walking trails.

Guest favorite

A sparkling pool is surrounded by a spacious patio, featuring lounge chairs and a vibrant red umbrella. Lush tropical landscaping creates a serene retreat, providing an inviting space for relaxation and leisure under a clear blue sky dotted with fluffy white clouds.

Home in Sarasota

4.96 out of 5 average rating, 125 reviews

Mid-Century Oasis with Pool in Arlington Park 1

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a mid-century gem offers a serene escape, providing a refreshing interplay of historical charm and modern luxury. Enjoy the separate sunroom/office for those working from home, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool.

Guest favorite

A bright and open outdoor space features a refreshing pool with a pineapple float. Surrounding the pool are multiple lounge chairs and a patio area, with a screened-in porch visible in the background. Sunlight reflects off the water, creating a cheerful atmosphere.

Home in Siesta Key

5 out of 5 average rating, 5 reviews

Designer Home| Sleeps 10| Walk to Beach & Village|

Steps from Siesta Key Beach, this beautifully renovated 3-bedroom, 3.5-bath home offers sophisticated coastal-inspired decor. The master suite has a private screened balcony overlooking the pool with an egg chair swing. A screened patio includes bar seating, a dining area, and a cozy lounge. The first-floor mudroom has a shower for easy beach cleanup. With its classic beach cottage feel and modern amenities, this home is the perfect coastal retreat. Book now!

Top guest favorite

Condo in Siesta Key

4.97 out of 5 average rating, 323 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

Top guest favorite

A modern pool home features a large outdoor space with a sparkling blue pool surrounded by stone pavers. The exterior showcases a combination of light-colored siding and expansive glass windows, providing views into the inviting interior. Lush greenery enhances the tranquil atmosphere.

Home in Siesta Key

5 out of 5 average rating, 9 reviews

Luxury Waterfront Home in Sarasota

Welcome to coastal elegance in Sarasota! - Stunning 4-bed, 4-bath pool home on Palm Island - Recently renovated with modern, open-concept layout - Gourmet kitchen featuring Italian Fulgor cooktop and marble island - Ground-floor master suite with luxury finishes - Sun-filled flex room for versatile use - Private dock access and large, boating-friendly lot - Close to Siesta Key Beach and Village, St. Armands Circle, and downtown Sarasota

Guest favorite

A refreshing pool area is framed by palm trees and overlooks Sarasota Bay. Lounge chairs with red and white stripes are positioned around the pool and hot tub, inviting relaxation. The serene water and lush greenery create a peaceful outdoor environment.

Home in Sarasota

4.8 out of 5 average rating, 10 reviews

Bayfront Beauty: Heated Pool, King size Bed

Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. You will have whole house except two rooms which will be locked and no one will be there. One bedroom with a king size bed. Full size kitchen, family room, pool and gorgeous view on the salty bay for nature lovers.

Guest favorite

A large heated outdoor pool is surrounded by lounge chairs, offering ample space for relaxation. The pool area is framed by palm trees, with a view of the condominium building and parked cars in the background, creating a welcoming environment.

Condo in Siesta Key

4.94 out of 5 average rating, 110 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

Guest favorite

A freeform pool is framed by lush tropical landscaping, featuring multiple waterfalls that flow into the water. The elevated home overlooks the pool area, complemented by large windows and a wraparound balcony.

Island in Sarasota

4.97 out of 5 average rating, 328 reviews

NEW 3/NTS JULY OPEN! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Guest favorite

The image shows a tranquil poolside setting with lounge chairs arranged beside a heated pool. A decorative tray with candles is placed in the foreground, surrounded by smooth stones. Soft lighting from the surrounding plants creates a relaxed atmosphere as evening approaches.

Apartment in Sarasota

4.96 out of 5 average rating, 27 reviews

Modern 2/1+ shared, heated pool +4 min Siesta

Welcome to your perfect Sarasota getaway! This is pet-friendly peaceful multifamily (3 apartment) home, offers a shared fenced garden, shared heated pool , and a prime location just 5 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.