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Holiday rentals with a pool in Sarasota Beach

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Top-rated rentals with a pool in Sarasota Beach

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Top guest favourite
A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.
Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

ValueLocationIndoor spaces

4.94 out of 5 average rating, 106 reviews
Guest favourite
Apartment in Siesta Key

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

FamilyLocationBathroom

4.79 out of 5 average rating, 110 reviews
Guest favourite
The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.
Apartment in Siesta Key

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

FamilyValueSolo travel

4.85 out of 5 average rating, 110 reviews
Top guest favourite
A covered patio area features modern wicker furniture with white cushions, positioned around a glass coffee table. The inviting space overlooks a pristine pool, surrounded by a protective screen. Lush greenery is visible in the background, enhancing the tranquil setting.
Home in Sarasota

Luxury Pool Family Oasis-Siesta Key/DT 3BR/2BA

Welcome to your home away from home! This renovated, spacious, and bright pool home will immerse you in a luxurious experience the minute you arrive. Located on a lush, quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in the USA), 10 minutes to downtown (with fantastic restaurants and shopping), and within walking distance of the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake Park, and the new UTC mall!

LocationValueCheckout

4.96 out of 5 average rating, 154 reviews
Guest favourite
A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.
Home in Sarasota

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

FamilyLocationNearby

4.8 out of 5 average rating, 189 reviews
Guest favourite
Apartment in Siesta Key

Gulf Views | Walkable | Spacious

Spacious Gulf-view 2BR condo perfect for families & groups—featuring a rare 2-queen guest room, king master, and plenty of room to spread out. Walk to the beach, restaurants, coffee, and more—no car needed. Easy beach access + FREE loungers make beach days effortless. Heated pool, fast WiFi & fully stocked with beach gear. Clean, spacious & comfortable in a prime, walkable location. (Daytime weekday construction nearby may cause intermittent noise in 2026.)

ValueLocationTV

4.92 out of 5 average rating, 166 reviews
Top guest favourite
Apartment in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

ValueLocationSleep quality

4.92 out of 5 average rating, 172 reviews
Guest favourite
A modern living area showcases a comfortable sectional sofa and armchair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a media console. Natural light floods the space through sliding glass doors that lead to a balcony, enhancing the open feel.
Apartment in Siesta Key

Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything

A spacious and quiet 2-floor, 2 bedroom, 2.5 bathroom condo that lives like home and is close to everything Siesta Key offers. Spread out and enjoy YOUR vacation! Your condo features large rooms, comfy and modern surroundings, (2) Master Bedrooms upstairs, and you are steps away from a gorgeous heated pool that you can view from your lanai. This is the perfect condo for you and your family to relax in and simply enjoy your time in Siesta Key!

LocationFamilySleep quality

4.88 out of 5 average rating, 179 reviews
Guest favourite
A spacious backyard features a heated private pool surrounded by a paved area. Lounge chairs are positioned around the pool, with umbrellas providing shade. Lush greenery and a fence frame the yard, creating a serene outdoor setting, ideal for relaxation.
Home in Gulf Gate Estates

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

FamilyLocationBathroom

4.8 out of 5 average rating, 138 reviews
Top guest favourite
Home in Sarasota

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

FamilyValueLaundry

4.98 out of 5 average rating, 130 reviews
Guest favourite
Flat in Downtown Sarasota

Central Downtown Apartment with Pool and Gym

Stay in the heart of downtown in this stylish 2 bed, 2 bath apartment. Enjoy a bright open layout, fully equipped kitchen, cozy living area, and two comfortable bedrooms including a private primary suite. Building amenities include a sparkling pool with games and fully equipped gym. Walk to top restaurants, shops, and nightlife. Perfect for business trips or weekend getaways!

FamilyLocationComfort

4.88 out of 5 average rating, 210 reviews
Top guest favourite
A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.
Apartment in Siesta Key

Breathtaking Beachfront Views in Siesta Key

Welcome to your slice of paradise on Siesta Key, where beachfront bliss meets laid-back island vibes! Situated in the heart of the world-renowned Siesta Key Beach, our condo offers a spectacular beachfront experience! Wake up to breathtaking views, step outside your door and feel the powdery sand, inviting you and your family to sink into relaxation, adventure, and sun!

FamilyValueAmenities

5.0 out of 5 average rating, 105 reviews

Popular amenities for Sarasota Beach rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.
Home in Sarasota

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

LocationFamilyDecor

5.0 out of 5 average rating, 110 reviews
Guest favourite
The outdoor area features a heated pool surrounded by lounge chairs, providing ample space for relaxation. A dining set is positioned nearby, accompanied by an umbrella for shade. Lush greenery and palm trees border the property, complementing the serene atmosphere.
Home in Sarasota

Rhodes Retreat - Beautiful Pool and Backyard Space

ValueLocationOutdoor spaces

4.91 out of 5 average rating, 124 reviews
Top guest favourite
A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.
Home in Sarasota

Oasis by Siesta Key Beach and Downtown SRQ w/pool

FamilyLocationCheck-in

4.94 out of 5 average rating, 143 reviews
Guest favourite
The exterior of a newly renovated home is shown, featuring a light-colored brick facade and a modern garage door. A well-maintained driveway leads to the entrance, which is accentuated by a bright orange door. Landscaping includes gravel beds and low-maintenance plants amidst partial cloud cover.
Home in Sarasota

Gorgeous renovation with pool, minutes from beach

LocationValueAir conditioning

4.88 out of 5 average rating, 103 reviews
Guest favourite
A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.
Home in Gulf Gate Estates

Beautifully Remodeled Home with Pool Near Siesta

FamilyValueLong stay

4.95 out of 5 average rating, 165 reviews
Top guest favourite
Home in Sarasota

Heated&Renovated Pool•Beach Retreat•15m to Siesta

FamilyLocationBeach

4.93 out of 5 average rating, 409 reviews
Superhost
An outdoor space showcases a heated saltwater pool with a calm blue hue, surrounded by comfortable lounge chairs. The area is framed by lush greenery and fencing, enhancing privacy. The backdrop features a gently lit sky at dusk, complementing the home's modern design.
Home in Sarasota

Retreat by the Bay-Heated Saltwater Pool

LocationFamilyParks

4.95 out of 5 average rating, 110 reviews
Top guest favourite
Home in Arlington Park

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

ValueLocationWifi

5.0 out of 5 average rating, 117 reviews

Apartment rentals with a pool

Guest favourite
A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.
Apartment in Siesta Key

Siesta Key Beach Front Condo

LocationValueView

4.91 out of 5 average rating, 137 reviews
Top guest favourite
A three-story condominium building is shown, featuring a combination of palm trees and lush green landscaping at the forefront. Balconies are visible on each level, with a red-tiled roof adding a distinct character to the architecture.
Apartment in Siesta Key

Seaside on Siesta Key Beach

LocationFamilyKitchen

4.95 out of 5 average rating, 127 reviews
Superhost
A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.
Apartment in Siesta Key

Crystal House on Siesta Key Beach

FamilyLocationNearby

4.88 out of 5 average rating, 146 reviews
Top guest favourite
Apartment in Siesta Key

Siesta Key Condo. Checkout our great rates!

ValueLocationAmenities

4.96 out of 5 average rating, 141 reviews
Guest favourite
The exterior of the condo features a serene pool area surrounded by tropical landscaping. Lounge chairs are positioned near the pool, with a tiki bar visible in the background, creating a relaxed atmosphere amidst the vibrant palm trees and colorful building.
Apartment in Siesta Key

5213A Calle Menorca - Siesta Key Village Condo

LocationValueOutdoor spaces

4.86 out of 5 average rating, 129 reviews
Top guest favourite
A bright and airy living space features a modern sofa facing a sleek coffee table. The open kitchen is visible in the background, showcasing white cabinetry and bar seating with stylish stools. Light fills the room through large windows, enhancing the spacious feel.
Apartment in Sarasota

Modern Coastal Oasis - Beach and Private Patio

LocationFamilyOutdoor spaces

4.96 out of 5 average rating, 164 reviews
Top guest favourite
A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.
Apartment in Siesta Key

Beachfront Siesta Key | Gulf View + Private Beach

FamilyLocationAccess

4.97 out of 5 average rating, 397 reviews
Guest favourite
A spacious living area is furnished with comfortable seating, including a mix of plush sofas and armchairs. A coffee table sits at the center, and a television is discreetly positioned on a stand. Natural light is welcomed through large windows, enhancing the room's brightness.
Apartment in Siesta Key

Siesta Key Beach Escape

LocationValueComfort

4.9 out of 5 average rating, 145 reviews

Other holiday rentals with a pool

Superhost
Flat in Siesta Key

Elegant 2BR + Den | Heated Pool | Near Beach

FamilyValueSleep quality

4.79 out of 5 average rating, 206 reviews
Superhost
A covered seating area is furnished with comfortable wicker chairs and lounge chairs featuring green cushions. Lush plants and palm trees enhance the outdoor space, while a view of the shared garden can be seen in the background. A book and a sun hat rest on a side table.
Flat in Sarasota

Minutes to Siesta or DT w/heated pool and Hot Tub

FamilyLocationGetting around

4.87 out of 5 average rating, 133 reviews
Guest favourite
A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.
Home in Arlington Park

Private Heated Pool Retreat for Two Families

ValueFamilyShared spaces

4.95 out of 5 average rating, 63 reviews
Guest favourite
A well-lit bedroom features a spacious bed with a light-colored bedspread. Two large windows offer views of the outdoors, framed by sheer curtains. A ceiling fan hangs above, providing airflow. A comfortable chair and a dresser add practical elements to the inviting space.
Home in Sarasota

The Palms Away

ValueFamilyCheck-in

5.0 out of 5 average rating, 39 reviews
Top guest favourite
Cottage in Lido Key

Studio by Lido Beach w heated pool

ValueLocationDecor

4.93 out of 5 average rating, 57 reviews
Guest favourite
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.
Flat in Sarasota

Modern 2BR Retreat · Heated Pool · Near Siesta

LocationFamilyGrill

4.94 out of 5 average rating, 90 reviews
Top guest favourite
Apartment in Gulf Gate Estates

10 Min to Siesta Key • Pool View • Pet Friendly

FamilyLocationParks

4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Siesta Key

Siesta Key House, Pool & Hot Tub, 1 mile to beach

FamilyLocationComfort

5.0 out of 5 average rating, 15 reviews

Destinations to explore