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Vacation rentals with a pool in Siesta Key

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Quick stats about vacation rentals with a pool in Siesta Key

  • Total vacation rentals

    Explore 1,830 vacation rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key vacation rentals start at R 982 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 28,790 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,530 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 280 rentals that welcome pets

  • Rentals with dedicated workspaces

    830 properties have a dedicated workspace

  • Wi-Fi availability

    1,810 of Siesta Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Siesta Key rentals

  • 4.8 Average rating

    Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Siesta Key

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

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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.
Condo in Siesta Key

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!

4.88 out of 5 average rating, 146 reviews
Top guest favorite
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.

4.94 out of 5 average rating, 106 reviews
Top guest favorite
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.
Condo in Siesta Key

Seaside on Siesta Key Beach

Seaside on Siesta is the perfect walkable location to everything you need for a seaside getaway! Located directly across the street from Siesta Key Beach. Walk or take the FREE trolley (trolley stop located feet from our front patio) to Siesta Key Village, Stickney Point, or Turtle Beach First floor unit so no need to wait on elevators. The spectacular white quartz beach and crystal clear water awaits you just outside your door! Search "Seaside on Siesta Tour" on Youtube for a video tour.

4.95 out of 5 average rating, 127 reviews
Guest favorite
Condo 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.

4.79 out of 5 average rating, 110 reviews
Guest favorite
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.
Condo 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.

4.85 out of 5 average rating, 110 reviews
Guest favorite
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.

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

Elegant 2BR + Den | Heated Pool | Near Beach

Welcome to your perfect getaway! This recently remodeled ground-floor apartment features a washer/dryer, dishwasher, microwave, 2 flat-screen TVs, and 1,200 sqft of space. With 2 bedrooms and a 3rd room (den, see photos), it comfortably sleeps 6 guests max. in beds (1 king, 2 queens) and includes a private breakfast patio. Gumbo Limbo is a mini resort with 2 duplexes, sharing a heated black-bottom lagoon-style pool. Enjoy free parking (2 cars max), beach chairs, sun umbrellas, and Wi-Fi.

4.79 out of 5 average rating, 206 reviews
Guest favorite
Condo in Siesta Key

Beach Retreat - Jamaica Royale Unit #52

Casually elegant condo fully remodeled in 2025, and very close to beach! One bedroom, one bath unit includes quartz kitchen counters, new appliances, king bed and relaxing patio. Perfect size for 2 guests! No need to cross busy roads to get to stunning white sand; just a 5 -10 minute walk along lush grounds which boast 3 heated pools. Beach gear provided, and unit is stocked with linens and kitchen utensils. Minutes away from Siesta Village and other wonderful dining and activities.

4.86 out of 5 average rating, 138 reviews
Top guest favorite
Condo 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!

4.92 out of 5 average rating, 172 reviews
Guest favorite
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.
Condo 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!

4.88 out of 5 average rating, 179 reviews
Top guest favorite
Home in Siesta Key

Heated pool & Infrared Sauna, 2 min to beach

Our 3-story home offers privacy for multiple families and is just 1 mile from Siesta Key Beach. Call the free shuttle for a quick ride to the Village for shopping and dining. Enjoy TVs in every bedroom, a full kitchen, laundry room, infrared sauna, and beach chairs. Two bedrooms have private baths. Relax in the heated pool and covered outdoor dining area while watching the game, surrounded by palm trees and salty air. SunfishBeachSiesta awaits!

4.98 out of 5 average rating, 104 reviews
Guest favorite
The open living space is highlighted by a circular dining table surrounded by four chairs. A turquoise sofa and coffee table are arranged in the living area, with a large TV mounted on the wall. Natural light fills the room through nearby windows, enhancing the airy atmosphere.
Apartment in Siesta Key

2/2 Beach House Apt. on Siesta Key. Heated Pool

Siesta Key waterfront apartment that sleeps 6. This split-plan, 2-bedroom, 2-bath “Beach House” features a full kitchen and recent updates. Bedroom 1 has a king bed, bedroom 2 has a queen, and the living room offers a sleeper sofa. Enjoy a 75” smart TV in the living room and a private screened lanai with canal views to Sarasota Bay. Located in a charming, quaint resort with a heated swimming pool, and guests enjoy free use of kayaks!

4.8 out of 5 average rating, 264 reviews

Popular amenities for Siesta Key rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
Home in Siesta Key

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!

4.91 out of 5 average rating, 131 reviews
Guest favorite
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

4.8 out of 5 average rating, 138 reviews
Top guest favorite
Home in Siesta Key

Siesta Key, FL - Casa Berano

4.91 out of 5 average rating, 129 reviews
Guest favorite
A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.
Home in Sarasota

Cozy Boho Bungalow Pool/Spa Downtown Sarasota

4.97 out of 5 average rating, 160 reviews
Top guest favorite
A custom pool is framed by elegant lounge chairs and tropical landscaping. Water features create gentle curves, while illuminated details enhance the space as the sunset casts a warm glow. A covered outdoor area is visible in the background, providing seating and entertainment options.
Home in Sarasota

Fruit /Botanical Garden Estate 2 ml to downtown EV

4.97 out of 5 average rating, 105 reviews
Guest favorite
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

4.91 out of 5 average rating, 124 reviews
Guest favorite
An inviting beach scene features a sun umbrella providing shade over a wooden lounge chair, set upon soft, sandy shores. The clear blue sky contrasts with the tranquil turquoise waters, creating a peaceful atmosphere near the shoreline.
Home in Siesta Key

Beachfront Getaway in Siesta Key

4.78 out of 5 average rating, 567 reviews
Guest favorite
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

4.88 out of 5 average rating, 103 reviews

Condo rentals with a pool

Guest favorite
Condo in Siesta Key

Gulf Views | Walkable | Spacious

4.92 out of 5 average rating, 166 reviews
Top guest favorite
A heated pool is surrounded by a tiled deck, with lounge chairs available for guests. Palm trees and blue umbrellas create a tropical atmosphere, while the beach and ocean are visible beyond the pool area under a clear blue sky.
Condo in Siesta Key

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

4.94 out of 5 average rating, 157 reviews
Top guest favorite
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.
Condo in Siesta Key

Beachfront Siesta Key | Gulf View + Private Beach

4.97 out of 5 average rating, 397 reviews
Top guest favorite
Condo in Longboat Key

Island Time: Open Columbus Day Weekend!

4.98 out of 5 average rating, 258 reviews
Top guest favorite
A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.
Condo in Siesta Key

Heated Pools & Spa · Private Beach + Bay Views

4.97 out of 5 average rating, 137 reviews
Guest favorite
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.
Condo in Siesta Key

5213A Calle Menorca - Siesta Key Village Condo

4.86 out of 5 average rating, 129 reviews
Top guest favorite
A landscaped pathway is flanked by vibrant flowering plants and palm trees. Neatly trimmed grass lines the walkway, leading to a serene courtyard. Soft lighting from a garden lantern adds to the peaceful ambiance of this tropical setting.
Condo in Siesta Key

Siesta Key Serenity At The Palm Bay Club

4.94 out of 5 average rating, 176 reviews
Guest favorite
A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.
Condo in Siesta Key

Sarasota Surf & Racquet Club Siesta Key Condo

4.82 out of 5 average rating, 152 reviews

Other vacation rentals with a pool

Guest favorite
Apartment in Siesta Key

New listing - Heated Pool, Private Patio!

4.96 out of 5 average rating, 28 reviews
Top guest favorite
Home in Siesta Key

Siesta Key Village Home

5.0 out of 5 average rating, 20 reviews
Guest favorite
A screened-in pool area features a clear blue pool surrounded by tropical greenery. Two lounge chairs with striped fabric are positioned nearby, alongside a shaded umbrella. The pool deck is spacious, inviting relaxation and leisure in a tranquil outdoor setting.
Home in Siesta Key

Siesta Key home 5 min from beach

4.95 out of 5 average rating, 59 reviews
Top guest favorite
Home in Siesta Key

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

5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Siesta Key

Sunny & Comfy ~ Steps to Siesta Key Beach ~ Pool!

4.97 out of 5 average rating, 33 reviews
Top guest favorite
A serene view of Siesta Key Beach is captured, showcasing soft white sands and gentle turquoise waves. Palm trees frame the scene, and various beach umbrellas are visible in the distance, hinting at a lively beach atmosphere under a clear blue sky.
Townhouse in Siesta Key

Gulf and Beach Views-Steps from Beach and Village

5.0 out of 5 average rating, 49 reviews
Top guest favorite
Home in Siesta Key

Bahama Mama | Tropical Retreat on Siesta Key

5.0 out of 5 average rating, 13 reviews
Guest favorite
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

4.95 out of 5 average rating, 63 reviews

When is the best time to visit Siesta Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 4,616 ZARR 6,041 ZARR 6,728 ZARR 5,288 ZARR 4,404 ZARR 4,551 ZARR 4,043 ZARR 3,683 ZARR 3,307 ZARR 3,405 ZARR 3,798 ZARR 4,469 ZAR
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

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