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Holiday rentals with a pool in South Sarasota

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Quick stats about holiday rentals with a pool in South Sarasota

  • Total holiday rentals

    Explore 270 holiday rentals in South Sarasota

  • Nightly prices starting at

    South Sarasota holiday rentals start at $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 7,410 verified reviews to help you choose

  • Family-friendly holiday rentals

    230 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wi-Fi availability

    270 of South Sarasota holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across South Sarasota rentals

  • 4.8 Average rating

    South Sarasota stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in South Sarasota

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

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Superhost
Home in Gulf Gate Estates

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

Welcome to The Salty Unicorn, your cheerful Sarasota escape just five miles from Siesta Key Beach. This fully renovated 3-bedroom home is designed for relaxation and fun, with a bright open layout, stylish coastal décor, and plenty of space to gather with family or friends. Start your mornings with coffee by the pool, spend sunny afternoons swimming or lounging in the spacious backyard, and end the day with dinner in the screened lanai. Whether you’re here for beach days, family time, or a peace

4.89 out of 5 average rating, 107 reviews
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.

4.94 out of 5 average rating, 100 reviews
Guest favourite
An indoor pool is enclosed within a screened area, offering a clear view of tranquil blue water and surrounding trees. Comfortable outdoor seating is visible, complemented by a sunlit patio space. Large glass doors provide access to the pool area, enhancing the open feel.
Home in South Sarasota

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

4.97 out of 5 average rating, 217 reviews
Guest favourite
An inviting private backyard features a sparkling heated pool surrounded by a spacious screened patio. Comfortable loungers are positioned nearby, with a shady area provided by the overhead structure. Lush greenery accents the space, enhancing the tranquil outdoor atmosphere.
Home in South Sarasota

Siesta Key FL: Heated Pool, Beaches, Family Fun

Escape to a stylish and spacious retreat near the world-famous Siesta Key Beach! This 3-bedroom, 2-bathroom home sleeps up to 10 guests, making it perfect for families, groups, or workcations. Relax by the private heated pool in the fenced backyard, whip up gourmet meals in the fully equipped kitchen, or explore Sarasota’s vibrant dining, shopping, and cultural attractions just minutes away. Whether you’re here to soak up the sun or create family memories, your Florida getaway starts here.

4.89 out of 5 average rating, 119 reviews
Superhost
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, 185 reviews
Top Guest favourite
The outdoor area features a uniquely shaped heated saltwater pool with clear blue water. Surrounding the pool are loungers placed on a bright, white deck, complemented by tropical plants and palm trees that enhance the tranquil environment.
Home in South Sarasota

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!

4.98 out of 5 average rating, 127 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

Light, bright and newly renovated. Beautifully decorated 3 bedroom home minutes from Siesta Key and downtown. The spacious modern kitchen has a slider that leads to covered porch and large pool with private fenced yard. A second slider from the porch leads to the master bedroom with master bath and walk in closet. Open living room and 2 additional big bedrooms make the house perfectly comfortable for 6. Everything you need is right here! Siesta Key Beach Distance - 16 Min; 6.1 Mi

4.88 out of 5 average rating, 101 reviews
Guest favourite
Home in South Sarasota

Roselawn St | Private Pool, Fire Pit + Patio!

BNB Breeze Presents: Roselawn Street! Located in the heart of Sarasota, just 10 minutes away from Siesta Key Beach, the location of this home is everything! This stunning oasis with a private pool and basketball court includes: • Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st • Miniature Basketball Court • Covered Outdoor Dining Area + Grill • Lightning Fast Wi-Fi (Perfect for Remote Work!) • Incredible Fire Pit w/ String Lights! • 2 Living Rooms

4.85 out of 5 average rating, 123 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

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!

4.94 out of 5 average rating, 140 reviews
Guest favourite
A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.
Home in Sarasota

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want!

4.94 out of 5 average rating, 168 reviews
Guest favourite
An outdoor dining area features a large table set with plates and glasses, surrounded by seating. A pool is visible nearby, framed by lounge chairs under a covered patio with ceiling fans. The walls are painted in a vibrant blue, enhancing the inviting atmosphere.
Home in Sarasota Springs

Sarasota Sandpiper: 4 Bed/3 bath + Pool

Your Ideal Getaway: All-Inclusive Comfort and Convenience Discover the perfect retreat that's close to everything you desire in a vacation. Whether you're seeking the beach, family-friendly activities, nightlife, mini golf or championship golf courses, you'll find it all at your doorstep. It's a place where you can unwind and savor life's simple pleasures. Embrace the great outdoors with an outdoor space that's perfect for relaxation and enjoyment.

4.91 out of 5 average rating, 202 reviews
Top Guest favourite
The pool area is enclosed by a screened lanai, featuring a clear blue pool with sunlight reflecting off its surface. Surrounding palm trees and greenery enhance the tropical atmosphere. Comfortable seating options are visible nearby, inviting relaxation and enjoyment.
Home in Sarasota

Endless Summer Escape Near SK!

Welcome to paradise! This 3/2 pool home showcases what Florida life is all about- comfort, relaxation and sun! With a screened in patio and pool area with an outdoor TV, hightop table, dining table with umbrella, a comfy couch, sun loungers, pool floats, and more, you will see how easy it is to unwind and relax here at the Endless Summer Escape! Did we mention you are about a 5 minute drive to Siesta Key beach!? We can't wait to host you!

4.93 out of 5 average rating, 123 reviews

Popular amenities for South Sarasota rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top Guest favourite
A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.
Home in Sarasota

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

4.98 out of 5 average rating, 119 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

4.91 out of 5 average rating, 122 reviews
Top Guest favourite
A screened-in pool area features a crystal-clear heated pool with lounge chairs positioned nearby. An umbrella provides shade over a seating area, surrounded by lush greenery and fencing that enhances privacy.
Home in Sarasota

Cozy 2BD/2BA with Heated Pool Near Siesta Key

4.95 out of 5 average rating, 242 reviews
Guest favourite
A private backyard features a heated in-ground pool surrounded by spacious pavers. Lounge chairs are positioned along one side, with a shaded table and umbrella nearby. Lush greenery lines the perimeter, providing a natural backdrop for relaxation and leisure.
Home in South Sarasota

The Pink Pineapple - Your Cozy Sarasota Home

4.92 out of 5 average rating, 25 reviews
Top Guest favourite
Home in Sarasota

4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key

5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in South Sarasota

"Siesta on Lee" - NEW SRQ Home w/ Heated Pool!

5.0 out of 5 average rating, 19 reviews
Top Guest favourite
Home in South Sarasota

Heated Pool + Spa + Mini Golf + Tiki near Siesta

5.0 out of 5 average rating, 68 reviews
Guest favourite
The outdoor area features a well-maintained pool bordered by lush greenery. Several loungers and a shaded seating area invite relaxation. A vibrant red umbrella provides sun protection, while the sky above showcases a mix of clouds and blue, enhancing the serene atmosphere.
Home in South Sarasota

Siesta Shore House

4.83 out of 5 average rating, 24 reviews

Condo rentals with a pool

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.
Condo in Siesta Key

Comfy Siesta Key Condo

4.85 out of 5 average rating, 110 reviews
Top Guest favourite
Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

4.92 out of 5 average rating, 170 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.
Condo in Siesta Key

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

4.88 out of 5 average rating, 175 reviews
Guest favourite
A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.
Condo in Gulf Gate Estates

Heated Pool Apartment Near Siesta Key | 1BR

4.87 out of 5 average rating, 154 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.
Condo in Siesta Key

Breathtaking Beachfront Views in Siesta Key

5.0 out of 5 average rating, 103 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.
Condo in Siesta Key

Crystal House on Siesta Key Beach

4.88 out of 5 average rating, 146 reviews
Guest favourite
Condo in Siesta Key

Beachwalk Townhouse with view of Gulf of Mexico

4.79 out of 5 average rating, 109 reviews
Guest favourite
A serene lanai view features a dining table with chairs overlooking the community pool. Lush palm trees frame the scene, while sunlight reflects off the water's surface. A doorway is visible, leading to the interior of the condo.
Condo in Sarasota

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

4.96 out of 5 average rating, 225 reviews

Other holiday rentals with a pool

Guest favourite
Home in Sarasota

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

5.0 out of 5 average rating, 16 reviews
Top Guest favourite
Home in Arlington Park

Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta

4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Sarasota

Trish's Beach Retreat W/ Pool/Spa by Siesta Keys#2

4.86 out of 5 average rating, 88 reviews
Top Guest favourite
A well-maintained pool area is enclosed by a screened lanai, featuring a refreshing turquoise pool surrounded by a spacious patio and two lounge chairs. Direct access to the house is visible, with additional outdoor seating for relaxing or dining nearby.
Bungalow in Sarasota

*Waterfront house with dock and heated pool

4.99 out of 5 average rating, 96 reviews
Top Guest favourite
A spacious kitchen showcases a large island with seating for four, surrounded by light-colored cabinetry and modern appliances. Natural light illuminates the area through large windows, providing a view of the outdoor pool. Decorative tiles and subtle backsplash add texture to the design.
Home in Siesta Key

Siesta Key Retreat 1mi to Beach!

4.96 out of 5 average rating, 48 reviews
Top Guest favourite
Home in Sarasota

Modern 4bd | Heated Pool | Hot Tub + Studio Suite!

5.0 out of 5 average rating, 22 reviews
Superhost
A private heated pool and spa are surrounded by tropical palm trees and lounge chairs. The pool's water reflects soft blue hues, while a spacious two-story structure provides a backdrop with large windows. The scene is illuminated by the evening sky.
Home in Sarasota

The Pearl on the Bay, a breathtaking Bayfront Home

4.77 out of 5 average rating, 13 reviews
Guest favourite
An outdoor dining area features a large rectangular table with seating for eight, complemented by a shaded lounge space. A heated pool is visible, along with a sunken hot tub and sun loungers. Lush greenery surrounds the area, providing a serene backdrop.
Villa in Arlington Park

Bohemian Inspired Villa with Golf Cart and SUV

4.88 out of 5 average rating, 67 reviews

When is the best time to visit South Sarasota?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$402 NZD$545 NZD$550 NZD$451 NZD$390 NZD$397 NZD$333 NZD$304 NZD$294 NZD$299 NZD$333 NZD$360 NZD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

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