Holiday rentals with a pool in Sarasota Springs

The outdoor pool area features a heated pool and spa, surrounded by a screened lanai. Lounge chairs are positioned nearby for relaxing. A hammock rests on the grass, inviting moments of leisure. Lush greenery enhances the tranquil environment.

4.95 out of 5 average rating, 102 reviews

Deja Blue Villa Salt Water Heated Pool & Spa

Featured Home: 🌊 Deja Blue Villa 🌊 From the beautiful, fully-equipped kitchen, to our fenced and heated pool patio, Deja Blue Villa is your perfect vacation home! Located only 20 minutes from Siesta Key Beach and 25 minutes from Lido Key Beach, this incredible stay includes: Private Heated Pool & Spa + Lounge Chairs & String Lights Pool Patio Mini Fridge + Serving Area Free Washer/Dryer Access, Detergent & Softener Included Gas Grill + Propane Coffee & Coffee Maker TV + Roku in Every Bedroom

5.0 out of 5 average rating, 18 reviews

Sarasota Retreat/Beaches/Pool/8.5mi. to Siesta Key

Welcome to your Sarasota retreat!! Enjoy a private heated pool home just 8.5 miles from the white sands of Siesta Key. With multiple bedrooms and an additional living room/lania, there’s plenty of space to spread out and relax. Start your mornings with coffee poolside, spend beach days exploring the coast and downtown dining, then unwind in comfort... Perfect for: • Families wanting space and a private pool • Couples looking for a warm-weather getaway Your perfect Florida vacation starts here...

4.91 out of 5 average rating, 127 reviews

Coastal Farmhouse - 3/2 with heated saltwater pool

Experience relaxation at this tranquil 3BD/2BA home with a heated pool, perfect for a family retreat! Prepare meals in the fully equipped kitchen or savor local delights on the screened-in lanai. Each bedroom boasts plush bedding, ensuring a restful night's sleep. Plus, a cozy living room. Conveniently located, just under 9 miles from Siesta & Lido Key Beach, Der Dutchman 2.2 miles and 2.5 miles from Yoder's Restaurant. Shopping and dining options at University Town Center, only 7.7 miles away.

An outdoor dining area features a wooden table set for four, overlooking a pristine pool. Lounge chairs are positioned nearby, providing a relaxing space for sunbathing. The screened patio ensures comfort while enjoying meals or relaxation outdoors.

4.98 out of 5 average rating, 162 reviews

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

Relax at this modern heated pool house located just 15 min from the famous Siesta Key Beach. Nested in a quiet neighborhood with a lot of privacy, the house has plenty of space for an entire family or a group of friends. An additional family room with a TV for kids. Relax by the pool in the spacious outdoor area or explore the beautiful downtown filled with restaurants. Recently renovated, this home offers handmade authentic Mexican tile flooring to compliment a cozy and contemporary design.

4.94 out of 5 average rating, 98 reviews

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.

A serene view of the pool area features clear blue water, framed by a brick border. Lush greenery surrounds the pool, with a statue placed amidst the landscaping. Sunlight filters through the trees, casting soft reflections on the water's surface.

4.98 out of 5 average rating, 123 reviews

The Oasis

Welcome to The Oasis, your Florida home away from home! Centrally located, between siesta key and st Armand’s circle, near many fantastic restaurants, grocery stores, and downtown. This home has everything you need for a fantastic stress free stay in Sarasota. A luxurious Italian style pool and garden area, a spacious indoor area with a full sized kitchen, king bed, queen bed, 2 twin beds and 2 twin air mattress. 3 smart tvs. We love this stunning and cozy home and we’re sure you will too!

5.0 out of 5 average rating, 11 reviews

Sunny Palm Villa

Welcome to Sunny Palm Villa! This family friendly 3 bedroom 2 bathroom home with a heated pool is just the place you have been looking for. A wonderful place to unwind and relax by the pool or one of the nearby beaches. Conveniently located 20 minutes from Siesta Key Beach or Lido Key Beach. Only 15 minutes from University Town Center shopping, Mote Aquarium and Nathan Bendersen Rowing Park. The Legacy Bike Trail and famous Dutch, Amish restaurants in Pinecraft only 5 minutes away.

A private pool area is enclosed by a screened-in lanai, featuring clear blue water reflecting sunlight. A patio umbrella and several chairs are positioned nearby, surrounded by lush greenery, creating a relaxing outdoor space.

4.98 out of 5 average rating, 94 reviews

GARDEN VIEW HOUSE WITH A POOL

Relax with the whole family at this peaceful place to stay. Private Garden Front Home. Located 7 miles to the Siesta Key, #1 beach in United States. 1 mile to Legacy Trail. Trail is 18.5 mile Connecting Sarasota and Venice, Florida. This 3 bedrooms 2 bath home offers everything you need for your next vacation getaway! The kitchen is equipped with everything needed to make your favorite home-cooked meals and host the family at the table or on the covered outdoor screened-in lanai!

A private heated pool is enclosed within a screened area, featuring clear blue water. Red Adirondack chairs are positioned nearby on a structured surface. A spacious yard is visible beyond the pool area, enclosed by a wooden fence for added privacy.

4.82 out of 5 average rating, 230 reviews

Heated Open Pool Home In Sunny Sarasota!

This home is perfect for hosting friends and family or just relaxing on your own! Spend a day in the surf and sun at the world famous Siesta Beach, shop at one of the many centrally located shopping centers , try local restaurants, or just take it easy in your own private and open pool and sitting area! Like making your own meal, step inside to an updated and fully stocked kitchen! Two living rooms, lots of space. Let this beautiful home be yours during your visit to Sarasota!

4.82 out of 5 average rating, 38 reviews

Quiet Family Home w/ Pool Near Pinecraft

Escape to a serene family retreat near Pinecraft and Yoders! This 3-bed, 2-bath home features a screened-in heated swimming pool for year-round enjoyment. Nestled in a quiet, family-friendly neighborhood, savor nearby Amish dining at Yoders and Der Dutchman. Siesta Key & Lido Key Beaches are only 8.7 miles away! Explore Marina Jack's at Bayfront Park in downtown Sarasota, where you can admire stunning boats and enjoy a leisurely stroll. Your perfect vacation awaits you!

Guest suite in Sarasota Springs

A compact kitchen is equipped with modern black and white appliances. A retro-style fridge stands beside a sleek black microwave. An artistic pineapple wall decor complements the minimalist cabinetry, while a neutral-toned rug adds warmth to the space. Light is provided by overhead fixtures.

4.99 out of 5 average rating, 88 reviews

Villa Palmette, 1 Bedroom, Nestled in the Palms

1 Bedroom in-law apartment with private entrance and easy up front parking, sleeps 2. There is a pull out but not great for adults more suited to kids . Minutes to Siesta Key, Downtown Sarasota and Lido Beach, with easy access to I75. This quiet apartment is tucked into lush tropical landscape. Attention to detail throughout with new bed, pull out couch , coffee bar, Internet, Prime, Netflix, plush towels, crisp linen, soft pillows.

4.98 out of 5 average rating, 123 reviews

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. 🌴

Popular amenities for Sarasota Springs rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 108 reviews

[The Bay St. Hideaway]Private Swimming Pool& Patio

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.

4.96 out of 5 average rating, 142 reviews

Luxury Pool Family Paradise-Siesta Key Beach/DT

5.0 out of 5 average rating, 11 reviews

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

Superhost

4.69 out of 5 average rating, 52 reviews

Near Legacy Trail, Family Friendly, Heated pool

A spacious kitchen and dining area features a large island with bar seating, complemented by a dining table that accommodates multiple guests. Natural light illuminates the room through large windows, while neutral tones and wood accents create a welcoming atmosphere.

5.0 out of 5 average rating, 46 reviews

Sarasota Paradise/Stunning Home/Heated Pool

A tranquil pool area features a curvy shape with clear blue water. A pink inflatable flamingo floats on the surface. Surrounding the pool, gray stone tiles create a sleek patio, with two lounge chairs positioned nearby, all set against a backdrop of tall green palm trees.

4.91 out of 5 average rating, 34 reviews

Suncoast Ranch SRQ Pool House

A heated pool is surrounded by lush greenery, featuring six lounge chairs and a large umbrella for shade. The patio area is accentuated with tropical plants, while a covered lanai is visible in the background, providing additional outdoor space.

4.99 out of 5 average rating, 99 reviews

You Private Tropical Paradise

Superhost

A screened-in pool area features a clear blue pool with a shallow entry. Sun loungers are positioned alongside the pool, and outdoor seating is arranged nearby. The space is bathed in natural light, creating an inviting atmosphere for relaxation.

4.83 out of 5 average rating, 59 reviews

[The Island Date Home]Heated Pool•Family Friendly•

Condo rentals with a pool

Condo in Gulf Gate Estates

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

4.89 out of 5 average rating, 192 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

4.96 out of 5 average rating, 157 reviews

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.

Condo in Sarasota

Your Modern Beachside Getaway!

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.

4.85 out of 5 average rating, 109 reviews

Comfy Siesta Key Condo

4.83 out of 5 average rating, 146 reviews

Condo in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

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.

4.97 out of 5 average rating, 132 reviews

Private Beach with Loungers · 2 Pools & Bay View

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.

4.88 out of 5 average rating, 146 reviews

Crystal House on Siesta Key Beach

5.0 out of 5 average rating, 109 reviews

Condo in Sarasota

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

A dining table is set with elegant glassware and neutral tableware. A decorative figurine of a crane stands between two tall candlesticks, with a soft ocean view visible through the screened lanai in the background.

4.92 out of 5 average rating, 102 reviews

Siesta Key Oasis with Gulf Views

Other holiday rentals with a pool

A living room area is furnished with a green sofa and two beige armchairs, complemented by a round ottoman. Light wood accents are featured, with a large area rug underfoot. Natural light filters through two windows, and a potted plant adds a touch of greenery.

4.94 out of 5 average rating, 35 reviews

Driftwood Cottage - 3 BR with Salt Water Pool

5.0 out of 5 average rating, 33 reviews

Belle of Sarasota

4.97 out of 5 average rating, 71 reviews

A modern cottage is set within a spacious, manicured lawn surrounded by trees. A circular driveway leads to the house, which features a dark metal roof and large windows. Lush greenery frames the property, emphasizing its serene outdoor environment.

Cottage in Sarasota

Bee Keepers Cottage

4.89 out of 5 average rating, 61 reviews

Pet-Friendly Pool Oasis Near Siesta Key Beaches

5.0 out of 5 average rating, 14 reviews

Good Vibrations Home

4.99 out of 5 average rating, 91 reviews

The Cottage at the Roost, SRQ Ranch Paradise

An inviting backyard showcases a pool surrounded by a concrete patio, featuring lounge chairs and a grill. Lush greenery and tropical palms create a serene environment. A shaded area with colorful seating offers a space for relaxation, enhancing the outdoor experience.

4.94 out of 5 average rating, 18 reviews

Tropical Oasis: Poolside Getaway

A spacious seating area features comfortable chairs surrounding a modern fire table. A clear view of the salt water heated pool is available through large glass doors. Outdoor furniture is positioned beside the pool, with lush greenery visible in the background.