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, 105 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

Home in Gulf Gate Estates

4.89 out of 5 average rating, 107 reviews

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

4.91 out of 5 average rating, 128 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.

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

4.98 out of 5 average rating, 132 reviews

Sunshine House, near Downtown, Legacy Trail, Beach

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

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.

5 out of 5 average rating, 134 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream A purpose-built luxury family vacation home designed by parents for unforgettable stays. Enjoy swing dining chairs, a glowing neon moss wall, backyard putt-putt, and a free heated saltwater pool (Nov 21–Apr 1st). 15 minutes to Siesta & Lido Key Beaches. ✔ Private heated saltwater pool ✔ Backyard mini golf & outdoor games ✔ Luxury covered lanai w/ high ceilings ✔ Super kid-friendly (toys, Pack ’n Plays) ✔ Jura Espresso Machine ✔ 65” Frame TV w/ YouTube TV

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, 125 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!

4.98 out of 5 average rating, 126 reviews

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!

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

4.95 out of 5 average rating, 253 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

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, 146 reviews

Luxury Pool Family Paradise-Siesta Key Beach/DT

Welcome to your home away from home! This renovated, spacious and bright pool home will immerse you into 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 USA), 10 minutes to downtown including fantastic restaurants and shopping and walking distance to the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake park and The new UTC mall!

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!

4.98 out of 5 average rating, 126 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

4.89 out of 5 average rating, 61 reviews

Pet-Friendly Pool Oasis Near Siesta Key Beaches

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

5 out of 5 average rating, 15 reviews

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

5 out of 5 average rating, 20 reviews

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

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.

4.95 out of 5 average rating, 242 reviews

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

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.

4.95 out of 5 average rating, 139 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

A private pool area is surrounded by a well-maintained yard featuring palm trees. Four lounge chairs are positioned near the pool, which is characterized by clear turquoise water. A white fence provides privacy around the space, enhancing the tranquil outdoor setting.

4.93 out of 5 average rating, 92 reviews

The Coral Cottage-heated pool, Siesta beach 15 min

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 out of 5 average rating, 47 reviews

Sarasota Paradise/Stunning Home/Heated Pool

Condo rentals with a pool

4.96 out of 5 average rating, 224 reviews

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

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.

4.97 out of 5 average rating, 392 reviews

Beachfront Siesta Key | Gulf View + Private Beach

4.83 out of 5 average rating, 148 reviews

Condo in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

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

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, 110 reviews

Comfy Siesta Key Condo

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, 195 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

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.

4.88 out of 5 average rating, 175 reviews

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

4.82 out of 5 average rating, 111 reviews

Condo in Sarasota

LJ's Cottage 2

Other holiday rentals with a pool

4.7 out of 5 average rating, 53 reviews

Near Legacy Trail, Family Friendly, Heated pool

4.8 out of 5 average rating, 99 reviews

The exterior of a single-story home is showcased, featuring a covered entryway with double doors. Lush greenery, including potted palm trees and trimmed shrubs, frames the entrance. A concrete path leads through a pebble-strewn area, offering a welcoming appearance on a sunny day.

Villa in Sarasota

Paradise Villa- Sarasota

4.87 out of 5 average rating, 45 reviews

Paradise Palms • Heated Pool • Near Siesta Key

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

5 out of 5 average rating, 5 reviews

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

4.96 out of 5 average rating, 46 reviews

NEW! Renovated Pool Home Mins 2 Siesta Key Beach

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.

4.95 out of 5 average rating, 37 reviews

Driftwood Cottage - 3 BR with Salt Water Pool

A private pool with a clear blue surface reflects the sky, surrounded by a fence and several trees. A shaded gazebo is positioned nearby, with an air of relaxation. Pool accessories float gently on the water, inviting calm moments by the poolside.