Vacation rentals with a pool in Sarasota

4.93 out of 5 average rating, 122 reviews

An outdoor area features a heated pool surrounded by a spacious deck. Lounge chairs are positioned nearby for relaxation, and a dining set offers seating for outdoor meals. A screened enclosure provides protection from insects while allowing natural light to filter through.

Home in Glen Oaks

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

5 out of 5 average rating, 122 reviews

Home in Bellevue Terrace

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

4.99 out of 5 average rating, 268 reviews

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guesthouse in Whitfield

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

4.98 out of 5 average rating, 227 reviews

Condo in Longboat Key

Sun-Kissed Memories!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

4.98 out of 5 average rating, 116 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!

5 out of 5 average rating, 122 reviews

A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.

Villa in Arlington Park

Luxury Villa with Pool, Game Room, Near Beach

Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. • Bedrooms: 4 private suites, plush linens to ensure restful nights. • Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. • Heated pool & sun loungers • Arcade-style game room • Fast Wi-Fi & 5-star cleanliness • Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today! VR24-00060

Home in Gulf Gate Estates

4.97 out of 5 average rating, 265 reviews

Your private retreat near Siesta Key Beach.

Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

4.97 out of 5 average rating, 367 reviews

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

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. If we are booked check out our additional units under our profile.

Home in Indian Beach-Sapphire Shores

A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.

4.94 out of 5 average rating, 133 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

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.

4.95 out of 5 average rating, 125 reviews

Luxury Family Pool Home Near Siesta Beach

Prepare to be enchanted by your new sanctuary! Immerse yourself in luxury at this spacious and bright pool home, recently renovated to perfection. Located on a peaceful street, it strikes the perfect balance between tranquility and convenience, with easy access to Sarasota's finest attractions. Unwind at Siesta Key Beach, indulge in downtown's culinary delights and shopping, and explore the famous Fresh Fish Waltz Market—all just minutes away!

4.98 out of 5 average rating, 101 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. 🌴

4.97 out of 5 average rating, 353 reviews

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Popular amenities for Sarasota rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 11 reviews

A clear swimming pool reflects the evening sky, surrounded by a spacious patio. Outdoor seating for dining is arranged under an umbrella, with chairs positioned nearby. Lush greenery provides privacy, and large glass doors lead to the inviting interior of the home.

Home in Southgate

Pool, Spa, & Private Gym in the Heart of Sarasota

Home in Downtown Sarasota

The Master Suite features a spacious bed with a headboard, accompanied by two bedside lamps and minimalist decor. A cozy bench is positioned at the foot of the bed. Natural light brightens the space, which includes an ensuite bathroom with a walk-in shower visible in the background.

5 out of 5 average rating, 44 reviews

Coastal Contemporary Pool Home

Superhost

A spacious game room features a pool table in the foreground, with a selection of arcade machines visible in the background. Large glass doors provide access to outdoor areas. Neutral-colored walls and tiled flooring enhance the airy atmosphere of the room.

Home in Port Charlotte

4.66 out of 5 average rating, 32 reviews

Florida Fun Home! Pool and Game Room

A well-lit living area is furnished with a sofa and armchair, accompanied by a round coffee table. Light drapes partially cover a large window, allowing natural light to fill the space. A decorative plant and two lamps enhance the cozy ambiance.

4.96 out of 5 average rating, 56 reviews

Haven on Helene pool house.

5 out of 5 average rating, 112 reviews

An inviting exterior view of Sunrise Villa showcases a well-maintained landscape featuring lush greenery and vibrant plants. A spacious driveway leads up to a garage, with decorative stone detailing accentuating the garden area. The home is framed by palm trees, contributing to the tropical ambiance.

Home in Bradenton

Sunrise Villa - Tropical 3 bedroom home with pool

Superhost

Home in Gillespie Park

4.82 out of 5 average rating, 131 reviews

Heated Saltwater Pool and Hot Tub, Walk Downtown.

5 out of 5 average rating, 9 reviews

Seabreeze Pool Retreat.

4.95 out of 5 average rating, 74 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!

Condo rentals with a pool

Condo in Gulf Gate Estates

The living area features a light-colored sofa complemented by an orange accent chair. A coffee table sits on a textured area rug, while wall art adds color to the red accent wall. Glass doors open to a view of outdoors, surrounded by greenery.

4.9 out of 5 average rating, 141 reviews

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR

4.99 out of 5 average rating, 101 reviews

The balcony features a cozy seating arrangement comprising two chairs and a coffee table, all set against a stunning ocean view. The turquoise waters and sandy beach are visible beyond the railing, offering a serene backdrop for relaxation.

Condo in Sarasota

6 Siesta Breakers - Condo, Ocean View, Heated Pool

4.83 out of 5 average rating, 126 reviews

Condo in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

4.89 out of 5 average rating, 137 reviews

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

4.91 out of 5 average rating, 151 reviews

A vibrant exterior showcases the entrance to Villa Maria, framed by palm trees and a charming fountain. The entrance features a set of red stairs leading to a welcoming sign, adding a decorative touch to the well-maintained surroundings.

Condo in Sarasota

Gateway Siesta Key Beach

4.85 out of 5 average rating, 102 reviews

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

4.88 out of 5 average rating, 127 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

4.96 out of 5 average rating, 185 reviews

A light-filled living area showcases a large white sectional sofa adorned with colorful throw pillows. A turquoise coffee table displays decorative shells, and a light-toned area rug is centered beneath. Artwork featuring vibrant coastal scenes is mounted on the walls, enhancing the relaxed ambiance.

Condo in Bradenton

The Seabreeze Cottage with peaceful water views

Other vacation rentals with a pool

4.97 out of 5 average rating, 29 reviews

A tranquil outdoor space features a heated pool surrounded by stone pavers. Comfortable lounge chairs are positioned nearby, and a modern fire pit offers seating. The restored stone house stands in the background, framed by palm trees under a clear blue sky.

Home in Bradenton

100 yr Old Stone Home + Pool + 9 miles to beaches

Apartment in Southside Village

4.9 out of 5 average rating, 20 reviews

Siesta key Beach 2 miles Fun in the sun, Gardinia

5 out of 5 average rating, 23 reviews

An aerial view captures a modern apartment complex adjacent to a calm waterway, framed by lush greenery. The sunset casts warm hues across the sky, while nearby city lights begin to emerge. Boating docks and waterfront properties are visible in the serene landscape.

Apartment in Sarasota

Zen and Paradise-Sarasota

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.

5 out of 5 average rating, 20 reviews

The Palms Away

4.95 out of 5 average rating, 22 reviews

Home in Siesta Key

Luxury Canal-Front Home + Heated Pool Near Beach

4.95 out of 5 average rating, 19 reviews

Home in Arlington Park

Heated Pool Near Siesta Key Beach and Downtown

4.94 out of 5 average rating, 32 reviews

An aerial view captures a light blue house with a spacious driveway and manicured lawn, surrounded by lush greenery and a serene canal. The home features a charming front porch and is set within a quiet neighborhood, showcasing the tranquil natural landscape.

Home in Port Charlotte

Peaceful waterfront home