Holiday rentals with a pool in Sarasota

4.97 out of 5 average rating, 258 reviews

Your private retreat near Siesta Key Beach.

Welcome to your private retreat! RELAX, UNWIND, AND MAKE LASTING MEMORIES in this coastal haven. 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

5 out of 5 average rating, 119 reviews

Home in Bellevue Terrace

Living The Dream - Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream! From the swings at the dining room table and the neon sign, to the moss wall and the private putt-putt course, Living the Dream is fully loaded and is the ultimate luxury vacation home! Located just 15 minutes away from both Lido Key and Siesta Key Beach, the stay includes: ✔ Backyard Putt-Putt Course ✔ Saltwater Heated Pool - heated at NO extra cost from Nov 21 - April 1st ✔ Super Kid Friendly ✔ Jura Espresso Machine ✔ 65" Frame TV w/ Youtube TV Included

4.95 out of 5 average rating, 524 reviews

A living area features wooden flooring with a large area rug at the center. Two gray armchairs are positioned near a media console, which supports a flat-screen television. Natural light is provided by windows adorned with sheer white curtains, and a green plant adds a touch of greenery.

Home in Arlington Park

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

4.99 out of 5 average rating, 246 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.

Guest house in Sarasota

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

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.

4.98 out of 5 average rating, 109 reviews

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, 218 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 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, 127 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.

Flat in Indian Beach-Sapphire Shores

A spacious living area is featured with a large flat-screen television mounted on the wall. Two comfortable chairs are placed adjacent to a round ottoman, decorated with a variety of plants and a small basket. Natural light filters in through large windows, offering a view of the surrounding landscape.

4.97 out of 5 average rating, 152 reviews

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt

Beach ready Apt!! 2 minutes from downtown Sarasota 7 mins - Airport Cornerr apartment Steps to the elevator 2 bicycles & 2 escooters Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb on a main road . Beside ARTS & DESIGN COLLEGE!! 60+ amenities from a secure room safe to a luxurious, indulgent bed. Essential amenities such as grocery stores/pharmacies/ & CVS. less than a mile away. Send me a message if you have any questions .

Apartment in Longboat Key

4.98 out of 5 average rating, 218 reviews

Oceanfront: January Availability!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located 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 onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort!

4.97 out of 5 average rating, 348 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.

Apartment 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. Enjoy 2 free bikes day rental with booking!

5 out of 5 average rating, 117 reviews

An aerial view captures a heated saltwater pool accompanied by a spa hot tub, surrounded by a stone patio and tropical landscaping. Loungers and Adirondack chairs are positioned for relaxation under a shaded umbrella. A serene pond and lush greenery create a tranquil backdrop.

Home in Bradenton

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

4.97 out of 5 average rating, 342 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

*DEC SALE! 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

A bright and inviting outdoor space features a saltwater pool surrounded by landscaped areas. A large umbrella provides shade over a white lounge chair, while additional seating is positioned around the pool deck, all enclosed by a wooden privacy fence.

4.99 out of 5 average rating, 68 reviews

Modern coastal downtown home w/saltwater pool

A private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

4.77 out of 5 average rating, 113 reviews

Pool house by the bay

5 out of 5 average rating, 22 reviews

Luxury Sport Vacation Pool House-Downtown Sarasota

The spacious backyard features a heated pool illuminated with purple lighting, surrounded by lounge chairs and umbrellas. A dining table for eight sits nearby, with a cozy fire pit area providing evening ambiance. Pool floats are present, enhancing recreational options.

4.97 out of 5 average rating, 34 reviews

Luxe Oasis Mins to Beach & Downtown w/Heated Pool

A screened lanai showcases a heated pool and spa, surrounded by twinkling string lights. Lounger chairs and outdoor dining furniture are positioned nearby. A grassy area is visible beyond the pool, while a pink inflatable floats in the water, enhancing the serene outdoor setting.

4.98 out of 5 average rating, 65 reviews

Coastal Home in Sarasota-8min from 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.

4.94 out of 5 average rating, 110 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

The vibrant outdoor space features a mini-golf putting green, surrounded by strategically placed lounge chairs and Adirondack seating. Illuminated by string lights, the heated pool area is complemented by cabana umbrellas, with a backdrop of the house showcasing lively decor and inviting lighting.

5 out of 5 average rating, 21 reviews

Private Tropical Oasis | Pool+Golf+Bocce+Fire+PETS

5 out of 5 average rating, 25 reviews

Palm Paradise • Private Office • Heated Pool & Spa

Apartment rentals with a pool

4.81 out of 5 average rating, 114 reviews

Apartment in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

4.85 out of 5 average rating, 100 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.

Apartment in Siesta Key

Comfy Siesta Key Condo

Apartment in Longboat Key

4.89 out of 5 average rating, 122 reviews

Sunset and beach view from your balcony Unit 403

4.89 out of 5 average rating, 160 reviews

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.

Apartment in Sarasota

6 min to Siesta Beach | Heated Pool | Lake View

Apartment in Longboat Key

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

4.89 out of 5 average rating, 198 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

4.96 out of 5 average rating, 172 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.

Apartment in Bradenton

The Seabreeze Cottage with peaceful water views

4.92 out of 5 average rating, 150 reviews

Apartment in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Apartment in Sunset Beach

4.95 out of 5 average rating, 150 reviews

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

Other holiday rentals with a pool

4.99 out of 5 average rating, 93 reviews

An airy dining area features a glass table supported by a unique wooden base, surrounded by four woven chairs. Natural light floods the open space, highlighting the modern kitchen with white cabinetry and high-end finishes, while a large pendant light adds a stylish touch.

Home in Siesta Key

Luxurious Private Retreat - Your Siesta Key Oasis!

The home's exterior showcases a modern design with a light-colored facade and a welcoming entrance. Lush green landscaping and decorative stone borders frame the property, while tall palm trees provide shade and a tropical feel. Light filters through the detailed window shutters.

5 out of 5 average rating, 90 reviews

Luxury Downtown Home+Spa & Pool+Near Beaches

5 out of 5 average rating, 10 reviews

Pool house with outdoor shower, 10 minutes from SK

Bungalow in Arlington Park

A private heated pool is surrounded by a protective mesh cage, featuring lounge chairs along the edges. The pool area connects to the home through large glass doors, with potted plants adding greenery to the scene. Sunlight reflects off the water's surface, creating a serene atmosphere.

4.84 out of 5 average rating, 56 reviews

Gorgeous Sarasota Private Home with Heated Pool

A clear view of the inviting swimming pool is presented, bordered by lounge chairs with red and white stripes. Palm trees sway gently in the background, framing the scenic vista of Sarasota Bay and lush greenery beyond.

4.86 out of 5 average rating, 14 reviews

Bayfront Beauty: Heated Pool, King size Bed

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.

5 out of 5 average rating, 41 reviews

Sunshine House- Sarasota Pool Retreat

5 out of 5 average rating, 55 reviews

An elegant gated entrance is framed by a tall tree, with sunlight filtering through the leaves. A gravel pathway leads through the gates, bordered by lush green grass and white fencing, creating a serene and inviting arrival to the property.

Farm stay in Sarasota

800 sq ft FARM Guest House nestled in the country