Holiday rentals with a pool in Vamo

An outdoor lanai is shown, featuring a seating area with two chairs and a dining table set for six. A vibrant area rug with floral patterns adds color beneath the furnishings. A private pool is visible, surrounded by a screened enclosure, with lush greenery in the background.

4.85 out of 5 average rating, 40 reviews

Siesta sunset - Pool - Close to beach

Welcome to your dream vacation getaway in Sarasota! This spacious 3/2 pool home is your perfect oasis, just minutes from the pristine shores of Siesta Key Beach. Immerse yourself in the Florida lifestyle, with a private pool and lanai for relaxation and outdoor dining. Enjoy a fully equipped kitchen, and tastefully decorated interiors that make this home a haven of comfort. Unwind in style after a day at the beach (10 min away) soak in the sunshine by the pool. Your Sarasota adventure awaits!

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, 108 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 spacious screened-in pool area is visible, featuring a uniquely shaped pool surrounded by natural stone flooring. Several lounge chairs are arranged around the pool for relaxation. Bright blue skies and fluffy white clouds can be seen above, enhancing the inviting outdoor space.

4.93 out of 5 average rating, 15 reviews

Freda’s Sarasota Oasis! Private Pool & Lounge Area

Relax with the whole family in this beautiful Sarasota home. Not only is there plenty of space inside with a mother in law suite, 2 kitchens, and huge gathering area, you will also enjoy 2,000 square feet of private outside space. The backyard is equipped with a large pool with swim up table & layout pad, a full bar, sitting area w/ TV, large dining table, and plenty of lounge chairs to catch some rays! 5.4 miles to Siesta Key Beach 6.8 miles to Turtle Beach 8.2 miles to Nokmis Beach

4.97 out of 5 average rating, 258 reviews

Your private retreat near Siesta Key Beach.

Welcome to your Private Retreat! Nestled at the end of a quiet street. This distinguished property guarantees a relaxing Florida vacation for everyone! Completely remodeled with Coastal-Modern Decor. 3 bedroom, 2 bath, amazing heated pool home and private back yard is located in the Gulf Gate Estate neighborhood. A short drive (less than 2 miles) to the white coastal sands of Siesta Key Beach, Gulf Gate shopping mall, grocery store, restaurants, cafes. Must be at least 25 years old

4.93 out of 5 average rating, 378 reviews

A bright and airy indoor space features a coastal-themed rug with a starfish design. Light-colored furniture and a wooden table provide a casual dining area, while large windows allow natural light to fill the room and offer views of the backyard.

Home in Pelican Cove

Beach Retreat•Renovated Pool Patio•Near Siesta Key

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

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 spacious living room is presented with neutral-toned sofas adorned with colorful cushions. A coffee table with decorative items is centered between the seating, while light enters through large windows framed by soft blue curtains. A decorative plant adds a touch of greenery.

5 out of 5 average rating, 34 reviews

Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!

Fantastic South Sarasota Location! Short drive to multiple beaches including World Famous Siesta Key & Siesta Village. To the South is Quaint Downtown Venice with shopping and restaurants. Sharkey’s Pier for Fishing, also the Shark Tooth Capital of the World! You could find fossilized, shark teeth and shells. The Legacy Trail is around the corner a favorite for bike riding. There are so many restaurants to choose from. If you like to cook Detwiler‘s Farmers Market is a must!

5 out of 5 average rating, 4 reviews

Luxury Waterfront Home in Sarasota w/ Pool & Dock

Exclusive Amenities Include: • Private Heated Saltwater infinity-edge Pool & Spa • Canal front with Breathtaking Intracoastal Views • 4 Bedrooms - 2 Primaries with Ensuite Bathrooms for a total of 3 Full Baths • Outdoor Lounge Area - Private Heated Pool with Baja Shelf, Gas Grill & Outdoor Kitchen • Private Boat Dock • Dock Fishing • Free WiFi & HD Smart TV’s • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Cart

4.85 out of 5 average rating, 177 reviews

A light-filled living area features a soft blue sofa adorned with decorative pillows. Large sliding glass doors open to a private screened lanai, enhancing the connection to the outdoors. A simple coffee table is centered on a cozy area rug, with a TV placed against the opposite wall.

Flat in Sarasota

Little gem just 6 min from Siesta+heated pool

★ Second floor 1 bedroom 1 bathroom apartment ★ "An incredible apartment and 6 star hospitality!" 🌴 Stylish Retreat Near Siesta Key & Heated Pool! Welcome to your perfect Sarasota getaway! This pet-friendly home offers a, heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

4.92 out of 5 average rating, 149 reviews

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

A sparkling screened pool surrounded by a spacious patio area features lounge chairs for relaxation. The pool area is complemented by a hot tub and offers views of the indoor living space through large glass doors, enhancing the indoor-outdoor connection.

4.95 out of 5 average rating, 21 reviews

Siesta Key Modern Retreat with Heated Pool & Spa

Immerse yourself in the elegance of modern living at this stunning contemporary home, designed with sophistication in mind. Perfect for families, couples, and business travelers, this property is your gateway to Sarasota's best - from the sun-kissed shores of Siesta Key Beach to the vibrant streets of downtown Sarasota. Embrace the luxury within and the adventures that lie just beyond. Discover more below!

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 Vamo rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A heated pool is framed by a screened enclosure, allowing for sunlit swims while providing shade. Comfortable lounge chairs are lined along the poolside, and greenery is visible in the background, creating a serene atmosphere for relaxation.

4.93 out of 5 average rating, 106 reviews

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

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!

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, 12 reviews

The Palms Away

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.96 out of 5 average rating, 149 reviews

Beautifully Remodeled Home with Pool Near Siesta

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

5 out of 5 average rating, 3 reviews

Gulf Gate Getaway – 2BR/2BA w/ Heated Pool

5 out of 5 average rating, 35 reviews

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Arlington Park

Sarasota Escape | Minutes to Beaches + Downtown

The outdoor space features a screened-in pool, surrounded by tropical landscaping and a putting green. A barbecue grill is positioned nearby, and several lounge chairs are visible, providing ideal spots for relaxation. The sky is adorned with warm hues of sunset.

4.97 out of 5 average rating, 32 reviews

Intercostal Oasis

Apartment rentals with a pool

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.

4.96 out of 5 average rating, 214 reviews

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

4.83 out of 5 average rating, 254 reviews

A living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.

Apartment in Siesta Key

Cozy 1BR Beach Condo on Siesta Key!

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

A welcoming living area features a green sofa adorned with colorful cushions. A large tropical mural displays flamingos and lush foliage. A round coffee table sits in front of the sofa, while a dining area with elegant chairs and a floral centerpiece is visible in the background.

4.86 out of 5 average rating, 197 reviews

♥ 1/2 mile to BEACH! ➸ KING in master ➸ POOL ♥

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

4.88 out of 5 average rating, 121 reviews

Sunset and beach view from your balcony Unit 403

Apartment in Longboat Key

4.99 out of 5 average rating, 165 reviews

Silver Sands By the Sea: Open Christmas!

A heated swimming pool is centrally located, surrounded by colorful lounge chairs in red, yellow, and green. The turquoise water is inviting under clear blue skies, with palm trees bordering the area. Nearby, several outdoor chairs are positioned for relaxation.

4.91 out of 5 average rating, 242 reviews

Near beach. Daily rentals. Pool. king bed

Other holiday rentals with a pool

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

5 out of 5 average rating, 78 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

A large, sparkling private pool is enclosed within a pool cage, allowing for safety and comfort. Sunlight reflects off the clear water, while a spacious patio area provides comfortable seating. Lush greenery and flower beds surround the pool, creating a serene outdoor space.

4.98 out of 5 average rating, 60 reviews

Serene&Clean! Great location! Heated pool!

An aerial view of a single-story home with a blue exterior and a metal roof highlights a private pool surrounded by a spacious patio. Lush landscaping and palm trees create a tropical atmosphere, while a shaded seating area under the umbrella invites relaxation.

5 out of 5 average rating, 42 reviews

Waterfront Retreat | Heated Pool & Boat Dock

4.73 out of 5 average rating, 11 reviews

The outdoor pool area features a spacious swimming pool alongside a hot tub. Surrounded by tall trees, the space offers a relaxing atmosphere with lounge chairs and umbrellas positioned around the pool deck. Clear blue skies enhance the inviting setting.

Villa in Sarasota

Charming 2/2 Village des Pins close to Siesta Key

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.

5 out of 5 average rating, 67 reviews

Breathtaking Beachfront Views in Siesta Key

A tropical outdoor area is seen with palm trees casting shadows on a gravel surface. Lounge chairs and tables are present, providing spaces for relaxation. A low wall with greenery around it surrounds the area, creating a private atmosphere.

5 out of 5 average rating, 5 reviews

Siesta Key Poolside Paradise”

4.75 out of 5 average rating, 4 reviews

Flat in Sarasota

2BR Beachfront Condo Steps To Turtle Beach | Pool