Vacation rentals with a pool in Vamo

A vibrant sunset lights up the sky in shades of orange and pink, framed by tall trees that line a quiet street. The silhouettes of palm trees add to the tropical ambiance, while homes are visible in the background, nestled among the lush landscaping.

4.92 out of 5 average rating, 102 reviews

Spectacular Sunsets! 15 min Siesta Key!

This villa is spacious and bright with lots of windows. The interior has just been updated. Tropical decor makes you feel like your’e at the beach. Huge flat screen TV. Tile flooring in the living areas and laminate in the bedrooms. Screened lanai overlooks palm tree and mature landscaping. Wireless fast speed internet included. It has everything you need for a short visit or extended stay. Fully equipped kitchen. Washer and Dryer. Beach chairs and towels. One car garage and driveway space.

4.93 out of 5 average rating, 374 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

☀Coastal Gem☀Heated pool & amazing location!☀

- Located in a quiet Sarasota neighborhood minutes from shopping, restaurants, & Siesta Key, this amenity packed home is perfect for families and beach enthusiasts! - Enjoy the pool and patio (renovated in July 2025) and comfy outdoor furniture in your fenced in backyard where you can bask in the sun. - Beautifully designed coastal interior w/ new appliances, Smart TVs, and fast WiFi. - Your on-site Superhost is available if needed to assist with making your stay enjoyable and worry free.

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.

4.96 out of 5 average rating, 120 reviews

Your Modern Beachside Getaway!

Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!

4.93 out of 5 average rating, 102 reviews

An inviting outdoor space features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned along the poolside, with lush greenery and tropical plants enhancing the landscape. A pergola provides shaded seating, creating a comfortable area for relaxation and entertainment.

Home in Arlington Park

Sea Esta | Private Saltwater POOL + Putting Green!

BNB Breeze Presents: Sea Esta! Experience this stunning, newly-renovated home in the heart of Sarasota, located just 10 minutes away from Siesta Key Beach! From the gorgeous interior, to the INCREDIBLE outdoor oasis, this home has everything that you and your loved ones need for your next dream vacation, including: • Private Heated Saltwater Pool! • E-Bikes (For Rent) • Resort-Like Back Yard w/ a Pergola, Turf + Putting Green • Pool + Beach Supplies • Fun Outdoor Swinging Dining Table

4.94 out of 5 average rating, 111 reviews

Rita Retreat - Beautiful 2/2 with private pool

Welcome to your dream vacation home! This charming rental offers a private pool and a lush green area for relaxation and fun. Situated just 4.6 miles away from the stunning Siesta Key beach, you'll have easy access to sun-kissed sands and sparkling waters. Seafood lovers will be delighted to find the renowned Phillippi Creek Oyster Bar nearby, offering some of the best seafood in town. Embrace the Florida lifestyle and make cherished memories in this wonderful retreat!

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.

4.93 out of 5 average rating, 105 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

A serene pool area is surrounded by lush greenery and wooden fencing. Aquamarine water reflects sunlight, while a few poolside lounge chairs in turquoise invite relaxation. Potted plants add a touch of color, and a floating pool accessory rests on the surface.

4.94 out of 5 average rating, 112 reviews

5Stars Tiki, Heated Pool, Close to Beaches and ALL

Beautiful home with amazing pool and landscape, 15 minutes from Siesta Key Beach, 25 minutes from Lido Key Beach and Venice Beach. Close to grocery stores, parks, biking trails, shopping and restaurants. Enjoy the pool, entertain your family in our tiki bar, meditate in our amazing backyard or rest in our tastefully decorated bedrooms. Two pets under 30 pounds are allowed. Our pet fee is $150/dog. Please enter your pet when you complete the reservation.

A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.

4.93 out of 5 average rating, 136 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ask for!

4.99 out of 5 average rating, 142 reviews

A light blue bedroom features a spacious bed with a floral-patterned blanket and a ceiling fan overhead. Double glass doors provide a view of the pool area outside. Storage options include a white dresser and closet, while a small table and chair are positioned nearby.

Guesthouse in Sarasota

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

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!

Charming 2BR/2BA Lakefront Home with Heated Pool – Just 2 Miles to Siesta Key Beach! Escape to this picturesque lakefront retreat, only 2 miles from the world-famous Siesta Key Beach. Perfect for families or groups, this spacious and beautifully furnished home offers a relaxing and memorable getaway. Lounge by the heated pool, soak in stunning lake views, or explore nearby attractions—this home is your ideal Sarasota vacation base.

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, 20 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, 338 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

Oct SALE! Private Sarasota #1 Luxery beach Villa

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 modern, one-story villa is showcased with a light-colored exterior. The front door is flanked by tropical palm trees and vibrant landscaping. A paved driveway leads to an attached garage, enhancing accessibility in this coastal retreat.

5 out of 5 average rating, 27 reviews

Ground floor home 2BD2BA garage Pool Private beach

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.

5 out of 5 average rating, 11 reviews

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

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, 33 reviews

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

A serene pool area features a rectangular swimming pool surrounded by a spacious deck. Lounge chairs are positioned for relaxation, while lush greenery and a wooden fence provide privacy. A decorative statue adds an elegant touch to the tranquil environment.

4.99 out of 5 average rating, 91 reviews

The Oasis

4.99 out of 5 average rating, 91 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

Relax in a Private Tropical Retreat on Siesta Key!

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, 148 reviews

Beautifully Remodeled Home with Pool Near Siesta

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, 126 reviews

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

5 out of 5 average rating, 32 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

Condo 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.

4.97 out of 5 average rating, 209 reviews

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

4.84 out of 5 average rating, 250 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.

Condo in Siesta Key

Cozy 1BR Beach Condo on Siesta Key!

4.8 out of 5 average rating, 106 reviews

Condo in Lido Key

LIDO KEY 1 BR/1Bath Heated Pool 16

A cozy living area is depicted, featuring a comfortable sofa and two light blue armchairs. A wooden coffee table is centered in the space, while a small TV is positioned on a decorative cabinet. Soft lighting from floor lamps enhances the inviting atmosphere.

4.86 out of 5 average rating, 152 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

4.88 out of 5 average rating, 117 reviews

A living room area features large sliding glass doors that open to a private balcony with views of the Gulf of Mexico. Soft gray furniture is arranged around a coffee table, and a flat-screen TV is located on a media console. Natural light fills the space.

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

4.91 out of 5 average rating, 190 reviews

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.

Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

4.96 out of 5 average rating, 138 reviews

The inviting living area features a brown leather sofa paired with a teal accent chair. A circular mirror is positioned above a coffee table, which holds magazines. A patterned rug sits beneath, and natural light filters through the sliding glass doors.

Condo in Bradenton

Cozy 2 bed/2.5 bath townhome

4.92 out of 5 average rating, 116 reviews

A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.

Condo in Siesta Key

Siesta Key Beach Front Condo

Other vacation rentals with a pool

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.

4.94 out of 5 average rating, 85 reviews

Deja Blue Villa Salt Water Heated Pool & Spa

5 out of 5 average rating, 7 reviews

Chic happens 3/2pool 5min from Siesta

A spacious living area is depicted with light-colored tiles. Two sofas, adorned with aqua and gray decorative pillows, face each other. A glass coffee table sits in between, and two lamps provide ambient lighting. A dining area with a circular table is visible in the background.

4.87 out of 5 average rating, 69 reviews

La Villa des Pins

An aerial view showcases the waterfront property, highlighting the building's proximity to the canal. Nearby greenery and water feature prominently, while the surrounding area includes various residential and commercial structures, indicating a vibrant community. The pool is visible, situated on the property.

4.96 out of 5 average rating, 26 reviews

Waterfront w/ Pool, mins to SK Beaches, bikes/sups

4.9 out of 5 average rating, 98 reviews

An inviting pool area is framed by a protective screen, with soft lighting illuminating the space. Lush plants hang from the ceiling, and a decorative piece is positioned on the wall, creating an atmosphere of relaxation and calmness.

Guesthouse in Sarasota

Cabana/Guest house w/spa/pool 5min to Siesta key.

A sign marking Siesta Beach as the '#1 Beach in the USA' is prominently displayed at the entrance. A sandy pathway leads to the beach, flanked by green vegetation and palm trees. Beachgoers and colorful umbrellas can be seen in the background, emphasizing the lively atmosphere.

4.88 out of 5 average rating, 69 reviews

A Hidden Gem in Paradise

A serene pool area is bordered by lush palm trees and vibrant greenery, providing a refreshing atmosphere. The clear blue sky is visible above the inviting water, with several lounge chairs placed around the pool, offering a perfect spot for relaxation.

4.96 out of 5 average rating, 47 reviews

Modern, Spacious Villa close to the Beach!FreeWiFi

An inviting outdoor space features a private pool, hot tub, and lounge chairs, surrounded by tropical landscaping. A built-in barbecue grill is situated nearby for outdoor dining. The bright living area includes plush seating and decor harmonizing with the coastal theme, complemented by natural light from large windows.