Vacation rentals with a pool in Gulf Gate Estates

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, 129 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!

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, 111 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!

4.97 out of 5 average rating, 258 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

4.93 out of 5 average rating, 380 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 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

It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

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, 353 reviews

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!

Superhost

A screened outdoor area features a shaped pool and a hot tub. Sun loungers sit along the edge, and a large umbrella provides shade over a seating area. The space is surrounded by greenery, contributing to a serene environment.

Guest suite in Sarasota

4.72 out of 5 average rating, 300 reviews

Prvt entry Suite-2nd Fl HotTub/pool & beach items

This location is * 8.6 * miles from Siesta Key Beach 18-22 min drive Entire upstairs private in-law suite sleeps (4) people (king bed & queen pullout couch) w/ bathroom, & kitchenette. I live on the property AND have a ADDITIONAL UNIT which is located directly below this room for rent. Shared areas for all guests are pool/hot tub, patio, and garage areas. The pool/hot tub operate within hours listed. The “stove” listed is a hot plate with three burners.

A serene community pool is surrounded by a fence and complemented by lounge chairs positioned nearby. The pool's clear blue water reflects the sunlight, while the yellow exterior of the building provides a warm backdrop. Windows with awnings complete the inviting atmosphere of the area.

4.94 out of 5 average rating, 159 reviews

ONLY $155/night in January!

2 BDRM/2 BTHRM condo very close to Siesta Key (3 min. drive or 20 min. walk). Totally UPDATED! Quality furnishings, super clean, ideal location. Have it all: Spacious condo in a peaceful setting. Just a few minutes drive over the south bridge to Siesta Key. Walking distance to great restaurants and shops on and off the key. Everything is within easy access by walking, car, bike, or free beach shuttle service. Come enjoy everything Sarasota has to offer.

A private backyard features a heated saltwater pool surrounded by a spacious patio area. Sun loungers are arranged along the edge of the pool, while trees and shrubbery provide a sense of seclusion. Soft clouds drift in the blue sky above.

4.95 out of 5 average rating, 120 reviews

Coastal Getaway *With Bikes & NEW Saltwater Pool*

Just outside of Downtown near the Legacy Trail, this home is located in a quiet neighborhood only 15 minutes from the Siesta Key Beach. The home stands out with its bright and airy design, brand new saltwater pool in the private backyard, and its breezy living room. The large master bathroom rain shower is perfect to wash off the leftover sand from the beach. You can also spend your evenings grilling out back or playing corn hole in the patio area.

A screened lanai encloses a private saltwater pool, featuring a shallow entry and a vibrant pink float. Two lounge chairs are positioned nearby, surrounded by greenery that enhances the serene pool area.

4.94 out of 5 average rating, 102 reviews

Minutes to Siesta Key, heated pool & tiki on water

Coral Harbor is conveniently located in Gulf Gate Estates, just 3 miles to the beach. The 1 acre property sleeps up to 12, with a private heated salt water pool, mature trees, lanai, sun deck, and bonus "Tiki" bar. You'll love the deck overlooking the lake to feed the turtles! The home has all the modern amenities you would expect from a vacation home. Minutes to Siesta Key, easy access to Venice Beach, Lido Beach, downtown Sarasota, AMI & more!

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.

4.79 out of 5 average rating, 229 reviews

The open living space is highlighted by a circular dining table surrounded by four chairs. A turquoise sofa and coffee table are arranged in the living area, with a large TV mounted on the wall. Natural light fills the room through nearby windows, enhancing the airy atmosphere.

Apartment in Siesta Key

2/2 Beach House Apt on Siesta Key

Siesta Key Waterfront Apartment. Sleeps 6. Split plan 2 bedroom, 2 full bathroom “Beach House” w/ a full kitchen & recently updated! Bedroom 1: King. Bedroom 2: Queen. Living room: Sleeper sofa. 75” smart TV in the living room. A private screened lanai overlooking canal to Sarasota Bay. This is located in a super cute, quaint resort w/ other units. FREE KAYAKS & SUPs FOR GUESTS!

Popular amenities for Gulf Gate Estates rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private hot tub is shown within a screened enclosure, featuring clear blue water. Two inflatable rings are floating on the surface. Lush greenery can be seen in the background, providing a natural setting for relaxation.

4.98 out of 5 average rating, 103 reviews

Location! Siesta 1 mile away. Home with HOT SPA.

The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.

4.89 out of 5 average rating, 167 reviews

5 minutes to private Siesta Key Beach + 2 pools

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, 111 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

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, 128 reviews

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

A spacious outdoor area surrounds a heated saltwater pool, which is enclosed by a screened-in patio. Several lounge chairs are positioned beside the pool, with a colorful inflatable float visible in the water. Lush greenery adds a natural backdrop in the distance.

5 out of 5 average rating, 69 reviews

Heated saltwater pool, Hot tub!7 min to Siesta Key

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

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, 116 reviews

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

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, 221 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

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.

4.96 out of 5 average rating, 214 reviews

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

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.

4.84 out of 5 average rating, 256 reviews

Cozy 1BR Beach Condo on Siesta Key!

An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.

4.92 out of 5 average rating, 144 reviews

Sea Shell Ocean View On Beach Walk Everywhere Pool

A detailed map highlights the location of Siesta Key, showcasing nearby points of interest and roadways. The Gulf of Mexico is indicated to the southwest, while the surrounding areas and other keys are marked, providing context for travel and exploration.

4.87 out of 5 average rating, 104 reviews

Bayside Sunrise Cottage on Siesta Key!

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.

4.89 out of 5 average rating, 130 reviews

Crystal House on Siesta Key Beach

Superhost

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 ♥

4.98 out of 5 average rating, 220 reviews

Condo in Longboat Key

Oceanfront: Open Tonite, $100/nt + Fees!

4.91 out of 5 average rating, 151 reviews

Cottage on Siesta Key Beachside & Stunning sunsets

Other vacation rentals with a pool

4.92 out of 5 average rating, 26 reviews

A serene swimming pool is highlighted with a clear, inviting blue water surface. Submerged seating areas offer relaxing spots within the pool. Sun loungers and a shaded area with an umbrella are positioned around the pool deck, creating spaces for leisure and enjoyment.

Bungalow in Sarasota

Sarasota Luxury house, 3BD, Siesta Key Beach

5 out of 5 average rating, 14 reviews

A modern living space is showcased, featuring a sectional sofa and a wooden coffee table. A wall-mounted television displays serene ocean imagery. The fully equipped kitchen, visible in the background, includes stainless steel appliances and a casual dining area with two chairs. Natural light enters through large windows.

Guesthouse in Sarasota

New! Siesta Beach Guest House with 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!

4.97 out of 5 average rating, 75 reviews

A heated pool is surrounded by lush greenery, with clear blue water inviting relaxation. Sunlight glimmers on the surface, and a cozy pool area is visible alongside a white two-story building. The space features a kayak resting against the pool's edge.

Apartment in Sarasota

Beechwood Suites A

A screened-in outdoor area features a spacious pool surrounded by a brick patio. Comfortable seating is visible in the background, alongside a bar area with stools. Lush greenery frames the space, providing a private atmosphere for relaxation.

4.98 out of 5 average rating, 45 reviews

Heated Pool and Hot tub 2 miles from Siesta Key

A screened swimming pool area is framed by a spacious patio with stone flooring. Four lounge chairs are positioned alongside the pool, which features inviting blue water. Lush greenery is visible beyond the enclosure, complemented by a vibrant sunset sky.

4.86 out of 5 average rating, 63 reviews

Siesta Key, Luxurious House W/ Heated Pool

A well-appointed backyard features a heated saltwater pool surrounded by elegant stone decking. Lush green artificial grass lines the pool area, enhancing the design. Comfortable lounge chairs are positioned nearby, offering a relaxing space for enjoyment under the shade of sleek umbrellas.

4.94 out of 5 average rating, 90 reviews

Private Heated Saltwater Pool & Spa 1 mi to Beach