Vacation rentals with a pool in Gulf Gate Estates

4.88 out of 5 average rating, 160 reviews

5 minutes to private Siesta Key Beach + 2 pools

Escape to this luxurious 1st-floor condo on Siesta Key, just 5 minutes from the award-winning Siesta Key Beach. Enjoy private access to its soft, white sand and turquoise waters. Perfect for families, the condo offers two heated pools, lighted tennis and pickleball courts, a fishing pier, gym, and sauna for endless fun and relaxation. Nestled in a tropical setting, it’s the ideal spot for your beach vacation, staycation, or a peaceful getaway. Everything you need for an unforgettable experience!

5 out of 5 average rating, 102 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, this incredible stay includes: ✔ Backyard Putt-Putt Course ✔ Private Heated Saltwater Pool w/ Lounge Chairs ✔ Covered Patio w/ String Lights ✔ Jura Espresso Machine ✔ 65" Frame TV w/ Youtube TV Included!

4.84 out of 5 average rating, 55 reviews

Siesta Key, Luxurious House W/ Heated Pool

Welcome! This wonderful home is the perfect place for you and your family! Located on a peaceful and quiet street, yet close to all of Sarasota's best attractions! Very close to Siesta Key Beach (#1 Beach in USA), and downtown Sarasota which includes many restaurants and shopping. As you step inside the house, you will immediately feel the comfort and relaxation of its inviting ambiance. The newly renovated, 4 bedroom/2 bathroom, beachy motif home is the perfect place for you and your family!

4.9 out of 5 average rating, 51 reviews

Flip off your flops at The Faded Oasis!

The Faded Oasis is a newly remodeled 3 bedroom/2 bath vacation home. Brand new with putting green in the backyard, 80 inch outside, so you can watch movies from the pool. Located in the upscale Gulf Gate community of Sarasota, FL -- just 2 miles from Siesta Key (the #1 beach in the USA). This beautiful home is ideal for families with kids or for groups of up to 3 adult couples (6 person max), and is close to numerous popular restaurants & shopping destinations and several golf courses close by

4.97 out of 5 average rating, 29 reviews

Right on the bay! Heated pool! King bed

Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. You will have whole house except two rooms which will be locked and no one will be there. One bedroom with a king size bed and sleeping sofa in the family room (if more than two guests coming). Full size kitchen, two family rooms, pool and gorgeous view on the salty bay for nature lovers.

5 out of 5 average rating, 11 reviews

Pristine, modern, with pool & 10 mins from Siesta

THE WHITE SANDS is a pristine and stylish vacation property, in the heart of the Gulf Gate Estates and only 10 minutes from Siesta Beach Enjoy this recently renovated house with enough room to host up to 8 people. Four bedrooms include (1) one king-size bed, (2) two full-size beds, (3) one queen-size bed, and (4) dedicated office space with futon Fully furnished outdoor patio next to a beautiful heated pool Plenty of restaurants are within walking distance from you (5 blocks). No pets allowed

4.95 out of 5 average rating, 110 reviews

Condo in Sarasota

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!

4.95 out of 5 average rating, 22 reviews

Peaceful Paradise only 2 miles from Siesta Key

Your own little paradise! Three bedroom, two bathroom house in a quiet Sarasota neighborhood. Enjoy your private oasis of a back yard with the FREE heated pool, hot tub, and fire pit, or enjoy the #1 ranked beach in the U.S. less than 10 mins away by car. You can’t beat this location; with a short drive to downtown Sarasota, St. Armonds Circle, Siesta Key Beach and Village, Nakomis Beach, & everything in between, you’ll never run out of things to do!

5 out of 5 average rating, 11 reviews

Sand Dollar Cottage|Heated pool|10mins to beach!

Sand Dollar cottage is the perfect place to relax after a day spent at the beach, exploring the local area of Siesta Key and Sarasota, or venturing further afield to the many desirable locations reachable from its ideal location of Gulf Gate village. If relaxing is not your vibe, the location of this property boasts the fact that you can walk to an array of nearby bars, cafes, restaurants, pizzerias and stores within a 5 minute walk.

4.96 out of 5 average rating, 27 reviews

Intercostal Oasis

Offering 30% discount for weekly rental for Hurricane Victims.. Welcome to Tropical Intercoastal Oasis in the heart of a boat-friendly paradise! This stunning 3-bedroom, 2-bathroom house is the perfect blend of modern amenities and Florida charm, making it an ideal retreat for families, friends, and even your four-legged companions. It is only minutes away from Siesta Key Beach, America’s #1 rated public beach.

4.97 out of 5 average rating, 329 reviews

Island in Sarasota

NEW 3/NTS JULY OPEN! Sarasota #1 Lux 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!