
Holiday rentals with a pool in Gulf Gate Estates
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Gulf Gate Estates
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Newly Renovated w Pool – 10 min to Siesta Beach
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

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

Beach Retreat•Renovated & Heated Pool•Near Siesta
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.

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.

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard
Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

Beautiful Pool Home minutes from Siesta Key
The Gulf Breeze Cottage is your home away from home. The tropically decorated interior sets the mood for a relaxing stay. From the minute you enter, you will know you have arrived in Paradise! Take a plunge in the private pool or relax on the loungers sipping a cool drink as you enjoy time with family and friends. And when your ready to explore, you are minutes to Siesta Key as well as the shops and restaurants of Gulf Gate Village.

Siesta Key-Private Family Pool Home-6 min to Beach
Welcome to a beautifully designed home in the heart of Sarasota's sought-after community. This newly renovated great Gulf Gate pool home has 2 bedrooms and 2 bathrooms and is in a fantastic location near Siesta Key, restaurants and shopping. Tucked away on a quiet street this home is perfectly situated, including a large heated pool with a covered lanai looking out onto a good sized yard.

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

Oasis on water near Siesta Key, Heated Pool, Tiki
Escape to Coral Harbor, a private 1-acre retreat in Gulf Gate Estates! This spacious 4-bed home sleeps 12, just 3 miles from Siesta Key. Enjoy a private saltwater pool, tiki bar, and firepit in your own waterfront paradise. Perfect for families and groups seeking a resort-style getaway with modern comforts and ample space to relax and connect.

Siesta Key Condo. Checkout our great rates!
Our beautiful Siesta Key condo is located a short stroll from the famous Siesta Key beach with its beautiful quartz sand and amazing sunsets. The Midnight Cove II condominium complex has private beach access with outstanding amenities and is very family friendly, come and enjoy the natural beauty this complex and all Siesta Key has to offer.

Private Siesta Beach House Oasis with Heated Pool.
Come enjoy the #1 rated beach in the USA. A contemporary style beach house that is located in a very conveniently located 10 min from Siesta Key beach. Within .5 miles you will find a mall, Cinebistro, trendy local bars, all major banks, Trader Joe’s, Publix, and a gas station. Drive way accommodates 2 cars with street parking as well.

Tranquil 3-Bed Pool Home Near Siesta Key
Welcome to this tranquil 3-bedroom, 2-bath home near Siesta Key Beach. - Cozy living area and fully equipped kitchen - Relaxing bedrooms with queen beds and twin daybed - Peaceful pool with cage and BBQ grill - Free parking, beach chairs, and cooler included - Minutes from top restaurants and Sarasota attractions
Popular amenities for Gulf Gate Estates rentals with a pool
House rentals with a pool

Pool House lots of Wonderful Wildlife

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

Sun-filled cottage with pool, walk to beach

Gulf Gate Oasis w/ Pool Near Siesta Key

The Sand Castle - Backyard Oasis Mins from Siesta!

Siesta Key Paradise-Pool Oasis

The Gecko House - Family Friendly

Spectacular Sunsets! 15 min Siesta Key!
Apartment rentals with a pool

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR

6 Siesta Breakers - Condo, Ocean View, Heated Pool

The Honeymoon Suite on Siesta Key Beach

Villa Maria: Minutes to Siesta Key!

On the Beach; Siesta Key SunBum Studio

Gateway Siesta Key Beach

Comfy Siesta Key Condo

Siesta Key Ground Floor Condo 2BR On Trolley Line
Other holiday rentals with a pool

Spacious Cozy Tropical Retreat!

Siesta Key Private Retreat -Screened Pool Haven

Charming Poolhouse · 1BR · Close to Siesta

Siesta Sands Serenity

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

Intercostal Oasis

Florida Oasis Fully Equipped • 12 Min to Beaches

Beachy Cottage close to Siesta | 3 Bed | Huge Pool
When is the best time to visit Gulf Gate Estates?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 196 | € 223 | € 237 | € 204 | € 183 | € 184 | € 186 | € 172 | € 160 | € 160 | € 172 | € 196 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about holiday rentals with a pool in Gulf Gate Estates

Total holiday rentals
Explore 130 holiday rentals in Gulf Gate Estates

Nightly prices starting at
Gulf Gate Estates holiday rentals start at € 35 per night before taxes and fees

Verified guest reviews
Over 3,860 verified reviews to help you choose

Family-friendly holiday rentals
120 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
130 of Gulf Gate Estates holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Gulf Gate Estates rentals

4.8 Average rating
Gulf Gate Estates stays are highly rated by guests – averaging 4.8 out of 5!
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- Anna Maria Island
- Siesta Beach
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- Lido Key Beach
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- Amalie Arena
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- Anna Maria Public Beach
- Jannus Live
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