Vacation rentals with a pool in Gulf Gate Estates

Complete Privacy Mid Century 2mi to #1 Beach Pool

Relax and take it easy at this beautiful old Florida home. Step outside to your own PRIVATE OASIS with towering palm trees, heated salt water pool, turf lawn and ping pong table! Located on a quiet cul de sac and a driveway that fits 4 cars. Featuring an open layout that looks out to the pool, 4 beds and paddle board with straps! Walking distance to 50+ shops and restaurants in Gulf Gate. Less than 2 mi to Siesta Beach and 5 mi to downtown. 25 mins to SRQ. Under an hour from PGD, PIE and TPA

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

Luxury 4B Home & Heated Pool, Resort for 10 guests

Minutes to Siesta Key Beach, this Sarasota home is made for effortless group getaways. Start your mornings by the private screened pool, unwind on the cabana daybed, and gather in bright open living spaces designed for connection. Enjoy a fully equipped kitchen, 3 full bathrooms, and a separate studio offering extra space and privacy. Centrally located with quick access to St. Armands Circle, The Ringling, and Mote Marine Laboratory & Aquarium—perfect for dining, culture, and family fun 🌴

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

Private Heated Saltwater Pool & Spa 1 mi to Beach

Welcome to Salty Palms Pool House. Your family will be close to everything when you stay at this CLEAN modern completely remodeled home 2024 only 1 mile off the sand of Siesta Key Beach. The backyard offers a private resort like oasis with a heated saltwater pool & spa, modern fire pit, heated outdoor shower and BBQ grill. New fully stocked kitchen with Quartz countertops, beverage fridge, all new appliances, & coffee bar. Smart TV and Fans in every room. W&D, Tankless h20 heater.

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.

Private heated pool, 3Bed, 2Bath, Siesta Key

Family oriented house; Heated pool; Kids scooters, bikes, beach toys, games, etc; 3bed/2bath/laundry; 1 crib; 10 minutes to Siesta Beach; 15 minutes to Siesta Village Restaurants/Shops. 20-25 minutes to Sarasota Airport, Lido Key Beaches & Shops, Venice; BONUS FEATURES: +Fast Wifi, +Cable TVs, +Netflix, +Disney, +Kids activity corner & games, +Kids safety net by pool is optional.

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. 🌴

JULY AVAIL! 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!

Captain's Cottage

"West of Trail" home close to Crescent Beach and Siesta Key with water access Right in the heart of South Sarasota, restaurants, groceries, shopping within minutes. Water access for kayaking right across the street from the house. Very private, great for walking and bike riding. One of the best kept secret locations in Sarasota. You will fall in love with the place!