Holiday rentals with a pool in Gulf Gate Estates

4.97 out of 5 average rating, 243 reviews

Your private retreat near Siesta Key Beach.

Your Private Retreat! Nestled at the end of a quiet dead-end street. This distinguished rental property guarantees a relaxing Florida vacation for everyone! Completely remodeled with Coastal-Modern Decor. 3 bedroom, 2 bath, amazing heated pool home and private back yard is located in the Gulf Gate Estate neighborhood. A short drive (less than 2 miles) to the white coastal sands of Siesta Key Beach, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Must be at least 25 years old

4.83 out of 5 average rating, 54 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!

4.98 out of 5 average rating, 66 reviews

Siesta Key: Pool |Spa| Game Room |Fire Pit|Grill

Welcome to our spacious, fully stocked home—just 3 miles from Siesta Key Beach (ranked #1 in USA) and minutes from downtown Sarasota, other great beaches, shopping, dining, golf, gyms, trails, and sightseeing spots! Whether you're a family, a group of friends, or a couple craving comfort and space, this beautifully furnished retreat offers the perfect blend of relaxation, fun, privacy, and convenience. You'll love how close you are to everything—yet tucked away in a peaceful residential area.

5 out of 5 average rating, 10 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

4.92 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.

4.96 out of 5 average rating, 146 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.

4.95 out of 5 average rating, 21 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!

4.98 out of 5 average rating, 58 reviews

Serene&Clean!Prime location!Amazing pool&patio!

Perfect for a multigenerational vacation, reunion with old friends or quiet escape! The home is clean and updated. It is located in a quiet residential neighborhood and within walking distance to many unique restaurants, boutiques and pubs. Whether you choose to unwind by the large private pool, hit a beautiful beach (beach gear is provided) or soak in the culture of downtown Sarasota and surrounding area, you are sure to have a lovely time!

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.

4.98 out of 5 average rating, 89 reviews

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.

4.97 out of 5 average rating, 328 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!