Family-friendly holiday rentals 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

4.98 out of 5 average rating, 179 reviews

Apartment in Sarasota

Near Siesta Key Beaches - Quiet 1 BR apt

Cozy, quiet & private getaway 2 mi. from the white sands of Siesta Key. Solar powered! Under a 100-yr. old live oak, keyless entry, 3-rm. apt., east side of our home. 10 min. to beaches, 3 min. to shopping, groceries, pubs, restaurants or cook at home: apt. size stove, fridge, toaster oven, full size microwave, coffee pot. Take a morning cup out to your fenced private patio and enjoy the tropical garden. Everything you need is here. Escape to this special retreat in a relaxed tranquil setting.

4.99 out of 5 average rating, 68 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, 12 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

4.96 out of 5 average rating, 248 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

4.96 out of 5 average rating, 362 reviews

Tiny home in Sarasota

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

4.96 out of 5 average rating, 147 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.

4.87 out of 5 average rating, 159 reviews

1.9 mi to Siesta Key, Beach Gear+Bikes+Restaurants

Power & high speed & 🛜 - Siesta Key 1.9 mi, mecca portal to shopping & dining (Vegan, Raw, Sushi, BBQ, Craft Beer, Italian... and more). 1.9 miles to the white sandy beaches of Siesta Key. Home: Updated kitchen, Bedrooms w/very comfortable beds. 2.5 bathrooms. SmartTVs, FIOS, streaming sports & Live TV channels (WiFi: over 200mbps). Large Kitchen, screened porch, and private yard. Beach Gear: Towels, Chairs, Cooler, Umbrella, & bikes! 11 mi to SRQ airport

5 out of 5 average rating, 12 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.

4.94 out of 5 average rating, 217 reviews

Guest suite in Sarasota

Sunshine Inn Paradise

Sunshine Inn Paradise Come as guests, stay as friends, leave as family! Step into your private oasis with a sparkling pool, outdoor shower, and deck surrounded by lush gardens. Whether you’re here to relax or explore, everything you need is here We don’t just offer a place to stay—we offer a place to belong. We can’t wait to welcome you as a guest and see you off as family.

4.97 out of 5 average rating, 330 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!