Family-friendly holiday rentals in Gulf Gate Estates

Guest suite in Gulf Gate Estates

A wide view of a sandy beach features clusters of beachgoers enjoying the sun. Colorful beach chairs and umbrellas are scattered across the white sand. The gentle waves of the blue ocean can be seen in the distance, with high-rise buildings lining the shore.

4.95 out of 5 average rating, 307 reviews

2 Miles to Siesta Key

Excellent Location. Private & Quiet - Private Entrance & Quiet Surroundings - Comfortable Bedroom & Bath with King Bed - Small Kitchenette fridge/freezer/microwave/coffee maker Private entrance to Guest Suite with full bathroom, kitchenette, sink and countertop, fridge and freezer, microwave, and coffee maker. This provides ample utility to prepare simple meals, but it is not suited for cooking. Located in Gulf Gate with over 150 shops including bakeries, coffee shops, restaurants and more..

Bungalow in Gulf Gate Estates

4.83 out of 5 average rating, 115 reviews

Beach Remedy Retreat near Siesta Key Beach

Unwind & Refresh! Our perfect 3/2 getaway is fully remodeled and our cozy retreat rests in the most ideal location for everything Sarasota has to offer! Just 2 mi. to Siesta Key Beach! Beach towels, chairs & toys provided. Grocery, restaurants and unique shops within 1.5 mi. Indulge in watching gorgeous sunsets, walks on the beach, shop/dine in the many cafes in our community. Extras for your use-hammock, outdoor grill, board games, books, large screened in patio. Family neighborhood. Enjoy!

Flat in Gulf Gate Estates

A bright living area is viewed, showcasing a cozy sofa adorned with decorative pillows. Light drapes frame large glass doors that open to a vibrant garden patio. Two comfortable chairs and a wooden table complement the space, creating a welcoming atmosphere for relaxation.

4.98 out of 5 average rating, 189 reviews

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.

A nautilus shell rests on the sandy beach, displaying striking orange and white stripes. The calm ocean waves gently lap at the shore, while a clear blue sky with scattered clouds provides a serene backdrop to this coastal scene.

4.96 out of 5 average rating, 122 reviews

Beachside Bliss: Family Paradise/Siesta Key3BR/2BA

Escape to this stunning, fully renovated 3BR/2BA home in the prestigious Gulf Gate Neighborhood, just 5 minutes from Siesta Key Beach – ranked the #1 beach in the U.S.! This spacious and airy retreat is designed for relaxation and making unforgettable memories. Enjoy an impeccably styled interior, modern amenities, and a prime location close to Sarasota’s best attractions. Indulge in top-rated restaurants, vibrant shopping centers, and endless beachside adventures-all just around the corner.

A vibrant sunset lights up the sky in shades of orange and pink, framed by tall trees that line a quiet street. The silhouettes of palm trees add to the tropical ambiance, while homes are visible in the background, nestled among the lush landscaping.

4.92 out of 5 average rating, 106 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.

4.88 out of 5 average rating, 264 reviews

Tiny home in Sarasota

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

4.97 out of 5 average rating, 270 reviews

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

Superhost

4.91 out of 5 average rating, 104 reviews

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.

4.98 out of 5 average rating, 112 reviews

Pool, Shuffleboard, EV charg, Near beach, UTC mall

Welcome to Vistalodgings Vista Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

An open living area is presented, featuring a blue couch and a wooden coffee table. A dining table with four chairs sits nearby, complemented by a kitchen with white cabinetry and modern appliances. A Christmas tree adds a seasonal touch, while windows allow natural light.

4.97 out of 5 average rating, 125 reviews

2 BR House 1.6 miles from Siesta Key Beach

Discover the charm of Sarasota in our newly remodeled 2BR/1BA vacation home. Just 1.6 miles from beautiful Siesta Key Beach! Enjoy your morning coffee on a brick patio surrounded by flowers and sunshine. Our comfy beds, blackout curtains, and quiet neighborhood ensure a sweet deep sleep. FIOS wifi and three smart TVs; a fully-equipped kitchen; and a sparkling new bathroom with two sinks, huge mirror, and marble shower offer all the comforts and convenience of home. We welcome you!

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.95 out of 5 average rating, 157 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.

A spacious backyard features a heated private pool surrounded by a paved area. Lounge chairs are positioned around the pool, with umbrellas providing shade. Lush greenery and a fence frame the yard, creating a serene outdoor setting, ideal for relaxation.

4.79 out of 5 average rating, 124 reviews

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 🌴☀️

Popular amenities for Gulf Gate Estates family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The backyard features a newly constructed pool accompanied by a hot tub, both surrounded by vibrant greenery and tropical landscaping. A sun shelf is present in the pool, while a patio area with seating is visible in the background under the shade of trees.

4.96 out of 5 average rating, 110 reviews

Sun-filled cottage with pool, walk to beach

4.98 out of 5 average rating, 157 reviews

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

4.98 out of 5 average rating, 112 reviews

A single-story house is presented with a light-colored exterior and a gently sloping roof. Lush greenery surrounds the property, including palm trees and ornamental shrubbery. A paved driveway leads to a two-car garage, while a clear blue sky completes the inviting exterior view.

Home in Nokomis

Peaceful Getaway just minutes from the beach

4.98 out of 5 average rating, 361 reviews

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!

A private backyard oasis is highlighted by a heated pool and a hot tub, surrounded by lush tropical landscaping. A shaded area with an umbrella and seating for outdoor dining is visible beside the pool, creating a serene environment for relaxation.

4.97 out of 5 average rating, 128 reviews

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

5 out of 5 average rating, 109 reviews

Home in Arlington Park

The Blessing House- Htd Pool/Spa, Close to Beaches

4.92 out of 5 average rating, 144 reviews

A mid-century structure is set among lush palm trees, showcasing a combination of wooden accents and large glass windows. A curved gravel driveway leads to the front entrance, inviting natural light into the living areas and offering a serene outdoor landscape.

Home in Saint Armands

St Armand's Mid-Century Oasis

A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.

4.98 out of 5 average rating, 143 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 113 reviews

Home in Arlington Park

Sea Esta | Private Saltwater POOL + Putting Green!

Superhost

A private heated pool is enclosed within a screened area, surrounded by landscaped greenery. Several lounge chairs are situated beside the pool on a sunlit deck, and the water displays a clear turquoise hue, inviting relaxation.

4.85 out of 5 average rating, 108 reviews

1.5mi to South SiEsta Key Bridge, Free Heated Pool

A bright living area features a comfortable cream-colored sofa and an accent chair, accompanied by a decorative rug. Natural light filters in through vertical blinds, enhancing the warm tones of the wood flooring. Bar stools line a small breakfast counter in the background.

4.96 out of 5 average rating, 92 reviews

Game Room • King Bed • Near Siesta Key Beach •

Apartment in Gulf Gate Estates

The studio features a modern kitchen with white cabinetry and a large countertop. A flat-screen TV is mounted on the wall, and natural light enters through sliding glass doors that lead to the private garden. A compact dining table and a plush blue ottoman add functionality.

4.96 out of 5 average rating, 137 reviews

Modern Studio · 5 min from Siesta Beach

Superhost

4.72 out of 5 average rating, 121 reviews

3 bdr house, Screened in Lanai, 3mi to Siesta Key

Apartment in Gulf Gate Estates

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

4.89 out of 5 average rating, 185 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

4.91 out of 5 average rating, 126 reviews

A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.

Home in Siesta Key

Siesta Key, FL - Casa Berano

A living room features two reclining genuine Italian leather couches arranged to face a wall-mounted 58" flat screen TV. Natural light enters through sheer curtains, highlighting the wood-burning fireplace and polished wooden flooring. A fan is centrally located above for ventilation.

4.84 out of 5 average rating, 237 reviews

Home away from home mins to Siesta Beach! 4/2

Family-friendly home rentals with a pool

A large, sparkling private pool is enclosed within a pool cage, allowing for safety and comfort. Sunlight reflects off the clear water, while a spacious patio area provides comfortable seating. Lush greenery and flower beds surround the pool, creating a serene outdoor space.

4.99 out of 5 average rating, 69 reviews

Serene&Clean! Large Pool! Minutes to Siesta Key!

An aerial view of Siesta Key displays a coastal neighborhood with a network of waterways. The vibrant blue water contrasts with the greenery and residential homes, highlighting the island's tranquil setting. The city skyline of Sarasota is visible in the distance, framing the picturesque scene.

4.99 out of 5 average rating, 102 reviews

Siesta Key Beach Getaway

A private caged pool area features a spacious swimming pool with crystal-clear water. Two loungers in bright blue are positioned beside the pool. A large inflatable ring floats in the water, and an outdoor seating area can be seen in the background, surrounded by greenery.

4.95 out of 5 average rating, 22 reviews

Paradise Getaway Pool house

A screened swimming pool area is framed by a spacious patio with stone flooring. Four lounge chairs are positioned alongside the pool, which features inviting blue water. Lush greenery is visible beyond the enclosure, complemented by a vibrant sunset sky.

4.85 out of 5 average rating, 81 reviews

Siesta Key, Luxurious House W/ Heated Pool

A screened lanai showcases a heated pool and spa, surrounded by twinkling string lights. Lounger chairs and outdoor dining furniture are positioned nearby. A grassy area is visible beyond the pool, while a pink inflatable floats in the water, enhancing the serene outdoor setting.

4.99 out of 5 average rating, 74 reviews

Coastal Home in Sarasota-8min from Siesta Key

A screened lanai encloses a private saltwater pool, featuring a shallow entry and a vibrant pink float. Two lounge chairs are positioned nearby, surrounded by greenery that enhances the serene pool area.

4.95 out of 5 average rating, 117 reviews

Coastal Paradise w/ Pool & Dock, Minutes to Siesta

4.94 out of 5 average rating, 64 reviews

Bay Breeze Cottage Min to Siesta Key Heated Pool