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, 304 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!

4.96 out of 5 average rating, 120 reviews

Beachside Bliss: Family Paradise/Siesta Key3BR/2BA

Vacation on the Siesta Key Beach! Private Family Home just 3 miles from Siesta Key Beach! This fully renovated 3BR/2BA retreat is located in the peaceful and prestigious Gulf Gate Estates. Everything inside is brand new, offering comfort and style for your perfect getaway. Relax with family, enjoy the famous white sand beaches of Siesta Key, explore nearby restaurants and shops, and unwind in your spacious private backyard—ideal for morning coffee or evening BBQs. Your vacation paradise awaits!

A well-lit dining area features a modern table with four chairs, complemented by a floral artwork on the wall. Natural light enters through French doors, enhancing the bright and open atmosphere. A stainless steel refrigerator is visible, maintaining a clean and functional kitchen space.

4.9 out of 5 average rating, 115 reviews

Tropical Paradise minutes to #1 Siesta Key Beach

Location! Just minute to the #1 Beach in USA , Siesta restaurant and shopping. This cozy 2 bedroom/1 bath home feels very modern, comfortable and very functional. Tropical landscaping .Fully equipped kitchen. Beautiful private fenced backyard with Yoga platform. Beach chairs available. Perfect for a budget oriented traveler looking for immaculate home and convenient location close to Hwy 41 Siesta Beach and shopping and walking distance to restaurants. Primary guest must be 25 years of age.

Apartment 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, 188 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.

4.95 out of 5 average rating, 411 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)

4.97 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

A well-appointed backyard features a heated saltwater pool surrounded by elegant stone decking. Lush green artificial grass lines the pool area, enhancing the design. Comfortable lounge chairs are positioned nearby, offering a relaxing space for enjoyment under the shade of sleek umbrellas.

4.91 out of 5 average rating, 102 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.

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, 121 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, 122 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 🌴☀️

4.97 out of 5 average rating, 119 reviews

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

Important for privacy-conscious guests: You are renting a fully private home. There are no shared spaces of any kind. Stylish 4BR home 9 minutes from Siesta Key. Private jacuzzi, equipped kitchen, fast Wi-Fi, and outdoor grill. Sleeps 8, 2 bathrooms. Pet-friendly with fee. Please note: A separate structure on the property has its own entrance and does not share space with the guest home.

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

4.98 out of 5 average rating, 157 reviews

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

4.97 out of 5 average rating, 377 reviews

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

Condo in Siesta Key

On the Beach; Siesta Key SunBum Studio

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, 360 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

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 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, 105 reviews

Spectacular Sunsets! 15 min Siesta Key!

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, 141 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 112 reviews

Home in Arlington Park

Sea Esta | Private Saltwater POOL + Putting Green!

A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.

4.94 out of 5 average rating, 156 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

4.86 out of 5 average rating, 139 reviews

Home in Longboat Key

Summer House longboat key

Condo 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.

4.97 out of 5 average rating, 134 reviews

Modern Studio · 5 min from Siesta Beach

Superhost

4.72 out of 5 average rating, 120 reviews

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

Condo 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, 184 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

A secluded backyard features a heated pool surrounded by lush greenery and flowering plants. Tropical palm trees and colorful potted plants enhance the tranquil atmosphere, while the tiled pool edge adds a touch of contemporary design.

4.84 out of 5 average rating, 308 reviews

Private Siesta Beach House Oasis with Heated Pool.

4.96 out of 5 average rating, 96 reviews

New King Bed, 4B/2B Paradise 10 mins to Siesta Key

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 113 reviews

Your DreamOasisAwaits: SiestaKeyEscape with 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!

A private pool area is surrounded by a clean white patio, featuring several lounge chairs arranged for relaxation. The light-colored exterior of the home is contrasted by green landscaping. A grill is positioned nearby, enhancing outdoor dining possibilities.

4.85 out of 5 average rating, 46 reviews

Gulf Gate Pool Home

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.

4.87 out of 5 average rating, 75 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, 72 reviews

Coastal Home in Sarasota-8min from Siesta Key

An aerial view of the heated pool is captured within a screened enclosure, showcasing its vibrant blue water. The surrounding patio is visible, framed by lush greenery, while patterns from the enclosure create contrasting shadows across the surface.

4.91 out of 5 average rating, 58 reviews

Private Home near Siesta Key

5 out of 5 average rating, 10 reviews

Modern Private Paradise-Pool House

A spacious outdoor area surrounds a heated saltwater pool, which is enclosed by a screened-in patio. Several lounge chairs are positioned beside the pool, with a colorful inflatable float visible in the water. Lush greenery adds a natural backdrop in the distance.