Family-friendly vacation rentals in Leeward

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Top-rated family-friendly rentals in Leeward

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Long Bay Hills

4.94 out of 5 average rating, 108 reviews

Flame Tree Cottage|Ocean view&pool.Walk to beach

Built in 2013. 1 bedroom 2 bathroom cottage with PRIVATE POOL. Sunrise & ocean view from the front deck and only 1/4 mile to the beach. Perfect for 2, but can sleep up to 6. Full kitchen, 2 bathrooms + outdoor shower. No bathtub. Propane Grill. AC in master bedroom. WIFI throughout & local cell provided. This quaint clutter-free 1200 square foot home is surrounded by indigenous foliage, cactus', succulents and native stonework. A rental car is recommended to explore all the island has to offer!

Guest favorite

A spacious living area features large glass sliding doors that open to a balcony, allowing natural light to illuminate the room. The white furnishings include a comfortable sofa bed and armchairs, with a small side table positioned nearby. Artwork adorns the walls, and a peaceful view of the ocean is visible through the glass doors.

Condo in Providenciales

4.91 out of 5 average rating, 120 reviews

Amazing Grace Bay Views, Terraces Pools & Location

This Pristine, private poolside studio condo is beautiful, turquoise, peaceful & tranquil - as is Turks & Caicos. It is special - cool, casual, chill and comfortable - like the Provo vibe. Live the Villa Estate lifestyle like its your own estate, pool, 6,000 sq ft deck with chaise lounges and umbrellas, and Hot Tub! Enjoy cocktails & dine on your private veranda or large terrazza deck & watch the sunrise/sunset while enjoying the 180 degree panoramic views of Grace Bay. ! In a word, Paradise.

Guest favorite

A bright and airy room features large windows allowing natural light to fill the space. A spacious bed adorned with floral accents is complemented by a cozy seating area. A television is mounted on a white cabinet, and a small plant adds green to the decor.

Apartment in Venetian Road Settlement

4.9 out of 5 average rating, 112 reviews

Cozy Studio Near Beaches w/ Gym & Pool Access

Welcome to your idyllic island retreat! Our centrally located unit offers the perfect blend of convenience and tranquility. Nestled at the heart of the island, you're just minutes away from pristine beaches, supermarkets, cultural hotspots and the airport. Unwind in our thoughtfully designed space, boasting island-inspired decor. Whether you seek adventure or relaxation, this rental is your gateway to a memorable island experience. Book now and make our home yours during your island getaway!

Top guest favorite

The expansive resort pool area features multiple sections, including a large main pool with a central gazebo. Vibrant palm trees surround the space, enhancing the tropical atmosphere, while sun loungers and umbrellas are positioned nearby for guest relaxation.

Condo in Providenciales

4.92 out of 5 average rating, 247 reviews

★★★★★ Modern Condo | Amazing Pool | On Site Spa

• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access *Pool under construction Sept & Oct • Hot tub • Highest Rated Spa on Island • Fully equipped kitchen • Private front patio • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Guest favorite

A thatched-roof gazebo is positioned near the water, surrounded by sandy ground and lush vegetation. Palm trees sway gently, and a calm body of water is visible in the background, reflecting the bright blue sky with fluffy clouds.

Loft in Long Bay Hills

4.88 out of 5 average rating, 178 reviews

Best deal on island! On the water w/pool!

♥♥ The studio is a secluded get-away place apart from the tourist areas. It overlooks the lake of Juba Sound National Park. The studio is only a 10-minute drive to the world-famous Grace Bay Beach and Longbay Beach (kiteboarding beach)! Restaurants and nightlife are also close by. The studio is in a secure, quiet location where you can relax and enjoy your vacation. This studio is ideal for singles, couples, and kiteboarders. You will need to rent a car for better convenience and freedom!

Top guest favorite

An outdoor pool area is illuminated by natural sunlight, featuring lounge chairs with blue cushions arranged around the pool. Palm trees provide shade, while ocean views extend in the background, showcasing the vibrant blue water and greenery of the hillside.

Condo in Turtle Cove

4.95 out of 5 average rating, 190 reviews

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝

🏖 NEWLY RENOVATED, SPACIOUS one bedroom condo with an ocean view at La Vista Azul Condo Resort. Located hillside in the exciting area of Turtle Cove, Providenciales, the unit is close to several excellent restaurants, cafes, bars, a casino, and a marina. Most notably, the studio is a 10 minute walks to Smith's Reef in the Princess Alexandra Park National beach. Smith’s Reef is located near Turtle Cove on the north coast of Providenciales, and about 3.5 miles (5.6 km) from Grace Bay 🏝

Top guest favorite

The exterior of the villa is surrounded by lush greenery, showcasing a white structure with a light-colored roof. A spacious balcony is visible, featuring seating arrangements and providing a view of the vibrant tropical landscape.

Apartment in Leeward Settlement

4.95 out of 5 average rating, 240 reviews

Romantic Apartment few steps from beach

Wake up to the soothing melody of a mockingbird in the garden, as gentle sunlight filters through the lush greenery. Sip your morning coffee on the balcony, overlooking the tropical garden and sparkling crystal-clear pool, where the peaceful ambiance sets the tone for a romantic escape. Afterward, take a leisurely stroll through the vibrant garden or wander just a few minutes to the nearest beach with turquoise waters and soft white sands, perfect for a tranquil start to your day.

Guest favorite

An aerial view captures the vibrant turquoise waters of Sapodilla Bay Beach, with calm waves gently lapping at the shore. Nearby, a wooden pier extends into the water, providing access to serene surroundings. The image includes markers indicating proximity to various local attractions.

Apartment in Providenciales

4.88 out of 5 average rating, 217 reviews

Tatis Ferguson Villas 2

Our new Modern Studio Apartment awaits offering its warm and friendly hospitality to you. If your choice is comfort and service at a reasonable price, come and let us show you our care for your simple and most extravagant desire to enjoy a getaway with your significant other or a getaway for yourself. What are you waiting for ? The location is in South Dock Road, 5 mins from the airport, 10 from sapodilla bay beach, a few mins away from restaurants and right behind a supermarket.

Superhost

A modern three-story building features spacious balconies with outdoor seating. Expansive glass windows reflect the sky, while an inviting lawn with well-maintained greenery surrounds the structure, creating a serene environment.

Condo in Grace Bay

4.81 out of 5 average rating, 130 reviews

Gated Condo in Grace Bay/ Short Walk to Everything

This studio in Grace Bay offers comfort and convenience. It's a few minutes walk to the beach, grocery stores, restaurants, activities, and a medical center. The Caicos Key condo is new and includes a 55-inch smart TV with Fire Stick, fast Wi-Fi, a dishwasher, and a washer/dryer combo. For your security, the property has a smart lock and is gated. Guests can also use the swimming pool and BBQ area. We aim to make your stay comfortable and can provide anything you need on demand.

Superhost

Villa in Long Bay Hills

4.92 out of 5 average rating, 128 reviews

VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY

Take it easy at this dreamy, unique and tranquil getaway. Villa Infini brings privacy and relaxation all in one. Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway. Bali like plunge pool that can create amazing insta-worthy moments. Located in Long Bay! A 5 minute walk to Long Bay Beach, a 5 minute drive to the nearest grocery store and a 5 minute drive to Grace Bay Beach. Everything is 5 minutes away!!

Top guest favorite

The infinity edge pool reflects the vibrant colors of the sunset, overlooking Juba Sound. Lush greenery surrounds the area, enhancing the serene atmosphere. The horizon features a calm waterway and the setting sun, creating a picturesque evening view.

Guesthouse in Long Bay Hills

4.99 out of 5 average rating, 178 reviews

Juba Sunset

Waterfront Private apartment that is fully furnished. Private deck. fantastic views overlooking Juba Sound. within 7mins to Grace Bay, world famous Grace Bay Beach and shops. Very quiet and safe area. Infinity edge pool included. Glorious sunsets. BBQ on the waterfront. Only a couple of mins away from popular Kite Surfing spot. There is also a Kayak available for guests use down on the waterfront. This is the only rental unit on property, you will be the only guests.

Guest favorite

A freshwater pool is set within a sunlit area, bordered by vibrant bougainvillea flowers. A shaded gazebo is visible in the background, furnished for relaxation. The surrounding landscape features greenery, enhancing the tranquil environment near the water.

Apartment in Cooper Jack Bay Settlement

4.93 out of 5 average rating, 138 reviews

Poco Villa

Situated in the Discovery Bay Canal "Poco Villa" is a separated complete studio with a view of the canal and access to a freshwater pool and sun decK with bar and barbeque. The accommodation is a one a/c unit with a full kitchen living room and tv. Its a peacefull place surrounded by water. There are two units for rent on this property the other "Coco Villa" both being double occupancy. We do suggest our guests have a vehicle rental to explore the island.