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
An outdoor area features a private pool surrounded by lush indigenous foliage. Comfortable lounge chairs are positioned nearby, with colorful towels neatly arranged. The scene overlooks a serene landscape, enhancing the inviting atmosphere for relaxation and enjoyment.
Cottage in Long Bay Hills
4.94 out of 5 average rating, 109 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
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, 248 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, 179 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
A rooftop terrace features multiple sun loungers and circular seating areas, complemented by blue umbrellas providing shade. The water of the pool reflects the sky above, creating a calming atmosphere. Lush greenery and distant rooftops are visible in the background, adding to the serene setting.
Condo in The Bight Settlement
4.95 out of 5 average rating, 112 reviews

Oasis | 1 BR Condo | Vista Azul | Pool & Wifi

Peaceful Palm Trees with a peek of Ocean View! 10 min walk to the beach or 10 min drive to Grace Bay. Located on 2nd floor of the higher buildings, this condo is a spacious studio with Queen Bed, full kitchen, living room, bathroom, washer and dryer, Wifi and free parking. The large balcony has a pretty view over soothing palm trees dancing in the breeze, with a peek at the ocean in the distance. A great place for morning coffee or relax after long day at the beach or by the pool.

Top guest favorite
A serene outdoor space features a sparkling pool surrounded by lush tropical plants and palm trees. Soft lighting illuminates the area, enhancing the inviting atmosphere. A shaded lounge chair rests nearby, offering a comfortable spot to relax and enjoy the peaceful surroundings.
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 villa is showcased, with its sleek design complemented by lush tropical landscaping. A private plunge pool is visible, surrounded by wooden decking and lounge chairs. A small outdoor dining area and a barbecue grill are also present, creating a relaxing outdoor living space.
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!!

Guest favorite
A covered balcony offers outdoor seating with two armchairs and a coffee table. Lush greenery surrounds the area, and a pool can be seen in the background. The tiled floor complements the natural elements of the space.
Condo in Providenciales
4.88 out of 5 average rating, 145 reviews

*Balcony View* Modern Studio C202

Welcome to our little piece of paradise in Providenciales, Turks and Caicos. We hope that you will enjoy our modern style condo as much as we do. Our condominium is situated at Queen Angel Resort, walking distance to the #1 beach in the world, Turtle Cove Marina, and Smith’s Reef the best snorkelling spot on the island. Turtle Cove is a tourist hot spot with many restaurants, excursions and attractions available. The condo has recently been fully renovated and remodelled.

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.

Top guest favorite
Guesthouse in Leeward Settlement
4.97 out of 5 average rating, 114 reviews

"The Nest Cozy Cottage"

“The Nest” Spacious and modern 1 bedroom cottage sits amongst a well-manicured garden with majestic swaying palms. Less than 150 steps away from the famous Grace Bay Beach. This cozy sanctuary is quiet and bears the true beauty of itself, it’s perfect for honeymooners or if you’re just seeking for some quiet and down time. Complete with high-speed internet, cable TV and all amenities one need for the perfect vacation, The Nest is where you want to be.

Superhost
Cottage in Leeward Settlement
4.91 out of 5 average rating, 123 reviews

Sandpiper Cottage, minutes from the beach

Kick back and relax in this delightful modern one bedroom cottage in the high end residential gated community of Leeward. Grace Bay Beach, most recently voted “The best in the world” is only a 4 minute walk away! This cozy cottage is perfect for a couple, wanting to relax and have some downtime. Complete with full kitchen, washer/dryer/ BBQ, high speed internet with cable TV and all amenities needed for the perfect getaway.

Superhost
An inviting interior space combines a comfortable green sofa with a vibrant orange wall. A queen bed is visible in the background, surrounded by natural light from glass doors. Decorative pillows add color, while a ceiling fan and art piece enhance the cozy atmosphere.
Guesthouse in Leeward Settlement
4.9 out of 5 average rating, 146 reviews

Pelican Cottage -Mins. to the Beach!! Car 4 Rent!

Nestled in the tranquil gated community of Leeward, on the heels of the Grace Bay area and the Grace Bay Beach, most recently ranked as the “The Best Beach in the World!”. The upscale Leeward community is within a 5-8 minute drive to the Grace Bay shopping and restaurant district, with about two dozen businesses, including a large grocery store, banks, liquor store, café, phone company, and bookstore.

Popular amenities for Leeward family-friendly rentals

Quick stats about vacation rentals that are family-friendly in Leeward

  • Total vacation rentals

    Explore 230 vacation rentals in Leeward

  • Nightly prices starting at

    Leeward vacation rentals start at R2,783 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 3,590 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    210 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    220 of Leeward vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Leeward rentals

  • 4.8 Average rating

    Leeward stays are highly rated by guests—averaging 4.8 out of 5!