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Family-friendly holiday rentals in Leeward

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 240 holiday rentals in Leeward

  • Nightly prices starting at

    Leeward holiday rentals start at £142 per night before taxes and fees

  • Verified guest reviews

    Over 4,510 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    220 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    230 of Leeward holiday rentals include wifi 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!

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 favourite
A bright dining area overlooks the marina, featuring a table with chairs positioned for scenic views. Lush greenery frames the outdoor space, while the tranquil blue water reflects the clear sky. The room is designed with floor-to-ceiling glass doors that enhance the open layout.
Flat in Venetian Road Settlement
4.94 out of 5 average rating, 120 reviews

OCEAN ORCHID

This fabulous penthouse apartment is located within the exclusive Turtle Tail Marina and next to the late singer Prince's house. This newly built 3 large en suite bedroom apartment offers beautiful ocean and marina views from every room and balconies. The outdoor BBQ area has views of the ocean and Flamingo Lake where you can socialize, chill and spot the odd pink flamingo. There is a large pool with loungers and a hammock for relaxing, kayaks are available to explore the small cays and beach.

Guest favourite
Villa in The Bight Settlement
4.97 out of 5 average rating, 147 reviews

Ideal private getaway villa | 250 yds to the beach

The perfect getaway villa, just 250 yards from Grace Bay beach, Gracehaven Getaway is tucked away from passing traffic in a little garden oasis of its own. It is an ideal venue to celebrate anniversaries, birthdays, or honeymoons, or just for a couple seeking a romantic, private setting. Enjoy your own private pool hidden away from main roads and just a 2-minute walk to the Grace Bay beach and Coral Gardens Reef. Easily walk to local restaurants or visit the nearby supermarket for groceries.

Top guest favourite
A charming home is surrounded by lush palm trees and vibrant tropical landscaping. The exterior features a combination of stucco walls and a tiled roof under a clear blue sky. A gravel path leads to the entrance, adding to the welcoming ambiance.
Home in Grace Bay
4.91 out of 5 average rating, 124 reviews

Tropical Carabas Villa!

Peaceful Villa Near Grace Bay Beach 🌴 Escape to this serene villa just minutes from Grace Bay Beach and steps from Coco Bistro. Enjoy a private pool, air-conditioned bedrooms, a fully equipped kitchen, and an outdoor grill for relaxing meals. Lounge with beach towels and chairs, stay connected with strong Wi-Fi, and soak in the lush tropical surroundings. The perfect mix of comfort, convenience, and tranquility for your getaway! 🌴 12% government tax is included in the listed price.

Guest favourite
A modern villa is framed by lush tropical landscaping, featuring vibrant flowers in shades of red and purple. A private pool is surrounded by lounge chairs and umbrellas, with a shaded seating area, inviting relaxation under clear blue skies.
Villa in Caicos Islands
4.92 out of 5 average rating, 111 reviews

Modern 4BR oasis on 1 acre, 1 min from the Beach

Legacy Palms Villa is an ideal oasis for visitors to Providenciales. Set on an acre of private land, this secluded location provides privacy and tranquility. Kick back and relax by the pool with tons of natural shade from the beautiful palm trees and natural island vegetation or take a 10 minute walk to the beach. The villa is also a short 5 minute drive to the popular Grace Bay strip where you can find many different restaurants, tourist attractions, shopping, and grocery stores.

Guest favourite
Apartment in Grace Bay
4.82 out of 5 average rating, 148 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.

Top guest favourite
An outdoor area features a rectangular swimming pool with clear water, surrounded by a deck area with lounge chairs. A striped umbrella provides shade, while views of the ocean and sandy beach create a serene backdrop. Lush greenery frames the space, enhancing the coastal ambiance.
Villa in Providenciales
4.99 out of 5 average rating, 139 reviews

Villa DelEvan 4A / 1-bedrm Beach front villa

Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.

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
4.9 out of 5 average rating, 148 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 favourite
A contemporary living area features a sleek white sectional sofa with plush cushions, positioned around a minimalist coffee table. Decorative pillows and a small vase with flowers add subtle color. Soft natural light brightens the space, enhancing the modern design.
Flat in Leeward Settlement
5 out of 5 average rating, 123 reviews

Luxury Spacious 1 Bed Condo close to the Beach

This 925 sqft luxury 1 bedroom, recently renovated condo provides all necessary amenities for your home away from home. 3 minutes drive from the famous Grace Bay Beach! Located in the exclusive Leeward area, a gated, secure residential area where all the major luxury villas are. The beach is a short stroll away & the main Grace Bay shopping / resort area is 5 minutes by car. The condo boasts a large pool, stunning modern finish and appliances. We recommend renting a car.

Top guest favourite
Guest house in Leeward Settlement
4.98 out of 5 average rating, 130 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.

Top guest favourite
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.
Apartment in Providenciales
4.92 out of 5 average rating, 271 reviews

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

• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub • Highest Rated Spa on Island onsite • 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 • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Guest favourite
Cottage in Leeward Settlement
4.89 out of 5 average rating, 149 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.

Top guest favourite
A serene beach scene is depicted, featuring soft, white sand gently meeting clear turquoise waters. Lush greenery lines the shore, and a clear blue sky with scattered clouds enhances the peaceful atmosphere. The shoreline extends into the distance, inviting exploration.
Flat in Providenciales
4.96 out of 5 average rating, 277 reviews

2 bedroom, 2 bathrooms, garden, beach 2 mins walk

We have two Garden apartments downstairs that we renovated. One two bedroom two bathroom, and one 1 bed 1 bathroom. Just a 3 minute walk from a white sandy beach. You can walk to Da Conch shack restaurant along the beach in 5-10 minutes. Off the beaten trail. We live upstairs with our our potcake Boxer. We are so sad to say we just lost our legend Buster who you would have read about in all of our reviews.

Popular amenities for Leeward family-friendly rentals