
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 $259 SGD per night before taxes and fees

Verified guest reviews
Over 4,230 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
230 properties feature pools

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
240 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.

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.

55 Oasis Cottage Nearby World's #1 Grace Bay Beach
55 Oasis Cottage is located in leeward Palms. This Settlement is located very near to the famed Grace Bay strip that is known for it’s beaches and tourist activities including shopping and dining. It only takes five minutes to drive to the world’s best beach and with only a fraction of what it cost to rent a Hotel room in this area, you can have the Grace bay experience at a fraction of the cost It is best to rent a Car. Please book with us, we’re looking forward to hosting you.

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.

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.

Cheers 🥂 Villa 🌴
Beautiful private Villa in a superb location. Just 2 minutes by car, or 10 minute walk to Grace Bay Beach & Shopping! Cheers Villa is a bright and inviting getaway, ideal for relaxing moments and quality time during your stay. We have all the essentials to enjoy the climate of Turks & Caicos. You can relax by the private pool after a day at the beach! 2 bedrooms (King & Queen) 2.5 bathroom. Each room has its own AC as well as the downstairs living space. 🚧 in the neighborhood.

Tropical Guest House
This stylish studio sits within a lush tropical garden behind a semi-detached villa. Enjoy cold AC, a well-equipped space, and your own private grill. Grace Bay Beach is just a 15-minute walk—or less than a minute by car—making it easy to enjoy one of the world’s most beautiful shorelines. Coco Bistro, a renowned island restaurant, and Coco Van are close by, with shops and a grocery store also within easy reach. A fantastic location, great value, and close to everything! 🏠🌴

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.

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!!

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.

"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.

★★★★★ 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

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.
Popular amenities for Leeward family-friendly rentals
Family-friendly home rentals with a hot tub

Charming Villa 360° Beach Nearby + Hot Tub

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝

Amazing Ocean views -Modern Condo -Balcony - Pool

Charming Studio at Gated Resort Amazing Rates!

🌴 YOUR STUNNING BEACH HOME IN PARADISE 🌞

Sea La Vie - #1 Beachside 4-Bedroom Villa

Pelican 12 Villa Off Longbay Kiteboarding beach

Ideal Honeymoon Villa
Family- and pet-friendly home rentals

Tree Stump Villa - Grace Bay

Tranquility Rest Near the Beach

25%Off July 27-29 Great Reviews Walk 2 Beach, Pool

BeachHaus Villa with ocean view and private pool

2Bedroom cozy home walking distance to the beach.

Hopewell Villa East/Pool & walk to Gracebay Beach

Ocean Seacret Views/Gated & Pool

2 Bdrm Condo Grace Bay a quick walk too the Beach
Family-friendly home rentals with a pool

Leeward Landing Villa

Sea Sun Relax - villa 5 min walk to Grace Bay

Sandy Feet poolside 1-bedroom near the beach

Blue Tang Villa (2 Bedroom)

Caicos Cove Villa Private Pool, BBQ near Grace Bay

Grace House Amazing home in the heart of Grace Bay

Leeward Condo - Sleeps 4

Beautiful Loft newly renovated
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