
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 $243 SGD 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.

Grace Bay villa | Pool | 3min walk to Beach & Reef
A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

🏖🏝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 🏝

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.

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.

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.

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!!

Large Luxury Modern Condo + pool + close to 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.

Leeward Landing Villa
Escape to paradise at Beach Landing Villa nestled in the heart of Leeward TCI. This luxurious villa is just minutes away from the pristine award-winning Grace Bay Beach offering a perfect blend of relaxation and adventure. Conveniently cruise your community in your 6-seater Golf Cart or pedal along with the (2) provided pedal bikes. Or relax out by the pool in your private back yard! Book your villa now for an unforgettable experience in paradise!

★★★★★ 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

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

Amazing Ocean views -Modern Condo -Balcony - Pool

Gabriella Luxury Villa - Opening Special Rates

🌴 YOUR STUNNING BEACH HOME IN PARADISE 🌞

Sea La Vie - #1 Beachside 4 Bedroom Villa

Ocean Pearl Villa

Ideal Honeymoon Villa
Family- and pet-friendly home rentals

Tree Stump Villa - Grace Bay

Private Pool Villa w/ Firepit, Outdoor Dining

2Bedroom cozy home walking distance to the beach.

Hopewell Villa East/Pool & walk to Gracebay Beach

Luz Maria Villa- 3 bed 3 bath, Pool and Hot Tub!

Waterfront Villa, Pool & Canal

Ocean Seacret, Pool Gated Clean Ocean & Canal view

Stunning Yacht Club, Walk to Beach, Great Reviews!
Family-friendly home rentals with a pool

Private Luxury Villa with Pool 5 Min to GB Beach

OCEAN ORCHID

Sea Sun Relax - villa 5 min walk to Grace Bay

Live Villa - 2 BDR in Grace Bay

Blue Tang Villa (2 Bedroom)

2 Bedroom Stunning Views

Follow Your Dreams Villa!

NEW Luxury Grace Bay villa|Pool | 2 min>Beach|Reef
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