
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.

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!

★★★★★ 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

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!

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.

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.

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.

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!!

*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.

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.

"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.

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.

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
Family-friendly home rentals with a hot tub

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

The Cottonwood House - Beach Villa

Shore Thing 1BR Beach Condo - Mins to Beach/Eatery

Amazing Modern Beachfront Studio w/ Pool Jacuzzi

Crystal Vista Suite

Couple’s Retreat - ocean view, pool and hot tub!

Sea More Getaway

Ideal Honeymoon Villa
Family- and pet-friendly home rentals

Baldwin Camp Rental- Villa #2

Poco Villa

Steady Winds Hideaway - Turtle Villa 1 King Bed

BeachHaus Villa with ocean view and private pool

Waterfront Villa, Pool & Canal

Ocean Seacret Views/Gated & Pool

Romantic Studio with Stunning Views

Gated Condo in Grace Bay/ Short Walk to Everything
Family-friendly home rentals with a pool

Villa Cocuyo Micro Villa with pool

Sea Sun Relax - villa 5 min walk to Grace Bay

Buttonwood 1 BR Updated Condo - BEACH -POOL - WIFI

“The Lighthouse”, Private Pool, Ocean Views, Beach

1 BR Apt w/pool - Long Bay Hills #2

Shore to Please - Large Studio Condo with Patio

OCEAN PEARL-Getaway Retreat- Near Leeward sunset

Very Large Studio & Porch, 5 mins Beach, Secluded
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!
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