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
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, 180 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 panoramic view captures the ocean on the horizon, framed by swaying palm trees. The foreground features a spacious terrace with blue umbrellas providing shade. Below, a row of white-roofed buildings is nestled among lush greenery, enhancing the serene coastal atmosphere.
Apartment in Providenciales and West Caicos
4.95 out of 5 average rating, 202 reviews

â˜€ïžđŸ– Modern Luxury Ocean View Studio Suite đŸâ˜€ïž

â˜€ïžđŸ– NEWLY RENOVATED, SPACIOUS STUDIO with an ocean view at La Vista Azul Condo Resort. Located hillside in the exciting area of Turtle Cove, Providenciales, the studio 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 â˜€ïžđŸ–

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, 244 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.

Superhost
The exterior of the guest house is shown, featuring a two-story structure with a spacious balcony and decorative wooden lattice. Surrounded by greenery, the building presents a welcoming entrance, blending modern architecture with natural elements under a clear blue sky.
Guesthouse in Long Bay Hills
4.89 out of 5 average rating, 115 reviews

Spacious Family Home, 5 Mins Walk To Beach, Quiet

Hawksbill is an affordable luxury two bedroom guest house located in a quiet part of Long Bay with access to a shared 15m swimming pool, kids play area and just a short 5 minutes walk to the Long Bay beach. We focus on providing quality accommodation, a home from home feel and an opportunity to truly relax, while getting your adrenaline fix. The quiet neighborhood gives you an opportunity to connect back in with nature and the Grace Bay area is just a short 10 minute drive away.

Superhost
A tranquil outdoor space features a bright blue pool surrounded by palm trees. Comfortable lounge chairs are positioned beside the pool, and a shaded bar area with a pink umbrella adds to the relaxing atmosphere. Lush greenery and colorful flowers enhance the tropical setting.
Cottage in Grace Bay
4.82 out of 5 average rating, 143 reviews

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! 🏠🌮

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, 130 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 favorite
An outdoor area features a swimming pool bordered by sun loungers and a shaded seating area. Umbrellas provide shade, while lush greenery and ocean views create a serene environment. The clear water of the pool reflects the blue sky, enhancing the inviting space.
Villa in Providenciales
4.99 out of 5 average rating, 112 reviews

Villa DelEvan 4B / 1-bedrm 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.

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, 180 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.

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, 249 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

Superhost
Cottage in Leeward Settlement
4.91 out of 5 average rating, 125 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, cafĂ©, 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 ïș©.ïș‡588 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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