Vacation rentals in Leeward

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Top-rated vacation rentals in Leeward

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Villa in The Bight Settlement
4.97 out of 5 average rating, 142 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 favorite
A large outdoor pool area is surrounded by lush tropical landscaping, featuring palm trees and vibrant greenery. An inviting bubble spa is situated within the pool. Comfortable lounge seating is arranged under a shaded cabana, providing a relaxing space for guests.
Apartment in Leeward Settlement
5 out of 5 average rating, 116 reviews

Luxury Spacious 1 Bed Condo close to the Beach

Just renovated: The perfect condo, and only 3 minutes 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. This 925 sqft luxury 1 bedroom, freshly renovated (Jan 2023), provides all necessary amenities for your home away from home.

Guest favorite
A private infinity pool stretches out towards the horizon, reflecting the vibrant turquoise waters of Chalk Sound. Lush palm trees frame the scene, while the tranquil landscape of the bay and clear blue sky creates a serene and inviting atmosphere.
Apartment in Providenciales
4.9 out of 5 average rating, 211 reviews

Beautiful Sunset Villa with Infiniti Pool

Beautiful Sunset Villa is nestled in the heart of Chalk Sound, Providenciales where guests are guaranteed a home away from home experience. It enjoys unique trade winds in a private and safe community close to restaurants and the beach. Beautiful Sunset Villa provides views of the famous Chalk Sound turquoise waters, featuring a private Infiniti pool, extensive pool deck, a dedicate kitchen and dining area with full air conditioning. View the video below! https://youtu.be/13YyhYECZQA

Superhost
An aerial view captures the vibrant turquoise waters of Sapodilla Bay Beach, with calm waves gently lapping at the shore. Nearby, a wooden pier extends into the water, providing access to serene surroundings. The image includes markers indicating proximity to various local attractions.
Apartment in Providenciales
4.86 out of 5 average rating, 250 reviews

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.

Guest favorite
A private villa features a sparkling pool surrounded by lush palm trees and a spacious patio. Comfortable lounge chairs are positioned near the water, while the interior of the villa can be seen through expansive glass doors, seamlessly integrating indoor and outdoor living.
Villa in Caicos Islands
4.95 out of 5 average rating, 132 reviews

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.

Guest favorite
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
4.83 out of 5 average rating, 152 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! 🏠🌴

Top guest favorite
A modern two-story villa is surrounded by lush greenery and vibrant flowers. The exterior features large glass doors leading to a balcony with seating. Palm trees add to the tropical ambiance, while a colorful sky creates a serene backdrop.
Villa in Providenciales
4.99 out of 5 average rating, 131 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
Villa in Long Bay Hills
4.9 out of 5 average rating, 145 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
Guesthouse 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 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, 268 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 favorite
Cottage in Leeward Settlement
4.9 out of 5 average rating, 144 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.

Guest favorite
Guesthouse in Leeward Settlement
4.91 out of 5 average rating, 158 reviews

Pelican Cottage -Mins. to the Beach!

Nestled in the tranquil, gated community of Leeward, just minutes from the Grace Bay area and Grace Bay Beach, frequently ranked “The Best Beach in the World”. This exclusive enclave offers both privacy and convenience. Leeward is only a 5–8 minute drive from the Grace Bay shopping and restaurant district, which includes a large grocery store and many other amenities.

Popular amenities for Leeward Settlement vacation rentals

Frequently Asked Questions

  • How much does it cost to stay in condo rentals in Leeward Settlement?

    Experience the best of Leeward Settlement with our condo rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Leeward Settlement?

    Yes! Work meets play with ease at over 120 vacation rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Leeward Settlement vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 280 vacation homes with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Leeward Settlement?

    Leeward Settlement has more than 240 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Leeward Settlement?

    Four-legged friends are welcome in Leeward Settlement. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do guesthouse rentals in Leeward Settlement have air conditioning?

    Absolutely! We offer over 10 guesthouse rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Leeward Settlement have wifi?

    Absolutely! We offer over 40 apartment rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Leeward Settlement have a bbq area?

    Absolutely! We offer over 60 villa rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Leeward Settlement have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Leeward Settlement?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a gym, over 90 homes with wifi, over 100 homes with a bbq area, over 90 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Leeward

  • Total vacation rentals

    Explore 330 vacation rentals in Leeward

  • Nightly prices starting at

    Leeward vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

  • Verified guest reviews

    Over 7,640 verified reviews to help you choose

  • Family-friendly vacation rentals

    240 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    280 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wi-Fi availability

    330 of Leeward vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Leeward rentals

  • 4.8 Average rating

    Leeward stays are highly rated by guests—averaging 4.8 out of 5!