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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Top guest favorite
Villa in Grace Bay
4.96 out of 5 average rating, 76 reviews

Ideal Honeymoon Villa

Luxurious Gated Villa near Grace Bay Beach– Private Pool & Jacuzzi♨️ Escape to this luxury villa, just 2 minutes by car or a 10-min walk from Grace Bay Beach. Relax in your private infinity pool or rooftop jacuzzi with ocean view. The villa features 2 outdoor balconies, a modern kitchen with new appliances, and fast fiber internet. Perfect for 2 guests, this private retreat offers comfort, style, and Super host service. Close to dining, shopping, and activities. Book your dream vacation today🌴

Top guest favorite
The modern villa features a two-story design with a spacious ground-level patio. A private pool reflects the blue sky, surrounded by tropical landscaping. Comfortable outdoor seating is visible on the terrace, offering a quiet space for relaxation.
Villa in The Bight Settlement
4.98 out of 5 average rating, 160 reviews

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.

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, 115 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.

Top guest favorite
Apartment in Providenciales and West Caicos
4.95 out of 5 average rating, 220 reviews

☀️🏖 Modern Luxury Ocean View Studio Suite 🏝☀️

☀️🏖 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 ☀️🏖

Guest favorite
An outdoor pool area surrounded by lush greenery features comfortable lounge beds and a circular seating arrangement. The sleek swimming pool reflects the sky, inviting relaxation under the sun. A wooden deck connects the lounging spaces to the water, offering a tranquil atmosphere.
Condo in Grace Bay
4.82 out of 5 average rating, 147 reviews

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.

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.

Superhost
A tranquil outdoor area features a sparkling pool surrounded by a spacious patio. Lush palm trees and colorful plants border the space, while seating arrangements are present. A gazebo with a bar completes the setting, providing shaded areas for relaxation and entertainment.
Home in Leeward Settlement
4.5 out of 5 average rating, 4 reviews

Perroquet | Family Villa Leeward

Villa Perroquet is the ideal place to enjoy a family-style vacation. Set 980 feet from the fabulous Leeward Beach, this villa offers a sparkling pool and large patio with coconut trees, sago palms, and plenty of seating. A poolside gazebo with built-in grill and shaded dining area creates the perfect setting for casual meals and barbeques. Electricity allowance included up to $300 per week. Excess usage is charged at current market rate plus 12% tax.

Top guest favorite
An aerial view captures a modern villa surrounded by lush greenery. The structure features a spacious patio with lounge chairs and a heated pool. Large overhanging awnings provide shade, and the white exterior contrasts with the vibrant natural landscape.
Home in Providenciales
4.96 out of 5 average rating, 376 reviews

Private Luxury Villa with Pool 5 Min to GB Beach

Villa Cocuyo offers complete privacy, comfort, and consistent 5⭐️ hospitality. Couples love the safe and secure , peaceful setting, private solar heated pool, modern interior, and garden oasis. Enjoy fast WIFI, premium amenities, and a spotless space designed for true relaxation. Our 5-star reviews reflect our dedication to exceptional hosting, attention to detail, and a worry-free, private island getaway close to everything including beach

Top guest favorite
Condo in Providenciales
4.92 out of 5 average rating, 267 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

Popular amenities for Leeward Settlement vacation rentals

Frequently Asked Questions

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

    Experience the best of Leeward Settlement with our villa rentals, starting at about $210 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 villa rentals in Leeward Settlement have air conditioning?

    Absolutely! We offer over 140 villa rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Leeward Settlement have wifi?

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

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

    Absolutely! We offer over 100 house 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 Villa Rentals in Leeward Settlement?

    Enhance your stay in our Villa Rentals with the most popular amenities: over 20 homes with a gym, over 60 homes with a bbq area, over 140 homes with wifi, over 140 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!