Villa vacation rentals in Leeward

Cheers 🥂 Villa 🌴

Beautiful private Villa in a superb location,surrounded with🌴.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.

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🌴

Gated Villa + Private Pool• Walk to GraceBay Beach

Popular for Families, Couples & Group Vacations! PRIVATE Sun Drenched Pool. Walk to Famous GraceBay Beach + shopping, dining, night-life, “Incredible space! Loved the outdoor/indoor living combo and comfy veranda.” Sarah Burton, OH, USA The villa is tucked away in a peaceful setting on a private gated street with only 4 villas! Features a PRIVATE pool perfect for relaxation, sunbathing, enjoying some cocktails & your favorite music. The Ultimate Escape. Unpack, Relax, Enjoy... Reserve Now!

Delightful Family Villa with Pool in Leeward

Slow down, discover our family's favourite spot for gathering and relaxation. Surrounded by luscious flora & access to the world's #1 Beach in 100 steps. Relax at our retreat while the trade winds whisper through the trees. Worries are forgotten, and memories are made in a home away from home. We offer our home as a family retreat. It features a private pool, outdoor shower, huge covered outdoor dining space, BBQ, three bedrooms, and three bathrooms. Relax and make memories of a lifetime!

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.

Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks

Classic Caribbean 3 Bedroom canal front villa in Leeward. Cotton House has been designed in the timeless, traditional Caribbean aesthetic and is solar powered. Located in the gated Leeward community (25 min from PLS airport - 8 min to Grace Bay), this canal front home exudes an easy living elegance. Each bedroom opens to a central courtyard, the serene heart of the home featuring fountain, ferns, climbing vines, and tropical trees. *Ask us about our 4 and 5 Bedroom options for this villa.

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!!

Blanca: Taylor Bay Beach-Ocean View

Get away from it all on a beautiful white powdery half-moon shaped beach! The villa offers spectacular turquoise ocean views and dreamy sunsets from the terrace & pool. A private/gated path brings you to the beach in 30 steps where your loungers await you. Located in the prestigious Sunset Bay Community, offering nightly private security patrol & guards. The Island Escapes Villa Managers will meet & greet you and offer an unparalleled level of service during your stay.

Swan Villa-2br 2Bath

This stunning canal-front villa, located in the prestigious Leeward neighborhood, offers a luxurious retreat. This villa features two bedrooms, two and a half bathrooms, a fully equipped kitchen, and a spacious living room, accommodating up to four guests with a king and queen bed. Please note that the owner keeps a boat at the dock. Occasionally, the captain or an assistant may stop by to clean or perform routine maintenance on the boat. (Edit June 7th, 2026)

Caya Villa 1 - 2 Bedroom - Modern Island Home

Caya Villas are welcoming, modern island fusion styled homes with endless roof deck views to the Caicos Bank. Nestled in the heart of beautiful Long Bay Beach, that’s home to the renowned Shore Club Resort and a less than a mile away from the worlds top beach, Grace Bay Beach. Our two adjacent villas in a gated property are your perfect getaway! 12% Government Tax is calculated in final payment. Follow @islehavenpropertiestci Tag #islehaventci

The Caicos House -5 mins to the Beach & Dining!

Daily Housekeeping included! …… Nestled in the tranquil gated community of Leeward, on the heels of the Grace Bay and the Grace Bay Beach, regularly 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 over two dozen businesses, including a large grocery store and bank.