House vacation rentals in Leeward

Gated Villa w Pool. Walk to GraceBay Beach & Shops

Super Popular for Families, Couples & Group Vacations! Steps to shopping, dining, night-life, and a short walk to Famous Grace Bay Beach. “Great space. Loved the outdoor/indoor living combo.” Jenny Bear, DE, USA The villa is tucked away in a peaceful setting on a private gated street with only 4 villas! Features a private plunge pool for kids and sunbathing or hanging out by the larger pool with some cocktails & your favorite music. The Ultimate Escape. Unpack, Relax, Enjoy... Reserve Now!

2 Bedroom Spectacular Views

Kick back and relax in this calm, stylish space. This modern 2-bedroom, 2-bathroom home is nestled along the serene Chalk Sound, offering peaceful seclusion with breathtaking views. FAR from the hustle and bustle of Grace Bay, it caters to guests looking to relax and reset. Enjoy spacious living, stylish finishes, and stunning water views from almost every room—perfect for those seeking comfort and tranquility. 15 mins to airport 20 mins to Grace Bay 5 mins to Taylor Bay & Sapoddila Bay Beach

The Sapphire Villa. Tropical Oasis. Make memories

This is where an unscripted holiday begins. At our Villa, we provide the canvas for luxury and privacy for the perfect getaway. Where dreams are fulfilled, and precious memories are made to live forever. Whatever you desire is within reach. Our Villa combines with the extraordinary tranquility of Turks and Caicos Islands for sophisticated, low-key luxury. Here is where to create your story within the privacy of your own home away from home in an exceptional place that becomes uniquely yours.

Villa Cocuyo Micro Villa with pool

"Discover a truly unique escape at our one-of-a-kind villa in the picturesque Blue Mountain. Crafted by a local architect, this exceptional residence is nestled on a half-acre of beautifully landscaped grounds, offering an exclusive retreat in a private and secure community. Admire the lush garden in the comfort of your own oasis. The villa boasts a distinctive design that is often imitated but never duplicated, showcasing the perfect blend of style, modern layout and local charm

PERIWINKLE | Charming Island Home|Near to Beach

Nestled in the Gated Upscale community of Leeward at the end of a quiet cul-de-sac is Periwinkle. Experience the true flavor of the Islands with us. Be cradled and relax in the lush native vegetation and enjoy the view from the many windows which decorate the home. Periwinkle is a short stroll away from the magnificent soul quenching Leeward Beach and a five minute drive to the heart of Grace Bay for great shopping and dining experiences. Escape to the quieter side of Paradise.

3 Bed Beach Oasis on Flamingo Lake w/Private Pool

Márohu is a stunning 3-bedroom modern Caribbean villa set within the exclusive neighbourhood of Turtle Tail, just a 10-minute drive from the world-renowned Grace Bay Beach. This spacious, well-equipped, and family-oriented villa offers expansive floor-to-ceiling views over Flamingo Lake from every room. You’ll experience the best of outdoor living with our own pool and sandy beach, ideal for lounging, a friendly game of cornhole, or exploring the lake with our included kayaks.

Moonrise, Turks and Caicos

Kick back and relax in this calm, stylish space. This Long Bay beach villa featuring 1800 sq feet of A/C space with views of the Caicos bank. Enjoy two spacious ensuite bedrooms and a large open living, dinning, kitchen area. The outdoor space features 3 sun decks, covered dinning, and a relaxing pool. It's a short 5 minute walk to the Long Bay beach access via a path. A 2 minute drive to South Bank and 10 minutes to Grace Bay beaches. Managed by Ski2Sea

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

The Lighthouse private cottage features a tower fashioned after a lighthouse affording stellar ocean views Private pool just outside living room doors! Deck & patio lounge w/ BBQ for fun & sun Nestled in the Thompson Cove Canal area and just a 3-minute walk to the beach WiFi, Smart TV with Netflix. Book now for a relaxing yet adventurous getaway! Kayaks, SUPs & snorkel gear included!

Charming Gecko House Island Vibes - Grace Bay

Perfect place for solo travelers and couples! Affordable and charming house situated in a quiet residential neighborhood in Grace Bay just a short 8 minute walk (less than a 3 minute ride) to the world famous Grace Bay Beach. And yes, we have a pool!!! Close to the beach and steps away from the very popular Coco Bistro Restaurant and Coco Van!