Luxury rentals in Leeward

Milestone Villa

Grace Bay sprawls beyond this picturesque 8-bedroom villa in Turks and Caicos. A pickleball court and gym, as well as kayaking and paddle boarding, ensure wellness is maintained, even on vacation. The crystalline ocean entices you in for a snorkel with vibrant marine life. Easily walk to the golf course, tennis courts, and postcard-worthy marina. Sip a glass of champagne on the terrace at sunset. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Television, Safe, Terrace, Ocean view • Bedroom 2: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Television, Safe • Bedroom 3: King size bed, Ensuite bathroom with shower/bathtub combo, Television, Safe, Terrace, Ocean view • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower, Television, Safe, Ocean view • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower, Television, Safe, Terrace, Ocean view • Bedroom 6: King size bed, Ensuite bathroom with stand-alone shower, Television, Safe, Ocean view • Bedroom 7: 2 Twin size beds, Shared access to hallway bathroom with Bedroom 8, Stand-alone shower, Television • Bedroom 8: King size bed, Shared access to hallway bathroom with Bedroom 7, Stand-alone shower, Television, Safe

Waterfront 5BR Villa - Kayak Sups Dock + Pool

Classic Caribbean 5 Bedroom canal front villa in Leeward. Cotton House has been designed in a timeless, traditional Caribbean aesthetic and is solar powered. Located in the gated Leeward community, this canal front home exudes an easy living elegance. 4 of the 5 bedrooms open up to a central courtyard, the serene heart of the home featuring a plunge pool, ferns and tropical trees. The 5th room, the prime loft is also accessed via the courtyard through a private staircase to the second storey.

Above Rocks Villa - Stunning Views from Every Room

Perched dramatically on the crystalline shores of Chalk Sound National Park, Above Rocks isn't just a villa – it's a private sanctuary overlooking one of nature's most breathtaking masterpieces. Above Rocks' two villas capture the spectacular panoramic views of Chalk Sound while offering both togetherness and privacy for up to 8 guests. Every window, terrace and thoughtfully designed space frames the mesmerizing waters dotted with mystical cays that seem to float across an endless azure canvas.

NEW Beachfront Estate | Sleeps 20 | 4 Pools | Gym

Brand New Liquid Villas 2. Beachfront estate with every bedroom oceanfront & private ensuite. Two striking onyx-designed villas combine into one seamless 20-guest retreat with 4 glass-edge pools, rooftop lounges, beachfront cabanas, kayaks, chef’s kitchens, a private gym, games room, and refined indoor-outdoor living. 10,000 sqft of private beachfront living with 360° rooftop ocean views. Gated for elevated privacy. Direct beachfront setting a rare luxury. Surrounded by 3 of Turks best beaches.

Luxury Ocean View Villa-Heated Pool-Minutes to GB

Welcome to Casa Cocuyo Luxe—a 5⭐️ Guest Favorite Private Villa. Wake up to ocean views, swim in your private heated pool then off to Gracebay Beach just minutes away. This spotless 3-bed, 3.5-bath luxury Villa features unmatched privacy, fast Wi-Fi, A/C, a sleek kitchen and beautiful indoor-outdoor living surrounded by lush gardens. Backed by 9+ years hosting and excellent reviews—ideal for couples, friends, and families wanting a quiet, secure, upscale getaway with easy access to everywhere.

Villa Katava - 3BDR/3.5BATH on Grace Bay

Villa Katava is a spectacular 3 BDR/3.5 Bath Villa in the heart of Grace Bay. This stunning retreat is designed for those seeking the perfect blend of luxury, comfort and convenience, making it ideal for families, friends, or couples. Villa Katava welcomes you with its contemporary design and elegant furnishings. Each bedrooms has its own ensuite bathroom. Flat-screen TVs in all bedrooms and living room. We are within walking distance to restaurants, supermarket, shops, spas, nightlife etc

Villa Khaya - Bespoke Waterfront Home

Set on the sparkling waterfront of Leeward Canal, Villa Khaya is a luxurious retreat with a relaxing ambiance. As you step through the glass doors into the villa, you’ll be surrounded by beautifully cut native limestone feature walls, custom designed mahogany woodwork, and an eye-catching vaulted ceiling all expertly crafted by TC Millwork. The open-plan living and dining areas blend seamlessly with the kitchen to create an airy space that leads through bi-fold glass doors onto the

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.

sugar apple

Welcome to Sugar Apple, a new breathtaking villa on the serene cul de sac of Kira Island. Sugar Apple sits directly on the Leeward Marina, allowing for the most breathtaking waterfront view. This exclusive property is just five minutes from the most acclaimed Grace Bay Beach.The villa has 4 bedroom room with ensuite facing garden or ocean view front. The property features outdoor and indoor dining, outdoor gas grill, fire pit, bicycles and private boat dock.

White Villas - Villa Near Ocean + Private Pool (6)

WHITE VILLAS (6) is a modern 2-bedroom, 3-bathroom retreat just a 3-minute walk from Long Bay Beach and 5 minutes from Grace Bay. Sleeping up to 5, it combines the privacy of a luxury villa with resort-style amenities. Integrated in the 15-villa WHITE VILLAS collection, it offers the upscale comforts and personalized service of a 5-star hotel—without the crowds or compromises. Ideal for beach lovers seeking space, style, and barefoot luxury in Turks & Caicos.

CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock

Welcome to Anara, an exceptional canal-front estate where modern elegance meets resort-style living. Thoughtfully designed for discerning guests and large groups, this expansive 9-bedroom with all King beds, 10-bathroom ensuite villa offers over 13,000 sq ft of refined indoor and outdoor living space, providing the perfect setting for unforgettable island stays. We have complimentary bikes, kayaks and Paddle boards

[LR] Gwynt A Mor

This luxury villa near Blue Mountain has extraordinary views of the north coast of Providenciales. Its high elevation offers a far reaching view to the northern ends of the island and cool breezes drift up from the ocean below. The villa's name, Gwynt A Mor, means Wind and Sea in Welsh. A gated driveway leads up to the 4-bedroom property. Limestone patios and pathways surround the villa and its gardens.