Luxury rentals in Leeward

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Top-rated luxury holiday rentals in Leeward

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Luxe
An aerial view of Villa Vieux Caribe showcases its traditional stone architecture against a backdrop of tranquil waters. The property is surrounded by lush greenery and features multiple decks, private docks, and a pool, reflecting the serene ambiance of the Caribbean at sunset.
Villa in Chalk Sound
4.97 out of 5 average rating, 29 reviews

Villa Vieux Caribe

Enjoy postcard-worthy ocean views at Villa Vieux Caribe. Set on lush grounds on the southern coast of Providenciales, the seven-bedroom stone villa has traditional stone architecture and panoramic views of Chalk Sound National Park and Caicos Banks. Snorkel just off the property’s beach in calm Taylor Bay, sunbathe on one of several decks, and retreat to private, hotel-like accommodations in the evening. The heart of the villa is its outdoor spaces, which range from a large deck to a terrace around the private pool. Steps lead from the house down to the beach, where you’ll find two private docks and two kayaks. The pool terrace even has a barbecue, wet bar and dining area, so you can enjoy the sunset over a drink and dine al-fresco. Relax in the hammock, or escape the heat thanks to the house’s ceiling fans and air conditioning. For your convenience, Wi-Fi access is available, too. Inside, Villa Vieux Caribe is light and airy, with fresh, neutral decor and high ceilings that let in the trade winds. The living room is calm, comfortable and traditional, with tile floors, cream-colored walls, dark wood and linen-toned upholstery. The kitchen has classic white beadboard cabinets and is open to the dining area, where you’ll find rustic woven rush chairs and antique pottery accents. Each of the villa’s seven bedrooms has an en-suite bathroom, air conditioning, a ceiling fan, television and safe. There are five bedrooms with king beds, and two bedrooms with two queen beds each. Two of the suites are located on a lower level and have their own private entrance, sitting room with kitchenette and deck; one of these suites is wheelchair-accessible. Swimming, snorkeling and boating are just steps away from Villa Vieux Caribe on Taylor Bay. There’s also a beach just a 2-minute walk away. By car, it’s a 10-minute drive to the grocery store or the international airport, and a 15-minute drive to downtown Providenciales. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Television, Safe, Ceiling Fan, Air Conditioning. En-suite bathroom with shower • Bedroom 2: King size bed, Television, Safe, Ceiling Fan, Air conditioning. En-suite bathroom with shower • Bedroom 3: King size bed, Television, Safe, Ceiling Fan, Air Conditioning. En-suite bathroom with shower • Bedroom 4: 2 Queen size beds, Television, Safe, Ceiling Fan, Air conditioning. En-suite bathroom with shower • Bedroom 5: 2 Queen size beds, Television, Safe, Ceiling Fan, Air conditioning. En-suite bathroom with shower • Bedroom 6: King size bed, Television, Safe, Ceiling Fan, Air conditioning. En-suite bathroom with shower • Bedroom 7: King size bed, Television, Safe, Ceiling Fan, Air conditioning. En-suite bathroom with shower

Luxe
A spacious living area features large glass doors that open to stunning ocean views. Comfortable seating is arranged around a glass coffee table. Colorful artwork adorns the walls, while hints of tropical greenery are visible outside, enhancing the serene setting.
Villa in The Bight Settlement
5 out of 5 average rating, 4 reviews

Seascape

Step from your pool terrace onto the sands of Grace Bay Beach and plunge into the crystalline sea. Sip cocktails under the sunset sky and relish a chef-prepared meal amid panoramic ocean views. Part of the Private Villa Collection at Grace Bay Club, this stand-alone house combines exclusive serenity, an attentive staff, and privileged access to the resort’s world-class amenities, including Anani Spa. The 2-level, 5,500-square-foot home is nestled amid lush hedges and palm trees, with 400 feet of beach frontage. Balancing vivid modern design with the age-old simplicity of a classic Caribbean beach cottage, the villa features a cool, open-concept interior with gourmet kitchen flowing gracefully onto the dining veranda and pool terrace. Watersports enthusiasts can select from the villa’s own kayaks, paddle boards, and 2-person pedal boat for an adventure on the bay, or cozy up with a drink and favorite film in the media room. The upstairs master suite features a private balcony with extraordinary vistas.   The villa is also just 3 minutes from Turtle Cove Marina and about 10 from Provo Golf Club. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower and bathtub, Dual Vanity, Television, Safe, Air conditioning, Private terrace, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Dual Vanity, Television, Safe, Air conditioning, Private balcony • Bedroom 3: King size bed, Ensuite bathroom with stand-alone rain shower, Dual Vanity, Television, Safe, Air conditioning, Private balcony • Bedroom 4: King size bed, Ensuite bathroom with stand-alone rain shower and bathtub, Dual vanity, Walk-in closet, Television, Air conditioning • Bedroom 5: King size bed, Ensuite bathroom with stand-alone rain shower, Dual Vanity, Television, Safe, Air conditioning FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • Life vests STAFF & SERVICES Included: • Butler Services • Local and Long-Distance Phone Calls from Villa Landline . 1 hour complimentary photo shoot with one free print • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below SHARED ACCESS TO AMENITIES AT GRACE BAY CLUB 

Luxe
An outdoor living area showcases a spacious teak deck, furnished with loungers and a coffee table. The backdrop features a modern house with a shaded upper deck, surrounded by lush greenery and a clear blue sky. Sunlight enhances the inviting atmosphere.
Villa in Grace Bay
5 out of 5 average rating, 15 reviews

Beach Cake

Step off the gorgeous teak deck to feel the sand between your toes at this beachfront upside-down-house in Turtle Cove. After a snorkeling adventure, head upstairs to relax in the pool lounge, where you can gaze out over the Caribbean from beneath the shaded overhang. Or, get a lay of the land from the third-floor sky deck. There are a few great restaurants within walking distance. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with semi-alfresco stand-alone shower & bathtub, Dual vanity, Television, Safe, Private terrace, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with semi-alfresco stand-alone rain shower, Dual vanity, Television, Shared terrace OUTDOOR FEATURES • Outdoor living space • More under “What this place offers” below STAFF & SERVICES Included: • $400/week air conditioning allowance Extra Cost (advance notice may be required): • Pool heating • Activities and excursions • Air conditioning charges above $400 allowance

Luxe
A classic Caribbean villa is presented with a two-story structure featuring a tiled roof and expansive balconies. Lounge chairs are arranged around a sleek pool, seamlessly extending to the surrounding greenery. Large windows allow natural light into the welcoming interior spaces.
Villa in Chalk Sound
5 out of 5 average rating, 35 reviews

Villa Sunset Close

Set in the private community of Silly Creek Estates, this luxury villa offers stunning views and a private lagoon-style beach. Sunset Close features a bright white interior with Caribbean accents. The spacious open-plan living area opens to the pool and fabulous view. Covered terraces on both floors are great for enjoying the breeze and the view. Just off the patio is a small beach with sun recliners. Take the villa’s kayaks or paddle boards to explore the mangroves and sea life in Silly Creek.

Luxe
Villa in Providenciales
5 out of 5 average rating, 9 reviews

NEW Liquid BEACH Villa · 5 beds · 2 Pools · 10 ppl

🌴 Beachfront Luxury in Turks & Caicos 🌴 Where modern architecture meets barefoot paradise. This brand-new villa defines elegance with two see-through glass pools. Step from your backyard onto the powder-soft beach, multiple balconies and a rooftop with 360° turquoise views. Inside, enjoy 4 ocean-view bedrooms with private ensuite, a chef’s kitchen. Featuring a private gym, lush tropical gardens, and a multi-game pool/ping-pong table. . Sleeps 10 in pure island luxury. 200m to Sapodilla ⛱️

Luxe
Villa in Chalk Sound
5 out of 5 average rating, 13 reviews

[LR] Hesperides House

Hesperides House is a brand new five-bedroom luxury waterfront accommodation in the Turks and Caicos Islands. Named for the mythical garden at the edge of the western world of ancient Greek lore, and the three nymphs of the golden light of sunset who tend to it, Hesperides House is a stunning contemporary residence that lives up to its namesake. Located on the sunny southwestern shore of Provo in exclusive Silly Creek Estates, the home is situated in a private gated community on the edge ...

Luxe
Villa in Providenciales
5 out of 5 average rating, 3 reviews

No Snow Here: Villa w/Pool & Golf Cart Near Beach

Ideally located within walking distance of Sunset Beach, this villa in the secure and private enclave of the Sunset Beach Villas community offers the perfect respite for your island escape. No Snow Here! includes complimentary concierge services, daily private resort style lounger and umbrella set up on Sunset Beach, and an electric beach cart for easy transport to and from the beach. Please note upon booking you will be required to sign a renter agreement and pay a security deposit.

Luxe
Villa in Providenciales
5 out of 5 average rating, 3 reviews

Skyline Villas - Villa Cosmo with Oceanview

Escape to a Haven of Luxury: Revel in your own Private Pool, Immerse in Nature with an Expansive Outdoor Space and Lush Gardens. Bask in Open-Plan Elegance with Breathtaking Ocean Views. Indulge in Superior Comfort with Top-Notch Byredo Bathroom Essentials and Chic Roche Bobois Furnishings. Enhance your Stay with State-of-the-Art Sonos Sound, Eco-Friendly Tesla Solar Power, Premium Miele Appliances, and Exquisite Jack Brown Outdoor Furniture. Experience the Ultimate Retreat.

Luxe
A modern waterfront villa is shown with a spacious terrace and swimming pool. Poolside loungers are arranged under the sun, while outdoor seating is situated near the water's edge. Lush palm trees frame the property, enhancing the coastal ambiance.
Villa in Leeward Settlement
4.86 out of 5 average rating, 14 reviews

Sugar Apple - Modern, Waterside Base

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.

Luxe
A light-filled living area features a gentle color palette, with a comfortable curved sofa and sleek coffee table. The large glass doors offer a view of the pool and ocean, while a contemporary ceiling design and textured wood accents enhance the space's modern aesthetic.
Villa in Long Bay Hills
5 out of 5 average rating, 3 reviews

Coco Rock - Villa Angelina

Set on the luxurious shores of Turks and Caicos, Villa Angelina is a serene spot for your next romantic getaway. Spend your mornings strolling along the beach. In the afternoon, hop in the plunge pool to cool off or head into town to check out the local restaurants and bars. At night, an alfresco dinner on the ocean-view patio is the perfect place to enjoy a meal, a bottle of wine, and the sea view. Copyright © Luxury Retreats. All rights reserved.

Luxe
The villa features a modern design set against a vibrant turquoise canal. Palm trees frame the expansive terrace, where lounge chairs are arranged invitingly. A private dock with stairs leading to the water enhances the outdoor experience, reflecting the tranquility of the surrounding tropical environment.
Villa in Leeward Settlement
5 out of 5 average rating, 4 reviews

Sunset Bay Villa - 10 mins away from Grace Bay

**This listing can be booked as an 8-bedroom villa or 5 bedroom villa . Please get in touch with the host for more information. Main House - 5 bedrooms Guest House - 3 bedrooms Total bedrooms - 8 Early booking Discount for 7 nights or more - Please get in touch with the host for more information The breathtaking Sunset Bay Villa is a brand-new villa that exemplifies what it means to enjoy a luxurious and carefree holiday by the canal.

Luxe
Lounge chairs are positioned under woven umbrellas on a spacious terrace, overlooking an infinity pool that merges with the vibrant ocean. The sky is clear, reflecting shades of blue, while lush greenery lines the edge of the pool area.
Villa in Providenciales
5 out of 5 average rating, 16 reviews

La Mer Villa West

Situated by oceanfront with uninterrupted views of the turquoise waters, La Mer West offers luxury villa rentals in Sapodilla Bay, Providenciales. The home provides a European touch to modern Caribbean architecture, unique to rental villas in Turks and Caicos Islands. This well-appointed, staffed villa is situated right on the ocean’s edge and offers a seamless blend of indoor and outdoor living across 7,500 square feet.

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