House holiday rentals in Leeward Settlement

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Top-rated house rentals in Leeward Settlement

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4.97 out of 5 average rating, 319 reviews

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 breathtaking views of the North Shore from the comfort of your own oasis. The villa boasts a distinctive design that is often imitated but never duplicated, showcasing the perfect blend of luxury and local charm.

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4.97 out of 5 average rating, 63 reviews

Cocodemer, a short walk to secluded Pelican Beach.

Cocodemer is a charming Caribbean style home, set in private, landscaped gardens within the gated community of Leeward, Providenciales. This colourful, Caribbean retreat is situated a short walk to secluded Pelican Beach. At this tranquil end of Grace Bay, visitors are tempted by unforgettable turquoise waters, pristine white sands and spectacular sunsets. Walk the shore in search of conch shells, watch Pelicans dive for fish, or simply relax with the sound of the waves lapping upon the shore.

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5 out of 5 average rating, 29 reviews

A Clean and Cozy Family Villa Steps From the Beach

Discover tranquility at Sea Villa, a 2-bedroom, 1-bathroom haven just steps from the beach. This cozy retreat is ideal for couples or small families seeking relaxation and adventure. Enjoy the complimentary golf cart for easy island exploration, and make the most of your stay with direct beach access. For added convenience, we offer car rentals at an affordable rate, so you can explore Turks and Caicos at your own pace. Experience comfort, convenience, and island charm at Sea Villa.

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4.96 out of 5 average rating, 69 reviews

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.

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4.9 out of 5 average rating, 103 reviews

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views

Located in a secluded Beachside property, 500 ft from Long Bay Beach, and 5-minutes drive from Grace Bay Resorts and shops, this spacious, private, 2-Bedroom\2-Bathroom unit can accommodate up to 6 guests, with a king size bed, 2 full size beds, and a queen sofa bed. It occupies 2nd and 3rd floor of our middle building, roughly 10 yards from the pool. With beautiful scenic views of the ocean and Long Bay Beach area, from its 3rd floor Livingroom and wrap-around balcony.

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4.95 out of 5 average rating, 109 reviews

Private Family Villa in Grace Bay w/pool + yard

Welcome to Villa Three O! When creating this space to share with guests, we were very intentional about how we wanted the home to feel + the convenience we want to be able to provide you with during your stay. Our goal is ensure our guests can arrive and begin to immediately relax and unwind in paradise. Whether you're a young family like ours, travelling with a group of couples or looking for the ultimate friends getaway, make Villa Three O your stay in Grace Bay!

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4.96 out of 5 average rating, 141 reviews

Follow Your Dreams Villa!

This a New Super Cool Upper Floor Loft Bedroom for one couple. Private Pool! Downstairs full Kitchen and 65" Giant TV entertainment area! Full Kitchen, Dishwasher, Laundry, all you need & more. Just behind Coco Bistro/Coco Van and 2 minutes by car to Beach! Grace Bay Beach that is! This is a Totally Private Villa for 2 Guests Only! Just landscaped with Palms around the Private pool! Great Location & New! Thanks for checking out "Follow Your Dreams!

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4.96 out of 5 average rating, 100 reviews

Sunny Paradise Long Bay

This airy, island-style, modern home is a 4-minute walk to the Leeward Marina where you can experience all the water-sports that the Turks & Caicos have to offer. The home is situated on private property with a complete electronic security system. The Property includes use of a gas grill on a 20x16ft sundeck, drink cooler, beach umbrellas, beach chairs, and use of beach towels, there are also two relaxing hammocks over an almond tree waiting for you.

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4.82 out of 5 average rating, 130 reviews

Tropical Guest House

Guest house, stylish and cozy with cold AC. Nested in a Tropical Nursery Garden on back of a semi-detached Villa. Well equipped! Studio. 15 Minute walk to beach, less than a minute by car. Best way to see all island and beaches is to rent a car!! Coco Bistro and Coco Van is just down the road! Easy access to all kind of shops and grocery store. Grill on your deck for your private use. Great Value location & close to Grace Bay Beach!

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4.98 out of 5 average rating, 168 reviews

“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!

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5 out of 5 average rating, 3 reviews

Newly Listed 2BR Canal Front

This Stunning canal waterfront villa, located in the esteemed Leeward neighborhood, boasts two bedrooms and two and a half bathrooms. Indulge in the awe-inspiring vistas and opulent facilities offered by this sophisticated sanctuary. Featuring expansive living spaces, a contemporary kitchen, and a secluded outdoor area, it presents an ideal setting for a tranquil escape.

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4.94 out of 5 average rating, 115 reviews

THE GECKO HOUSE awesome pool 🌞 - Grace Bay

One of very few affordable stand alone houses with a beautiful pool and beautiful gardens! This uniqueness lovely house is located in a quiet residential neighborhood in Grace Bay just a short 8 minute walk (less than a 3 minute ride) to the beach and walking distance to many of the islands attractions, shops, restaurants and activities.