Holiday houses in Leeward Settlement

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Top-rated holiday rentals in Leeward Settlement

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Guest favourite

Villa in The Bight Settlement

4.98 out of 5 average rating, 108 reviews

Modern villa | Pool | 3-mins walk to Beach & Reef

A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins. Nearby grocery supermarket & shops. Inflatable paddleboards available

Guest favourite

Villa in Leeward Settlement

5 out of 5 average rating, 30 reviews

Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool

*Great for couples and families - Pool - Heated SPA - On the canal - Sups - 5 min to the beach* Piccolo Ponte is an elegant 3 bedroom canal front Caribbean property that sits on an acre of private tropical garden where friends and family gather together to relax and enjoy a laid-back vacation island-style. Located directly on the clear and turquoise canals of the prestigious Leeward Settlement, just a few minutes away from Blue Haven Marina and many beach accesses and watersports operators.

Superhost

Villa in Providenciales

4.9 out of 5 average rating, 122 reviews

Gardenia Villa

Gardenia Villa. This contemporary Oasis is perfect for a small family or couples, located steps away from the world’s #1 Grace Bay Beach. The villa entrance opens to a bright entryway leading to the living room area with a spectacular view through a wall of sliding doors to the covered deck and pool. The open plan is perfect for entertaining with the dining and kitchen area all part of the living space. The upstairs consist a master King and second queen sized bedrooms both ensuite baths.

Guest favourite

Rental unit in Long bay

4.95 out of 5 average rating, 73 reviews

Villa Kendara~BOOK SEP SALE~Gated~SeaFront GH~View

Private~Gated~Seafront~Unique Loc~Beautiful by Nature~ Panoramic Sea & Bay Views~A+ Sunrises/Sunsets~Pool~5 min to Grace Bay Beaches, Stores, Restaurants, Marina~Exclusive "Johnson Guide to Provo"~Fully Equipped Apt~Loaded with Supplies~CoralStone Deck, Pergola for Shade, BBQ, AC, Fans, TV, DVD, Phone, Wi-Fi, Snorkel Gear, Portable Beach Chairs & Umbrella~Island Partner Discounts for Car Rental, Water Sports/Eco-Tours, Cruise, Massages~LOFT FOR KIDS~Swim, Snorkel, KiteBoard, PaddleBoard

Guest favourite

Villa in Long Bay Hills

4.97 out of 5 average rating, 93 reviews

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!!

Guest favourite

Home in Grace Bay

4.95 out of 5 average rating, 101 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!

Guest favourite

Condo in Providenciales

4.91 out of 5 average rating, 213 reviews

★★★★★ Modern Condo | Amazing Pool | On Site Spa

• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub • Highest Rated Spa on Island • Fully equipped kitchen • Private front patio + grill • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Guest favourite

Condo in Grace Bay

4.98 out of 5 average rating, 160 reviews

Luxury 1 Bedroom - Central Grace Bay

The perfect location, and only a 5-7 minute walk to world famous Grace Bay Beach! Located in the heart of Grace Bay near Seven Stars Resort and the Ritz Carlton Resort. 5-7 minute walk to the beach. 4 minute walk to the grocery store, and 10 minute walk to the best restaurants and shopping on the island. No rental car is needed. This 790 sq. ft. luxury one bedroom, newly built condo (Nov 2020), provides all necessary amenities for your home away from home.

Guest favourite

Condo in Grace Bay, Providenciales

4.99 out of 5 average rating, 123 reviews

1 Bedroom Luxury Grace Bay Condo

The perfect location, and only a 7 minute walk to world famous Grace Bay Beach! Located in the heart of Grace Bay near Seven Stars Resort and the Ritz Carlton Resort. 7 minute walk to the beach. 4 minute walk to the grocery store, and 10 minute walk to the best restaurants and shopping on the island. No rental car is needed. This 790 sq. ft. luxury one bedroom, newly built condo (Nov 2020), provides all necessary amenities for your home away from home.

Guest favourite

Home in Grace Bay

4.97 out of 5 average rating, 127 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!

Guest favourite

Rental unit in Grace Bay

4.83 out of 5 average rating, 127 reviews

Crescent #1 Grace bay (beach 2 min walk)

Our small studio apartment is setup in a new house (built 2020) with its own private access, nice and quiet neighbourhood. Studio is close to the main attractions, bars, groceries, restaurants and about 2 minutes walking distance to the nicest beach in the world Grace Bay beach. No car needed. Place is good for couples and solo adventurers. Apartment is a open concept only door for the bathroom.

Guest favourite

Rental unit in Leeward Settlement

4.95 out of 5 average rating, 234 reviews

Leisure in Paradise

Wake up on a Mocking bird singing in the garden, sun rays sparkling through the lush green while you drink your cup of tea or coffee on your private screened patio. Take a walk in the topical garden and have a refreshing swim in crystal clear pool or take a short walk (3 minute) to the turquoise ocean and white sandy beach.