Holiday houses in Leeward Settlement

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Top-rated holiday rentals in Leeward Settlement

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Guest favourite

Guesthouse in Long bay

4.96 out of 5 average rating, 70 reviews

Villa Kendara~BK 8/17 On~Gated~SeaFront GH~View

Private~Gated~Seafront~Unique Loc~Beautiful by Nature~Panoramic Water & Bay Views~A+ Sunrises/Sunsets~5 min to Grace Bay, Stores, Restaurants, Marina~Exclusive ”Johnson Guide to Provo & Car Travel Guide~LOFT FOR KIDS~Fully Equipped~Loaded with Supplies~Pool, 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~Swim, Snorkel, KiteBoard, PaddleBoard

23 – 30 Nov

$4,096 AUD total

Guest favourite

Apartment in Leeward Settlement

4.95 out of 5 average rating, 44 reviews

NEW! Luxury Modern 1Bd Condo

The perfect large condo, and only 3 minutes from the famous Grace Bay Beach! Located in the exclusive Leeward area, a gated, secure residential area where all the major luxury villas are. The beach is a short stroll away & the main Grace Bay shopping / resort area is 5 minutes by car. The condo boasts a large pool, stunning modern finish and appliances. This 900 sq. ft. luxury one bedroom, freshly renovated condo (in Feb 2023), provides all necessary amenities for your home away from home.

7 – 14 Sept

$3,178 AUD total

Guest favourite

Apartment in Leeward Settlement

5.0 out of 5 average rating, 13 reviews

Beautiful Loft newly renovated

Experience the vacation of a lifetime in our stunning loft in Providenciales, Turks and Caicos. Boasting a proximity location where all celebrities stay in Leeward, this newly renovated modern apartment features sleek design, a fully equipped kitchen, and a large private balcony. Immerse yourself in tranquility, steps away from pristine beaches and exquisite dining. Ideal for a romantic escape or a peaceful island adventure! The best restaurants on island are a 5 minute drive away!

27 Oct – 3 Nov

$2,991 AUD total

Guest favourite

Villa in Long Bay Hills

4.98 out of 5 average rating, 85 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!!

12 – 19 Oct

$6,308 AUD total

Guest favourite

Condo in Leeward Settlement

5.0 out of 5 average rating, 22 reviews

Grace’s Condo In Leeward Settlement

Caribbean Diamond Residences is a quiet condominium located inside the exclusive and secured Leeward Settlement. Our ground floor Condo is a short 5-7 minute walk from the beautiful and picturesque Sunset Beach. The complex offers a walk-in pool, plenty of chaise loungers, outdoor furniture and BBQ grills to enjoy. We are a short 5-minute drive down Grace Bay Road to all the shopping and activities that Grace Bay has to offer, or a 15-20 minute bike ride along the sidewalk.

6 – 13 Dec

$3,534 AUD total

Guest favourite

Villa in Leeward Settlement

4.94 out of 5 average rating, 17 reviews

Ocean Pearl-Brand new villa/pool, near beach/ferry

Newly built 2 bed 2bath stand alone guest villa is located in a Leeward gate. It's closer to all the activities, restaurants, golf, Grace bay, water sports, excursion pickup points, enjoy and relaxation in beautiful island. It's 11 minutes walk away from sunset, pelican beach, marina. , pool, barbecue, We provide pre-arrival and island support and assist with all local reservations for excursions, water sports and restaurants, car rental safer place to stay in island.

31 Aug – 7 Sept

$5,068 AUD total

Guest favourite

Condo in Providenciales

4.9 out of 5 average rating, 198 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

4 – 11 Jan

$7,271 AUD total

Guest favourite

Home in Grace Bay

4.98 out of 5 average rating, 113 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!

22 – 29 Jan

$5,634 AUD total

Guest favourite

Home in Grace Bay

4.81 out of 5 average rating, 126 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!

27 July – 3 Aug

$2,777 AUD total

Guest favourite

Cottage in Leeward Settlement

4.96 out of 5 average rating, 69 reviews

Sandpiper Cottage, minutes from the beach

Kick back and relax in this delightful modern one bedroom cottage in the high end residential gated community of Leeward. Grace Bay Beach, most recently voted “The best in the world” is only a 4 minute walk away! This cozy cottage is perfect for a couple, wanting to relax and have some downtime. Complete with full kitchen, washer/dryer/ BBQ, high speed internet with cable TV and all amenities needed for the perfect getaway.

6 – 13 Feb

$3,450 AUD total

Guest favourite

Guest suite in Leeward Settlement

4.96 out of 5 average rating, 69 reviews

Erisa Studio near Grace Bay Beach

Erisa Studio, with small kitchen, is located at less than 15min walk of Grace Bay Beach, 3 min in car of restaurants and shopping area. Adjacent to the Provo Golf Club. Short drive to Longbay Beach. Apple TV, mobile phone, beach towels, beach chairs, and cooler are provided. Bicycle can be rented at $10/day. The studio is attached to the main residence and has its own entrance. Your space is totally private.

18 – 25 Oct

$1,685 AUD total

Guest favourite

Apartment in Grace Bay

4.85 out of 5 average rating, 115 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.

10 – 17 Mar

$2,211 AUD total