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Villa holiday rentals in Leeward Settlement

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Top-rated villa rentals in Leeward Settlement

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Villa in Providenciales and West Caicos

4.84 out of 5 average rating, 125 reviews

Secluded 3 BR Villa on Taylor Bay -Place De La Sol

The luxury of privacy is what this villa is all about. A few steps through a private tropical path takes you to the pristine waters and powder sand beach that is Taylor Bay. This Villa is split between the main villa which hosts 2 bedrooms, living room, bathroom and kitchen/dining. The Master Suite is located across the patio with it's private bathroom and outdoor/indoor shower. Sunsets are 2nd to none and should be done at least once beachside since the villa faces west. **12% TCI Tax Included

Villa in Caicos Islands

4.94 out of 5 average rating, 99 reviews

Cheers 🥂 Villa 🌴

Beautiful private Villa superb location, 2 minutes by car, or 10 minute walk to Grace Bay Beach & Shopping! Cheers Villa is filled with love ❤️ where you can relax in peace during your holiday. Coco Bistro Restaurant down the road, situated in a Tropical Nursery.We have all the essentials to enjoy the climate of Turks & Caicos. You can relax by the pool after a day at the beach! 2 bedrooms (K&Q) has its own bathroom and A/C, upper outdoor balcony!Free Internet! Private pool, A/C downstairs also

Guest favourite

Villa in The Bight Settlement

4.98 out of 5 average rating, 114 reviews

Grace Bay villa | Pool | 3min 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 plus several restaurants. Large grocery supermarket & shops are nearby.

Villa in Grace Bay

4.89 out of 5 average rating, 108 reviews

Calico Villa

"CALICO VILLA is a luxurious Villa located in Grace Bay, just behind Coco Bistro & Coco Van. Grace Bay beach is a 2 minute ride by car, or approx a 12 minute walk. This Newly built 3 bed/3 bath Villa can accommodate up to 6 guests. You can relax by your own "Private Pool & Outdoor Shower" after a day at the beach! Each bedroom has its own bathroom & AC, Main floor AC! 2 Adjoining Upper outdoor balconies. Also a Rooftop Terrace! Fast Internet! Highly desired vacation Villa & Super Host Service!

Guest favourite

Villa in Leeward Settlement

5 out of 5 average rating, 33 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.

Guest favourite

Villa in TC

4.88 out of 5 average rating, 108 reviews

Waterfront Point Villa - A Taste of Island Living

This beautiful 3 bedroom, 2.5 bath waterfront villa at the end of a secluded cul-de-sac in a quiet neighborhood is the perfect place to enjoy a taste of island life. With 300-plus feet of waterfront, you can take in the view from wrap-around balconies, kayak, paddle board, and snorkel in the crystal clear canal, or go for a dip in the private pool. The bright, airy rooms have split-air units and ceiling fans to keep them cool and comfortable. Many amenities will make you feel right at home.

Villa in Providenciales, Long Bay Beach

5 out of 5 average rating, 23 reviews

Private Villa w chef, gym, pickleball, bocci & mor

WHITE VILLA is a luxurious retreat located in Long Bay Beach (5 min. from Grace Bay). A 3-minute stroll takes you straight to the beach, equipped with chairs, kayaks and stand-up-paddle boards. With no current, no coral, no waves, and no danger, it’s absolutely perfect for beach lovers and kiteboarders. Our cluster of 10 villas allows us to offer services and amenities you’d normally only find in a 5-stars hotel. ps: This unit is White Villas co-owner's home that he rents out when is away.

Guest favourite

Villa in Providenciales

4.91 out of 5 average rating, 127 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

Villa in Long Bay Hills

4.96 out of 5 average rating, 99 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

Villa in Providenciales

4.95 out of 5 average rating, 108 reviews

Villa DelEvan 4D / 1-bedrm 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.

Villa in Long Bay Hills

4.83 out of 5 average rating, 110 reviews

Long Bay Beach Private Pool Villa with VIP Extras!

A luxurious stay in a 2-story villa w/high ceilings, huge windows & designer finishes - 3 stylish bedrooms all with ensuite bathrooms & superb ocean views from upstairs - You'll have a gorgeous private pool & sun lounge area all to yourselves - 5-min drive to world-famous Long Bay Beach & 10-min to the famous Grace Bay - Fully-fenced in and gated property - Good fiber Wi-Fi, laptop-friendly workspaces for remote worker & washer & dryer.

Guest favourite

Villa in Leeward Settlement

4.89 out of 5 average rating, 46 reviews

Sea Sun Relax - villa 5 min walk to Grace Bay

Location, location, location! Stay at this recently renovated 1,650 sq. feet, 3 bed, 2 baths Caribbean house with a large private pool, close to the beach, in the prestigious Leeward gated community at the eastern tip of Providenciales island, in the beautiful Turks and Caicos. The house is 450 meters /4 min. walk away from one of the best beaches in the world (Grace Bay beach consistently gets top ratings from Trip Advisor).

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Popular amenities for villa rentals in Leeward Settlement

Free parking on premises

Air conditioning

Private villa rentals

Guest favourite

Villa in Leeward Settlement

4.98 out of 5 average rating, 54 reviews

Unique, Modern Cozy & Private | 2 minutes to Beach

Guest favourite

Villa in Providenciales

4.98 out of 5 average rating, 43 reviews

Modern Cottage with Chalk Sound Views

Villa in Leeward Settlement

5 out of 5 average rating, 4 reviews

New Listing! Modern Comfort! Private Pool!

Villa in Leeward Settlement

4.75 out of 5 average rating, 16 reviews

Our Home on the Water - I Land Time Villa

Guest favourite

Villa in Cooper Jack Bay Settlement

4.93 out of 5 average rating, 15 reviews

Villa Tayo Canal Front with Pool 5BR

Villa in Turtle Cove

4.8 out of 5 average rating, 66 reviews

Nirvana's Nest

Villa in Long Bay Hills

5 out of 5 average rating, 4 reviews

Blue Lotus Villa - Long bay Luxury Sea View Villa

Villa in Providenciales

4.9 out of 5 average rating, 20 reviews

Best views on island!

Luxury villa rentals

Guest favourite

Villa in Providenciales

5 out of 5 average rating, 49 reviews

WALK TO BEACH IN 2! RECLINE … RELAX … RECHARGE …

Guest favourite

Villa in Providenciales

5 out of 5 average rating, 29 reviews

Villa & Studio: ocean view & private pool

Villa in Providenciales

4.84 out of 5 average rating, 79 reviews

BeachHaus Villa with ocean view and private pool

Guest favourite

Villa in Long Bay Hills

5 out of 5 average rating, 28 reviews

Hang Five Surf Villa in Long Bay

Guest favourite

Villa in Providenciales

4.88 out of 5 average rating, 26 reviews

Designer Artist’s Retreat - Stunning Interior/View

Guest favourite

Villa in Grace Bay

4.85 out of 5 average rating, 39 reviews

Sunny ☀️ Place

Guest favourite

Villa in Providenciales

4.95 out of 5 average rating, 76 reviews

Blanca: Taylor Bay Beach-Ocean View

Guest favourite

Villa in Providenciales

4.98 out of 5 average rating, 85 reviews

Villa Jayla

Villa rentals with a pool

Villa in Long Bay Hills

4.89 out of 5 average rating, 9 reviews

Luxury villa, steps to the beach, private pool.

Villa in Turtle Cove

5 out of 5 average rating, 6 reviews

Blue Water Villa w/ Private Pool Providenciales

Villa in Providenciales

4.76 out of 5 average rating, 46 reviews

Canal Front Luxury Villa!

Villa in Providenciales

4.86 out of 5 average rating, 29 reviews

The Caicos House -5 mins to the Beach & Dining!

Guest favourite

Villa in Providenciales

4.96 out of 5 average rating, 51 reviews

White Osprey Villa

Guest favourite

Villa in Long Bay Hills

5 out of 5 average rating, 9 reviews

New Luxury Caribbean Villa with Private Pool

Villa in Long Bay Hills

4.8 out of 5 average rating, 41 reviews

Peaceful island getaway in Long Bay (New Studio)

Villa in Providenciales

5 out of 5 average rating, 6 reviews

Villa Alee: Pool & Golf Cart, Walkable to Beach

Quick stats about villa rentals in Leeward Settlement

Total rentals
140 properties
Nightly prices starting at
$148 SGD before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
130 properties are a good fit for families
Rentals with a pool
130 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace

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