Villa holiday rentals in Leeward Settlement
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Top-rated villa rentals in Leeward Settlement
Guests agree: These villas are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Leeward Settlement villa rentals
Private villa rentals
Villa in Leeward Settlement
4.98 out of 5 average rating, 54 reviewsUnique, Modern Cozy & Private | 2 minutes to Beach
Villa in Providenciales
4.98 out of 5 average rating, 43 reviewsModern Cottage with Chalk Sound Views
Villa in Leeward Settlement
5 out of 5 average rating, 4 reviewsNew Listing! Modern Comfort! Private Pool!
Villa in Leeward Settlement
4.75 out of 5 average rating, 16 reviewsOur Home on the Water - I Land Time Villa
Villa in Cooper Jack Bay Settlement
4.93 out of 5 average rating, 15 reviewsVilla Tayo Canal Front with Pool 5BR
Villa in Turtle Cove
4.8 out of 5 average rating, 66 reviewsNirvana's Nest
Villa in Long Bay Hills
5 out of 5 average rating, 4 reviewsBlue Lotus Villa - Long bay Luxury Sea View Villa
Villa in Providenciales
4.9 out of 5 average rating, 20 reviewsBest views on island!
Luxury villa rentals
Villa in Providenciales
5 out of 5 average rating, 49 reviewsWALK TO BEACH IN 2! RECLINE … RELAX … RECHARGE …
Villa in Providenciales
5 out of 5 average rating, 29 reviewsVilla & Studio: ocean view & private pool
Villa in Providenciales
4.84 out of 5 average rating, 79 reviewsBeachHaus Villa with ocean view and private pool
Villa in Long Bay Hills
5 out of 5 average rating, 28 reviewsHang Five Surf Villa in Long Bay
Villa in Providenciales
4.88 out of 5 average rating, 26 reviewsDesigner Artist’s Retreat - Stunning Interior/View
Villa in Grace Bay
4.85 out of 5 average rating, 39 reviewsSunny ☀️ Place
Villa in Providenciales
4.95 out of 5 average rating, 76 reviewsBlanca: Taylor Bay Beach-Ocean View
Villa in Providenciales
4.98 out of 5 average rating, 85 reviewsVilla Jayla
Villa rentals with a pool
Villa in Long Bay Hills
4.89 out of 5 average rating, 9 reviewsLuxury villa, steps to the beach, private pool.
Villa in Turtle Cove
5 out of 5 average rating, 6 reviewsBlue Water Villa w/ Private Pool Providenciales
Villa in Providenciales
4.76 out of 5 average rating, 46 reviewsCanal Front Luxury Villa!
Villa in Providenciales
4.86 out of 5 average rating, 29 reviewsThe Caicos House -5 mins to the Beach & Dining!
Villa in Providenciales
4.96 out of 5 average rating, 51 reviewsWhite Osprey Villa
Villa in Long Bay Hills
5 out of 5 average rating, 9 reviewsNew Luxury Caribbean Villa with Private Pool
Villa in Long Bay Hills
4.8 out of 5 average rating, 41 reviewsPeaceful island getaway in Long Bay (New Studio)
Villa in Providenciales
5 out of 5 average rating, 6 reviewsVilla Alee: Pool & Golf Cart, Walkable to Beach
Quick stats about villa rentals in Leeward Settlement
Total rentals
140 properties
Nightly prices starting at
$187 NZD 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
Destinations to explore
- Grace Bay Holiday rentals
- Grand Turk Holiday rentals
- Taylor Bay Holiday rentals
- North Caicos Holiday rentals
- Long Bay Beach Holiday rentals
- Sapodilla Bay Holiday rentals
- Chalk Sound Holiday rentals
- Turtle Cove Holiday rentals
- Salt Cay Holiday rentals
- Santo Domingo Holiday rentals
- Santiago de los Caballeros Holiday rentals
- Las Terrenas Holiday rentals
- Villa rentals Turks and Caicos Islands
- Villa rentals Turks and Caicos Islands
- Villa rentals Providenciales
- Villa rentals Providenciales
- Villa rentals Grace Bay
- Rentals with a patio Leeward Settlement
- Apartment rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Rentals with a fireplace Leeward Settlement
- House rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with pools Leeward Settlement
- Monthly Rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Beachfront rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Pet-friendly rentals Leeward Settlement
- Villa rentals Caicos Islands
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