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 villa rentals in Leeward Settlement
Private villa rentals
Villa in Providenciales
4.7 out of 5 average rating, 10 reviewsTC Villas -Villa Cerulean -Waterfront Chalk Sound!
Villa in Providenciales
4.96 out of 5 average rating, 67 reviewsSapodilla Bay - Walk to the Beach!
Villa in Providenciales
4.92 out of 5 average rating, 50 reviews‘My Little Hideaway’ at Lucayan Cays
Villa in Cooper Jack Bay Settlement
5 out of 5 average rating, 4 reviewsCheerful 3 bedroom Villa canal front with pool.
Villa in Turtle Cove
4.8 out of 5 average rating, 66 reviewsNirvana's Nest
Villa in Providenciales
4.86 out of 5 average rating, 22 reviewsThanksgiving in Paradise! 3bedroom Villa with Pool
Villa in Grace Bay
4.88 out of 5 average rating, 17 reviewsYour own private oasis in Grace Bay w/pool !
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 Grace Bay
5 out of 5 average rating, 3 reviewsContemporary 3 Bed 2.5 Bath Villa minutes from the
Villa in Providenciales, Long Bay Beach
4.75 out of 5 average rating, 28 reviewsSeaside Villa 3 -Chef, Gym, Pickleball & Much More
Villa in The Bight Settlement
4.94 out of 5 average rating, 17 reviewsShades of Blue Grace Bay Beach
Villa in Long Bay Hills
4.97 out of 5 average rating, 29 reviewsOcean Dream Studio Blue
Villa in Long Bay Hills
5 out of 5 average rating, 28 reviewsHang Five Surf Villa in Long Bay
Villa in Long Bay Hills
5 out of 5 average rating, 4 reviewsBlue Lotus Villa - Long bay Luxury Sea View Villa
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 Leeward Settlement
4.98 out of 5 average rating, 54 reviewsUnique, Modern Cozy & Private | 2 minutes to Beach
Villa in Long Bay Hills
5 out of 5 average rating, 5 reviewsOceanfront Turquoise Dream Villa
Villa in Turtle Cove
5 out of 5 average rating, 6 reviewsBlue Water Villa w/ Private Pool Providenciales
Villa in Leeward Settlement
4.75 out of 5 average rating, 16 reviewsOur Home on the Water - I Land Time Villa
Villa in The Bight Settlement
5 out of 5 average rating, 18 reviewsWalk to Grace Bay Beach ~ 3 bedroom en-suite
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!
Quick stats about villa rentals in Leeward Settlement
Total rentals
140 properties
Nightly prices starting at
$145 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
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 washing machine and dryer Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Rentals with a patio Leeward Settlement
- Flat rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- House rentals Leeward Settlement
- Rentals with a firepit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Pet-friendly rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Rentals with a fireplace Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Beachfront rentals Leeward Settlement
- Rentals with pools Leeward Settlement
- Rentals with beach access Leeward Settlement
- Monthly Rentals Leeward Settlement
- Villa rentals Caicos Islands
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