Villa vacation rentals in Leeward Settlement
Find and book unique villas on Airbnb
Top-rated villa rentals in Leeward Settlement
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation 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 Providenciales
4.9 out of 5 average rating, 20 reviewsBest views on island!
Villa in Caicos Islands
4.63 out of 5 average rating, 8 reviewsSweet Escape Villa Waterfront Kayak + SUV BOAT Opt
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 Estate - Stunning Interior/View
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 in Providenciales
4.96 out of 5 average rating, 50 reviewsRockspray Villa | On Point in Ocean | Waterfront |
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
$110 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 Vacation rentals
- Grand Turk Vacation rentals
- Taylor Bay Vacation rentals
- North Caicos Vacation rentals
- Long Bay Beach Vacation rentals
- Sapodilla Bay Vacation rentals
- Chalk Sound Vacation rentals
- Turtle Cove Vacation rentals
- Salt Cay Vacation rentals
- Santo Domingo Vacation rentals
- Santiago de los Caballeros Vacation rentals
- Las Terrenas Vacation 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 hot tub Leeward Settlement
- House rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with a fireplace Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Beachfront rentals Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Rentals with pools Leeward Settlement
- Rentals with a patio Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
- Monthly Rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Pet-friendly rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Apartment rentals Leeward Settlement
- Villa rentals Caicos Islands
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom