House vacation rentals in Leeward Settlement
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Top-rated house rentals in Leeward Settlement
Guests agree: these houses 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 house rentals
House rentals with a pool
Home in Grace Bay
5.0 out of 5 average rating, 17 reviewsVilla in Providenciales
Home in Grace Bay
5.0 out of 5 average rating, 18 reviewsGrace Bay/ New Luxurious home 3+ Bedrooms & Pool
Home in The Bight Settlement
5.0 out of 5 average rating, 66 reviews2b/2b BEACH HOUSE STEPS to GRACE BAY! WiFi,AC,Pool
Home in Grace Bay
5.0 out of 5 average rating, 4 reviews3 King Bedroom Villa, Grace Bay - Sanmar Villa
Home in Leeward Settlement
4.84 out of 5 average rating, 25 reviewsCaribbean Serene Escape with Pool, 5 mins to Beach
Home in Long Bay Hills
4.9 out of 5 average rating, 21 reviewsLUXURy Villa: Ocean View. Private Pool! Chef avail
Home in Leeward Settlement
4.92 out of 5 average rating, 26 reviewsPelican Paradise Villa - Leeward Beach
Home in Long Bay Hills
4.85 out of 5 average rating, 33 reviewsSunSeaSand 3Bdrm Oceanview Home -Long Bay Hills
Weekly house rentals
Home in Long Bay Hills
4.83 out of 5 average rating, 18 reviewsVision Kite- Longbay beach house
Home in Providenciales
4.84 out of 5 average rating, 127 reviewsFerguson Tatis Villas 1
Home in Long Bay Hills
5.0 out of 5 average rating, 23 reviewsPrivate water front villa – 5 mins from Grace Bay!
Home in Providenciales and West Caicos
4.88 out of 5 average rating, 95 reviewsParadise Villa #4, (Studio)
Home in Leeward Settlement
4.76 out of 5 average rating, 17 reviewsVista Blue Rental-Grace Bay Beach just 4 mins away
Home in Long Bay Hills
4.94 out of 5 average rating, 17 reviewsPeaceful 1BR Private Cottage w/ HotTub Beach Front
Home in The Bight Settlement
5.0 out of 5 average rating, 7 reviewsStudio 400 steps to Grace Bay
Home in Long Bay Hills
5.0 out of 5 average rating, 35 reviews2 BR Ocean View- Private Pool- Flame Tree Villa #2
Private house rentals
Home in Providenciales
5.0 out of 5 average rating, 10 reviewsTC Villas -Sea Edge Villa -Romantic & Luxurious
Home in Long Bay Hills
4.81 out of 5 average rating, 53 reviewsPonciana House 3Bed Villa, Ridgetop Sea View, Pool
Home in Cooper Jack Bay Settlement
5.0 out of 5 average rating, 14 reviewsWaterfront House - Upstairs
Home in Providenciales
5.0 out of 5 average rating, 14 reviewsSoak in the views - Luxuriate in the surroundings
Home in Whitby
4.99 out of 5 average rating, 77 reviewsFlamingo's Nest at Whitby Beach (North Caicos)
Home in Providenciales
4.9 out of 5 average rating, 59 reviewsBlue Breezes
Home in Caicos Islands
4.82 out of 5 average rating, 51 reviewsCozy 1 bedroom Villa in Providenciales
Home in TC
4.88 out of 5 average rating, 105 reviewsSea More Getaway (with Pool, Hot Tub and BBQ!!)
Quick stats about house rentals in Leeward Settlement
Total rentals
80 properties
Rentals with a pool
70 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
$191 CAD before taxes and fees
Destinations to explore
- Grace Bay Vacation rentals
- Grand Turk Vacation rentals
- Taylor Bay Vacation rentals
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- Guesthouse rentals Turks and Caicos Islands
- House rentals Turks and Caicos Islands
- Guesthouse rentals Turks and Caicos Islands
- House rentals Turks and Caicos Islands
- Guesthouse rentals Providenciales
- House rentals Providenciales
- Guesthouse rentals Providenciales
- House rentals Providenciales
- House rentals Grace Bay
- Rentals with a firepit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Monthly Rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Luxury rentals Leeward Settlement
- Rentals with a patio Leeward Settlement
- Villa rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Beachfront rentals Leeward Settlement
- Rentals with pools Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
- Apartment rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
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