House holiday 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.
Holiday rentals for every style
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Popular amenities for house rentals in Leeward Settlement
House rentals with a pool
Home in Grace Bay
5.0 out of 5 average rating, 16 reviewsVilla in Providenciales
13–20 Feb
Home in Grace Bay
5.0 out of 5 average rating, 16 reviewsGrace Bay/ New Luxurious home 3+ Bedrooms & Pool
6–13 Nov
Home in Grace Bay
5.0 out of 5 average rating, 4 reviews3 King Bedroom Villa, Grace Bay - Sanmar Villa
7–14 Oct
Home in Long Bay Hills
4.89 out of 5 average rating, 19 reviewsLUXURy Villa: Ocean View. Private Pool! Chef avail
27 Mar – 3 Apr
Home in The Bight Settlement
5.0 out of 5 average rating, 63 reviews2b/2b BEACH HOUSE STEPS to GRACE BAY! WiFi,AC,Pool
28 Aug – 4 Sep
Home in Grace Bay
4.86 out of 5 average rating, 14 reviewsFleur de Mer ii - Gracebay, TCI
20–27 Apr
Home in Leeward Settlement
4.83 out of 5 average rating, 24 reviewsCaribbean Serene Escape with Pool, 5 mins to Beach
8–15 Feb
Home in Leeward Settlement
4.92 out of 5 average rating, 26 reviewsPelican Paradise Villa - Leeward Beach
29 Sep – 6 Oct
Weekly house rentals
Home in Long Bay Hills
4.83 out of 5 average rating, 18 reviewsVision Kite- Longbay beach house
15–22 Sep
Home in Long Bay Hills
5.0 out of 5 average rating, 22 reviewsPrivate water front villa – 5 mins from Grace Bay!
11–18 Oct
Home in Providenciales
4.85 out of 5 average rating, 123 reviewsFerguson Tatis Villas 1
16–23 Apr
Home in Providenciales and West Caicos
4.88 out of 5 average rating, 95 reviewsParadise Villa #4, (Studio)
12–19 Sep
Home in Leeward Settlement
4.76 out of 5 average rating, 17 reviewsVista Blue Rental-Grace Bay Beach just 4 mins away
16–23 Aug
Home in Venetian Road Settlement
4.93 out of 5 average rating, 14 reviewsBrighter Days Villa
30 Aug – 6 Sep
Home in The Bight Settlement
5.0 out of 5 average rating, 6 reviewsStudio 400 steps to Grace Bay
8–15 Feb
Home in Long Bay Hills
5.0 out of 5 average rating, 35 reviews2 BR Ocean View- Private Pool- Flame Tree Villa #2
31 Oct – 7 Nov
Private house rentals
Home in Long Bay Hills
4.81 out of 5 average rating, 53 reviewsPonciana House 3Bed Villa, Ridgetop Sea View, Pool
25 Mar – 1 Apr
Home in Providenciales
4.9 out of 5 average rating, 21 reviewsTC Villas -Coriander Cottage -Steps to Grace Bay
16–23 Nov
Home in Long Bay Hills
4.94 out of 5 average rating, 17 reviewsPeaceful 1BR Private Cottage w/ HotTub Beach Front
28 May – 4 Jun
Home in Cooper Jack Bay Settlement
5.0 out of 5 average rating, 11 reviewsWaterfront House - Upstairs
2–9 Jul
Home in Whitby
4.99 out of 5 average rating, 76 reviewsFlamingo's Nest at Whitby Beach (North Caicos)
27 Mar – 3 Apr
Home in Providenciales
4.93 out of 5 average rating, 55 reviewsPeaceful new 3 bedroom home
21–28 Oct
Home in Providenciales
4.9 out of 5 average rating, 58 reviewsThe Blue Breezes
13–20 Feb
Home in TC
4.88 out of 5 average rating, 104 reviewsSea More Getaway (with Pool, Hot Tub and BBQ!!)
19–26 Jan
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 SGD before taxes and fees
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
- Santiago de los Caballeros Holiday rentals
- Santo Domingo Holiday rentals
- Las Terrenas Holiday rentals
- House rentals Turks and Caicos Islands
- Guest house rentals Turks and Caicos Islands
- House rentals Turks and Caicos Islands
- Guest house rentals Turks and Caicos Islands
- Guest house rentals Providenciales
- House rentals Providenciales
- Guest house rentals Providenciales
- House rentals Providenciales
- House rentals Grace Bay
- Family-friendly rentals Leeward Settlement
- Villa rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
- Monthly Rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Flat rentals Leeward Settlement
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