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
Get the amount of space that is right for you
Popular amenities for house rentals in Leeward Settlement
House rentals with a pool
Home in Long Bay Hills
5.0 out of 5 average rating, 16 reviews1 BR Apt w/pool - Long Bay Hills #2
18–25 Dec
Home in Grace Bay
5.0 out of 5 average rating, 15 reviewsGrace Bay/ New Luxurious home 3+ Bedrooms & Pool
26 Aug – 2 Sep
Home in Grace Bay
5.0 out of 5 average rating, 4 reviews3 King Bedroom Villa, Grace Bay - Sanmar Villa
5–12 Oct
Home in The Bight Settlement
5.0 out of 5 average rating, 62 reviews2b/2b BEACH HOUSE STEPS to GRACE BAY! WiFi,AC,Pool
30 May – 6 Jun
Home in Grace Bay
4.86 out of 5 average rating, 14 reviewsFleur de Mer ii - Gracebay, TCI
4–11 Dec
Home in Long Bay Hills
4.89 out of 5 average rating, 19 reviewsLUXURy Villa: Ocean View. Private Pool! Chef avail
9–16 Jan
Home in Leeward Settlement
4.83 out of 5 average rating, 24 reviewsCaribbean Serene Escape with Pool, 5 mins to Beach
1–8 Aug
Home in Long Bay Hills
4.84 out of 5 average rating, 32 reviewsSunSeaSand 3Bdrm Oceanview Home -Long Bay Hills
22–29 Oct
Weekly house rentals
Home in Long Bay Hills
4.83 out of 5 average rating, 18 reviewsVision Kite- Longbay beach house
5–12 Jan
Home in Providenciales
4.84 out of 5 average rating, 122 reviewsFerguson Tatis Villas 1
17–24 Aug
Home in Long Bay Hills
5.0 out of 5 average rating, 22 reviewsPrivate water front villa – 5 mins from Grace Bay!
24–31 Dec
Home in Providenciales and West Caicos
4.88 out of 5 average rating, 95 reviewsParadise Villa #4, (Studio)
9–16 Jan
Home in Leeward Settlement
4.76 out of 5 average rating, 17 reviewsVista Blue Rental-Grace Bay Beach just 4 mins away
24–31 Jan
Home in The Bight Settlement
5.0 out of 5 average rating, 6 reviewsStudio 400 steps to Grace Bay
27 Jun – 4 Jul
Home in Venetian Road Settlement
4.93 out of 5 average rating, 14 reviewsBrighter Days Villa
7–14 Nov
Home in Providenciales
4.91 out of 5 average rating, 79 reviewsWaterfront house in Providenciales
2–9 Dec
Private house rentals
Home in Long Bay Hills
4.81 out of 5 average rating, 52 reviewsPonciana House 3Bed Villa, Ridgetop Sea View, Pool
23–30 Jan
Home in Providenciales
4.9 out of 5 average rating, 21 reviewsTC Villas -Coriander Cottage -Steps to Grace Bay
16–23 Nov
Home in Cooper Jack Bay Settlement
5.0 out of 5 average rating, 11 reviewsWaterfront House - Upstairs
27 Oct – 3 Nov
Home in Whitby
4.99 out of 5 average rating, 75 reviewsFlamingo's Nest at Whitby Beach (North Caicos)
19–26 Feb
Home in Providenciales
4.89 out of 5 average rating, 57 reviewsThe Blue Breezes
13–20 Feb
Home in Caicos Islands
4.82 out of 5 average rating, 49 reviewsCozy 1 bedroom Villa in Providenciales
20–27 Feb
Home in TC
4.88 out of 5 average rating, 104 reviewsSea More Getaway (with Pool, Hot Tub and BBQ!!)
30 Mar – 6 Apr
Home in Caicos Islands
4.85 out of 5 average rating, 13 reviews! ! NEW ! ! Designers Dream Marina's Beach House
8–15 Aug
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
€ 131 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
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- Las Terrenas Holiday rentals
- House rentals Turks and Caicos Islands
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- 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
- Rentals with a firepit Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Monthly Rentals Leeward Settlement
- Luxury rentals Leeward Settlement
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- Rentals with a hot tub Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
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- Villa rentals Leeward Settlement
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