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, 16 reviewsVilla in Providenciales
Nov 22 – 29
Home in Grace Bay
5.0 out of 5 average rating, 16 reviewsGrace Bay/ New Luxurious home 3+ Bedrooms & Pool
Sep 21 – 28
Home in Grace Bay
5.0 out of 5 average rating, 4 reviews3 King Bedroom Villa, Grace Bay - Sanmar Villa
Oct 8 – 15
Home in The Bight Settlement
5.0 out of 5 average rating, 63 reviews2b/2b BEACH HOUSE STEPS to GRACE BAY! WiFi,AC,Pool
Jul 27 – Aug 3
Home in Grace Bay
4.86 out of 5 average rating, 14 reviewsFleur de Mer ii - Gracebay, TCI
Mar 20 – 27
Home in Leeward Settlement
4.83 out of 5 average rating, 24 reviewsCaribbean Serene Escape with Pool, 5 mins to Beach
Mar 12 – 19
Home in Leeward Settlement
4.92 out of 5 average rating, 26 reviewsPelican Paradise Villa - Leeward Beach
Aug 19 – 26
Home in Long Bay Hills
4.85 out of 5 average rating, 33 reviewsSunSeaSand 3Bdrm Oceanview Home -Long Bay Hills
Oct 17 – 24
Weekly house rentals
Home in Long Bay Hills
4.83 out of 5 average rating, 18 reviewsVision Kite- Longbay beach house
Sep 16 – 23
Home in Long Bay Hills
5.0 out of 5 average rating, 22 reviewsPrivate water front villa – 5 mins from Grace Bay!
Mar 30 – Apr 6
Home in Providenciales
4.85 out of 5 average rating, 123 reviewsFerguson Tatis Villas 1
Oct 16 – 23
Home in Providenciales and West Caicos
4.88 out of 5 average rating, 95 reviewsParadise Villa #4, (Studio)
Mar 28 – Apr 4
Home in Leeward Settlement
4.76 out of 5 average rating, 17 reviewsVista Blue Rental-Grace Bay Beach just 4 mins away
Jan 16 – 23
Home in Venetian Road Settlement
4.93 out of 5 average rating, 14 reviewsBrighter Days Villa
Sep 21 – 28
Home in The Bight Settlement
5.0 out of 5 average rating, 6 reviewsStudio 400 steps to Grace Bay
Nov 27 – Dec 4
Home in Caicos Islands
4.82 out of 5 average rating, 49 reviewsCozy 1 bedroom Villa in Providenciales
Aug 7 – 14
Private house rentals
Home in Long Bay Hills
4.94 out of 5 average rating, 17 reviewsPeaceful 1BR Private Cottage w/ HotTub Beach Front
Nov 3 – 10
Home in Cooper Jack Bay Settlement
5.0 out of 5 average rating, 11 reviewsWaterfront House - Upstairs
Jul 3 – 10
Home in Providenciales
4.93 out of 5 average rating, 55 reviewsPeaceful new 3 bedroom home
Feb 10 – 17
Home in Whitby
4.99 out of 5 average rating, 76 reviewsFlamingo's Nest at Whitby Beach (North Caicos)
Apr 21 – 28
Home in Providenciales
4.9 out of 5 average rating, 58 reviewsBlue Breezes
Feb 13 – 20
Home in TC
4.88 out of 5 average rating, 104 reviewsSea More Getaway (with Pool, Hot Tub and BBQ!!)
Aug 5 – 12
Home in Providenciales
5.0 out of 5 average rating, 3 reviewsNEW Tropical Private Pool Villa, Beach 5min Drive
Mar 7 – 14
Home in Long Bay Hills
5.0 out of 5 average rating, 6 reviewsGorgeous Villa with Pool and Privacy (2Br2Ba)
Nov 4 – 11
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
R2,599 ZAR before taxes and fees
Destinations to explore
- Grace Bay Vacation rentals
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- House rentals Providenciales
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- House rentals Providenciales
- Guesthouse rentals Providenciales
- House rentals Grace Bay
- Rentals with a fire pit Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
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- Kid-friendly rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
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