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
Aug 22 – 29
Home in Grace Bay
5.0 out of 5 average rating, 16 reviewsGrace Bay/ New Luxurious home 3+ Bedrooms & Pool
Sep 27 – Oct 4
Home in Grace Bay
5.0 out of 5 average rating, 4 reviews3 King Bedroom Villa, Grace Bay - Sanmar Villa
Oct 19 – 26
Home in Leeward Settlement
4.92 out of 5 average rating, 26 reviewsPelican Paradise Villa - Leeward Beach
May 14 – 21
Home in Leeward Settlement
4.83 out of 5 average rating, 24 reviewsCaribbean Serene Escape with Pool, 5 mins to Beach
Apr 3 – 10
Home in The Bight Settlement
5.0 out of 5 average rating, 64 reviews2b/2b BEACH HOUSE STEPS to GRACE BAY! WiFi,AC,Pool
Jul 28 – Aug 4
Home in Long Bay Hills
4.89 out of 5 average rating, 19 reviewsLUXURy Villa: Ocean View. Private Pool! Chef avail
Feb 6 – 13
Home in Long Bay Hills
4.85 out of 5 average rating, 33 reviewsSunSeaSand 3Bdrm Oceanview Home -Long Bay Hills
Mar 9 – 16
Weekly house rentals
Home in Long Bay Hills
4.83 out of 5 average rating, 18 reviewsVision Kite- Longbay beach house
Sep 20 – 27
Home in Long Bay Hills
5.0 out of 5 average rating, 23 reviewsPrivate water front villa – 5 mins from Grace Bay!
Nov 11 – 18
Home in Providenciales
4.84 out of 5 average rating, 124 reviewsFerguson Tatis Villas 1
Oct 16 – 23
Home in Leeward Settlement
4.76 out of 5 average rating, 17 reviewsVista Blue Rental-Grace Bay Beach just 4 mins away
Apr 9 – 16
Home in Providenciales and West Caicos
4.88 out of 5 average rating, 95 reviewsParadise Villa #4, (Studio)
Apr 14 – 21
Home in Venetian Road Settlement
4.93 out of 5 average rating, 14 reviewsBrighter Days Villa
Aug 16 – 23
Home in Long Bay Hills
4.91 out of 5 average rating, 94 reviewsSea La Vie - Beachside 2 bdr Unit #4, Ocean views
Sep 14 – 21
Home in Long Bay Hills
5.0 out of 5 average rating, 35 reviews2 BR Ocean View- Private Pool- Flame Tree Villa #2
Nov 5 – 12
Private house rentals
Home in Whitby
4.99 out of 5 average rating, 76 reviewsFlamingo's Nest at Whitby Beach (North Caicos)
Nov 29 – Dec 6
Home in Cooper Jack Bay Settlement
5.0 out of 5 average rating, 12 reviewsWaterfront House - Upstairs
Jul 2 – 9
Home in Providenciales
4.9 out of 5 average rating, 59 reviewsBlue Breezes
Sep 22 – 29
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 Long Bay Hills
5.0 out of 5 average rating, 6 reviewsGorgeous Villa with Pool and Privacy (2Br2Ba)
Sep 16 – 23
Home in Grace Bay
4.95 out of 5 average rating, 21 reviewsCaya Villa 1 - 2 Bedroom - Modern Island Home
Feb 25 – Mar 4
Home in Caicos Islands
4.85 out of 5 average rating, 13 reviews! ! NEW ! ! Designers Dream Marina's Beach House
Sep 18 – 25
Home in Providenciales
5.0 out of 5 average rating, 9 reviewsCallaloo Cottage- Beachfront Paradise!
Jul 29 – Aug 5
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
$140 before taxes and fees
Destinations to explore
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- House rentals Grace Bay
- Rentals with a washer and dryer Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Apartment rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Fitness-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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- Monthly Rentals Leeward Settlement
- Rentals with a hot tub Leeward Settlement
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