House vacation rentals in Leeward Settlement
Find and book unique houses on Airbnb
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 Long Bay Hills
5.0 out of 5 average rating, 17 reviews1 BR Apt w/pool - Long Bay Hills #2
Jan 14 – 21
Home in Grace Bay
5.0 out of 5 average rating, 16 reviewsVilla in Providenciales
Mar 5 – 12
Home in Grace Bay
5.0 out of 5 average rating, 16 reviewsGrace Bay/ New Luxurious home 3+ Bedrooms & Pool
Apr 27 – May 4
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 27 – Aug 3
Home in Leeward Settlement
4.92 out of 5 average rating, 26 reviewsPelican Paradise Villa - Leeward Beach
Oct 11 – 18
Home in Leeward Settlement
4.83 out of 5 average rating, 24 reviewsCaribbean Serene Escape with Pool, 5 mins to Beach
Dec 29 – Jan 5
Home in Long Bay Hills
4.85 out of 5 average rating, 33 reviewsSunSeaSand 3Bdrm Oceanview Home -Long Bay Hills
Oct 25 – Nov 1
Home in Grace Bay
4.86 out of 5 average rating, 14 reviewsFleur de Mer ii - Gracebay, TCI
Sep 30 – Oct 7
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 10 – 17
Home in Providenciales
4.84 out of 5 average rating, 124 reviewsFerguson Tatis Villas 1
Nov 26 – Dec 3
Home in Leeward Settlement
4.76 out of 5 average rating, 17 reviewsVista Blue Rental-Grace Bay Beach just 4 mins away
Oct 27 – Nov 3
Home in Providenciales and West Caicos
4.88 out of 5 average rating, 95 reviewsParadise Villa #4, (Studio)
Mar 3 – 10
Home in Venetian Road Settlement
4.93 out of 5 average rating, 14 reviewsBrighter Days Villa
Sep 8 – 15
Home in Caicos Islands
5.0 out of 5 average rating, 4 reviewsTwo Bedroom Villa, Long Bay, Providenciales - Eden
Nov 26 – Dec 3
Home in The Bight Settlement
5.0 out of 5 average rating, 7 reviewsStudio 400 steps to Grace Bay
Jan 6 – 13
Private house rentals
Home in Cooper Jack Bay Settlement
5.0 out of 5 average rating, 11 reviewsWaterfront House - Upstairs
Jan 17 – 24
Home in Whitby
4.99 out of 5 average rating, 76 reviewsFlamingo's Nest at Whitby Beach (North Caicos)
Nov 15 – 22
Home in Providenciales
4.9 out of 5 average rating, 58 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!!)
Jul 27 – Aug 3
Home in Providenciales
5.0 out of 5 average rating, 3 reviewsNEW Tropical Private Pool Villa, Beach 5min Drive
Dec 8 – 15
Home in Long Bay Hills
5.0 out of 5 average rating, 6 reviewsGorgeous Villa with Pool and Privacy (2Br2Ba)
Mar 5 – 12
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 Grace Bay
4.95 out of 5 average rating, 21 reviewsCaya Villa 1 - 2 Bedroom - Modern Island Home
Sep 9 – 16
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
- Grace Bay Vacation rentals
- Grand Turk Vacation rentals
- Taylor Bay Vacation rentals
- North Caicos Vacation rentals
- Long Bay Beach Vacation rentals
- Sapodilla Bay Vacation rentals
- Chalk Sound Vacation rentals
- Turtle Cove Vacation rentals
- Salt Cay Vacation rentals
- Santiago de los Caballeros Vacation rentals
- Santo Domingo Vacation rentals
- Las Terrenas Vacation rentals
- House rentals Turks and Caicos Islands
- Guesthouse rentals Turks and Caicos Islands
- House rentals Turks and Caicos Islands
- Guesthouse rentals Turks and Caicos Islands
- Guesthouse rentals Providenciales
- House rentals Providenciales
- Guesthouse rentals Providenciales
- House rentals Providenciales
- House rentals Grace Bay
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
- Rentals with beach access Leeward Settlement
- Villa rentals Leeward Settlement
- Beachfront rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Monthly Rentals Leeward Settlement
- Apartment rentals Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Luxury rentals Leeward Settlement
- House rentals Caicos Islands
- Guesthouse rentals Caicos Islands
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom