Holiday houses in Leeward Settlement
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Top-rated holiday rentals in Leeward Settlement
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Holiday rentals for every style
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Popular amenities for Leeward Settlement holiday rentals
Other great holiday rentals in Leeward Settlement
Home in Leeward Settlement
5.0 out of 5 average rating, 25 reviewsPiccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 – 10 Dec
Villa in Leeward Settlement
5.0 out of 5 average rating, 30 reviewsPerroquet | Family Villa near Leeward Beach
27 Sept – 4 Oct
Home in Leeward Settlement
4.98 out of 5 average rating, 50 reviewsCocodemer, a short walk to secluded Pelican Beach.
21 – 28 Oct
Villa in Leeward Settlement
5.0 out of 5 average rating, 22 reviewsCaribbean Luxury Waterfront Villa w Housekeeping
27 July – 3 Aug
Guest suite in Leeward Settlement
5.0 out of 5 average rating, 24 reviewsThe Sandbox (UNIT 1)
17 – 24 July
Villa in Caicos Islands
4.92 out of 5 average rating, 36 reviewsPrivate Pool Luxury Villa, 5min to Grace Bay beach
16 – 23 Oct
Home in Providenciales
5.0 out of 5 average rating, 16 reviewsVilla Rae House in Long Bay Hills~walk to beach
15 – 22 July
Home in Leeward Settlement
4.95 out of 5 average rating, 61 reviewsPERIWINKLE | Charming Island Home|Near to Beach
13 – 20 Jan
Quick stats about holiday rentals in Leeward Settlement
Total rentals
290 properties
Rentals with a pool
240 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
5.2K reviews
Nightly prices starting at
$169 AUD before taxes and fees
Destinations to explore
- Grace Bay Holiday rentals
- Grand Turk Accommodation & holiday rentals
- Taylor Bay Holiday rentals
- North Caicos Accommodation & holiday rentals
- Long Bay Beach Accommodation & holiday rentals
- Sapodilla Bay Accommodation & holiday rentals
- Chalk Sound Holiday rentals
- Turtle Cove Holiday rentals
- Salt Cay Holiday rentals
- Santiago de los Caballeros Holiday rentals
- Santo Domingo Accommodation & holiday rentals
- Las Terrenas Accommodation & holiday rentals
- Luxury rentals Leeward Settlement
- Apartment rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Villa rentals Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Beachfront rentals Leeward Settlement
- House rentals Leeward Settlement
- Rentals with a washing machine and dryer Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Monthly Rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
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