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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Guest suite in Leeward Settlement
Handfield's Hideaway Cozy One Bedrm
1 bedroom, 2 beds, 1 private bathroom
1–6 Aug
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4.92 out of 5 average rating, 102 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds
18–23 Aug
4.92 out of 5 average rating, 130 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds
23–28 Aug
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds
16–21 Aug
4.91 out of 5 average rating, 53 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds
14–19 Aug
4.89 out of 5 average rating, 28 reviews
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds
2–7 Aug
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds
3–8 Aug
4.92 out of 5 average rating, 25 reviews
Flat in Leeward Settlement
Marbella Suite 1 | Caribbean Elegance & Luxury
3 bedrooms, 4 beds
1–6 Aug
New place to stay
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds
2–7 Aug
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa: Private Pool near Grace Bay
4 bedrooms, 5 beds
11–16 Aug
4.95 out of 5 average rating, 22 reviews
Flat in Leeward Settlement
Marbella Suite 2 | Caribbean Elegance & Luxury
2 bedrooms, 2 king beds
1–6 Aug
New place to stay
Superhost
Home in Leeward
Channel Villa - Elegant Canal-Front Retreat
4 bedrooms, 4 beds
13–18 Aug
4.83 out of 5 average rating, 6 reviews
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms, 6 beds
5–10 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms, 4 beds
1–6 Aug
4.89 out of 5 average rating, 37 reviews
Villa in Providenciales
NEW- Aqua Blu Beach Villa Oceanfront "The Jasmine"
4 bedrooms, 4 king beds
7–12 Aug
New place to stay
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds
1–6 Aug
4.76 out of 5 average rating, 17 reviews
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds
1–6 Aug
4.84 out of 5 average rating, 32 reviews
Superhost
Home in Long Bay Hills
LUXURy Villa: Ocean View. Private Pool! Chef avail
4 bedrooms, 5 beds
17–22 Aug
4.93 out of 5 average rating, 80 reviews