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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite
Guest house in Leeward Settlement
"The Nest Cozy Cottage"
1 bedroom, 1 bed, 1 private bathroom
12–17 Jul
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4.98 out of 5 average rating, 130 reviews
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
5.0 out of 5 average rating, 45 reviews, 3 bedrooms, 6 beds, 2 bathrooms
11–16 Jul
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4.96 out of 5 average rating, 24 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Aug
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4.95 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 3 bathrooms
9–14 Jul
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5.0 out of 5 average rating, 30 reviews, 5 bedrooms, 5 beds, 4 bathrooms
13–18 Jul
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
4.91 out of 5 average rating, 23 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
13–18 Jul
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
4.92 out of 5 average rating, 129 reviews, 3 bedrooms, 3 beds, 3 bathrooms
12–17 Jul
Guest favourite
Villa in Caicos Islands
*NEW* Villa Seadream - UESE 16
4.94 out of 5 average rating, 31 reviews, 4 bedrooms, 4 beds, 4 bathrooms
9–14 Jul
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4.89 out of 5 average rating, 9 reviews, 4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, No bathroom
9–14 Jul
Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4.9 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
9–14 Jul
Superhost
Home in Leeward Settlement
Gentry House
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
10–15 Jul
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
4.84 out of 5 average rating, 32 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
9–14 Jul
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 6 beds, 4 bathrooms
12–17 Jul
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
16–21 Jul
Guest favourite
Villa in Caicos Islands
Modern Canal Front Villa in Leeward
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 4 bathrooms
20–25 Jul
Superhost
Home in Long Bay
Turkcation Villa with Curated Tropical Living
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 3 bathrooms
26–31 Jul