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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
13–18 Jul
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4.98 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, 4 bathrooms
13–18 Jul
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 45 reviews
Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
4 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
5.0 out of 5 average rating, 8 reviews
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 beds, 4 bathrooms
13–18 Jul
4.9 out of 5 average rating, 52 reviews
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds, 3.5 bathrooms
14–19 Jul
4.91 out of 5 average rating, 23 reviews
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
2 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
4.94 out of 5 average rating, 88 reviews
Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Villa in Providenciales
Amazing Waterfront Villa on Leeward Canals
5 bedrooms, 7 beds, 3.5 bathrooms
14–19 Jul
4.99 out of 5 average rating, 67 reviews
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
13–18 Jul
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
18–23 Aug
4.98 out of 5 average rating, 53 reviews
Guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
2 bedrooms, 2 queen beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms, 6 beds, 4 bathrooms
5–10 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
15–20 Jul
4.76 out of 5 average rating, 17 reviews
Guest favourite
Villa in Caicos Islands
*NEW* Villa Seadream - UESE 16
4 bedrooms, 4 king beds, 4 bathrooms
2–7 Aug
4.94 out of 5 average rating, 31 reviews