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Search results; Over 1,000 homes in Leeward Settlement

Top guest favourite
Flat in Leeward Settlement
Large Luxury Modern Condo + pool + close to beach
1 bedroom, 1 bed, 1.5 private bathrooms
15–20 Sept
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4.97 out of 5 average rating, 117 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
14–19 Sept
4.91 out of 5 average rating, 58 reviews
Luxe
Villa in Leeward Settlement
Sunset Bay Villa - 10 mins away from Grace Bay
5 bedrooms, 5 beds, 5.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 35 reviews
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
4.61 out of 5 average rating, 18 reviews
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds, 3.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 26 reviews
Guest favourite
Villa in Leeward Settlement
*NEW* Villa Serenity - UESE 5
4 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
4.94 out of 5 average rating, 17 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Sept
4.9 out of 5 average rating, 30 reviews
Guest favourite
Villa in Leeward Settlement
Live style villa
4 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
4.89 out of 5 average rating, 38 reviews
Luxe
Villa in Leeward Settlement
*NEW* Upper East Side Enclave # 18
4 bedrooms, 4 king beds, 4 bathrooms
14–19 Sept
4.91 out of 5 average rating, 33 reviews
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds, 2 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 46 reviews
Guest favourite
Villa in Leeward
Waterfront Villa | Pool, Dock Near Grace Bay
4 bedrooms, 7 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 14 reviews
Villa in Leeward Settlement
Private Waterfront Lifestyle Villa -Turks & Caicos
4 bedrooms, 4 king beds, 4.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 66 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 34 reviews
Guest favourite
Villa in Caicos Islands
Waterfront Villa &Pool - Cotton House-Sups -Kayak
4 bedrooms, 5 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 34 reviews
Guest favourite
Villa in Caicos Islands
Modern 4BR oasis on 1 acre, 1 min from the Beach
4 bedrooms, 5 beds, 3.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 111 reviews
Villa in Leeward Settlement
Piccolo Ponte | 3 BR Canal Front | Pool & Hot Tub
3 bedrooms, 3 beds, 3 bathrooms
14–19 Sept
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