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Search results; Over 1,000 homes in Leeward Settlement

Superhost
Guest house in Leeward Settlement
Lois Estates: 2 Bed Unique Home - Long Bay
2 bedrooms, 1 bed, 2.5 private bathrooms
1–6 Sept
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Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
7–12 Sept
4.91 out of 5 average rating, 57 reviews
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms, 6 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
7–12 Sept
4.92 out of 5 average rating, 132 reviews
Luxe
Villa in Leeward Settlement
*Brand-new* Villa Terra Blue - Walk to Beach
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 34 reviews
Guest favourite
Home in Leeward Settlement
Sapphire Sands –Lotus Villa #3 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Sept
4.97 out of 5 average rating, 30 reviews
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
1–6 Sept
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 34 reviews
Villa in Leeward Settlement
Private Waterfront Lifestyle Villa -Turks & Caicos
4 bedrooms, 4 king beds, 4.5 bathrooms
1–6 Sept
4.92 out of 5 average rating, 65 reviews
Superhost
Villa in Leeward
Waterfront Villa | Pool, Dock Near Grace Bay
4 bedrooms, 7 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Leeward Settlement
Blue Diamond Villa, Waterfront Escape with Hot tub
3 bedrooms, 3 king beds, 3.5 bathrooms
15–20 Sept
4.86 out of 5 average rating, 7 reviews
Guest favourite
Villa in Leeward Settlement
*NEW* Upper East Side Enclave # 18
4 bedrooms, 4 king beds, 4 bathrooms
7–12 Sept
4.9 out of 5 average rating, 31 reviews
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
4.61 out of 5 average rating, 18 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
12–17 Sept
4.9 out of 5 average rating, 29 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
2–7 Sept
4.92 out of 5 average rating, 111 reviews
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Sept
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Townhouse in Grace Bay
Luxury 4Bed/4.5Bath Home w/ Private Pool Gracebay
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 10 reviews