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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
14–19 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
5.0 out of 5 average rating, 30 reviews, 5 bedrooms, 5 beds, 4 bathrooms
14–19 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
16–21 Aug
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
14–19 Aug
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 5 beds, 3 bathrooms
26–31 Aug
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
14–19 Jul
Superhost
Home in Providenciales
Grace Bay, Pool, Great Reviews! (#2,3)
4.73 out of 5 average rating, 33 reviews, 6 bedrooms, 8 beds, 8 bathrooms
14–19 Aug
Home in Long Bay Hills
Twins Villa - Mellizo B
2 bedrooms, 2 beds, 2 bathrooms
14–19 Jul
Guest favourite
Flat in Leeward Settlement
15 mins walk to restaurants and beach
4.93 out of 5 average rating, 14 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
Top guest favourite
Flat in Leeward Settlement
Luxury Paradise 1 Bedroom condo+pool in Grace Bay
5.0 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 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
Guest house in Long bay
Villa Kendara~SALE 8/15-9/25~Beach~Prvt~Gate~View
4.94 out of 5 average rating, 95 reviews, 2 bedrooms, 4 beds, 1 bathroom
15–22 Aug
Top guest favourite
Home in Grace Bay
#10 The Enclave
4.96 out of 5 average rating, 28 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
10–15 Oct
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
4.89 out of 5 average rating, 149 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Villa in Leeward Settlement
Delightful Family Villa with Pool in Leeward
4.75 out of 5 average rating, 60 reviews, 3 bedrooms, 5 beds, 3 bathrooms
14–19 Jul
Top guest favourite
Villa in Grace Bay
Ideal Honeymoon Villa
4.96 out of 5 average rating, 78 reviews, 1 bedroom, 1.5 bathrooms
14–19 Jul
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
16–21 Jul
Top guest favourite
Apartment in Providenciales
★★★★★ Modern Condo | Amazing Pool | On Site Spa
4.92 out of 5 average rating, 270 reviews, 2 bedrooms, 2 beds, 2 bathrooms
3–8 Aug
Flat in Long Bay Hills
Lush 2-Story Villa, Poolside Bliss Near Beach
4.81 out of 5 average rating, 27 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
30 Jul – 4 Aug