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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
,
4.98 out of 5 average rating, 130 reviews
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
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
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
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
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
7–12 Jul
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
17–22 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
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 Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
4.91 out of 5 average rating, 68 reviews, 3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4.95 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 3 bathrooms
7–12 Jul
Guest favourite
Flat in Caicos Islands
Guest Apartment near Grace Bay Beach
4.97 out of 5 average rating, 104 reviews, 1 bedroom, 3 beds, 1 bathroom
7–12 Jul
Top guest favourite
Home in Grace Bay
#10 The Enclave
4.96 out of 5 average rating, 27 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
4–9 Aug
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
Superhost
Home in Long Bay Hills
LUXURy Villa: Ocean View. Private Pool! Chef avail
4.92 out of 5 average rating, 79 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
23–28 Jul
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
5.0 out of 5 average rating, 30 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Leeward Settlement
25%Off July 27-29 Great Reviews Walk 2 Beach, Pool
4.75 out of 5 average rating, 103 reviews, 2 bedrooms, 2 beds, 2 bathrooms
20–25 Aug
Superhost
Villa in Long Bay
Hakuna Matata Villa
4.87 out of 5 average rating, 75 reviews, 3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
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
7–12 Jul