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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
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4.98 out of 5 average rating, 130 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
12–17 Jul
4.92 out of 5 average rating, 129 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
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
4.9 out of 5 average rating, 52 reviews
Top guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Aug
4.96 out of 5 average rating, 24 reviews
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds, 2.5 bathrooms
8–13 Jul
4.84 out of 5 average rating, 32 reviews
Top 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
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
16–21 Jul
Flat in Long Bay Hills
Lush 2-Story Villa, Poolside Bliss Near Beach
2 bedrooms, 2 queen beds, 2.5 bathrooms
12–17 Jul
4.81 out of 5 average rating, 27 reviews
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed, 1 bathroom
20–25 Jul
4.9 out of 5 average rating, 148 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
8–13 Jul
4.95 out of 5 average rating, 21 reviews
Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
4.91 out of 5 average rating, 68 reviews
Superhost
Villa in Leeward Settlement
Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Long Bay Hills
LUXURy Villa: Ocean View. Private Pool! Chef avail
4 bedrooms, 5 beds, 4.5 bathrooms
23–28 Jul
4.92 out of 5 average rating, 79 reviews
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
2 bedrooms, 5 beds, 2 bathrooms
8–13 Jul
4.94 out of 5 average rating, 88 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
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Place to stay in Leeward Settlement
Minutes from Grace Bay
1 bedroom, 1 queen bed, 1 bathroom
9–14 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Grace Bay
#10 The Enclave
2 bedrooms, 3 beds, 2.5 bathrooms
4–9 Aug
4.96 out of 5 average rating, 27 reviews