filters

Search results; Over 1,000 homes in Leeward Settlement

Photo 1 of 19
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 bed, 1 private bathroom
19–24 Sept
,
4.89 out of 5 average rating, 159 reviews
Photo 1 of 29
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
25–30 Sept
4.91 out of 5 average rating, 58 reviews
Photo 1 of 29
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
13–18 Oct
4.92 out of 5 average rating, 132 reviews
Photo 1 of 29
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
18–23 Oct
5.0 out of 5 average rating, 34 reviews
Photo 1 of 29
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
25–30 Sept
4.97 out of 5 average rating, 35 reviews
Photo 1 of 29
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
28 Sept – 3 Oct
4.9 out of 5 average rating, 31 reviews
Photo 1 of 22
Superhost
Home in Leeward Settlement
25% Off September Great Reviews Walk 2 Beach, Pool
2 bedrooms, 2 beds, 2 bathrooms
3–8 Oct
4.71 out of 5 average rating, 108 reviews
Photo 1 of 29
Guest favourite
Guest house in Long bay
Villa Kendara~SALE~OCT 3-10~Beach~Privt~Gated~View
2 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.94 out of 5 average rating, 97 reviews
Photo 1 of 20
Top guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
2 bedrooms, 2 queen beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 8 reviews
Photo 1 of 29
Superhost
Home in 144645
Villa Starfish
4 bedrooms, 7 beds, 3.5 bathrooms
28 Sept – 3 Oct
4.61 out of 5 average rating, 18 reviews
Photo 1 of 29
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
30 Sept – 5 Oct
4.92 out of 5 average rating, 13 reviews
Photo 1 of 21
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.84 out of 5 average rating, 32 reviews
Photo 1 of 29
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 19 reviews
Photo 1 of 14
Top guest favourite
Home in Grace Bay
#10 The Enclave
2 bedrooms, 3 beds, 2.5 bathrooms
26–31 Oct
4.97 out of 5 average rating, 30 reviews
Photo 1 of 29
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
3 bedrooms, 5 beds, 3 bathrooms
5–10 Oct
4.98 out of 5 average rating, 42 reviews
Photo 1 of 29
Superhost
Home in Providenciales
Grace Bay, Pool, Great Reviews! (#2,3)
6 bedrooms, 8 beds, 8 bathrooms
28 Sept – 3 Oct
4.74 out of 5 average rating, 35 reviews
Photo 1 of 29
Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.9 out of 5 average rating, 73 reviews
Photo 1 of 29
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
2 bedrooms, 5 beds, 2 bathrooms
23–28 Sept
4.94 out of 5 average rating, 90 reviews
Photo 1 of 15
Home in Leeward Settlement
Luxe 1BR Canal Suite w/ Pool • Near Grace Bay
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept