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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 bedrooms, 5 beds, 4 bathrooms
14–19 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
16–21 Aug
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
14–19 Aug
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Leeward Settlement
Guest House 2B&2B near Grace Bay Beach & Long Bay
2 bedrooms, 5 beds, 2 bathrooms
28 Jul – 3 Aug
4.94 out of 5 average rating, 88 reviews
Superhost
Villa in Providenciales
The Caicos House -5 mins to the Beach & Dining!
3 bedrooms, 5 beds, 2.5 bathrooms
14–19 Jul
4.84 out of 5 average rating, 32 reviews
Superhost
Home in Providenciales
Grace Bay, Pool, Great Reviews! (#2,3)
6 bedrooms, 8 beds, 8 bathrooms
14–19 Aug
4.73 out of 5 average rating, 33 reviews
Top guest favourite
Home in Grace Bay
#10 The Enclave
2 bedrooms, 3 beds, 2.5 bathrooms
3–8 Oct
4.96 out of 5 average rating, 28 reviews
Guest favourite
Guest house in Long bay
Villa Kendara~SALE 8/15-9/25~Beach~Prvt~Gate~View
2 bedrooms, 4 beds, 1 bathroom
15–22 Aug
4.94 out of 5 average rating, 95 reviews
Top guest favourite
Flat in Leeward Settlement
Luxury Paradise 1 Bedroom condo+pool in Grace Bay
1 bedroom, 1 king bed, 1 bathroom
16–21 Jul
5.0 out of 5 average rating, 93 reviews
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
16–21 Jul
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
3 bedrooms, 5 beds, 3 bathrooms
26–31 Aug
4.97 out of 5 average rating, 36 reviews
Guest favourite
Villa in Leeward Settlement
Delightful Family Villa with Pool in Leeward
3 bedrooms, 5 beds, 3 bathrooms
14–19 Jul
4.75 out of 5 average rating, 60 reviews
Guest favourite
Flat in Leeward Settlement
15 mins walk to restaurants and beach
2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
4.93 out of 5 average rating, 14 reviews
Home in Long Bay Hills
Twins Villa - Mellizo B
2 bedrooms, 2 beds, 2 bathrooms
14–19 Jul
Flat in Long Bay Hills
Lush 2-Story Villa, Poolside Bliss Near Beach
2 bedrooms, 2 queen beds, 2.5 bathrooms
30 Jul – 4 Aug
4.81 out of 5 average rating, 27 reviews
Guest favourite
Villa in Leeward Settlement
*NEW* Upper East Side Enclave # 18
4 bedrooms, 4 king beds, 4 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 25 reviews
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed, 1 bathroom
28 Jul – 2 Aug
4.9 out of 5 average rating, 148 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
4.9 out of 5 average rating, 69 reviews