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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
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
14–19 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
12–17 Jul
Guest favourite
Guest house in Long bay
VillaKendara~8/15-9/26@30%OFF~Beach~Prvt~Gate~View
4.94 out of 5 average rating, 95 reviews, 2 bedrooms, 4 beds, 1 bathroom
15–21 Aug
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
3–8 Oct
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 5 beds, 3 bathrooms
26–31 Aug
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
4.9 out of 5 average rating, 148 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
Top 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
26–31 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
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
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
Guest suite in Leeward Settlement
The Sandbox (UNIT 1)
4.99 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul
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
17–22 Aug
Guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Jul
Superhost
Villa in Leeward Settlement
Canal Front 3BR Villa and dock+ Pool+Sups+Kayaks
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 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
Top guest favourite
Villa in Grace Bay
Ideal Honeymoon Villa
4.96 out of 5 average rating, 78 reviews, 1 bedroom, 1.5 bathrooms
31 Aug – 5 Sept