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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
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
14–19 Aug
4.96 out of 5 average rating, 24 reviews
Guest favourite
Villa in Providenciales
Blue Flamingo Villa - Paradise Is a Lifestyle!
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
3 bedrooms, 3 beds, No bathroom
18–23 Aug
4.98 out of 5 average rating, 53 reviews
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
16–21 Jul
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5 bedrooms, 6 beds, 4 bathrooms
13–18 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
17–22 Aug
4.92 out of 5 average rating, 79 reviews
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, 34 reviews
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4 bedrooms, 5 beds, 3 bathrooms
27 Aug – 1 Sept
4.95 out of 5 average rating, 21 reviews
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5 bedrooms, 6 beds, 5.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Villa in Leeward Settlement
Canal-Front Pool Luxury Villa with Private Dock
5 bedrooms, 6 beds, 5.5 bathrooms
5–10 Aug
4.96 out of 5 average rating, 23 reviews
Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Leeward Settlement
Beach Daze Villa - Your Tropical Vacation Awaits
3 bedrooms, 6 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
3 bedrooms, 6 beds, 2 bathrooms
14–19 Jul
5.0 out of 5 average rating, 45 reviews
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
3 bedrooms, 4 beds, 3.5 bathrooms
13–18 Jul
4.91 out of 5 average rating, 23 reviews