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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Guest suite in Leeward Settlement
Handfield's Hideaway Cozy One Bedrm
1 bedroom, 2 beds, 1 private bathroom
25–30 Jul
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4.92 out of 5 average rating, 102 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
4.92 out of 5 average rating, 130 reviews, 3 bedrooms, 3 beds, 3 bathrooms
18–23 Aug
Flat in Leeward Settlement
Marbella Suite 1 | Caribbean Elegance & Luxury
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Jul
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5.0 out of 5 average rating, 31 reviews, 5 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
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
16–21 Aug
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
4.92 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
3–8 Aug
Flat in Leeward Settlement
Marbella Suite 2 | Caribbean Elegance & Luxury
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
22–27 Jul
Guest favourite
Villa in Leeward Settlement
Villa Solymar Waterfront 4bedroom Villa with Pool
5.0 out of 5 average rating, 32 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
Home in Providenciales
NEW-Aqua Blu Beach Villa Oceanfront "The Orchid"
New place to stay, 4 bedrooms, 4 beds, 5 bathrooms
31 Jul – 5 Aug
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4.9 out of 5 average rating, 10 reviews, 4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
Luxe
Villa in Leeward Settlement
Aqua Bliss Villa
4 bedrooms, 4 beds, 5 bathrooms
22–27 Jul
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4.92 out of 5 average rating, 26 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
Guest favourite
Villa in Long Bay Hills
Private Pool Villa w/ BBQ, & Fire Pit + Near Beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
27 Jul – 1 Aug
Superhost
Home in Long Bay Hills
LUXURy Villa: Ocean View. Private Pool! Chef avail
4.93 out of 5 average rating, 80 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
17–22 Aug
Guest favourite
Villa in Providenciales
Blue Flamingo Villa - Paradise Is a Lifestyle!
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Oct
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 5 beds, 3 bathrooms
26–31 Aug
Guest favourite
Villa in Leeward Settlement
Golden Palms – Lotus Villas #2 Privacy, Pool, BBQ
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
27 Jul – 1 Aug
Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
4.9 out of 5 average rating, 69 reviews, 3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Superhost
Home in Leeward Settlement
Blue Tang Villa (5 Bedroom Main House)
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
23–28 Aug