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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Villa in Leeward Settlement
Sea Sun Relax - villa 5 min walk to Grace Bay
3 bedrooms, 4 beds, 2 private bathrooms
27 Jul – 1 Aug
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4.9 out of 5 average rating, 69 reviews
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
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
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
Guest favourite
Home in Leeward Settlement
Caicos Cove Villa Private Pool, BBQ near Grace Bay
4.95 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 3 bathrooms
27 Aug – 1 Sept
Luxe
Villa in Providenciales
Villa Khaya - Bespoke Waterfront Home
4.89 out of 5 average rating, 9 reviews, 4 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
Guest favourite
Villa in Providenciales
Blue Flamingo Villa - Paradise Is a Lifestyle!
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Jul
Guest favourite
Villa in Leeward Settlement
Canal-Front Pool Luxury Villa with Private Dock
4.96 out of 5 average rating, 23 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
5–10 Aug
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
Villa in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, No bathroom
18–23 Aug
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
Villa Solymar Waterfront 4bedroom Villa with Pool
5.0 out of 5 average rating, 30 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
Superhost
Villa in Leeward Settlement
Waterfront 5BR Villa - Kayak Sups Dock + Pool
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 6 beds, 4 bathrooms
5–10 Aug
Top guest favourite
Villa in The Bight Settlement
New private villa |Pool |300yds to Grace Bay beach
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 2 beds, 2 bathrooms
4–9 Aug
Guest favourite
Home in Leeward Settlement
Vacay Vibez Villa Luxury Water Front with Pool
4.91 out of 5 average rating, 23 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
14–19 Jul
Guest favourite
Home in Leeward Settlement
Blue Tang Villa Estate (7 Bedroom)
4.92 out of 5 average rating, 12 reviews, 7 bedrooms, 8 beds, 7.5 bathrooms
23–28 Aug
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
13–18 Jul
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 Leeward
Luxury Waterfront Villa | Dock, Pool & Pickleball
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
16–21 Aug