Vacation rentals with a pool in Leeward Settlement
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Leeward Settlement
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Leeward Settlement rentals with a pool
House rentals with a pool
Home in TC
4.97 out of 5 average rating, 159 reviews“The Lighthouse”, Private Pool, Ocean Views, Beach
Home in Leeward Settlement
4.98 out of 5 average rating, 53 reviewsCocodemer, a short walk to secluded Pelican Beach.
Home in Leeward Settlement
5.0 out of 5 average rating, 25 reviewsPiccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
Home in Providenciales
4.97 out of 5 average rating, 86 reviewsSunny Paradise Long Bay
Home in Providenciales
5.0 out of 5 average rating, 22 reviewsSea Villa @ The Sun and Sea Villas
Home in Grace Bay
4.98 out of 5 average rating, 42 reviewsHopewell Villa East/Pool & walk to Gracebay Beach
Home in Grace Bay
4.95 out of 5 average rating, 93 reviewsPrivate Family Villa in Grace Bay w/pool + yard
Home in Grace Bay
5.0 out of 5 average rating, 18 reviewsVilla in Providenciales
Condo rentals with a pool
Condo in Grace Bay
4.8 out of 5 average rating, 100 reviewsAffordable Grace Bay condo near the beach
Condo in Providenciales and West Caicos
4.86 out of 5 average rating, 392 reviews🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞
Condo in Providenciales
4.92 out of 5 average rating, 106 reviewsRomantic Escape with Stunning Pools & Sunset Views
Condo in Providenciales
4.85 out of 5 average rating, 101 reviews*Balcony View* Renovated Modern Studio C202
Condo in Turtle Cove
4.95 out of 5 average rating, 140 reviews🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝
Condo in Providenciales
4.88 out of 5 average rating, 164 reviewsSea Dreams - Jr 1 bdrm with Panoramic Ocean views!
Condo in Leeward Settlement
5.0 out of 5 average rating, 23 reviewsGrace’s Condo In Leeward Settlement
Condo in Grace Bay
4.89 out of 5 average rating, 18 reviewsLuxe Studio - Grace Bay - (5-Min walk to Beach)
Quick stats about vacation rentals with a pool in Leeward Settlement
Total rentals
240 properties
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
200 properties are a good fit for families
Total number of reviews
3.8K reviews
Nightly prices starting at
$110 before taxes and fees
Destinations to explore
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