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 Providenciales
4.97 out of 5 average rating, 318 reviewsVilla Cocuyo Micro Villa with pool
Home in Grace Bay
4.95 out of 5 average rating, 22 reviewsWelcome to Hope's Cottage!
Home in The Bight Settlement
5 out of 5 average rating, 77 reviews2b/2b BEACH HOUSE STEPS to GRACE BAY! WiFi,AC,Pool
Home in Grace Bay
5 out of 5 average rating, 37 reviewsGrace Bay/ New Luxurious home 3+ Bedrooms & Pool
Home in TC
4.98 out of 5 average rating, 168 reviews“The Lighthouse”, Private Pool, Ocean Views, Beach
Home in Providenciales
5 out of 5 average rating, 29 reviewsSea Villa @ The Sun and Sea Villas
Home in Providenciales
4.9 out of 5 average rating, 103 reviewsSea La Vie - Beachside 2 bdr Unit #4, Ocean views
Home in Grace Bay
4.95 out of 5 average rating, 21 reviewsVilla in Providenciales
Condo rentals with a pool
Condo in Turtle Cove
4.93 out of 5 average rating, 102 reviewsAllies Rest - Seaflowers townhome
Condo in Turtle Cove
4.94 out of 5 average rating, 156 reviews🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝
Condo in Caicos Islands
4.97 out of 5 average rating, 34 reviewsLil Chill -A cozy 1-Bedroom Unit near the beach
Condo in Providenciales and West Caicos
4.86 out of 5 average rating, 412 reviews🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞
Condo in Wheeland Settlement
4.95 out of 5 average rating, 114 reviewsCouple’s Retreat with ocean views and hot tub!
Condo in Providenciales
4.88 out of 5 average rating, 106 reviewsThe Yacht Club ≋ 1 Bedroom (C3)
Condo in Providenciales
4.87 out of 5 average rating, 106 reviewsAmazing GraceBay Views, Pools,Location PH Studio
Condo in Providenciales
5 out of 5 average rating, 8 reviewsNEW! Romantic Getaway, 3 Mins to the Beach !
Quick stats about vacation rentals with a pool in Leeward Settlement
Total rentals
270 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
4.6K reviews
Family-friendly rentals
220 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Destinations to explore
- Grace Bay Vacation rentals
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- Taylor Bay Vacation rentals
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- Long Bay Beach Vacation rentals
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- Chalk Sound Vacation rentals
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- Rentals with pools Turks and Caicos Islands
- Rentals with pools Turks and Caicos Islands
- Rentals with pools Providenciales
- Rentals with pools Providenciales
- Rentals with pools Grace Bay
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- Rentals with a hot tub Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
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