
Vacation rentals with a pool in Fairfield County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Fairfield County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Fairfield County rentals with a pool
House rentals with a pool
Superhost

Home in Litchfield
4.82 out of 5 average rating, 105 reviewsThe Getaway-HOST & Co.
Top guest favorite

Home in Stratford
5 out of 5 average rating, 8 reviewsAkasa Ocean Front Oasis- Seasonal Pool, Grill
Top guest favorite

Home in Cheshire
5 out of 5 average rating, 135 reviewsPool House
Guest favorite

Home in Wolcott
5 out of 5 average rating, 5 reviewsAmazing Oasis Private Pool, BBQ, Pool Table.
Top guest favorite

Home in New Milford
5 out of 5 average rating, 11 reviewsPrivate Dock & Pool - Candlewood Lake
Guest favorite

Home in Putnam Valley
4.93 out of 5 average rating, 27 reviewsThe Barger Wixon House
Guest favorite

Home in North Salem
4.94 out of 5 average rating, 34 reviewsNorth Salem Home with Pool & Great Yard
Top guest favorite

Home in Roxbury
5 out of 5 average rating, 17 reviewsBright Mid-Century Modern Retreat-90 min from NYC
Condo rentals with a pool

Condo in Danbury
4.72 out of 5 average rating, 18 reviewsQuaint spacious unit, A+ location
Superhost

Condo in Hartford
3.75 out of 5 average rating, 4 reviewsBeautiful 2 bedrooms/ 2 bath Condo
Superhost

Condo in Farmington
4.81 out of 5 average rating, 53 reviewsFarmington -NEWLY UPDATED NEAR UCONN HC and WEHA

Condo in Wallingford
5 out of 5 average rating, 3 reviewsCozy and charming retreat in quiet area of Wlfd.
Guest favorite

Condo in Mount Sinai
5 out of 5 average rating, 34 reviews1856 Trading House close to water
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Gilgo Beach
- United Nations Headquarters
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art
- Astoria Park
- Robert Moses State Park