
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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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.
CrystalRating, 5 stars9 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Top guest favorite

Home in Stratford
5 out of 5 average rating, 8 reviewsAkasa Ocean Front Oasis- Seasonal Pool, Grill
JcRating, 5 stars4 weeks ago
Amazing time front of the ocean, enjoying time with kids and familly. The pool seems great but was too cold for us in this early time of the year.
Top guest favorite

Home in Cheshire
5 out of 5 average rating, 135 reviewsPool House
CindyRating, 5 stars1 month ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Guest favorite

Home in Wolcott
5 out of 5 average rating, 5 reviewsAmazing Oasis Private Pool, BBQ, Pool Table.
AmandaRating, 5 stars1 week ago
Glenda was friendly and had great communication from Start to Finish. This was a nice location for a family fun weekend. Although the drive is close enough to stores if you need anything (target/stopnshop/bjs etc), the property is in a quiet and safe neighborhood. The yard is a great place to hang out and relax with the fire pit or have fun in the pool. And when the weather was crappy the pool table and hanging out in the basement den was nice. Everything in the house is labeled and easy to find. We enjoyed the space and would definitely recommend. Thanks again! 😊
Top guest favorite

Home in New Milford
5 out of 5 average rating, 11 reviewsPrivate Dock & Pool - Candlewood Lake
WarkiriaRating, 5 stars1 week ago
I had such a fantastic experience staying at this Airbnb! The home was exactly as described—clean, cozy, and beautifully decorated. The location was perfect—close to everything I needed, but still quiet and peaceful for a relaxing getaway. Waking up and drinking coffee with the beautiful view of Candlewood lake was breathtaking. The host was incredibly welcoming and responsive. I would definitely stay here again and would recommend anyone to stay here. I would also recommend you to take your boat or even rent one near by,absolutely incredible!!!
Guest favorite

Home in Putnam Valley
4.93 out of 5 average rating, 27 reviewsThe Barger Wixon House
ChrisRating, 5 stars4 weeks ago
Stayed for West Point graduation. House was awesome. Hosts were more awsomelierist….. Highly recommend. GO ARMY! BEAT navy!
Guest favorite

Home in North Salem
4.94 out of 5 average rating, 34 reviewsNorth Salem Home with Pool & Great Yard
EliezerRating, 5 stars6 days ago
It is second time my family and I have stayed in this house, and we love coming here! the house is clean, well maintained, and stocked with everything we could ever need to enjoy our visit. Susan is very responsive and eager for us to make the most of our time. we hope to visit again soon
Top guest favorite

Home in Roxbury
5 out of 5 average rating, 17 reviewsBright Mid-Century Modern Retreat-90 min from NYC
SidRating, 5 stars4 months ago
My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.
Condo rentals with a pool

Condo in Danbury
4.72 out of 5 average rating, 18 reviewsQuaint spacious unit, A+ location
EmilyRating, 5 stars1 month ago
Will was pleasant, easy to reach for quick fixes and very communicative! He answered any questions we had and was incredibly helpful with locating the apartment as the map location was a little off. The apartment was beautiful, well decorated and clean! We stayed for 16 days and had little to no issues. I am confident anyone else would find this place to be worth the price!
Superhost

Condo in Hartford
3.75 out of 5 average rating, 4 reviewsBeautiful 2 bedrooms/ 2 bath Condo
BrentRating, 5 stars117 months ago
Sheryl was great. I was in town for a conference and my schedule got thrown off by traffic on 95. She was very understanding and flexible with making my arrival time work. Once we met to get keys and a quick tour of the place she remained a phone call away but otherwise left us to enjoy the space. The other inhabitants of the place were very laid back and nice - that being said I was so busy with a conference that I was barely around. Not the Ritz but a HUGE savings over staying at any hotel downtown even if it's not right downtown. Splurge on some cabs and you are still saving money.
Superhost

Condo in Farmington
4.81 out of 5 average rating, 53 reviewsFarmington -NEWLY UPDATED NEAR UCONN HC and WEHA
DenisRating, 5 stars7 months ago
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

Condo in Wallingford
5 out of 5 average rating, 3 reviewsCozy and charming retreat in quiet area of Wlfd.
JoeRating, 5 stars4 weeks ago
Cristina's home was great for our stay! She was extremely helpful even before we checked in, providing clear instructions on where to park and the location of the entrance. She even left out some toys for our son to play with during our time there. It's small space, but what we needed and exactly as described in the listing. We would absolutely stay here again, when we come back to the area!
Guest favorite

Condo in Mount Sinai
5 out of 5 average rating, 34 reviews1856 Trading House close to water
JohnRating, 5 stars5 months ago
Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.
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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