
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 Woodbury
4.95 out of 5 average rating, 19 reviews2 homes in one (in-law design) w/salt water pool
ChristineRating, 5 stars8 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
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.
Guest favorite

Home in Hampton Bays
4.95 out of 5 average rating, 129 reviewsPeaceful Retreat in Immaculate Architect’s House
TheanoRating, 5 stars1 month ago
We had an amazing stay at Michael’s Airbnb this past weekend! The space was exactly as described—clean, cozy, and well-equipped with everything we needed. Michael was a fantastic host: super responsive, thoughtful, and made us feel completely at home. The location was perfect for a relaxing getaway, and the setting was even more beautiful in person. Would absolutely stay here again—thank you for a wonderful experience, Michael!
Top guest favorite

Home in Cheshire
5 out of 5 average rating, 135 reviewsPool House
CindyRating, 5 stars1 week 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 Newburgh
4.84 out of 5 average rating, 86 reviewsEntire Home (private pool), Event Friendly
BernardRating, 5 stars1 week ago
The place is fun comfortable, private peaceful completely enjoyable. The hoste was great and response quickly.
Guest favorite

Home in Litchfield
4.99 out of 5 average rating, 84 reviewsHilltop House w/POOL/SPA- HOST & Co.
DanielRating, 5 stars3 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Superhost

Home in Roxbury
5 out of 5 average rating, 22 reviewsZoom Map 5* Town Roxbury! "Tophet Pool" PoshPadsCT
AllanRating, 5 stars21 months ago
Beautiful home, exactly how it was described and looked even better in person. Incredible surrounding areas and activities. Steven was helpful throughout the stay and incredibly flexible. Wonderful host! Will definitely be planning a yearly visit.
Guest favorite

Home in New Paltz
4.93 out of 5 average rating, 135 reviewsHarrison Field Pool 10AcreViews Bike2Town Hike
EmmaRating, 5 stars1 week ago
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!
Condo rentals with a pool

Condo in Danbury
4.72 out of 5 average rating, 18 reviewsQuaint spacious unit, A+ location
EmilyRating, 5 stars1 week 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 stars116 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 stars6 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
New place to stayCozy and charming retreat in quiet area of Wlfd.
JoeRating, 5 stars1 week 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.

Condo in Hampton Bays
4.95 out of 5 average rating, 42 reviewsA Unique Piece of Paradise, Water Front pool
ElysiaRating, 5 stars9 months ago
We really enjoyed our stay. The unit was just enough space for my husband and I and our two daughters. Having a kitchen to prepare quick breakfasts in the morning before heading out for the day and having the pool and beach in the late afternoons gave us everything we needed to start and end busy days at the Hamptons Classic or visiting family. We are hopeful to visit again!
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- Times Square
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- United Nations Headquarters
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- USTA Billie Jean King National Tennis Center
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