Vacation rentals with a pool in Fairfield County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Fairfield County rentals with a pool

House rentals with a pool

Superhost
A saltwater pool features a vibrant blue surface and is surrounded by a spacious terrace. Sun loungers are positioned along the poolside, and a fenced area provides safety. Lush greenery creates a serene backdrop, enhancing the outdoor space for relaxation.
Home in Woodbury
4.95 out of 5 average rating, 19 reviews

2 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
The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The 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
A contemporary home is depicted with a clear blue pool in the foreground, surrounded by a spacious wooden deck. Lush greenery and autumn foliage frame the property, while sliding glass doors provide views of the interior.
Home in Hampton Bays
4.95 out of 5 average rating, 129 reviews

Peaceful 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
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool 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
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh
4.84 out of 5 average rating, 86 reviews

Entire 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
A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop 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
A spacious pool area is surrounded by lush greenery and autumn foliage. The inviting swimming pool reflects the clear sky, with lounge chairs placed around its perimeter. A charming house with a covered porch in the background adds to the serene setting.
Home in Roxbury
5 out of 5 average rating, 22 reviews

Zoom 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 reviews

Harrison 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

A balcony offers a view of the surrounding landscape under a bright sun. The sky features a mix of clouds and blue, while a wooden railing surrounds the space. Below, other buildings and trees are visible, creating a sense of tranquility.
Condo in Danbury
4.72 out of 5 average rating, 18 reviews

Quaint 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
A spacious living area features large glass doors leading to a balcony, allowing natural light to fill the space. Two comfortable sofas in neutral tones are arranged around a coffee table, complemented by a simple area rug. A decorative plant adds a touch of greenery to the setting.
Condo in Hartford
3.75 out of 5 average rating, 4 reviews

Beautiful 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
A clean and inviting bedroom features a spacious bed with neutral bedding, accent pillows, and soft bedside lighting. Built-in shelves are displayed with decorative items, and a window allows natural light to brighten the area, complemented by light curtains.
Condo in Farmington
4.81 out of 5 average rating, 53 reviews

Farmington -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!
A stylish living room features a dark accent wall with a large TV displaying floral imagery. A low, wooden sideboard adds texture, complemented by decorative items. A cozy, light-coloured couch is paired with a patterned area rug, creating an inviting atmosphere.
Condo in Wallingford
New place to stay

Cozy 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
Two people are seen swimming in a calm body of water, surrounded by gentle ripples reflecting sunlight. Lush greenery lines the distant shoreline, creating a serene backdrop against the shimmering surface.
Condo in Mount Sinai
5 out of 5 average rating, 34 reviews

1856 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.
A clear swimming pool is seen with a shimmering blue surface, reflecting the sky above. Loungers are arranged around the pool area, offering views of Shinnecock Bay beyond the pool, framed by a protective fence and grassy landscaping.
Condo in Hampton Bays
4.95 out of 5 average rating, 42 reviews

A 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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