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
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.
Top guest favorite
The exterior of the home features a spacious pool, adjacent to a deck with seating options. The two-story house showcases large windows and sliding doors, reflecting natural light. Lush green grass frames the area, enhancing the inviting outdoor retreat.
Home in Stratford
5 out of 5 average rating, 8 reviews

Akasa 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
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 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
A private fenced in-ground pool is surrounded by a lush green lawn and a white picket fence. Poolside, a colorful umbrella provides shade over a dining table. Sun loungers and a pool cover are visible, with the house in the background adding to the serene outdoor setting.
Home in Wolcott
5 out of 5 average rating, 5 reviews

Amazing 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
A spacious lakefront retreat is depicted, featuring a newly remodeled pool surrounded by a green lawn. Large windows provide expansive views of Candlewood Lake and surrounding trees, while outdoor seating is arranged near the pool for relaxation.
Home in New Milford
5 out of 5 average rating, 11 reviews

Private 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
A spacious backyard is depicted, featuring two red Adirondack chairs positioned around a fire pit. The house, characterized by a gray exterior, is surrounded by lush grass and trees. The scenic view includes a nearby barn and the surrounding hills in the background.
Home in Putnam Valley
4.93 out of 5 average rating, 27 reviews

The 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
A serene backyard scene is presented, featuring a sparkling pool surrounded by gray lounge chairs. Lush green trees create a privacy barrier in the background, while a garden area and fencing add to the charm of the outdoor space.
Home in North Salem
4.94 out of 5 average rating, 34 reviews

North 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
A serene outdoor view showcases a lush, landscaped yard bordered by trees. An inground heated pool, currently closed for the season, is visible alongside the greenery. A modern home with expansive windows reflects the natural surroundings, creating a peaceful retreat.
Home in Roxbury
5 out of 5 average rating, 17 reviews

Bright 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

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 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
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 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
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 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!
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
5 out of 5 average rating, 3 reviews

Cozy 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
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.

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