
Holiday rentals with a pool in Bridgeport
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Bridgeport
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Popular amenities for Bridgeport rentals with a pool
House rentals with a pool

Peaceful Retreat in Immaculate Architect’s House
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!

Enchanted Escape | POOL, LAKE, Concierge Services
We had such a great experience staying at this Airbnb. The house was beautiful, super clean, and the view was just perfect honestly even better than the photos. What really made our stay stand out though was the host, Sunny. He was amazing so helpful, kind, and incredibly thoughtful. As a Muslim family, we really appreciated how respectful and considerate he was. He made sure we had our privacy and went out of his way to make everything as easy and comfortable as possible for us. It honestly felt like staying at a friend’s place. We’d definitely come back and highly recommend this spot to anyone looking for a peaceful, welcoming place to stay.

Stylish+Modern Cape w/Saltwater Pool-5min to Beach
My group of 8 loved staying here for a holiday weekend. The house was very cozy and clean, and we had such a relaxing time in the house. The kitchen was large enough for all of us to sit around the island, and the living room was a perfect spot to sit and talk. The backyard is really beautiful, large, and private. We were not able to use the pool due to the cold weather, but it looked beautiful in our pictures. The hosts, David and Michiko were amazing to interact with! They were extremely responsive to our messages and questions, and they provided very detailed instructions and information about the property and surrounding area. They genuinely want their guests to have the best experience, and I would definitely book this house again. Thank you David and Michiko!

The Barger Wixon House
Stayed for West Point graduation. House was awesome. Hosts were more awsomelierist….. Highly recommend. GO ARMY! BEAT navy!

Riverfront Cottage Retreat & Pool 35 mins from NYC
Fabulous getaway, beautiful surroundings, hard to believe we were just a few minutes from highways and downtown and civilization! Responsive host, many amenities -- pool, bbq, outdoor dining, waterfall, river view, soaking tub, sun loungers, spacious kitchen, dreamy sofa.

Bright Mid-Century Modern Retreat-90 min from NYC
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.

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Only complaint would be the noise from road during the morning commute

Summer Out East
My family and I had the most amazing time celebrating two birthdays as well as New Year’s. The pictures do not do this house justice. This house was so amazing for our family of nine. The beds were so comfortable, the rooms were very spacious, the two sunroom rooms were perfect (my family would hang out in the tiny sunroom with the bar in it every single morning. It was everyone’s favorite room.). One thing that was the best bonus was the built-in speaker system throughout the house on the main level. My brother-in-law is a DJ and knew how to use the system, which was amazing because we would have dance parties. The only thing I would ask Constantine to do is to possibly give instructions on how to use it because it is a definite bonus. We even had a bonfire one night as well as a BBQ. Even though we came during winter this place was perfect.
Condo rentals with a pool

Watersedge resort time share Westbrook ct
Andrew’s place was awesome. Just steps to a beautiful pool and the ocean! Couldn’t have asked for a better place.

Quaint spacious unit, A+ location
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!

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA
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!

Cozy and charming retreat in quiet area of Wlfd.
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!

Waterfront Elevated Bungalow - Spectacular Views
If we don't give a good review, can we keep this to ourselves?! Patti was a perfect host; the views were fantastic, whether from the outdoor porch or inside through the French doors looking out on the water. Access to the small beach and pool were excellent and we were close to several good restaurants (many of which Patti suggested, including some on the water) for take-out during the pandemic. Wifi was great and everything was very clean and as advertised. We generally fly for vacations and long weekends but had to stay closer to home this year and this was a perfect choice.

1856 Trading House close to water
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 Unique Piece of Paradise, Water Front pool
This was my second time at Susan’s. The location on the bay with the beautiful views and sparkling clean pool will bring me back again. The house is always extremely clean and comfortable. Great location to walkable Rumba’s Restaurant. Susan is very reachable and a pleasure to rent from. I highly recommend it.
Quick stats about holiday rentals with a pool in Bridgeport
Total rentals
10 properties
Nightly prices starting at
$66 NZD before taxes and fees
Total number of reviews
390 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 properties include access to Wi-Fi
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- Columbia University
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Rye Beach
- Citi Field
- Yankee Stadium
- Gilgo Beach
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art
- USTA Billie Jean King National Tennis Center
- Central Park Zoo
- Point Lookout Beach District Park
- Cooper's Beach, Southampton
- Robert Moses State Park
- Dunewood
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Astoria Park
- Thunder Ridge Ski Area
- Bethpage State Park