
Vacation rentals with a pool in Bridgeport
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Bridgeport
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Bridgeport rentals with a pool
House rentals with a pool

North Fork paradise between beaches and vineyards
We had a lovely stay at Karine’s cute house! The kitchen was very nicely outfitted, beds were super comfortable, and the big wood-burning fireplace was excellent! We appreciated all the cool artwork around the house, and Karine’s wonderful photography book! We got to enjoy lots of bird life, and we were lucky to have a bit of snow. What a beautiful and peaceful spot. We can’t wait to come back in warmer weather to enjoy the pool and lovely big deck and yard!

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.

Long Island Getaway w/ Heated Pool & Lake
This was the best stay we have ever had at an Airbnb. The place was clean. The entertainment system world class. The kitchen was phenomenal. The pool and backyard were fantastic. I would stay again and, in fact, may do so.

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.

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.

Huge Family House w/Waterviews
We live in the neighborhood of Liz’s house and held a 3 day reunion of 17 old friends staying both in her place and ours. Yes, it’s even better than the pictures! Lots of large, spacious rooms for gathering, wonderful outdoor pool with tons of seating, exceptional kitchen where of course everyone tended to congregate. Am already thinking about a future large family gathering. Liz was a gracious, helpful and generous host. We can testify from long experience living a few houses away that the neighborhood, beaches and sound make a wonderful setting for a gathering. Very appreciative that Liz and family share their house with others this way.

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Tiffany’s property was amazing! The porch, pool, fire pit, and hot tub all workout out wonderfully for us. Just a heads up if you plan to Uber places throughout the city (like we did) they could take anywhere from 5-25 minutes to get so plan ahead. My only thing of note was that the tap water—even with the Brita filter—was undrinkable to us. We would recommend bringing a couple of plastic water jugs for your stay. Otherwise the stay was amazing and highly recommend!
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.

Charming Bayfront Condo
Stop whatever you’re doing in the area and take 10 minutes to walk across the street to enjoy the sunset. I guarantee it’s addictive. Spent a post-Labor Day weekend with some friends and had an amazing time. The condo is centrally located between downtown Southampton, Bridgehampton and Sag Harbor and all that those areas have to offer. Several beaches, both bay-side and ocean-side, are also close by, but we mostly ended up lounging by the pool. The condo itself is spacious which is only further amplified by the amount of natural light reflecting off the bright interiors that let you know you’re near the beach. There are plenty of towels—both bath and beach—and there is ample beach equipment that you can use. The kitchen is fully stocked for cooking/dining at home, and there’s an outdoor patio equipped with a grill and dining furniture. Hostess could not have been nicer or more responsive, so I will definitely want to stay here again.

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!

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 vacation rentals with a pool in Bridgeport
Total rentals
10 properties
Nightly prices starting at
G$8,392 GYD 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
Wifi availability
10 properties include access to wifi
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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
- USTA Billie Jean King National Tennis Center
- Bronx Zoo
- Central Park Zoo
- The Metropolitan Museum of Art
- Cooper's Beach, Southampton
- Point Lookout Beach District Park
- Robert Moses State Park
- Astoria Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Dunewood
- Bethpage State Park
- Thunder Ridge Ski Area