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

2 homes in one (in-law design) w/salt water pool
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!!

Great Family Times in this 5 Bedroom House
My family and I had a beautiful stay and I couldn’t have asked for a better rental. The Airbnb was huge with more than enough room for everyone and the backyard was large and spacious enough to have everyone eat comfortably. If I ever need another large rental you can bet I’m gonna check here first.

Hamptons Retreat | Pool, Volleyball, Jacuzzi
Great place to explore the Hamptons!

MCM in the Hudson Valley
Beautiful home. Great vibes with cool art and decorations. Nearby the Fishill Farm, and the Beacon metro north. Highly recommended to stay here.

Home in Bellport Village w Pool
This home was great for us, our daughter, son-in-law and six month old grandson, not to mention our Vizsla. We were visiting the Island for a family celebration in Babylon and this home was worth the 30 minute drive further east. Immaculate, well designed inside and out. And downtown Bellport a short drive to restaurants, coffee shops houses and shops. We’d return in a heartbeat - highly recommended.

4 bedroom house with pool (Kids & Dog Friendly)
Bettys home was a wonderful place for our 7 family members to stay. It was very comfortable and well equipped, with thoughtful amenities and lots of room. The fenced in yard was great for our dog, and the neighborhood quiet and close to the lovely towns of Warwick and Sugar Loaf. Betty was extremely responsive and kind enough to let us check in a few hours early. We would definitely stay here again!!

Pool House
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.

Entire Home (private pool), Event Friendly
I had a wonderful stay at this Airbnb! The space was clean, comfortable, and had all the amenities I needed. The host was friendly and very responsive, making check-in and check-out easy. The location was also perfect. Highly recommend this place!
Condo rentals with a pool

Cherry Grove 1 bedroom condo w/heated pool!
Great place, exactly as advertised. Terrific location near ferry dock (making arrival/check-in extremely easy and fast, which was a relief after a long trip to get to Fire Island), near the little main hub of Cherry Grove… minutes or less to the general store, restaurants, bars. 5 minute walk to the beach. Although there is some bar noise at night, the unit is well sound-insulated. Hosts extremely friendly and communicative, full of info and recommendations. They take pride in their place and in being great hosts. Cozy place with very good value for Fire Island. The pool was a nice plus - salt water pool, lit at night. Met some of the other residents in the building who were extremely friendly and fun. Bed was very comfy. We slept in a lot. Wi-Fi worked perfectly. Nice desk in the bedroom for the few times work called. Roku TV. Lots of board games Bedroom has AC which worked great. Beach chairs and towels included. Coin laundry on site worked well. Great value. Would definitely return!

Lovely 2 bedroom Entire Home Across Time Square
The location of this stay is amazing! There is a beautiful view of the city line just outside the building door. Walkable to the ferry and a 20min car ride into the city. Great location for a group of 6! I would highly recommend walking to bagels on pine (10min walk from the Airbnb) for breakfast.

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
The space is adorable, and we loved the history of the rental and the community. The location was perfect for us—close to everything and secluded all at the same time. Also Jeff is an amazing host and made us feel welcome/at home. The next time we have to head to NY for a family visit we will definitely try to stay here again.

Quaint spacious unit, A+ location
Will's place is located in a quiet condo village, where the common areas are well kept. The place was clean, bed comfortable, and the shower had good water pressure. This space was perfect for me and my husband.

Studio with skyline view, 15 mins to city via bus
Denny has a fantastic place! The view cannot be beat, and it's very convenient to get to Manhattan. Clean facilities, clear communication, and all of the amenities you would want. You would not be disappointed by choosing this.
Quick stats about vacation rentals with a pool in Stamford
Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
790 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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- Radio City Music Hall
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Tenement Museum
- Riverside Park
- Comedy Cellar
- Yale University
- Apollo Theater
- Gilgo Beach
- St. Nicholas Park
- Yankee Stadium
- Citi Field
- Inwood Hill Park
- MetLife Stadium
- Bronx Zoo
- Astoria Park
- Rockefeller Center
- Dunewood
- United Nations Headquarters