Vacation rentals with a pool in Stamford

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Popular amenities for Stamford rentals with a pool

House rentals with a pool

Guest favorite
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

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

ChristineRating, 5 stars7 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!!
Guest favorite
Home in Massapequa
4.93 out of 5 average rating, 123 reviews

Great Family Times in this 5 Bedroom House

JorgeRating, 5 stars3 weeks ago
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.
Superhost
Home in Hampton Bays
4.94 out of 5 average rating, 127 reviews

Peaceful Retreat in Immaculate Architect’s House

ClareRating, 5 stars2 weeks ago
Michael was a great host, friendly, flexible and helpful. The house is beautiful and has all the amenities you would expect. We loved staying there and would definitely like to stay again.
Superhost
Home in Hampton Bays
4.77 out of 5 average rating, 84 reviews

Hamptons Retreat | Pool, Volleyball, Jacuzzi

ThalitaRating, 5 stars1 week ago
Aida’s house is very nice place to stay for a getaway in the Hamptons. Amazing outdoor area. Great for traveling with kids. Aida is a great host!
Guest favorite
Home in Hopewell Junction
5 out of 5 average rating, 18 reviews

MCM in the Hudson Valley

AlbaRating, 5 stars7 months ago
Beautiful home. Great vibes with cool art and decorations. Nearby the Fishill Farm, and the Beacon metro north. Highly recommended to stay here.
Top guest favorite
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
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.
Guest favorite
Home in Newburgh
4.88 out of 5 average rating, 80 reviews

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars6 days ago
Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.
Top guest favorite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars1 month ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Condo rentals with a pool

Condo in Cherry Grove
5 out of 5 average rating, 3 reviews

Cherry Grove 1 bedroom condo w/heated pool!

RobertRating, 5 stars8 months ago
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!
Condo in Weehawken Township
4.3 out of 5 average rating, 10 reviews

Lovely 2 bedroom Entire Home Across Time Square

MichaelaRating, 5 stars29 months ago
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.
Superhost
Condo in Hampton Bays
4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars55 months ago
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.
Guest favorite
Condo in Mount Sinai
5 out of 5 average rating, 33 reviews

1856 Trading House close to water

JulieRating, 5 stars3 months ago
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.
Condo in Danbury
4.71 out of 5 average rating, 17 reviews

Quaint spacious unit, A+ location

LindaRating, 5 stars9 months ago
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.

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

    800 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

Destinations to explore