Vacation rentals with a pool in Milford

Find and book unique homes with a pool on Airbnb

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Popular amenities for Milford rentals with a pool

House rentals with a pool

Top guest favorite
Home in North Fork
4.97 out of 5 average rating, 205 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars3 weeks ago
We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!
Top guest favorite
Home in North Fork
4.87 out of 5 average rating, 126 reviews

The Perfect North Fork Escape

RenataRating, 5 stars1 month ago
Laurie’s home was the perfect size for our girls weekend to celebrate the bride. The patio was extensive and comfortably fit all of us for a hibachi chef and dinner. It was a quick drive from the house to the wineries, which was fantastic.
Guest favorite
Home in Holmes
4.91 out of 5 average rating, 11 reviews

Enchanted Escape | POOL, LAKE, Concierge Services

AnxhelaRating, 5 stars1 week ago
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.
Top guest favorite
Home in Roxbury
5 out of 5 average rating, 17 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars3 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.
Guest favorite
Home in Greenwich
4.95 out of 5 average rating, 43 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

LucyRating, 5 stars3 weeks ago
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.
Guest favorite
Home in North Fork
4.92 out of 5 average rating, 87 reviews

Modern farmhouse w/ pool, beach, horses and winery

SteveRating, 5 stars3 weeks ago
Travis and Morgan’s home is exactly like the photos. It’s spacious, well maintained and has most everything you’ll need for your stay. They are quick to respond to questions. Great central location for heading to downtown Riverhead for the aquarium or lunch, a quick 5 minute ride to Harbes and 10 to the north fork Waterdrinker location and 20-ish minutes to Greenport for a nice day trip. The kitchen is well equipped with plenty of cookware, dishes, utensils and a variety of spices. There’s room to spread out between the 3 bedrooms and the two living areas and the heated pool is a great bonus especially with kids in the mix. The yard is well kept and great for a well behaved pup to run around. Our only really issue with the home was the lack of dark blinds or curtains in the bedrooms. It got pretty bright once the sun rose each morning aka early mornings The en-suite bath is pretty tight for us tall folks. We had a great time and will definitely consider staying there again.
Superhost
Home in Ridgefield
4.82 out of 5 average rating, 22 reviews

Log House, sits on 3acres. A retired mini farm.

TaylorRating, 5 stars1 month ago
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)
Top guest favorite
Home in Madison
5 out of 5 average rating, 35 reviews

Waterfront Beach House with pool

RachelRating, 5 stars1 week ago
Came with a few friends and we were all so amazed at how beautiful the house was. Very clean and the views were breathtaking. The pool was perfect and everything was just so amazing the whole weekend. Meaghan was very responsive when answering questions and flexible. Perfect host.. Highly recommend!!!

Condo rentals with a pool

Condo in Westbrook

Watersedge resort time share Westbrook ct

AbbieRating, 5 stars48 months ago
Andrew’s place was awesome. Just steps to a beautiful pool and the ocean! Couldn’t have asked for a better place.
Condo in Wallingford
New place to stay

Cozy and charming retreat in quiet area of Wlfd.

JoeRating, 5 stars1 week 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
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.
Condo in Danbury
4.72 out of 5 average rating, 18 reviews

Quaint spacious unit, A+ location

EmilyRating, 5 stars2 weeks 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!

Quick stats about vacation rentals with a pool in Milford

  • Total rentals

    10 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    530 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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