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

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.

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.

Modern farmhouse w/ pool, beach, horses and winery
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.

Log House, sits on 3acres. A retired mini farm.
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)

Waterfront Beach House with pool
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!!!

Family Oasis 4bd/2ba Private Yard & POOL!
We had a great time. We like to walk for exercise, the neighborhood was awesome. The house was great and we would love to stay again.

Breathtaking Panoramic Waterfront
A spacious property in a wonderful location. The house was exactly as advertised. Karen is an excpetionally responsive host. Our family (6 adults, 4 children) felt entirely comfortable there, and the kids especially enjoyed the pool.

Modern artist retreat near beach
Do to family circumstance, we could not use our reservation. Everything leading up to the check-in was above and beyond. Mary showed genuine concern for us and was understanding.
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!

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
We really enjoyed our stay. The unit was just enough space for my husband and I and our two daughters. Having a kitchen to prepare quick breakfasts in the morning before heading out for the day and having the pool and beach in the late afternoons gave us everything we needed to start and end busy days at the Hamptons Classic or visiting family. We are hopeful to visit again!
Quick stats about holiday rentals with a pool in Milford
Total rentals
10 properties
Nightly prices starting at
$46 AUD before taxes and fees
Total number of reviews
530 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Beach
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Rye Beach
- Gilgo Beach
- Rye Playland Beach
- Bronx Zoo
- Cooper's Beach, Southampton
- Robert Moses State Park
- Dunewood
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Thunder Ridge Ski Area
- Bethpage State Park
- Woodmont Beach
- Quotonset Beach
- Rye Town Beach
- Giants Neck Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach