
Vacation rentals with a pool in Westerly
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Westerly
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Westerly rentals with a pool
House rentals with a pool

3 BR/Pool. Walk to Beach & Town!
From the beginning of my booking Adam provided a real friendliness to ensure we had a great visit. Went the extra mile to help with getting situated with a 2 year old...and I would recommend this place to ANYone. It was perfect beach vibe with an amazing pool, great bikes/chairs/etc for enjoyment...and it's a 5 min walk to town (for the true Montauk experience). Loved it and thank you Adam!!!

Niantic Getaway w/ Pool, Spa & Many Activities
We (short-term owners of three years) had a fantastic week-long stay with a group of 7! The house was impeccably clean and well-stocked with everything we needed. Check-in was a breeze, and the hosts were incredibly attentive, kind, and quick with helpful suggestions. The variety of games and activities—especially the record player, fire pits, hot tub, and air hockey—kept us entertained. All amenities were ready for use, making our stay truly enjoyable. Highly recommend! Jennifer and Erich, well done. Thank you

A Mystic Dreamscape: Pool, Winery, Mystic Aquarium
Shelone was spacious and comfortable. Ideal for big families or a group trip. My family and I felt cozy in her home on our weekend getaway in CT. We were celebrating my birthday and my family surprised me with a birthday brunch. Shelones kitchen had everything equipped to make a full family meal. The rooms were comfortable and accurately described in the pictures. Living room area perfect for comfy gathering with family. The location of the house is in a quiet neighborhood but a short 8 min drive away from Mystic and 20 min drive to Mohegan soon. I traveled with small children, and let Shelone know. The house was equipped with all amenities needed for a family with young children, play pen, stool, hair chair, games. Thank you Shelone for hosting us ! We definitely enjoyed our time in your home.

Bailey House
It was a lovely stay. Great location. House felt like a home and had great vibes.

Modern East Hampton Home w/ Heated Saltwater Pool
Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.

Waterfront Oasis Pool EPIC Views
Our family just had a wonderful time at Stacy and Mario‘s house. The house was immaculate, comfortable and extremely well appointed. The views were beautiful especially the sunsets. The hosts were extremely responsive and considerate

Exclusive Sag Harbor Compound
Benjamins place was a wonderful stay for our family. Coming from the City it was amazing to have so much grass with peace and quiet. It is a short walk to the Main Street and Sag Harbor downtown. We had planned to go out and enjoy some activities during the couple of days we stayed but instead found the place so relaxing we spent most of it in the home. The separate house was nice for a master bedroom and quiet. We would highly recommend this house to anyone wanting to have a relaxing and quiet vacation in the Hamptons near Sag Harbor. Hope to be back again!

Secluded Luxury: New Gunite Pool, Walk to Bay
Beautiful home, really well stocked and super comfortable. Warm, clean and lots of amenities. Comfortable beds, good showers, big lovely kitchen. Lots of space. We had a great stay. Thanks :)
Condo rentals with a pool

Villa Flora @ Norwich Inn & Spa
Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!
Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi
Natalie was a great host, super communicative which was very much appreciated. The place was beautiful and a perfect stay for 2 couples!

Cozy Vacation Villa 5 minutes from Mohegan
The stay was very peaceful, friendly neighbors. The scenery was great, Desiree was there for any concerns we had, and with timely response. I would anyone that want a pleasurable stay while in Norwich, this is the place to be. Thanks again, for a wonderful stay. William & Potreen

Mohegan Sun Escape-Hot Tub/Pool/Golf & Norwich Spa
Nat was incredibly friendly, welcoming, and easy to communicate with! Her cute and clean little condo was the perfect spot for my husband and I to get away for his 40th birthday weekend! Conveniently located near the casinos and our favorite- spas! Thank you Nat!

Beachside Waterview 2Br Condo w/ Pool in Greenport
We had a great stay! Instructions were clear and the home had everything we needed.

1BR Condo w/ Bay Views + Jacuzzi Tub
Clean, comfortable, friendly atmosphere. Jenny and Ania were super helpful from booking until checkout. I would definitely stay with them again. Thank you for making the vacation with my son so wonderful.
Home rentals with a private pool
Enchanting Home with Large Decks and Heated Pool
Beautiful home worked perfect for our wedding visit. Loved sitting on the deck! Beautiful landscaping and very private! We were very confortable and able to relax between events and visit. Donna wad very flexible and allowed us to enter early so a dew of our family members could do s little remote eork. I hope to rent here again in the future! As a special surprise we saw the northern lights from the deck one night!!
East Hampton Ranch with Access to Clearwater Private Beach
We had a wonderful stay at Peter's home. It was beautifully decorated, very comfortable and a quick drive to Springs. Access to the private clearwater beach was a plus! Thank you for sharing your beautiful home with us.

Explore the Water & Woods at a Relaxing Retreat
Absolutely beautiful home and wonderful experience!! The host was quick to respond and the amenities were excellent. There was zero lack! Would definitely return for another stay!
Saltbox with Separate Poolhouse in Northwest Woods
Mike’s place made for the perfect Hamptons vacation. The location was the perfect starting point for day trips to Montauk and the harbors and we enjoyed the short walk to the beach daily… but there really is no need to leave this amazing property. Our family cannot stop raving about the amazing outdoor setup that we took full advantage of every day. Mike was very responsive and provided a detailed guide for the house and excellent recommendations for the area. We would 100% book again when we’re in the area and would recommend this place to anyone looking for an amazing Hamptons experience.
Quick stats about vacation rentals with a pool in Westerly
Total rentals
10 properties
Nightly prices starting at
G$35,566 GYD before taxes and fees
Total number of reviews
590 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- New York Vacation rentals
- Jersey Shore Vacation rentals
- Pocono Mountains Vacation rentals
- South Jersey Vacation rentals
- Philadelphia Vacation rentals
- Montreal Vacation rentals
- House rentals Westerly
- Rentals with a fireplace Westerly
- Kid-friendly rentals Westerly
- Rentals with outdoor seating Westerly
- Rentals with a washer and dryer Westerly
- Beachfront rentals Westerly
- Rentals with a kayak Westerly
- Rentals with a patio Westerly
- Waterfront rentals Westerly
- Rentals with a hot tub Westerly
- Rentals with breakfast Westerly
- Rentals with a fire pit Westerly
- Cottage rentals Westerly
- Family-friendly rentals Westerly
- Pet-friendly rentals Westerly
- Condo rentals Westerly
- Fitness-friendly rentals Westerly
- Rentals with beach access Westerly
- Beach house rentals Westerly
- Apartment rentals Westerly
- Rentals with pools Washington County
- Rentals with pools Rhode Island
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Beach
- Charlestown Beach
- Southampton Beach
- Brown University
- Foxwoods Resort Casino
- Easton Beach
- Napeague Beach
- Cooper's Beach, Southampton
- Shinnecock Hills Golf Club
- TPC River Highlands
- Roger Williams Park Zoo
- Ocean Beach Park
- Point Judith Country Club
- Amagansett Beach
- Oakland Beach
- Blue Shutters Beach
- Quotonset Beach
- Ninigret Beach
- South Shore Beach
- South Jamesport Beach
- Groton Long Point Main Beach
- Fort Adams State Park
- Second Beach
- Clinton Town Beach