
Vacation rentals with a pool in Westbrook
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Westbrook
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 Westbrook 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!!

The Perfect North Fork Escape
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

Modern beach getaway ocean views
Beautiful home- everything appeared brand new and in excellent condition. Courtney was great to communicate with- and kind enough to let us check in a little bit early since the place was open. We are definitely hoping to come back again!

Quaint Chalet w/Salt-heated Pool
Wonderful weekend stay. Charming.

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.

Garden Level Suite with Beautiful Pool
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!

East Hampton Oasis - Pool and Hot Tub
Tim is hands down the most responsive host we’ve ever dealt with through Airbnb. He was communicative, helpful and caring. We loved our experience and will be back!!!

Iconic Litchfield Home in Town Center
The house was beautiful! We loved the charm of the old floors and the cozy farm style. The house was so clean, we all noticed and appreciated the time it must have taken to clean. Thank you for a wonderful stay!
Condo rentals with a pool

Villa Flora @ Norwich Inn & Spa
There is nothing more frustrating than not being able to have a decent shower while you are on vacation. That was absolutely not the case here. The hot water and water pressure in both bathrooms was exceptional. This is a great place in a great area. We will definitely try to get back here.

CASiNO, Spa, Hot Tub, Pool, Private Villa, Kingbed
Wonderful stay, lots of small added touches that made a big difference. My 13-year-old son loved it. Convenient and quiet.

Oceanfront Condo – Incredible Spring Rates!
We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!

Montauk Waterfront Condo w/ Sunset Views
Absolutely wonderful stay and host. I've stayed at dozens of Airbnbs and this is one of my favorites! Doug's place is even better in person than the photos. We were a little nervous taking our first trip away with our baby, but it was extremely clean and comfortable, and Doug was so kind and responsive. The condo complex has a lovely boardwalk for taking walks, and the deck furniture was so comfortable to lounge in and take in the beautiful view. We hope to be back!

Peaceful Oasis steps from Mohegan Sun
This place has everything you need and a lot more. All of furniture is new and comfortable especially the huge king bed. Bathroom and shower was super clean and comfortable. Linens and towels are top notch. The TV in the bedroom and living room is a plus. The private outdoor patio is comfortable and relaxing. 5 min to Mohegan Sun. I could go on and on about this place it is amazing and a great value. You won't be disappointed!

Deluxe Studio Apt@The Montauk Manor
Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

The N-V ...The Spa at the Norwich Inn.
We stayed in town for an event at Mohegan Sun. The flexible check in was helpful as we got in late at night. The place was clean and welcoming.

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf
Thank you for the last minute booking and for answering all of my questions so quickly
Quick stats about vacation rentals with a pool in Westbrook
Total rentals
20 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
240 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- New York Vacation rentals
- Boston Vacation rentals
- Cape Cod Vacation rentals
- Jersey Shore Vacation rentals
- Pocono Mountains Vacation rentals
- South Jersey Vacation rentals
- Philadelphia Vacation rentals
- Kid-friendly rentals Westbrook
- Waterfront rentals Westbrook
- Rentals with a washer and dryer Westbrook
- Pet-friendly rentals Westbrook
- Cottage rentals Westbrook
- Family-friendly rentals Westbrook
- Apartment rentals Westbrook
- House rentals Westbrook
- Beachfront rentals Westbrook
- Fitness-friendly rentals Westbrook
- Rentals with a patio Westbrook
- Rentals with a fireplace Westbrook
- Rentals with beach access Westbrook
- Rentals with a hot tub Westbrook
- Rentals with outdoor seating Westbrook
- Beach house rentals Westbrook
- Rentals with a fire pit Westbrook
- Condo rentals Westbrook
- Rentals with pools Middlesex County
- Rentals with pools Connecticut
- Rentals with pools United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses 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
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Bushnell Park
- Sunken Meadow State Park
- Sherwood Island State Park
- The Connecticut Golf Club
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes