Vacation rentals with a pool in Middlesex County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Middlesex County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

The exterior of a modern wooden house features a sloping roof and a welcoming front porch. Lush green grass surrounds the structure, complemented by small shrubbery thoughtfully arranged near the entrance. Three large windows provide natural light to the interior.

Bungalow in East Hampton

4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

Dive into the saltwater pool, set amid professionally landscaped grounds. Later, head for the multiple outside entertaining areas for a meal from the built-in outdoor grill. Round off the day with a soak in the claw foot tub in the marbled bathroom. The pool is available from May to September, and the temperature is regulated at 87 degrees. Check with the host for additional requirements. Walk to the Clearwater Beach Association's private beach, just a few blocks from the house, with a local grocery store also close. East Hamptons village is 12 minutes away, with recommended restaurants including Roudy Hall and Citta Nova.

Superhost

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

Home in East Hampton

4.86 out of 5 average rating, 206 reviews

HeatedPool-Walk2Beach-Yard4Pup-Peaceful-Clean-Easy

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.Registry 23-625

Top guest favorite

A stone pathway leads to a sparkling pool surrounded by lush greenery. Flowering plants in pots frame the pool area, while lounge chairs and a shaded umbrella provide seating options. Tall trees offer privacy, creating a serene outdoor retreat.

Guesthouse in Southbury

4.93 out of 5 average rating, 319 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Top guest favorite

A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.

Home in Southold

5 out of 5 average rating, 11 reviews

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Top guest favorite

The expansive patio area features a large pool with a unique shape, surrounded by sun loungers and shaded seating options. A hot tub is positioned nearby, and additional amenities include a fire pit and a shaded cabana. The enclosed space is accentuated by landscaped elements.

Home in East Haddam

4.98 out of 5 average rating, 52 reviews

Spacious 5 bdrm, 6 bth, 30 min to beach & casinos

Spacious 5 bedroom 6 bath sleeps 14 -WHAT YOU’LL LOVE- • Private resort style patio, including STUNNING POOL, HOT TUB, fireplace and firepit, bar and grill, 65" TV, outdoor bathroom and shower. • Open concept floor plan that is great for groups and families. • Authentic New England experience. • Fun game room for adults and kids with wet bar and mini fridge • Quiet street and neighborhood. NY times listed East Haddam in their “52 places to love” in 2021 1 mile to East Haddam Center

Guest favorite

The image showcases a multi-story condo building set amidst neatly trimmed hedges. Sun loungers and patio umbrellas are positioned around a seasonal pool, which can be seen in the foreground. The design features white balconies and large windows, contributing to a light and airy appearance.

Condo in Greenport

4.92 out of 5 average rating, 138 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Superhost

An open dining area features a rustic wooden table surrounded by modern chairs. A chandelier hangs above, complementing the natural light from large windows. A cozy living space with a fireplace and plush seating is visible in the background. Warm wood beams add character to the ceiling.

Home in Litchfield

4.9 out of 5 average rating, 50 reviews

Woodland Country Retreat-Pool+FirePit-nearWineries

20% off JULY/AUG MONTHLY- Leave your worries at the front door of this New England gateway. An open, airy interior may make you feel like staying at home reading all day long, but there's so much to explore nearby. Head out to Black Rock State Park for a scenic hike through lush forests, followed by a leisurely afternoon sampling wines at local vineyards. Gather at this stylish home by the firepit w/loved ones. Pool deck area in rear of house is closed, under maintenance work until 5/26/25

Guest favorite

The studio features a queen-sized bed adorned with a floral-patterned blanket. A comfortable sofa and armchair are positioned nearby, along with a small table. Natural light filters through a nearby door, illuminating the warm wood flooring.

Condo in Montauk

4.83 out of 5 average rating, 176 reviews

Coastline View Studio

This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

Guest favorite

A clear view of a gunite pool reveals crystal blue water, surrounded by a spacious lawn. Four lounge chairs are positioned nearby, and the house is seen in the background, framed by lush hedges and trees, with a deck that offers steps leading up to the entrance.

Home in Cutchogue

4.92 out of 5 average rating, 25 reviews

North Fork Farmhouse with Saltwater Pool

Enjoy spectacular sunsets from the great room and deck overviewing your secluded hedged yard and saltwater pool. Located in the heart of the North Fork this 1820s farmhouse with modern amenities is nestled amongst vineyards and farmland with dramatic views in every direction. Quaint villages, premier restaurants, wineries, farms and beaches surround you. A truly magical, peaceful paradise for you and your group. Note pool is open May through mid October.

Guest favorite

Home in Cutchogue

4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Guest favorite

A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.

Home in Litchfield

4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

Nestled just outside the center of Bantam, this immaculate 3 bedroom 2.5 bath home with a pool is the ultimate retreat. The home is perfectly located for enjoying the area's top attractions, like lake activities, skiing at Mohawk, hiking the trails of White Memorial, Litchfield's Village Green where you can enjoy fine dinning, shopping and visit historic sites. Pool is open and heated May 15th to Sept 15th.

Superhost

An aerial view captures the serene coastline of Fairfield, Connecticut, showing a sweeping sandy beach alongside lush green trees and shrubbery. A tranquil waterway is visible, surrounded by a variety of homes and the inviting blue of the distant ocean.

Home in Fairfield

4.71 out of 5 average rating, 7 reviews

Modern Beach Area Vacation Home With Pool

This modern, spacious home has everything you need: comfortable sleeping spaces, open concept kitchen and dining areas, a pool & back yard for enjoying the summer sun. Plus location is well located within walking distance to town, train stations, beaches, restaurants, shopping, historic points, etc.