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Vacation rentals with a pool in Middlesex County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Middlesex County rentals with a pool

House rentals with a pool

An open-concept kitchen and dining area features modern furnishings, including a long dining table surrounded by black chairs. Large windows offer views of greenery, allowing natural light to fill the space. A sleek kitchen island with bar stools complements the contemporary design.
Home in Newton
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars42 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
The spacious living and dining area features a light-colored sofa, a wooden coffee table, and a dining table surrounded by chairs. Soft lighting enhances the open layout, creating a relaxed ambiance. A large painting and decorative elements are also visible in the surroundings.
Home in Worcester
4.83 out of 5 average rating, 6 reviews

Full house in Worcester.

ElizabethRating, 5 stars14 months ago
Albert was an accommodating host. His place had everything we needed. It was an easy, comfortable stay for a very reasonable price!
Top guest favorite
A private heated pool is surrounded by lush greenery, providing a tranquil setting. Loungers are positioned nearby, and a blue lane divider is visible across the pool. Sunlight reflects off the water, enhancing the serene atmosphere.
Home in Newton
5 out of 5 average rating, 19 reviews

Villa with private Pool in Boston's Elite Enclave

JonRating, 5 stars3 weeks ago
Great option when staying in Newton and right down the street from an incredible entrance to a hiking trail. Serge was a great host and kept us informed the entire trip.
Home in Revere
4.8 out of 5 average rating, 54 reviews

Boston 15 min away.

MelissaRating, 5 stars11 months ago
This is the third year we were able to rent Ediangela’s house. As always it’s beautiful and clean. The pool is spotless. Plenty of space for big groups and absolutely perfect for families with kids of all ages. There’s so much to do on the property itself. She is so kind and responsive. It’s always been amazing every time we stay. It’s becoming our summer staple to come and stay by the pool for a few days of vacation. 10/10 absolutely worth renting this space. This year we brought two 10 year olds, a 5 year old, and a 2 year old, with 4 adults. They had the best time in the little play houses and pool. The adults had a great time as well. If you’re looking for a low key - big fun spot where you don’t have to run around to entertain, this is perfect! Everything you need or may need is on site or minutes away if you need to shop. Including the actual beach. I sincerely hope we get the chance to make it year 4 next summer!
Top guest favorite
The exterior of a two-story house is displayed, featuring white siding and red shutters. A well-maintained front yard is visible, showcasing green grass and shrubs. A brick pathway leads to the front door, framed by two planters with greenery.
Home in Arlington
4.94 out of 5 average rating, 34 reviews

Beautiful Spacious 4BRM House!

NicholasRating, 5 stars2 weeks ago
I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽
A serene outdoor area features a blue saltwater pool surrounded by brick pavements and lush greenery. The space is complemented by a cozy seating arrangement and French doors leading into the carriage house, creating an inviting atmosphere for relaxation.
Home in Worcester
4.78 out of 5 average rating, 32 reviews

Beautiful & Historic Cottage, Steps to Elm Park

AmyRating, 5 stars1 month ago
location was easy to find in a nice residential area just outside of the city, very clean, owner responded quickly to messages
Superhost
A welcoming entrance is displayed with a polished brick pathway leading to a well-maintained white house. The front features large black-framed windows and a pair of bold red doors flanked by pots of colorful flowers, complemented by lush green landscaping.
Home in Canton
4.88 out of 5 average rating, 26 reviews

Hidden Gem near Boston w/ Private lake access

MeganRating, 5 stars3 days ago
This property was one of the best airbnbs we have stayed at. Clean and cozy and felt right at home. There was plenty for the kids to do so we didn’t have to limit screen time because they wanted to be enjoying the amenities available! Jody was quick to respond with any/all questions or concerns we had. We would highly recommend to everyone especially those with children!
Guest favorite
A vibrant outdoor pool area features a clear blue pool surrounded by a spacious patio. Lounge chairs are neatly arranged alongside the pool, with manicured shrubs and flowers adding color to the landscape. A privacy fence partially encloses the space, creating a secluded atmosphere.
Home in Waltham
4.9 out of 5 average rating, 51 reviews

Quiet/Private Neighborhood

DevRating, 5 stars2 days ago
This is one of the most well thought out properties we have stayed at. There was everything & more. In fact some of things provided for us we could never have even thought of. Michelle is responsive & accommodated all requests. Definitely spoiled us & raised the bar. Loved it & look forward to being back.

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