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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

A rectangular pool is surrounded by a spacious patio, complemented by a green seating area nearby. The house features a two-story structure with a balcony and steps leading down to the pool area. Lush trees and greenery create a serene environment.
Home in Newton
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars40 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 stars12 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, 14 reviews

Villa with private Pool in Boston's Elite Enclave

LucyRating, 5 stars3 days ago
Serge was helpful with marathon weekend details and was very responsive. House is as described, quite spacious and easily sleeps 8 adults. The game room includes billiards, darts, a massage chair, and 3 comfortable theater chairs. The kitchen is fully equipped with everything needed to prepare large family meals. It’s a 30 minute walk to the Newton Center green line train stop, which is recommended for transportation to and from downtown Boston. The price was a little high, but everything in the area was increased for marathon weekend. Would recommend.
Home in Revere
4.8 out of 5 average rating, 54 reviews

Boston 15 min away.

MelissaRating, 5 stars9 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!
Guest favorite
A well-maintained swimming pool is featured in the backyard, surrounded by a patio. Lush greenery and mature trees offer privacy. The two-story house is visible in the background, with large windows allowing light to enter. A basketball hoop is positioned adjacent to the pool area.
Home in Arlington
4.93 out of 5 average rating, 29 reviews

Beautiful Spacious 4BRM House!

SusanRating, 5 stars2 days ago
Maxine anticipated every possible need and so much more available. She went beyond any host I have ever stayed with and I travel quite often. I highly recommend Maxine's place
Top guest favorite
A refreshing pool area features a clear blue water, surrounded by a concrete patio. Two lounge chairs are positioned beside the pool, complemented by colorful flotation devices resting on the water. Lush green hedges provide privacy, enhancing the outdoor experience.
Home in Norwood
4.97 out of 5 average rating, 36 reviews

the house of id; vintage shop, accessible space

NatalieRating, 5 stars2 weeks ago
This has to be the neatest little place on Airbnb in the Boston area, and that's something to be said. Paige and Dara described the place and the experience perfectly, were a dream to communicate with, and were overall humorous hosts. Their in-house shop was very entertaining for us. We will absolutely be staying here again in the future.
Top guest favorite
The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.
Home in Weston
4.98 out of 5 average rating, 91 reviews

Spacious vacation unit in premium suburban town

RanuRating, 5 stars4 weeks ago
Thank you Scott for hosting us! The location was perfect for our son’s therapy intensive, and it was peaceful, calm, and a bonus that it was right near the park. Projector worked well, comfortable desk upstairs for working, strong internet, and a great layout for a family. Our kids really enjoyed the books, and we loved the open layout, as well as the backyard space. We also appreciated the fresh eggs — thank you!
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
4.77 out of 5 average rating, 30 reviews

Beautiful & Historic Cottage, Steps to Elm Park

CassandraRating, 5 stars2 months ago
Exactly as pictured - beautiful small one level renovated old carriage house. Such a cute aesthetic and a great neighbourhood. Some ants but nothing worrisome. Host was incredibly responsive and very helpful. They even had a new hot tub! Many towels available (usually uncommon for airbnbs). Thermostat was easy to use and kept the place at a comfortable temperature. Linens were lovely - soft and cosy and a range of many pillows to choose from. Couches were very long and could host a small gathering with ease. Tv was easy to direct and easy to connect our Firestick to. Book and binder with many local recommendations. Kitchen had just about anything you could possibly need!! Cookie sheets? Blender? Large salad bowls? Platter boards? Garlic salt? Slow cooker? They had it!! We visited during an ice storm and the hosts were very kind and responsive - helpful that they live next door. They also have a landscaping team to help shovel and salt the driveway/sidewalks. Thank u thank u thank u!!!!

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