
Holiday rentals with a pool in Essex County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Essex County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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House rentals with a pool
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Home in Gloucester
4.73 out of 5 average rating, 15 reviewsMansion in Gloucester with Pool
MaryRating, 5 stars5 months ago
My family and I were fortunate enough to spend the thanksgiving holiday here. It was the perfect space for a group gathering. Would highly recommend!

Home in Revere
4.8 out of 5 average rating, 54 reviewsBoston 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!

Home in Salem
5 out of 5 average rating, 4 reviewsmodern Tudor in beautiful Salem nh
MaxineRating, 5 stars2 days ago
Andre’s home was absolutely gorgeous all around 100%, and then some. Andre has great communication with the guests, and was truly amazing. Andre also accommodated a later checkout for us, and we are beyond grateful for that also. Every room In this home and the large fenced in back yard with a pool was awesome. Definitely recommend a stay here at this incredible Airbnb! If I could rate Andre over 5 ⭐️ I certainly would have. Thank you for sharing your home with us! We had a wonderful time.
Guest favourite

Home in Waltham
4.89 out of 5 average rating, 45 reviewsQuiet/Private Neighborhood
JeffRating, 5 stars2 weeks ago
Our stay at Michelle's was absolutely fantastic! I can't say enough good things about the house and the amenities. The kitchen was fully stocked and she really seemed to think of everything, including a gift basket! I stay at a lot of Air B&Bs and the small touches Michelle put on the house and the amount she cared for her guests was second to none! I could not recommend staying here more.
Guest favourite

Home in North Andover
4.92 out of 5 average rating, 12 reviewsPeaceful New England Retreat Close to It All
AmyRating, 5 stars6 months ago
The home was so lovely and comfortable - perfect for our family. It had so many amenities, and comfortable sleeping spaces. It looks exactly like the pictures. We will definitely return!
Top Guest favourite

Home in Andover
5 out of 5 average rating, 24 reviews3 Bedroom home with complete privacy near downtown
CecileRating, 5 stars5 months ago
My family and I stayed for the Thanksgiving weekend. We had a great time and made lots of fun memories. Katherine’s home is beautiful and well appointed. Traditional with a touch of whimsy! Andover is a lovely town and proximity to Boston is a plus.

Home in Revere
4.38 out of 5 average rating, 13 reviewsDiscover Your Perfect Getaway!
AlexaRating, 5 stars6 months ago
The description/images of the location are exactly what you get. Staying there felt like home. Only thing that caught us off guard on our second night was having other guests below that live there. We were never bothered by the couple below- you may hear their dog but it stops rather quickly. Again no issues and it was lovely staying here.

Home in Seabrook
4.91 out of 5 average rating, 47 reviewsFamily friendly beach house
LauraRating, 5 stars5 months ago
Loved our stay at this beautiful beach cottage. Hated to leave, can't wait to go back. Thank you sharing your space.
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- Hampton Beach
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- Boston Common
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- TD Garden
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- York Harbor Beach
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- Faneuil Hall Marketplace
- Prudential Center
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- Symphony Hall
- Boston Public Library
- Quincy Market
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