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

Guest favourite
Home in Old Saybrook
5 out of 5 average rating, 13 reviews

Beautiful Shoreline home in parklike setting

NishaRating, 5 stars6 months ago
Patricia was the perfect host. Her home is beautiful and peaceful, perfect for a family holiday. We loved spending time in the pool and it’s a perfect location to explore the CT coast. We would definitely be back. Many thanks Patricia.
Guest favourite
Home in Guilford
5 out of 5 average rating, 5 reviews

Peaceful private home with pool and pond

JoannaRating, 5 stars7 months ago
Jenny's house was a peaceful getaway from the city for us! We enjoyed the big, beautiful kitchen and outdoor dining set-up, and had plenty of space for 4 grown-ups and an active toddler. The living spaces were comfortable and well designed. Quick drive into Guilford and also to Madison. Jenny was also very responsive, helpful and friendly.
Home in Killingworth
4.75 out of 5 average rating, 4 reviews

11 Mi to Powder Ridge Mountain: Connecticut Home

EmiliaRating, 5 stars8 months ago
We had an amazing time at the house. The pool was so big and the kids enjoyed themselves. The house was beautiful so much space. Our family will be coming back and recommend to anyone to stay.
Home in Westbrook
4.73 out of 5 average rating, 132 reviews

Secluded Family escape w/ pool & jacuzzi

GaryRating, 5 stars4 months ago
Great getaway ! perfect for a guys vacation. Very private.
Home in Madison
4.79 out of 5 average rating, 38 reviews

Beautiful 1820 Colonial, Madison, CT

AngieRating, 5 stars8 months ago
My husband and I stayed with our 19-month-old son for three nights and it was a perfect choice! Susan had a toys and books that he loved, as well as a sandbox and pool outside - and the home was stocked with everything we needed for our stay. We used the location as a jumping off point for other activities and then had quiet afternoons at the house while my husband rode his bike (we saw lots of other cyclists!). If you are vegan or vegetarian, check out the Shoreline Diner in Guilford - it was delicious.
Home in East Hampton
4.83 out of 5 average rating, 6 reviews

Country escape w/pool, waterfall - 2h NYC/Boston

TaraRating, 5 stars31 months ago
We had such a wonderful time in this home. We loved the pool and used it everyday. We also loved the outdoor space. Perhaps the outdoor space is understated in the advertisement for the house, it is truly magnificent. The air conditioners worked very well and kept things cool inside even on the especially hot days. Thank you for a wonderful experience!
Guest favourite
Home in Madison
5 out of 5 average rating, 7 reviews

The Modernist | Patio & Pool | Beach (5-min drive)

RyanRating, 5 stars6 months ago
My family had an incredibly relaxing vacation at this beautiful property. It's even better than the pictures portray. There are many areas to relax in and outside the home and its extremely easy to hop on 95 and get to any of activities you're looking to do. Highly recommend this property to anyone looking to have a relaxing time away with the option to enjoy all the activities the CT shoreline has to offer.

Condo rentals with a pool

Guest favourite
Condo in Norwich
5 out of 5 average rating, 28 reviews

Modern Loft Villa, 1 mile to Mohegan Sun

KimberlyRating, 5 stars1 week ago
Convenient location and really came through when we needed a last minute place to stay to celebrate my father’s 90th birthday. Beautiful calming aesthetic decorated in gray and cream with gold accents. Plenty of space for our family. Appreciate the thoughtful touches of coffee, toothbrushes, and shower amenities, as well as a collection of board games for entertainment. A truly pleasant stay!
Superhost
Condo in Greenport
4.83 out of 5 average rating, 125 reviews

Seaside Escape w Pool, Private Beach + Patio

ShirleyRating, 5 stars3 months ago
Lovely stay in greenport! Short drive from major north fork activities. Can imagine its even better during the busy season!
Guest favourite
Condo in Norwich
4.95 out of 5 average rating, 20 reviews

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi

DoloresRating, 5 stars5 days ago
Villa Maisonet was the staycation that we needed, all around 10. The home was warm, welcoming and picturesque. Home away from home to celebrate an intimate anniversary, thank you Natalie! We will definitely book Villa Maisonet again.
Guest favourite
Condo in Norwich
4.98 out of 5 average rating, 167 reviews

Peaceful Oasis steps from Mohegan Sun

DougRating, 5 stars2 days ago
Christina, your condo was perfect. My wife and I had a great time..just as described. Your condo was very clean and smelled amazing. It was a perfect location from both clubhouses, the inn and spa as well as the Mohegan sun. We can wait to return. Thanks again.
Guest favourite
Condo in Norwich
4.98 out of 5 average rating, 124 reviews

The Vacay Villa

SuzanneRating, 5 stars2 weeks ago
I booked Krista’s place pretty last minute for just 1 night to surprise my friend for her 60th birthday as we were heading to Mohegan for dinner and a show! It was super cute, on the grounds of the Norwich Day Spa, and the clubhouse was super cute and convenient! I would definitely stay here again! Thanks Krista for also being super kind extending checkout and a few hours earlier for check in! It was very much appreciated!!! 😊
Guest favourite
Condo in Greenport
5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

KaitlinRating, 5 stars5 months ago
Overall relaxing stay and trip to Greenport. Sherri is very communicative and her instructions and listing is clear and accurate. The condo is well decorated and clean and has everything you need for a nice weekend. One thing to note- we were aware check in is between 3 and 5 pm based on the listing (wound up being around 4) but it would be nice for it to be earlier. Still 5 stars though!
Superhost
Condo in Hampton Bays
4.95 out of 5 average rating, 42 reviews

A Unique Piece of Paradise, Water Front pool

ElysiaRating, 5 stars5 months ago
We really enjoyed our stay. The unit was just enough space for my husband and I and our two daughters. Having a kitchen to prepare quick breakfasts in the morning before heading out for the day and having the pool and beach in the late afternoons gave us everything we needed to start and end busy days at the Hamptons Classic or visiting family. We are hopeful to visit again!
Guest favourite
Condo in Norwich
4.88 out of 5 average rating, 230 reviews

The N-V ...The Spa at the Norwich Inn.

AlejandraRating, 5 stars4 months ago
We enjoyed our stay in the villa at the Norwich Inn. The surroundings were so peaceful and the loft was very comfortable. The hot tub and suana were perfect for relaxing on a fall day, we loved staying here!

Home rentals with a private pool

Guest favourite
Bungalow in East Hampton
4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

KateRating, 5 stars4 months ago
We had a wonderful stay at Peter's home. It was beautifully decorated, very comfortable and a quick drive to Springs. Access to the private clearwater beach was a plus! Thank you for sharing your beautiful home with us.
Guest favourite
Home in Water Mill
4.92 out of 5 average rating, 125 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

BillRating, 5 stars1 month ago
Lovely place, great for having friends and family for a home cooked meal
Guest favourite
Home in East Hampton
4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars4 months ago
Beautiful home worked perfect for our wedding visit. Loved sitting on the deck! Beautiful landscaping and very private! We were very confortable and able to relax between events and visit. Donna wad very flexible and allowed us to enter early so a dew of our family members could do s little remote eork. I hope to rent here again in the future! As a special surprise we saw the northern lights from the deck one night!!
Home in East Hampton
5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

KatieRating, 5 stars31 months ago
Mike’s place made for the perfect Hamptons vacation. The location was the perfect starting point for day trips to Montauk and the harbors and we enjoyed the short walk to the beach daily… but there really is no need to leave this amazing property. Our family cannot stop raving about the amazing outdoor setup that we took full advantage of every day. Mike was very responsive and provided a detailed guide for the house and excellent recommendations for the area. We would 100% book again when we’re in the area and would recommend this place to anyone looking for an amazing Hamptons experience.
Superhost
Home in East Hampton
4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

LarryRating, 5 stars44 months ago
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.
Guest favourite
Home in East Hampton
4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

JulianaRating, 5 stars5 months ago
We had an amazing time staying at this house! It was in a great location, well-stocked with everything we needed, and the host was incredibly responsive. The check-in process was seamless, making our stay even more enjoyable. My family and I had a wonderful experience, and we would definitely book again!
Guest favourite
Home in Southampton
5 out of 5 average rating, 81 reviews

Best of Country and Beach Living

DavidRating, 5 stars5 months ago
My family had a great stay. Mary Ann was sweet and helpful. Very comfortable home with tons of amenities that we enjoyed. The kids really liked helping to feed the chickens and all the natural wild life at the property. Highly recommend for family or groups.
Guest favourite
Home in Southampton
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars5 months ago
One could not ask for a better hosts than Christina and Phil - they are extremely communitive, proactive and helpful. Their house is beautiful - gourmet kitchen, in-ceiling speakers throughout the house, nice deck, pool and a picturesque location. The master bedroom has access to the back deck and a great shower. We had all three bedrooms full and everyone enjoyed their stay. We did not take advantage of the kitchen, but if we come back to the Hamptons we would stay here for longer and cook some meals. We are art collectors, so definitely appreciated the works Christina & Phil have amassed. The one thing I would bring to the attention of future renters is that you definitely know you are in somebody else's home - this is the first time we have unpacked only to find that every drawer was full, so we had to place stuff on top of the dresser or on the few open shelves in the closet. That said - totally worth it and would definitely recommend this Airbnb. Hope to be back soon!

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