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 East Hampton
4.88 out of 5 average rating, 107 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

IanRating, 5 stars3 weeks ago
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.
Superhost
Home in East Hampton
4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

BrittanyRating, 5 stars7 months ago
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Guest favourite
Home in Southampton
4.93 out of 5 average rating, 14 reviews

Southampton Escape, Heated Pool, hot tub, 3 bed,

LaurenRating, 5 stars10 months ago
The house was great! Our two infants loved the large deck and pool. So close to town and the beach. It was a perfect getaway!
Top guest favourite
Home in East Hampton
5 out of 5 average rating, 36 reviews

Stunning Central E. Hampton Home w/ gunite pool.

DonnaRating, 5 stars3 months ago
Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!
Top guest favourite
Home in East Marion
5 out of 5 average rating, 12 reviews

Long Island home w/ large pool

TautraRating, 5 stars2 months ago
My stay here was phenomenal! From the host’s response time, down to the amenities that were placed throughout the house. As soon as you walk in, it felt like home. The house is spacious and highly functional. The design of the house offers a perfect blend of modern mixed with nostalgic elements. The best stay by far. Would love to book again!
Guest favourite
Home in Southampton
4.96 out of 5 average rating, 167 reviews

POOL in APRIL! Waterview, Free For Dogs! Kayaks

MeganRating, 5 stars5 days ago
Right off of 27 so it is super easy to get to. House is on a nice private street with beach access. We walked to the beach several times a day to let the kids play and the dogs run wild. It was beautiful. House is exactly as described and Roger and Amy were great at responding. Quiet neighborhood. Only about 5 minutes outside of Southampton town.
Guest favourite
Home in East Hampton
4.84 out of 5 average rating, 31 reviews

Private East Hampton Estate

CokiRating, 5 stars7 months ago
Marks home was beautiful, peaceful and near to so many great areas. The pool and backyard were wonderful and relaxing. We loved it! Highly recommend!

Condo rentals with a pool

Superhost
Condo in Norwich
4.84 out of 5 average rating, 150 reviews

Villa Flora @ Norwich Inn & Spa

DebraRating, 5 stars6 months ago
There is nothing more frustrating than not being able to have a decent shower while you are on vacation. That was absolutely not the case here. The hot water and water pressure in both bathrooms was exceptional. This is a great place in a great area. We will definitely try to get back here.
Top guest favourite
Condo in Norwich
4.98 out of 5 average rating, 101 reviews

CASiNO, Spa, Hot Tub, Pool, Private Villa, Kingbed

RachelRating, 5 stars5 days ago
Wonderful stay, lots of small added touches that made a big difference. My 13-year-old son loved it. Convenient and quiet.
Superhost
Condo in Greenport
4.84 out of 5 average rating, 128 reviews

Oceanfront Condo – Incredible Spring Rates!

DanielleRating, 5 stars2 weeks ago
We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!
Guest favourite
Condo in Norwich
4.96 out of 5 average rating, 26 reviews

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

NatashaRating, 5 stars3 weeks ago
Loved our stay, Natalie was an excellent host. Already figuring out when we can return.
Top guest favourite
Condo in Norwich
4.98 out of 5 average rating, 174 reviews

Peaceful Oasis steps from Mohegan Sun

JohnRating, 5 stars4 days ago
This place has everything you need and a lot more. All of furniture is new and comfortable especially the huge king bed. Bathroom and shower was super clean and comfortable. Linens and towels are top notch. The TV in the bedroom and living room is a plus. The private outdoor patio is comfortable and relaxing. 5 min to Mohegan Sun. I could go on and on about this place it is amazing and a great value. You won't be disappointed!
Top guest favourite
Condo in Norwich
4.98 out of 5 average rating, 132 reviews

The Vacay Villa

HeatherRating, 5 stars1 month ago
Had a wonderful stay! It was so cute and cozy and just what we needed for a wonderful weekend getaway. My daughter and I had a great mix of fun at local wineries, concert and dancing at Mohegan Sun just minutes away and a wonderful relaxing time at the spa just a short walk away. We also took a trip to Mystic for some shopping and a great dinner and still managed to have some nice wind down time in front of the fire watching a comedy on Netflix. The condo had everything we needed as well as great touches of snacks and coffee plus all sorts of creamers. Would definitely come back again!!!
Guest favourite
Condo in Greenport
4.92 out of 5 average rating, 138 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

RoxanaRating, 5 stars6 months ago
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.
Guest favourite
Condo in Norwich
4.88 out of 5 average rating, 233 reviews

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

CaitlinRating, 5 stars1 week ago
We stayed in town for an event at Mohegan Sun. The flexible check in was helpful as we got in late at night. The place was clean and welcoming.

Home rentals with a private pool

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 stars6 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!!
Top 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 stars7 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
Bungalow in East Hampton
4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

KateRating, 5 stars6 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 Southampton
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars7 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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