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

Superhost
Home in Hampton Bays
4.79 out of 5 average rating, 103 reviews

Private completely fenced in property. Near beach.

KarenRating, 5 stars2 weeks ago
This is a beautifully furnished large home with lots of extras, including very well outfitted gym, hot tub and pool (although the pool was not open yet during our visit). The backyard is huge and our dogs loved it. All of the bedroom are spacious and well appointed. It is a great entertaining house or a family with kids. We loved and in fact have already re-booked it for another visit!
Guest favourite
Home in East Hampton
4.88 out of 5 average rating, 106 reviews

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

IanRating, 5 stars2 days 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.
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 131 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.
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!
Guest favourite
Home in East Hampton
5 out of 5 average rating, 5 reviews

The Hideaway

NikkiRating, 5 stars7 months ago
Dorina’s home was the calm, peaceful reprieve from the city we were looking for. Her home was so comfortable and she went above and beyond to make sure we had everything we needed. The backyard was a little oasis with a large pool (with floats!), several (6 I think) lounger chairs, two 6 top tables in different areas and a functioning grill. We spent most of our time here! Dorina was fast to respond, helpful with recommendations and overall what you hope to have in a host. We would definitely come back to Dorina’s home!
Top guest favourite
Home in East Marion
5 out of 5 average rating, 11 reviews

Long Island home w/ large pool

LoreleiRating, 5 stars4 months ago
This house was fantastic! We cooked a full Thanksgiving dinner here! The house was well stocked with everything we needed, from kitchen essentials to paper products. The layout of the house was great. Jane was very accommodating and made things easy for us! The house was immaculate and met all of our needs. I hope it’s available next Thanksgiving! Perfect location! Close to town, yet quiet and private! It was my granddaughter’s first Thanksgiving and I’m so glad we had this house to celebrate in!
Guest favourite
Home in East Hampton
4.84 out of 5 average rating, 31 reviews

Private East Hampton Estate

CokiRating, 5 stars6 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!
Superhost
Home in Southampton
4.93 out of 5 average rating, 44 reviews

New Southampton mega home with heated gunite pool!

SamuelRating, 5 stars2 months ago
Great place to stay and great host !

Condo rentals with a pool

Superhost
Condo in Greenport
4.83 out of 5 average rating, 126 reviews

Oceanfront Condo – Incredible Spring Rates!

ShirleyRating, 5 stars4 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, 22 reviews

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

ChristopherRating, 5 stars1 month ago
I would highly recommend Natalie’s place for anyone looking to spend time in the Norwich area. Our group of 6 adults had a great overnight, and being 4 minutes from Mohegan was incredibly convenient. Natalie was incredibly responsive, and it’s clear she puts a lot of thought into curating a space that makes her guests feel at home!
Top guest favourite
Condo in Norwich
4.98 out of 5 average rating, 172 reviews

Peaceful Oasis steps from Mohegan Sun

BriannaRating, 5 stars1 day ago
This was by far one of the best Airbnbs I have ever stayed at and I have stayed at quite a few! Christina provided clear instructions in advance of how to access the property so no time was wasted trying to figure out how to access anything. I also had mentioned it was an anniversary surprise and Christina went out of her way to decorate and provide wine which my fiancé absolutely loved! There were also many board games provided along with smart tvs in the living room and bedroom which was perfect for any staycation. Also no need to stress if you forget a toiletry because most were also provided which was extremely convenient! Not only was the place extremely accommodating but it was also unbelievably clean and the decor was so fun and welcoming! If you are also planning on going to the casino or the spa at Norwich Inn the location is beyond perfect! I absolutely will be staying here again for future staycations and will recommend it to absolutely anyone!
Top guest favourite
Condo in Norwich
4.98 out of 5 average rating, 131 reviews

The Vacay Villa

HeatherRating, 5 stars2 weeks 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!!!
Top guest favourite
Condo in Greenport
5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

KaitlinRating, 5 stars7 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 stars7 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 Greenport
4.92 out of 5 average rating, 137 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MariaRating, 5 stars5 months ago
Irinas place was exactly as she described. She answered all inquiries in a timely manner. We will definitely be back.
Guest favourite
Condo in Norwich
4.88 out of 5 average rating, 232 reviews

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

RosemaryRating, 5 stars1 week ago
very clean and close to attractions. clear communication with host throughout stay. would def recommend.

Home rentals with a private pool

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 stars46 months ago
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.
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 stars6 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 stars5 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 East Hampton
4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars5 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!!
Guest favourite
Home in Southampton
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars6 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!
Home in East Hampton
5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

KatieRating, 5 stars33 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.

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