
Vacation rentals with a pool in Dennis Port
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Top-rated rentals with a pool in Dennis Port
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Popular amenities for Dennis Port rentals with a pool
House rentals with a pool

"Cape Escape" luxury home w/pool & beach access.
We have stayed in multiple houses / penthouses throughout the U.S. , however, this home surpassed them all. Jennifer was amazing from the beginning of the booking with answering my questions and went above and beyond to make this special occasion memorable. The house is well equipped! The sounds of birds chirping in the morning , the breeze, and the view of the pond when drinking coffee was so serene. The space in the house was more than I expected with everyone having lots of space to enjoy all the designated areas for playing board games, Video game room( so cool) , reading , watching tv - there was a room for everyone’s enjoyment from our 12 year old, 17, 25, to my 78 year old parents. The well thought out toiletries in every bathroom, spa slippers and robes in each bedroom, ear plugs located by the bedside, laundry room that has labeled racks of beach items and games , kitchen with all its wonderful amenities- I can do on and on. We WILL be back !

Mansion with Heated Pool Near Ocean
The place was nice and spacious. Great for large family gatherings. The pool was nice and although the water was not heated (which may partially have been due to the weather), Zachary and his team were very responsive and helped troubleshoot pool temperature. Overall we had a great stay!

Modern Cape, Private Salt Water Pool, Beaches-Golf
Our stay with Walt was incredible! The place came exactly as described and matched all of the photos. It also had all of the necessary ammenities when hosting large group of 11 people. Plenty of places to sleep, plenty of blankets and towels. Walt was extremely responsive and easy to communicate with when I had questions while we were in his residence. 10/10 would recommend!!

4 BD slice of Harwich Heaven
Chris is always a great host. He communicates. Is considerate of our soccer schedule and accommodations. He even wishes our boys good luck at their soccer tournament! He is understanding and a great host. We really enjoy staying here. I highly recommend staying here. He’s a great host.

Cape House with Pool by Canal
This home was great for our family. The pool and backyard are beautiful, and the house was clean and welcoming. There are a lot of activities in the area. I would stay here again!

Home in Hyannis Port
Our family of five had a wonderful stay! We picked the location because it was in the middle of the Cape and easy for us to explore the coast. The house is newly renovated and in pristine condition. The beds were comfortable and the bathrooms were fresh and new. We had plenty of space and felt right at home. The host was very responsive. We highly recommend!

Winslow Acres [heated] Pool Escape; pool May 15
Our family loved this retreat!!

Large Home Heated Swimming Pool Private Beach
We had a great stay at this place! The house was exactly as described—clean, comfortable, and well-stocked with everything we needed. Check-in was smooth, and the host provided clear instructions throughout. The neighborhood was quiet and convenient, with easy access to local attractions and restaurants. Would definitely recommend this spot to anyone visiting the area!
Condo rentals with a pool

Comfy Cape Escape! Spacious, Cozy, Close to Beach!
Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.

Ocean Edge: 2 bed/2 bath - Pools & Resort Access
Had a great weekend at Josh’s place! Smooth booking process, great communication, easy checkin. The space was clean and exactly as advertised. I’d definitely recommend both Josh as a host and this location as a Cape getaway!

Condo in Falmouth MA
The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.

Cape Cod, South Yarmouth July 19-26. Sleeps 8
Loved the location and the apartment was facing the water, which meant a light cool breeze most of the time all day and night. The 2 bedroom apt was very clean and spacious and the 5 of us did not get in each of our ways. While inside, we did not hear any noise from our next door neighbors and sliding doors silenced any outdoor noise. The AC was cold and very comfortable. Amenities including additional outdoor access to a peaceful water area with picnic tables, Adirondack chairs was a huge plus. Indoor pool helped too with two little ones. Beach parking passes at a discount. Staff was very nice and accommodating. Parking was easy and plenty of spaces. Would recommend and we would stay again.

Beachfront Complex in Hyannis
I loved our stay . The place inside was bigger than I was expecting. They have so many dishes, glasses, towels, blankets, chairs, etc to use. The place was great, just wish our weather was better. Thank you for being so helpful before and during our stay . Hope to return next year .

Ocean Edge Resort/Pool access/2bedroom-2bath Condo
We really enjoyed our stay. Great condition, really clean, easy parking, and great location right at the Ocean Edge resort. Rob was an excellent host, super communicative and responsive. Would stay again!

Golf Course Views and Pools
My wife and I wanted a little end of summer get away and we couldn’t have been happier choosing Alexa’s condo at Ocean Edge! The condo was beautifully decorated, very clean, and everything we could have wanted for our short vacation. Alexa was always very responsive and friendly, we’ll certainly be keeping her in mind for our next cape vacation! Highly recommend for small families and couples!

Escape to the Cape
We had a fantastic time at Betsy and Jon’s place on Juniper Circle. The location was perfect for us, a short walk to the private beach and even closer to the pool and tennis courts. The property was clean, comfortable and spacious. The kitchen was well equipped and we found it great that there were things for the beach and tennis equipment. The area was quiet but neighbours were friendly. We loved the town of Brewster with lots to do within a short distance. Betsy was very responsive, we’d recommend her place for a relaxing stay.
Quick stats about vacation rentals with a pool in Dennis Port
Total rentals
120 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
660 reviews
Family-friendly rentals
40 properties are a good fit for families
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
110 properties include access to wifi
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Owen Park Beach
- Coast Guard Beach
- Onset Beach
- Inman Road Beach
- Nickerson State Park
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Cahoon Hollow Beach
- Kalmus Park Beach
- White Horse Beach
- Peggotty Beach
- Cape Cod National Seashore
- Forest Beach
- Linnell Landing Beach
- Ridgevale Beach