
Holiday rentals with a pool in Dennis Port
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Top-rated rentals with a pool in Dennis Port
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House rentals with a pool

5-bedroom Cape with a pool and yard games.
We enjoyed our stay very much ~ the house and large fenced yard w/deck (perfect for pup) are amazing & the hosts were very kind, accommodating & responsive. The location was great with a short ride to local beaches and/or Chatham for a fun day of shopping or night out. The host’s welcome basket with treats & seltzers were a great surprise after a long day of travel. We loved playing ping pong in the garage! I do suggest the listing bedroom descriptions & photos be updated as we were pleased to find a king bed in the master BR (vs the queen shown) and a full bed (vs the twin) in the downstairs guest-room. Perhaps renovations are underway so we were pleasantly surprised! The only improvements I would suggest are adding a screen door to the deck & heat for the pool, having more wine glasses (the kitchen was wonderfully stocked otherwise), & adding amenities like blankets, washcloths, a hair dryer, beach/pool towels & chairs (we brought our own). We hope to be back next year!!

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10
Kimberly was a fantastic host. Her home was beautiful and well-maintained. It fit our group of 6 well and had lots of amenities for our baby (pack n play, stroller, baby gates, high chair)! There were beach chairs, beach & bath towels, and linens available which was unique from other places nearby and very helpful as we flew in. The location was great with a couple of stores nearby, several beaches, and restaurants. Kimberly was very responsive and accommodating as we navigated our stay. It was a great first trip to Cape Cod & we’ll definitely stay here again. I’d recommend trying Grumpy’s which is within 5 minutes & checking out a whale watching tour!

"Cape Escape" luxury home w/pool & beach access.
I can not say enough about how wonderful this house was to stay at for my son's wedding weekend. This house was very clean and organized. The hosts were extremely thoughtful with how everything was laid out. They thought of everything that you would need or might forget. The outdoor space was great!! My grandchildren and kids floated around the pool and played yard games. I did not hear "I am bored" and that was wonderful. We had so much space to get ready for the wedding and were able to get wonderful pictures of my son getting ready for his wedding. There are so many places in the house to either gather together or to go off and do something else. Two kids were playing chess while the younger ones were down playing with the video games and my dad and the men were watching the Masters. We had plenty of space for everyone to hang out. My entire family enjoyed this house and can't wait to go back.

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠
This place worked out wonderfully for the 6 adults and 3 grandchildren we had with us, my 4 year old granddaughter even got her own room and loved it, along with the pool!! It was very clean and family friendly and stocked with more than we expected. There is also food and shops within walking distance. We enjoyed it immensely!! Thank you Michael, you have a wonderful place!!

4 BD slice of Harwich Heaven
My friends and I always wanted to visit Cape Cod and Chris’ home felt just like that place to stay in. He was very responsive and helped me a lot with recommendations! If I were to come back, I would stay here again. The house was very spacious, can’t complain there!

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!

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!

Oceanview/pool&spa/private beach! 5 bedrms, 4 bath
We loved our stay in Justin’s home. The house is well-stocked, beds are comfortable, and our family had plenty of room. Justin was very responsive and helpful with any questions. Renting towels and sheets was new for us, but it was easy and all set up for us when we arrived. We loved the huge front porch and enjoyed coffee and the quiet neighborhood outdoors each morning. We would definitely return if we make another trip that way.
Condo rentals with a pool

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!

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access
Chris is an unbelievable host.

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 holiday rentals with a pool in Dennis Port
Total rentals
120 properties
Nightly prices starting at
$155 AUD 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
Wi-Fi availability
110 properties include access to Wi-Fi
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Coast Guard Beach
- Owen Park Beach
- Onset Beach
- Nickerson State Park
- Inman Road Beach
- Pinehills Golf Club
- White Horse Beach
- Oyster Harbors Beach
- Kalmus Park Beach
- Ridgevale Beach
- Chapin Memorial Beach
- Peggotty Beach
- Scusset Beach
- Lighthouse Beach
- Forest Beach
- Linnell Landing Beach