
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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Popular amenities for Dennis Port rentals with a pool
House rentals with a pool

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl
Joshua's place was the PERFECT place for our dad's 70th birthday! The 9 kids had an amazing time between the pool and game barn there was constant entertainment for all ages! If you have a big family/group this is the spot!

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.
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 !

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠
We had a wonderful stay here in New Seabury! The house is beautiful, spacious and just as described. The heated pool was an added bonus! Michael provided prompt and clear communication when needed. I would absolutely stay here again!

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!

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!!
Apartment 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.

Hidden Hideaway
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.

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!
Quick stats about holiday rentals with a pool in Dennis Port
Total rentals
120 properties
Nightly prices starting at
₹8,616 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