Vacation 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

Top guest favorite
Home in Sandwich
4.99 out of 5 average rating, 82 reviews

"Cape Escape" luxury home w/pool & beach access.

JanelleRating, 5 stars3 weeks ago
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 !
Superhost
An outdoor area showcases a heated pool surrounded by lounge chairs and a shaded seating arrangement. The back of a large two-story home is visible, with multiple windows indicating spacious interiors. Green trees line the background, adding a natural element to the setting.
Home in Plymouth
4.82 out of 5 average rating, 17 reviews

Mansion with Heated Pool Near Ocean

AnayRating, 5 stars2 weeks ago
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!
Guest favorite
A spacious heated saltwater pool is surrounded by a large deck featuring colorful lounge chairs and an umbrella. The attractive two-story house stands in the background, framed by lush greenery and trees, creating a peaceful outdoor setting.
Home in Brewster
4.97 out of 5 average rating, 34 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

MichaelRating, 5 stars2 weeks ago
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!!
Superhost
The exterior of the home is presented with natural wood siding, complemented by green shutters. Solar panels are mounted on the roof. A welcoming front porch leads to the main entrance, while a garage is visible to the left amidst well-maintained landscaping.
Home in Harwich
4.8 out of 5 average rating, 15 reviews

4 BD slice of Harwich Heaven

KimberlyRating, 5 stars8 months ago
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.
Top guest favorite
A spacious backyard features a large swimming pool surrounded by a well-maintained lawn. Comfortable lounge chairs are arranged along the pool's edge, while a charming shed is visible in the background. Lush greenery borders the area, enhancing the outdoor setting.
Home in Buzzards Bay
5 out of 5 average rating, 27 reviews

Cape House with Pool by Canal

SamanthaRating, 5 stars9 months ago
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!
Top guest favorite
An in-ground pool is surrounded by a spacious patio, featuring several blue lounge chairs. Lush greenery frames the area, with a clear blue sky overhead. The pool’s water reflects the sunlight, creating a refreshing ambiance for relaxation and entertainment.
Home in Hyannis Port
5 out of 5 average rating, 13 reviews

Home in Hyannis Port

Ryan & LindsayRating, 5 stars1 week ago
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!
Superhost
A well-maintained swimming pool reflects the greenery surrounding it, bordered by a stone deck. Poolside seating arrangements include a black metal table with chairs and a blue lounge chair. A red umbrella offers shade, while the exterior of the home features a wooden deck and bright lounge furniture.
Home in Yarmouth Port
4.91 out of 5 average rating, 43 reviews

Winslow Acres [heated] Pool Escape; pool May 15

TamiRating, 5 stars1 week ago
Our family loved this retreat!!
Superhost
The outdoor area features a heated fiberglass pool with a curved design, surrounded by a concrete patio. Sun loungers and a shaded seating area under an umbrella are visible, along with a grassy section and the home's exterior, showcasing large windows and a door leading inside.
Home in East Sandwich
4.92 out of 5 average rating, 65 reviews

Large Home Heated Swimming Pool Private Beach

SahilRating, 5 stars2 weeks ago
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

Guest favorite
A charming, single-story building is visible from the road, featuring a gray exterior and a white picket fence that encloses a well-kept yard. Leafy trees provide shade, and clear blue skies are overhead, creating a welcoming ambiance for guests.
Condo in Dennis Port
4.84 out of 5 average rating, 76 reviews

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

ChrisRating, 5 stars9 months ago
Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.
Guest favorite
The living room features two comfortable sofas adorned with colorful cushions, situated around a wooden coffee table on a vibrant area rug. Natural light fills the space, highlighting the dining area and fully equipped kitchen visible in the background.
Condo in Brewster
4.88 out of 5 average rating, 40 reviews

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

JasonRating, 5 stars8 months ago
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!
Superhost
The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.
Condo in Falmouth
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
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.
Superhost
A spacious lawn alongside the river features several lounge chairs arranged for guest relaxation. The water reflects the clear blue sky, while boats are visible along the shore. The pathway leads to a low wooden railing that borders the scenic waterfront.
Condo in West Yarmouth
4.75 out of 5 average rating, 4 reviews

Cape Cod, South Yarmouth July 19-26. Sleeps 8

RickyRating, 5 stars35 months ago
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.
Superhost
The outdoor swimming pool is framed by a spacious deck lined with lounge chairs and blue umbrellas. A gazebo is situated in the background, providing shade. Bright blue skies and scattered clouds enhance the open atmosphere of the recreational area.
Condo in Hyannis Port
4.82 out of 5 average rating, 17 reviews

Beachfront Complex in Hyannis

ErinRating, 5 stars10 months ago
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 .
Guest favorite
Condo in Brewster
5 out of 5 average rating, 72 reviews

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

DonnyRating, 5 stars8 months ago
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!
Superhost
Condo in Brewster
4.86 out of 5 average rating, 44 reviews

Golf Course Views and Pools

DavidRating, 5 stars9 months ago
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!
Superhost
Condo in Brewster
4.91 out of 5 average rating, 23 reviews

Escape to the Cape

PaulRating, 5 stars9 months ago
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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