Vacation rentals with a pool in Dennis Port

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Dennis Port rentals with a pool

House rentals with a pool

Superhost
An inground pool is surrounded by lush greenery, featuring vibrant flowering plants and bushes. The clear blue water reflects the sky, while stairs lead into the pool. A natural stone patio borders the pool area, enhancing the outdoor space.
Home in Orleans
4.92 out of 5 average rating, 26 reviews

5-bedroom Cape with a pool and yard games.

CatherineRating, 5 stars9 months ago
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!!
Guest favorite
The exterior of the two-story home is showcased, featuring a spacious deck with ample seating and a swimming pool in the foreground. A colorful pool float rests on the water, while greenery surrounds the property, enhancing the cozy outdoor space.
Home in East Dennis
4.8 out of 5 average rating, 5 reviews

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10

LaurenRating, 5 stars1 week ago
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!
Guest favorite
An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.
Home in New Seabury
5 out of 5 average rating, 21 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

DonnaRating, 5 stars2 days ago
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!!
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 stars2 weeks 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, 44 reviews

Winslow Acres [heated] Pool Escape; pool May 15

AllyRating, 5 starstoday
perfect location for us to stay in while attending a wedding. Having the pool and activities were a great bonus too.
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, 66 reviews

Large Home Heated Swimming Pool Private Beach

SahilRating, 5 stars3 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!
Guest favorite
A classic colonial home is set on a large green lawn, surrounded by trees. The expansive front porch features white railings and multiple seating areas. An American flag gently flutters to the side, while colorful flowers add a touch of vibrancy to the landscape.
Home in Chatham
4.97 out of 5 average rating, 39 reviews

Oceanview/pool&spa/private beach! 5 bedrms, 4 bath

BarbaraRating, 5 stars8 months ago
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.
Top guest favorite
A private, gated pool is surrounded by a concrete deck and bordered by lush greenery. The sparkling blue water is enhanced by a bright yellow floating ring. In the background, a spacious sunroom and outdoor seating areas are visible, offering convenience and leisure options.
Home in Cotuit
4.95 out of 5 average rating, 115 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

JorgeRating, 5 stars2 weeks ago
Beautiful house. Kid friendly Really close to the beach Amazing hosts

Condo rentals with a pool

Superhost
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!
Top guest favorite
The living area features a light-colored sofa paired with matching armchairs. A small table holds fresh flowers. Soft lighting from lamps creates a comfortable environment. Large sliding doors provide natural light and open to an outdoor patio with a dining set.
Condo in Brewster
4.97 out of 5 average rating, 72 reviews

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

LucasRating, 5 stars1 week ago
Chris is an unbelievable host.
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

    R1,807 ZAR 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

Destinations to explore