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Vacation rentals with a pool in Dennis

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Popular amenities for Dennis rentals with a pool

House rentals with a pool

Guest favorite

Home in Mashpee

4.9 out of 5 average rating, 20 reviews

Beautiful Mashpee Home with Pool

JudyRating, 5 stars3 months ago
The house was beautiful, better than expected! It was very spacious with lovely high ceilings in all the rooms. the bedrooms were all large and delightfully decorated, as were the two sitting rooms. In fact the layout worked really well for our family group: master bedroom with en suite for us grandparents, first floor bedrooms for one couple and their two kids with shared bathroom and extra sitting area with TV, and the garden room -with an enormous bed!- and ensuite bathroom for the other couple. The pool was a very good size with comfortable loungers and the large table on the terrace was perfect for mealtimes. The kitchen was fully equipped and there were an enormous range of dishes and utensils! The various beaches we visited were all within easy reach and Mashpee Commons was only a short drive away with a range of restaurants and shops. Nicole was very responsive and answered our questions quickly. We had a wonderful time and the house exceeded our expectations!
Superhost

Home in New Seabury

5 out of 5 average rating, 7 reviews

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

MadisonRating, 5 stars2 months ago
Prescott’s house is such a relaxing place to stay with a big group. The house has a very pretty view and is very clean and peaceful. We are very grateful for such a nice stay at this beautiful house. The BBQ outside didn’t work great but other than that we had a wonderful time! Thank you Prescott.
Superhost

Home in Orleans

4.92 out of 5 average rating, 25 reviews

5-bedroom Cape with a pool and yard games.

CatherineRating, 5 stars3 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

Home in Sandwich

4.99 out of 5 average rating, 80 reviews

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

LaurenRating, 5 stars3 months ago
We stayed at the Cape Escape for 5 nights with 7 adults and two young children, and it was perfect. The setting and location of the house was private and serene. The house was well stocked including plenty of beach towels, chairs, baby gear, coolers, wagons, beach toys and more. We used the provided high chair as well. I especially loved the soaps and lotions and extra bath toiletries which made it feel like a hotel. There were multiple areas where our family could gather and eat. Dinners on the back porch st sunset were the best. We hope to be back next year!!
Guest favorite

Home in Plymouth

4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars2 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Superhost

Home in Barnstable

4.88 out of 5 average rating, 34 reviews

Paradise home in centerville

LindaRating, 5 stars2 months ago
We loved our stay at this home. Even in mid-October we were able to take advantage of the pool. The jacuzzi was also wonderful and the outdoor set up made you feel as if you were at a resort! The house was clean and there was plenty of room for indoor mingling. We had a wonderful time.
Superhost

Home in Bourne

4.75 out of 5 average rating, 4 reviews

Cozy Cape Cod House - Stroll or Bike the Canal

AlexandraRating, 5 stars8 months ago
Excellent accommodation, I was in winter but in summer it should be the maximum
Guest favorite

Home in Buzzards Bay

5 out of 5 average rating, 27 reviews

Cape House with Pool by Canal

SamanthaRating, 5 stars3 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!

Condo rentals with a pool

Superhost

Condo in Dennis Port

4.8 out of 5 average rating, 5 reviews

2BR Presidential Cape Cod Resort Ocean Front

MelanieRating, 5 stars27 months ago
The place and location were great. Dave definitely was a great communicator and explained everything prior to arrival. This was a time share so the facility has no reflection on Dave’s reputation. The deck and the pool were the only things that could have been cleaner.
Guest favorite

Condo in Dennis Port

4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

NupurRating, 5 stars3 months ago
Perfect little studio for two people! Great location - close to beaches and restaurants and there’s even a pool! Michael was super responsive and the place was exactly like the pictures!
Guest favorite

Condo in Brewster

4.97 out of 5 average rating, 178 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

KathleenRating, 5 stars3 weeks ago
It is always comforting to stay at Anna’s condo. It feels like home with well thought out amenities, clean spaces, quiet surroundings and such a helpful host. It is a great space for families and has all you need to cook in. I highly recommend staying here.
Guest favorite

Condo in West Dennis

4.89 out of 5 average rating, 28 reviews

1BR 2nd Floor Condo with pool

MarjorieRating, 5 stars2 months ago
Excellent location, clean, comfortable place to spend some time on the Cape. Perfect for my husband and I.
Guest favorite

Condo in Dennis Port

4.84 out of 5 average rating, 76 reviews

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

ChrisRating, 5 stars3 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

Condo in Dennis Port

4.84 out of 5 average rating, 58 reviews

Stylish & Modern Studio Condo - Steps to the Beach

RachelRating, 5 stars1 month ago
Great spot with just a 5 min walk to the beach. Cute and cozy which is just what I needed. Super clean and well maintained. Very much enjoyed my stay!
Superhost

Condo in West Dennis

4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

JennyRating, 5 stars1 month ago
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.
Guest favorite

Condo in Brewster

5 out of 5 average rating, 71 reviews

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

KevinRating, 5 stars3 months ago
We had a great stay with Rob in his cottage at Ocean Edge! The place had clearly been recently updated and it utilized space well such that it lived much bigger then its footprint. While it rained the whole time we were there, we could see Ocean Edge being a fun community for active folks. We highly recommend you stay here!

Quick stats about vacation rentals with a pool in Dennis

  • Total rentals

    220 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    2.5K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

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