
Vacation rentals with a pool in Dennis
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Dennis
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Dennis rentals with a pool
House rentals with a pool

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

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!!

Cape Cod multi-structure family compound with Pool
We absolutely loved our stay!! This home, (compound actually with three separate homes) was so beautiful! So much room for our party of 8 adults to spread out and enjoy during our family reunion! The main house is stunning with fabulous views of the 10th fairway of the Ocean Course from the expansive family room and back decks. The kitchen of the home is very large, clean and well stocked. The three and half baths of this home are very clean and updated. The two smaller cottages of the compound are also comfortable, clean and give your group lots of privacy. The pool and hot tub are fantastic and get sun most of the day. This property is truly a gem! Highly recommend!!!

Our families slice of heaven
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

Cape Oasis with large pool + lots of privacy.
The house was exactly as described and pictured. Located in a quiet neighborhood—enjoyed taking morning and evening walks for exercise. It was exceptionally clean, kitchen was well-equipped, spacious bedrooms with comfortable beds, plenty of towels and linens, roomy enough for everyone to enjoy private time. The pool was a big plus for family fun and there was plenty of space on the patio/deck to enjoy a meal cooked on the grill. Cortney was very responsive and provided helpful info on restaurants, shopping, and nearby beaches. We had everything we needed for a relaxing and comfortable stay in Sandwich.

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
Chris' home was clean, bright and very well-stocked. He was timely in communication, and the area was perfect. Beaches, dining and shopping were all within walking distance or a quick drive. It's a great location for taking the ferry to either Martha's Vineyard or Nantucket. We certainly hope to return!

Private Heated Pool, Wifi, AC, Grill & Firepit
Best airbnb I’ve ever stayed in! Flexible check in and check out, even left snacks, water and a note for us. Would for sure go back
Condo rentals with a pool

P-Town Beach Beauty on the Bay. Water View!
We had a wonderful time at Rob's place in Provincetown this February. If you are looking for a quiet place on the East End in the off season this is an exceptional spot. Beautiful water views from the condo. A gorgeous beach with some of the best views in Provincetown is right across the street. Condo was perfectly cleaned upon arrival and exactly as described. Couldn't ask for more.

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

1BR 2nd Floor Condo with pool
Excellent location, clean, comfortable place to spend some time on the Cape. Perfect for my husband and I.

Luxury Waterfront Getaway
Michael's place is spacious, well-appointed, and very comfortable. The views from the living room are amazing, and the breeze from the bay is wonderful. I would definitely recommend staying here.

Private 3bdrm Condo Tashmoo Woods
What a relaxing and wonderful stay! Barbara’s place was welcoming and even better than the pictures. The house has everything you need and the addition of the community pool was the cherry on top. The host was extremely responsive and helpful. We look forward to returning to Barbara‘s place the next time my family and I visit MV.

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.

Modern, clean waterviews
This was my second stay at Garrett’s and the place was just as nice as I remembered (plus a a few upgrades). Garrett’s always quick to respond to inquiries, unit had just about everything we needed including beach towels and location is great as it’s a short bike ride from center town and peaceful/quiet if you’re looking for a balanced vacation.

Martha’s Vineyard Condo * Near Ferry
Great location and a nice quaint spot for one or two ! Great value for the area as well
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
2.4K reviews
Family-friendly rentals
90 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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