
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

Sandy Bottoms Bungalow
Catherine is a wonderful host. She truly went above and beyond to make sure our family stay was comfortable, fun and memorable. She had several gifts for our kids and many many snacks, the kids absolutely LOVED it!! Highly responsive, friendly and provided great recommendations for things to do / where to eat in the area. The house is gorgeous, perfectly clean and equipped with everything a family needs!! Thank you Catherine for a fantastic stay and we can’t wait to visit again soon!

Luxury House private pool oceanview 4 King Bd
Absolutely beautiful place. Every bedroom beautifully Decorated and Beds Incredible. Clean comfortable and great location Kelly

north wildwood beach block house pool use
The whole process from reservations, to our stay then to check-out was easy and straightforward. This was to be a quiet weekend with my daughter and no (grand)kids. It was that and more. Great location. Very clean and well equipped. You can book this with confidence.

Wilde Rose By The Bay - Salt water Inground pool
This is a lovely home in a peaceful and safe neighborhood, perfect for families. We would stay again! It really is just steps to the beach. The kitchen was well stocked with spices and supplies to prepare meals. Everything was in working condition. The pool is beautiful! I loved the lights at night. The entire pool area is gated and locked, good to know for little ones. The shower had great water pressure. The outdoor shower has hot water too! The TV was very easy to use and had many options. Of note, the entire upstairs could accommodate a second family with a mini fridge, half bathroom, two beds, separate entrance, sofa/tv/table/patio - the photos really don’t do this home justice. I was very impressed when I walked inside. My kids LOVED the adorable spiral staircase to get upstairs! We had no problems with it, but it would be hard to keep little climbers off of it. The master bedroom is downstairs, something to consider with littles that wake up in the night and need to get down.

Cape May Modern with Heated Pool/Porch Sleeps 16!
Our stay at Frank & Liz's home was perfect! The home was beautiful and pristine with wonderful amenities. They were very easy to communicate with and had very clear instructions for the stay! Every bedroom and bathroom was beautiful and clean! Its a great location with easy walks to both the beach and the historic and quaint downtown! Will definitely be looking to stay there again!

Hot Tub Backyard Oasis, Private Beach, Local Pool
The house was even nicer than it appeared in the pictures. The living area is spacious and the bedrooms and bathrooms comfortable for our family's needs. The outdoor area was very enjoyable as well. It is evident that Heather has put a lot of care into creating a welcoming vacation home.

Dodd House Beach Home w/private pool and hot tub
Lynn and Brian’s house was amazing. It was perfect for our large group! The house had everything we needed and more. The hot tub and outdoor area were a huge plus! The house was very clean and they supplied us with sheets and towels which was a huge help. Brian was very responsive and super easy to communicate with. Couldn’t have asked for a better house or hosts!

Beautiful Beach House in Rehoboth
We had a wonderful stay at Autumn's house. The house itself was really lovely - clean, spacious, comfortable, and beautifully decorated. And the location was unbeatable: near enough to the beach and restaurants in town to walk everywhere, but in an adorable and quiet neighborhood. (We were visiting in the off season, so probably things are more hectic in the summer, but I would absolutely pick this house over other options in the future). Autumn was also very communicative and responsive. A great find all around.
Condo rentals with a pool

Beach block condo, pool/spa, 2 parking, 4 bdrms
The house was very spacious and accommodating. Great location near the beach and boardwalk. The host always responded quickly and was very easy going. We would definitely stay here again.

Ocean View Condo—Pool, Elevator, Linens, towels
Three of us women friends spent a week in early October. Wonderful! Fun! Relaxing! The condo was bright and cheery, even nicer than the pictures. Comfy, close to beach, We loved eating on the patio, especially in the morning. Spotted a dolphin(s) from the porch with binoculars, spouting as he/she moved along. And a hawk low in the vegetation next to small boardwalk. Nice details that made us feel welcome, bottle of wine with a note, keurig coffee and hot chocolate, use of beach chairs. Lovely and set up thoughtfully for guests. Hope to visit again!

1 BED/1 BATH HEATED POOL BEACH CONDO FOR RENT
The accommodations were private and serene, providing a peaceful retreat. The location was convenient, with a short 15-minute walk to the vibrant boardwalk and sandy beaches. We appreciated the thoughtful gesture of welcome snacks, which were especially comforting after our long journey. The rocking chairs on the property offered a relaxing spot to unwind after our beach days. We enjoyed exploring the local dining scene, with standout meals at Vegas Diner and Russo’s Market. The sandwich I ordered at Russo’s Market was truly exceptional, the largest I’ve ever encountered. This was the perfect weekend getaway for my wife and me, offering a balance of relaxation, convenience, and local experiences.

Cozy Wildwood Crest Beach - Poolside Condo
Just returned from my 6th stay at Erica’s condo. Most of the units are owner occupied with only a few rentals. It’s perfect for those looking for a chill relaxing environment. Just a few blocks to the beach, Centennial Park (has live music series!), and Sunrise Park. Erica is an awesome host, the condo is perfect and well maintained. We’re already booked again for next year!

Renovated Condo Near Outlets, 3.5 Miles to Beach
The condo was easy to find and easily accessible!! The location is a short drive from the beach and very quiet!! We loved that the balcony was enclosed by a screen to help minimize the bugs and heat; There were plenty of utensils and cookware to assist you with cooking during your stay. Overall, Our stay was enjoyable and We would recommend this booking to our friends and family. We look forward to booking again!!

Surfside 2 Bedroom Condo with a Pool!
I’ve stayed at this place multiple times. Great location and the perfect size. Would highly recommend!

Cozy Condo
We really enjoyed our stay at the condo! Maria was helpful and responsive. All amenities were as described. We’d we happy to stay at this location again.

Lovely Two bedroom condo with community pool.
Airui was a great host. Beautiful place, nice view, very close to stores and restaurants. Airui was very responsive and the apartment was super clean :)
Quick stats about vacation rentals with a pool in Dennis
Total rentals
20 properties
Nightly prices starting at
$110 CAD before taxes and fees
Total number of reviews
580 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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