Family-friendly holiday rentals in Dennis Port

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Dennis Port family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Chatham
4.95 out of 5 average rating, 279 reviews

Slate House - a modern waterfront getaway

ChristyRating, 5 stars3 weeks ago
We enjoyed our stay—it was a quick 5-minute car ride to Main Street. We also enjoyed watching wildlife in the river! I wish we had brought our binoculars!
Guest favourite
Home in Eastham
4.99 out of 5 average rating, 80 reviews

The Penney House Retreat/Hot Tub Gardens, Peace

KathleenRating, 5 stars10 months ago
The Penny's House is close to all the beaches, great restaurants and the bike path is accessible via the back of the property which we loved. Her house is beautiful and the kitchen was fully stocked with all cookware you needed to make family dinners together. My family was very comfortable with out stay here! Thanks, Kathleen,Jack and family
Superhost
Home in South Chatham
4.85 out of 5 average rating, 59 reviews

Perfect for Group w/ Kids & Dogs w/ Hot Tub

KevinRating, 5 stars1 month ago
Stayed for a weekend with a few friends right before the Cape busy season and had a great time. Check-in was extremely easy, all instructions and rules were clear and reasonable, and check-out was very convenient and straight forward. The house matched all the pictures and was exactly as described, and everything was clean and well stocked. In the future I’ll look to stay at a Del Mar managed location again!
Flat in Dennis Port
5 out of 5 average rating, 16 reviews

BEACHfront RESORT OCEAN VIEW HANDICAP acc. CapeCod

EricRating, 5 stars11 months ago
Amazing stay and great host, thanks Eleonora!
Superhost
Home in West Dennis
4.79 out of 5 average rating, 171 reviews

Walk2Beach, HotTub, FirePit, PetsOk

NatalieRating, 5 stars1 month ago
Great stay! Place is in a quiet residential area, yet centrally located and easy to get places. Nice yard and hot tub was a plus (clean and good temp). We didn’t have a chance to use the fire pit, but outdoor furniture and sitting area was nice with space for everyone. House was very clean, beds comfortable. Host was very responsive. Would definitely stay again.
Guest favourite
Home in Dennis
4.92 out of 5 average rating, 50 reviews

Cape Cod Lakefront Home

JustinRating, 5 stars9 months ago
Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.
Top guest favourite
Home in Centerville, Barnstable
4.97 out of 5 average rating, 155 reviews

Luxury House 0.25 mi from Craigville Beach

AngieRating, 5 stars4 weeks ago
I had a wonderful experience staying at this Airbnb. The place was exactly as described—clean, cozy, and well-stocked with all the essentials. The host was friendly, responsive, and made check-in and out super easy. The neighborhood was quiet and felt very safe, with great local spots just a short walk or drive away. I’d absolutely stay here again and recommend it to anyone looking for a comfortable and convenient stay!
Guest favourite
Home in East Falmouth
4.9 out of 5 average rating, 60 reviews

Peaceful waterfront home with dock/ hot tub

ConorRating, 5 stars10 months ago
We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!

Family- and pet-friendly home rentals

Superhost
Cottage in Sandwich
4.86 out of 5 average rating, 400 reviews

Oceanfront Cottage w/Private Beach ~ Lil’ Sea Sass

YmanRating, 5 stars4 days ago
Great stay! The place was clean, cozy, and just like the photos. The host was kind and helpful. I’d definitely stay here again.
Guest favourite
Home in Brewster
4.81 out of 5 average rating, 100 reviews

Walk to Beach, Restaurants and Ocean Edge.

AnitaRating, 5 stars2 months ago
We had a great weekend at Elizabeth's place in Brewster. For us, the location was perfect with a beautiful walking beach <1/2 a mile down a quiet side street as well as being able to ride our bikes a short distance down a dirt road abutting the property to easily access the Cape Cod Rail Trail. The house was warm and cozy, with comfortable beds, and a well-stocked kitchen with everything needed to cook meals throughout our stay. We especially appreciated being about to bring our pup along and she enjoyed running out on the Brewster flats at low tide to chase seagulls and splash around at the edge of the ocean. We would happily come back to enjoy this wonderful spot again hopefully very soon!
Top guest favourite
Home in Brewster
4.98 out of 5 average rating, 187 reviews

SeaPeace Cottage-East Brewster Deck,Firepit,W/D AC

PaulRating, 5 stars8 months ago
We attended a wedding at the Ocean Edge Resort and we found Paige's home to be convenient to the venue and activities and a great alternative to staying on property. The home was clean and neat and had everything we needed. The weather turned out beautiful so we took full advantage of the outdoor space. I would highly recommend Paige's home to anyone who likes to be close to the beach, restaurants and golf, but far enough away to be quiet and peaceful.
Guest favourite
Cottage in Yarmouth
4.97 out of 5 average rating, 127 reviews

Walk 7/10 mile to Beaches*Summer Fri to Fri*

SharonRating, 5 stars3 weeks ago
Comfortable and cozy cottage to stay in. Bonnie was great at communicating, and the offer (didn't have to ask) to check in early was greatly appreciated. Even though the weather (Nor'easter) wasn't the best, the cottage was great. The gas fireplace was used and added to the warmth of the cottage. Little things that the cottage was stocked with was very helpful (dog bowls) even if weren't used. Just knowing the cottage has little details will have me renting again. Thank you!
Superhost
Home in Wellfleet
4.85 out of 5 average rating, 105 reviews

A Cape Escape with Water Views from Every Room

JonathanRating, 5 stars5 months ago
We stayed at Rob's place for a few days for New Year's Eve and it was great. The house was very comfortable for a few couples to hang out, cook some meals and enjoy the beautiful views. At low tide you can walk from the house down to the marsh and follow some rough trails or walk a little further to Lt. Island for some sandy beach. The wood stove made it great winter haven, to sit by the fire and enjoy the views of the tides rolling in and out. The architecture of the house is also interesting and reminiscent of other Wellfleet modernist homes.
Top guest favourite
Cottage in West Yarmouth
4.84 out of 5 average rating, 240 reviews

Charming Cottage near Beach and Ferry.

SaraRating, 5 stars2 weeks ago
We traveled to the cape for a youth soccer tournament and wanted to find a place with room for our family and dog. Daniel's cottage was perfect for our family of 4 - a nice cozy cottage with beach access, all the comforts of home, and a great location. Daniel was a great host - proactive friendly location and a clean house with everything we needed.
Guest favourite
Flat in Brewster
4.83 out of 5 average rating, 116 reviews

A quiet, private, unique spot in a great location!

CarlRating, 5 stars2 weeks ago
Second time there- we really enjoyed the cozy space and room for our dog. Space is great for a quick getaway to the cape.
Guest favourite
Home in Chatham
4.96 out of 5 average rating, 210 reviews

Studio cottage in Chatham Ma.

JeanetteRating, 5 stars1 month ago
Absolutely adorable! Would stay here again! Be sure to read the details when you get there (my fault I learned you can’t take 2 hot showers back to back…they do tell you that but I missed it). Great location. Perfect crash pad for a weekend as wedding guests!

Family-friendly home rentals with a pool

Cottage in Dennis Port
4.84 out of 5 average rating, 25 reviews

Adorable 2BR cottage with pool.

ColeenRating, 5 stars11 months ago
This is our 2nd stay at Marie’s cottage. We love the peaceful environment (patio area especially), the pool, the proximity to the local beach (1 mile) & the proximity to Nauset Beach (20 mins) and the outdoor shower.
Top guest favourite
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

EmilyRating, 5 stars7 months ago
This place was INCREDIBLE!! Marla and her family were so responsive and so welcoming!! This house was the cleanest I have ever stayed in. The furniture was so comfortable and cozy. I would HIGHLY recommend staying here! I hope to come back in the near future!! Thank you Marla and family for being such amazing hosts!!
Top guest favourite
Flat in Hyannis Port
4.84 out of 5 average rating, 51 reviews

1 bdrm 4ppl apartment,stairs,pool,no meals,deck

MichaelRating, 5 stars10 months ago
We stayed in the tree house suite. It had a lovely deck surrounded by trees and a great view of the sky. Craig and Ginny are as friendly a couple you will ever meet--always quick to answer questions and offer some great suggestions, Craig even offered to drop us off at a few places. They were so kind they felt like old friends. The beach is beautiful and a five minute walk away--which is great because they charge 25 bucks to park. So do the easy walk, and Ginny will provide chairs, towels, and umbrellas. Hyannis itself is a great place to walk around with lots of shops and great restaurants. We also took a ferry to Nantucket which was delightful, as well. I would visit them again without question. Go. You won't be disappointed. Michael and Rebecca
Cabin in Falmouth
4.66 out of 5 average rating, 596 reviews

Waterside Guest House

AidenRating, 5 stars2 weeks ago
Super responsive, great host. Very friendly, offered us the local newspaper with deals on places to go and everything. incredible space, right along the water. Thank you, Ron!
Top guest favourite
Cottage in Dennis Port
4.89 out of 5 average rating, 80 reviews

Bright and Lovely Cottage With Community Pool

KaylaRating, 5 stars2 weeks ago
Sonja's place was great for a weekend away! It was walkable to both the beaches of Dennisport as well as the center of Dennisport for the restaurants and shops. We had a lovely stay and really appreciate the help Sonja gave when we had questions!
Superhost
Apartment 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.
Home in Dennis Port
4.76 out of 5 average rating, 38 reviews

private pool, spacious, quiet private home,

SashaRating, 5 stars9 months ago
We loved our stay! The house is super family-friendly, the pool was amazing, and we found the house very cozy. There were plenty of cooking utensils/pots, which made cooking easy and a great grill and fire pit. Communication with Joe was super easy too.
Guest favourite
Cottage in Dennis Port
4.91 out of 5 average rating, 32 reviews

Cute Dennis Port Cottage with pool & A/C

KarenRating, 5 stars10 months ago
Perfect place to stay on the Cape. The house was clean and adorable, everything you need is there in a small little quiet area. It’s a quiet place in the middle of everything. We mostly ate in the area, and the food was great. We could get to Hyannis in a short drive. We took the Ferry to Martha’s Vineyard . Drove up to Provincetown and had a fun time watching the fisherman bring in their catch at the Chatham fish pier. We saw the seals as the tried to catch the fish that fell in the water. So this place is the perfect place to get away and be in the middle of everything you want on the Cape.

Quick stats about holiday rentals that are family-friendly in Dennis Port

  • Total rentals

    360 properties

  • Nightly prices starting at

    ₹6,031 before taxes and fees

  • Total number of reviews

    9.4K reviews

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    40 properties have a pool

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

Destinations to explore