Family-friendly holiday rentals in Dennis

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Dennis

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Tiny home in Dennis Port

4.81 out of 5 average rating, 436 reviews

★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes

Welcome to SAND PEBBLE COTTAGE! We are PET FRIENDLY! This 300sq.ft "TINY HOUSE" is 0.4 mi from the ocean beach & 1/2 mi from Dennisport village At the end of a cul-de-sac, this tiny cottage has everything you need ✅ 4/10mi to beach & village ✅ Kitchen w/marble counters ✅ Combo W/D unit ✅ TV ✅ Deck w/furniture & charcoal BBQ ✅ Parking-2 cars ✅ Separate bedroom ✅ Full A/C ✅ Bring your sheets/towels-we do not provide linens ✅ Pet friendly-only 1 pet as the cottage is tiny $25/nt

1–8 Mar

$187 SGD per night

Guest favourite

Guest suite in Yarmouth

4.85 out of 5 average rating, 249 reviews

Old Cape Cottage

I'm the Resident Host here for this simple old cape cottage moved over here from Nantucket years ago now used as airbnb furnished in antiques early attic has a cozy warm feeling about it located near lewis bay or nantucket sound Walking less than 10 minutes from two local beaches Cottage is best suited for one or 2 adults Has two bedrooms each room has one full bed in it. Bathroom off hall between bedrooms Linens towels provided Secured parking area Beds made up in advance No cleaning fees jon

30 Nov – 7 Dec

$218 SGD per night

Guest favourite

Cottage in Dennis

4.94 out of 5 average rating, 102 reviews

Steps to the Beach Kid Friendly

Sip your coffee on the patio or at the water with the sandpipers , spend some family time at the swings, making sandcastles or swimming in the warmer waters of Nantucket sound. It's all just footsteps from your door! Nip back to the cottage to cool off before heading out to enjoy the local attractions. You’ll also be just 3 miles from the bike trail! Return for a blissful end to your day watching a beautiful Cape Cod beach sunset and enjoying the starry sky. *Positive reviews required please

9–16 May

$378 SGD per night

Guest favourite

Place to stay in Wellfleet

4.98 out of 5 average rating, 164 reviews

WoodsideTiny House near Wellfleet Bay

Our tiny house tucked under trees is the perfect getaway. Walk past our orchard to get to your "Romantic Hideaway". This special rental has a private, sunny deck, a Nordic shower, stained glass windows and a library of books/vinyls. Set back from a quiet road on our property, this little gem is walking distance to Wellfleet's center, harbor & many restaurants, & just minutes drive from National Seashore beaches & ponds. A fun time in bustling Provincetown awaits you only 15 miles down the road!

9–16 Oct

$226 SGD per night

Guest favourite

Cottage in Dennis

4.95 out of 5 average rating, 191 reviews

The Strandloper / Beachwalker Cottage

This very clean and spacious 1 bedroom cottage has AC, is within walking distance to two public Nantucket Sound Beaches and is centrally located on Cape Cod. The vaulted ceilings and ample array of windows gives off natural light and a sense of space. FYI The cottage's name, The Strandloper, the Beachwalker, is a member of an extinct tribe of Khoikhoi Bushmen who lived on seafood gathered along the beaches of Southern Africa. Walking beaches is just as special today as it was a millennium ago.

10–17 Oct

$275 SGD per night

Guest favourite

Apartment in Dennis

4.99 out of 5 average rating, 172 reviews

Studio, 300 yards to Glendon Beach; Seahorse#2

Newly renovated, 250 sq ft studio at Near Beach Rentals. 300 yards to Glendon Beach means you can head to the beach in the morning and you're close enough to walk back for lunch. Fully furnished studio includes a queen bed and a fold down couch, kitchen with stove, fridge, coffee maker and microwave, air conditioning, 40" smart TV, newly renovated bathroom, Wifi, and access to the shared courtyard with grills and furniture. **(6) total units makes NBR a great place for larger gatherings!!!

12–19 Oct

$171 SGD per night

Guest favourite

Cottage in Dennis

4.94 out of 5 average rating, 216 reviews

Walk to Beach - Experience Dennis Beach House - AC

A quaint, cozy, well-decorated & well-equipped Cape Cod cottage located .2 miles away from Sea St Beach and a variety of other bars/restaurants, coffee shops and more. The house sleeps 5 people comfortably and has 1 small bathroom. Kitchen is fully stocked. 4-6 bath towels will be provided. The house has many smart home tech amenities, central air, Temperpedic mattresses, and a lovely & large outdoor space/back deck. First time booking on Airbnb? Save using link: www.airbnb.com/c/brianm30025

16–23 Dec

$230 SGD per night

Guest favourite

Flat in Harwich

4.9 out of 5 average rating, 263 reviews

The Secret Garden

Bright and spacious garden level apartment. One floor living, one queen bedroom, private bath, living room with queen pullout and limited kitchenette. Tranquil setting. Your own entrance and patio. A mile to Pleasant Bay, Eastward Ho golf course and Wequassett Inn, shopping, restaurants and beach. Your own private patio. Walk the labyrinth, gardens and fairy gardens. Take an outdoor shower. Cable TV in bedroom as well as living room plus wifi. The hosts live on the top floor of the home.

6–13 Mar

$194 SGD per night

Guest favourite

Home in Dennis

4.92 out of 5 average rating, 168 reviews

SUMMERS OFF CAPE HOUSE

All new paver patio and landscaping with enormous back yard. Spacious home on large corner lot just 5 minute walk to downtown Dennis Port or Inman Beach. Fully stocked kitchen. Huge LR w/ 2 couches, large fireplace and TV/DVD. BD#1 has a queen bed with a 1/2 bath ensuite. BD#2 has a queen bed. BD#3 has 2 twin over full bunk beds as well as pack n'play for infants. Covered front porch, screened in side porch, gas and charcoal grill, horseshoe pit and spacious outdoor shower.

22–29 Dec

$237 SGD per night

Guest favourite

Home in Dennis

4.98 out of 5 average rating, 247 reviews

Shirley's Place - Pet Friendly Sleeps Six!

Cozy, clean and bright! PET FRIENDLY! (PRE APPROVAL required) All amenities provided for an enjoyable and relaxing family vacation or quick get-a-way! Three car driveway and private outdoor shower. Five minute walk to Dennis Port Main Street shopping, restaurants, yoga, Pet Salon, and Town playground. South Side Beaches and Ponds just 1 mile away as well as Cape Cod Bike Trail Yarmouth to Provincetown minutes away! Pet friendly beaches mid September - Mid May.

29 Oct – 5 Nov

$265 SGD per night

Guest favourite

Guest house in Yarmouth

4.96 out of 5 average rating, 183 reviews

One bedroom guest house on beautiful Cape Cod

Second level guest apartment with one bedroom, bathroom, kitchen, large walk-in closet and living room. Just about everything you need to feel at home. There is A/C in the bedroom and the living area is well vented and has a large ceiling fan. Two golf courses are within 3/4 of a mile, public access beach and boat ramp are within 1 mile. You will also find kayaking, bike trails, walking trails and many other Cape Cod amenities just a short drive away.

21–28 Mar

$235 SGD per night

Guest favourite

Flat in Barnstable

4.99 out of 5 average rating, 231 reviews

Your dog will love it here and you will too.

If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

19–26 Feb

$179 SGD per night