Family-friendly vacation rentals in Plymouth

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Plymouth

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

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Guest favorite

Apartment in Plymouth

4.82 out of 5 average rating, 328 reviews

The Harbor House - In The Center of Downtown

Amazing location in the heart of historic downtown Plymouth. Enjoy everything Plymouth has to offer right outside your door! Walk to restaurants, pubs, breweries, historical sites, antique shops, art studios, museums, beaches, parks, whale watching and deep sea fishing. The Harbor House is a remodeled, sparkling clean apartment offering all the comforts of home in a private 2 bedroom setting. Includes private parking, WiFi, smart TV, full kitchen and more in a safe, fun and convenient location.

Nov 19 – 26

R4,080 ZAR per night

Guest favorite

Place to stay in Wellfleet

4.97 out of 5 average rating, 166 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!

Oct 21 – 28

R3,137 ZAR per night

Guest favorite

Cabin in Cohasset

4.92 out of 5 average rating, 286 reviews

Lionsgate at Cohasset

Lionsgate is the perfect retreat to refresh the soul. Newly remodeled fully stocked kitchen with comfortable amenities provide a home away from feel. Enjoy a roaring fire in a rustic cabin during the winter or the coolness of a mini split in the summer. Cohasset, jewel of the South Shore is a quintessential New England seaside village located half way between Boston and Cape Cod. The ocean offers abundant recreation opportunities as well as plentiful parks for hiking and biking. A must visit.

Oct 8 – 15

R2,974 ZAR per night

Guest favorite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 308 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

Nov 29 – Dec 6

R2,168 ZAR per night

Guest favorite

Home in Plymouth

4.91 out of 5 average rating, 109 reviews

Spring & Summer dates still available, book NOW!

Warm weather and beach days are headed your way soon! Enjoy beaches, the Waterfront & Downtown - we are steps from both. Check out our walk-through video on You Tube. Type WhaleTailInt 2019 in the search for a virtual tour of the entire house. We are less than a block from many beaches, restaurants, nightlife and historical touring. Hop on the "T" and day trip to Boston for museums and culture, or head to Cape Cod for beaches galore and souvenir shopping! Summer is on the way so book today!

Feb 1 – 8

R6,277 ZAR per night

Guest favorite

Cottage in Plymouth

4.93 out of 5 average rating, 222 reviews

Ocean View Cottage

Charming cottage with an ocean view in a private setting seaside community with updated kitchen that does NOT include a stove however there is a cooktop, microwave and toaster oven, 3/4 bathroom w a shower. Firestick/RokuTV. It is ONE room, open concept with a comfortable memory foam easy fold out king couch. The cottage is separate from the house and has its own entrance w own parking for 2 cars. 1 mile from the beach and 5 miles from downtown. **PLEASE NOTE ONLY 2 PERSON OCCUPANCY**!!

Nov 15 – 20

R3,263 ZAR per night

Guest favorite

Home in Plymouth

4.92 out of 5 average rating, 171 reviews

Our Secret Garden

This beautiful 2.5 acre fully fenced in private property has gardens, an in-ground pool & pool house with an outdoor heated shower. Our home offers 2 kitchens, dining room seating 12, a great room, 3 bedrooms with private sitting areas & lower level with 2 bunk beds (bottoms are full beds) & exercise area. Outside are 2 grills & chiminea. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod. POOL can be HEATED for $500.00/Visit.

Feb 3 – 10

R7,666 ZAR per night

Guest favorite

Cottage in Plymouth

4.93 out of 5 average rating, 113 reviews

Shifting Sands Beachfront Cottage with Parking

A true oceanfront cottage experience awaits at the Shifting Sands! Beaches, sunsets, relaxation, and nearby Plymouth are part of this cottage experience. The Shifting Sands is the place to enjoy a magnificent sunrise or sunset, stargaze, take a leisurely stroll on the beach, or grill & eat oceanside. Your outdoor living room is the ocean & an unspoiled beach with our cottage perched in front offers incredible views! You can drive right up to the cottage & park & you're vacation starts.

Jan 21 – 28

R7,601 ZAR per night

Guest favorite

Home in Middleborough

4.94 out of 5 average rating, 296 reviews

Private retreat setting on 4 acres 1

Gatherings, parties, events, reunions, etc. with 8 or more total sleepers /non sleepers MUST be discussed prior to booking. A 5 minutes from Rte. 495, secluded, 2 bedroom 1200 sq.ft. apartment. Amenities include -- in-ground pool, horseshoe pits, tennis/basketball court, fully lit for night time use. Central air, full bath, eat in kitchen, Juliet balcony, private drive & entrances, 2 HD flat screen TV"s, Netflix, On Demand WIFI. Very comfortable for two or a couple with children.

Mar 2 – 9

R1,904 ZAR per night

Guest favorite

Home in Plymouth

4.94 out of 5 average rating, 211 reviews

PLYMOUTH CENTER - The Captain's House #1

A true downtown gem. Sparkling clean PRIVATE 1,600 sq ft HOUSE. Unbeatable location with all that Plymouth has to offer literally outside the door - restaurants, the harbor and historic sites (yet on a quiet street). Stylish, renovated 5 bedroom, 2 full bathrooms, laundry, a huge front porch and hidden backyard courtyard. Full kitchen, dining room, and living room. Park 2-3 cars in driveway. Central AC. A guest favorite that rarely disappoints.

Jan 27 – Feb 3

R7,730 ZAR per night

Guest favorite

Apartment 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!

Jan 30 – Feb 6

R2,476 ZAR per night

Guest favorite

Home in Plymouth

4.96 out of 5 average rating, 140 reviews

1 of a Kind Pond-Front Home, Minutes from Downtown

Pond-Front property boasts unparalleled privacy and charm. 5 minutes from shopping and downtown Plymouth. Located on a peninsula of land, water views are plentiful. Both ponds are tested yearly and safe for swimming, fishing, etc. Bring your furry friend to run in the back yard, your kids to play, or simply your friends to relax and catch some sun. Opportunities are endless!

Oct 24 – 31

R8,978 ZAR per night