
Family-friendly holiday rentals in Oak Bluffs
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Oak Bluffs
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Bluffs family-friendly rentals
Family-friendly home rentals with a hot tub

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course

Vineyard Meadow Writer's Cottage

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

Oak bluffs cottage Perfect place to honeymoon!

Charming Cape House with Private Hot Tub !

Valentine's Retreat Hot Tub Fire Pit Trails Beach

Spacious 2BR by the Sea in Falmouth

Seacoast Shores Oasis-Steps From Private Beach Bay
Family- and pet-friendly home rentals

Sunny, Spacious Vineyard Retreat

Katama Barn

Sweet Vineyard Haven Cottage

Sweet 3BR Cape in West Tisbury, MV

Lambert's Cove Retreat, Water view, Beach pass

Secluded Up Island Cottage

Walk to Town! 4 blocks to harbor and beach!

The Sea-Cret Garden, Guest Apartment
Family-friendly home rentals with a pool

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

Private 3bdrm Condo Tashmoo Woods

Beautiful Edgartown Colonial with heated pool.

Waterside Guest House

Falmouth, Cozy Studio Near Old Silver Beach

Sunny 2bedroom condo w pool, walk to town

Private Pool, near beaches, 3 BR/3 BA, Central Air

Lovely two - story private cottage.
Quick stats about holiday rentals that are family-friendly in Oak Bluffs
Total rentals
540 properties
Nightly prices starting at
£59 before taxes and fees
Total number of reviews
13K reviews
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
250 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- South Jersey Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Rentals with outdoor seating Oak Bluffs
- Rentals with a washing machine and dryer Oak Bluffs
- Apartment rentals Oak Bluffs
- Rentals with a kayak Oak Bluffs
- Hotel rentals Oak Bluffs
- Rentals with breakfast Oak Bluffs
- House rentals Oak Bluffs
- Rentals with a fireplace Oak Bluffs
- Rentals with pools Oak Bluffs
- Boutique hotel rentals Oak Bluffs
- Rentals with a patio Oak Bluffs
- Fitness-friendly rentals Oak Bluffs
- Rentals with lake access Oak Bluffs
- Rentals with an EV charger Oak Bluffs
- Bed and breakfasts Oak Bluffs
- Rentals with a hot tub Oak Bluffs
- Pet-friendly rentals Oak Bluffs
- Private suite rentals Oak Bluffs
- Flat rentals Oak Bluffs
- Beachfront rentals Oak Bluffs
- Rentals with a firepit Oak Bluffs
- Waterfront rentals Oak Bluffs
- Rentals with beach access Oak Bluffs
- Family-friendly rentals Dukes County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Cape Cod
- Mayflower Beach
- Cape Cod National Seashore
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Point Judith Country Club
- Easton Beach
- Oakland Beach
- Coast Guard Beach
- Horseneck Beach State Reservation
- White Horse Beach
- Second Beach
- Roger Williams Park Zoo
- Chapin Memorial Beach
- Pinehills Golf Club
- Nauset Beach
- Island Park Beach
- Lighthouse Beach
- The Breakers
- South Shore Beach
- Goddard Memorial State Park