
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!

2 Acre Waterfront Oasis Overlooking Waquoit Bay

Charming Cape House with Private Hot Tub !

Valentine's Retreat Hot Tub Fire Pit Trails Beach

On HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach
Family- and pet-friendly home rentals

Walk to OB Town & Beach | Family & Dog Friendly

Sweet Vineyard Haven Cottage

Lambert's Cove Retreat, Water view, Beach pass

Charming Cottage

Downtown Edgartown Home

Cozy Vacation Getaway On Bike Path

Charming Vacation Home in Oak Bluffs.

Bucolic, modern home near town, beaches
Family-friendly home rentals with a pool

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

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

Private 3bdrm Condo Tashmoo Woods

Beautiful Edgartown Colonial with heated pool.

Falmouth, Cozy Studio Near Old Silver Beach

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

Sunny 2bedroom condo w pool, walk to town

Private Pool, near beaches, 3 BR/3 BA, Central Air
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
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Private suite rentals Oak Bluffs
- Rentals with a fireplace Oak Bluffs
- Rentals with outdoor seating Oak Bluffs
- Rentals with a hot tub Oak Bluffs
- Pet-friendly rentals Oak Bluffs
- Rentals with breakfast Oak Bluffs
- Rentals with a kayak Oak Bluffs
- Rentals with lake access Oak Bluffs
- Rentals with a patio Oak Bluffs
- Rentals with beach access Oak Bluffs
- Flat rentals Oak Bluffs
- House rentals Oak Bluffs
- Beachfront rentals Oak Bluffs
- Bed and breakfasts Oak Bluffs
- Boutique hotel rentals Oak Bluffs
- Apartment rentals Oak Bluffs
- Hotel rentals Oak Bluffs
- Fitness-friendly rentals Oak Bluffs
- Rentals with a firepit Oak Bluffs
- Rentals with a washing machine and dryer Oak Bluffs
- Rentals with pools Oak Bluffs
- Waterfront rentals Oak Bluffs
- Rentals with an EV charger 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
- White Horse Beach
- Second Beach
- Horseneck Beach State Reservation
- Roger Williams Park Zoo
- Chapin Memorial Beach
- Island Park Beach
- Pinehills Golf Club
- Nauset Beach
- Lighthouse Beach
- South Shore Beach
- Inman Road Beach
- The Breakers