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Kid-friendly holiday rentals in Oak Bluffs
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Oak Bluffs
Guests agree: these family-friendly rentals 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
Kid-friendly house rentals
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Home in Edgartown
5 out of 5 average rating, 128 reviewsClose to Edgartown Village Center!
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Home in Edgartown
4.92 out of 5 average rating, 144 reviews✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path
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Home in West Tisbury
4.97 out of 5 average rating, 132 reviewsSecluded Up Island Cottage
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Home in Edgartown
4.89 out of 5 average rating, 115 reviewsEdgartown Village: Walk to Everything
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Home in Oak Bluffs
5 out of 5 average rating, 18 reviewsVineyard Vacation, 3-Bedroom, Hot-tub, Golf course
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Home in Oak Bluffs
4.9 out of 5 average rating, 31 reviewsNautical Oasis Walking Distance to Downtown OB
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Home in Oak Bluffs
5 out of 5 average rating, 17 reviewsDiscounted Price! Walk to OB, AC, WiFi, New Home!
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Home in Oak Bluffs
4.97 out of 5 average rating, 75 reviewsArrowsmith Cottage-Oak Bluffs near Eastville Beach
Family-friendly apartment rentals
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Rental unit in New Bedford
4.99 out of 5 average rating, 106 reviewsOne Bedroom in-law near beach with breakfast
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Rental unit in Edgartown
4.94 out of 5 average rating, 182 reviewsThe Osprey - Short walk to Edgartown & beach
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Rental unit in Tisbury
4.83 out of 5 average rating, 294 reviews"Island Home" 1 BR Suite w/Harbor View- downtown
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Rental unit in Falmouth
4.99 out of 5 average rating, 146 reviewsModern Luxury Apt. | 7 min from Commons
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Rental unit in Barnstable
4.99 out of 5 average rating, 242 reviewsYour dog will love it here and you will too.
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Rental unit in Fairhaven
4.97 out of 5 average rating, 220 reviewsHistoric Fairhaven Village Garden-Level Suite
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Rental unit in East Falmouth
4.96 out of 5 average rating, 293 reviewsIn-law apt. with all the amenities of Home.
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Rental unit in Tisbury
4.84 out of 5 average rating, 164 reviewsQuaint Vineyard Escape
Family-friendly apartment rentals
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Apartment in New Seabury
4.97 out of 5 average rating, 115 reviewsSleep 6 @ New Seabury w/ Pool Access, All Seasons!
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Apartment in New Bedford
4.81 out of 5 average rating, 118 reviewsModern Downtown Condo!
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Apartment in Tisbury
4.91 out of 5 average rating, 58 reviewsSunny 2bedroom condo w pool, walk to town
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Apartment in Oak Bluffs
4.7 out of 5 average rating, 10 reviewsOcean View Gem, Walk to it All, No Car Needed!
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Apartment in Vineyard Haven
5 out of 5 average rating, 18 reviewsRelax....You're on Island Time......
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Apartment in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
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Apartment in Tisbury
4.98 out of 5 average rating, 46 reviewsShort Walk into Town - Nice Comfortable Reasonable
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Apartment in Tisbury
4.79 out of 5 average rating, 24 reviewsLovely studio above garage
Quick stats about holiday rentals that are kid-friendly in Oak Bluffs
Total rentals
140 properties
Nightly prices starting at
£117 before taxes and fees
Total number of reviews
5.1K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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