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
Home in Oak Bluffs
4.94 out of 5 average rating, 116 reviewsThe Lighthouse
17–24 Sep
Home in Tisbury
4.98 out of 5 average rating, 248 reviewsSunny, Spacious Vineyard Retreat
14–21 Sep
Home in Oak Bluffs
4.78 out of 5 average rating, 217 reviewsCentral location for your vacation
22–29 Oct
Home in Edgartown
5.0 out of 5 average rating, 116 reviewsClose to Edgartown Village Center!
18–25 Oct
Home in West Tisbury
4.98 out of 5 average rating, 183 reviewsWest Tisbury Escape, Long Point Beach
14–21 Oct
Home in West Tisbury
4.98 out of 5 average rating, 122 reviewsSecluded Up Island Cottage
18–25 Sep
Home in Edgartown
4.92 out of 5 average rating, 140 reviews✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path
5–12 Oct
Home in Oak Bluffs
5.0 out of 5 average rating, 13 reviewsCoastal Chic Cape Centrally Located Oak Bluffs, MA
12–19 Nov
Family-friendly apartment rentals
Flat in Tisbury
4.92 out of 5 average rating, 102 reviewsHarbor view apartment, a quick walk from the ferry
5–12 Jun
Flat in Tisbury
4.89 out of 5 average rating, 132 reviewsMartha's Vineyard Pied-á-terre #2 Vineyard Haven
10–17 Nov
Flat in Falmouth
4.98 out of 5 average rating, 118 reviewsModern Luxury Apt. | 7 min from Commons
14–19 Oct
Flat in Tisbury
4.83 out of 5 average rating, 288 reviews"Island Home" 1 BR Suite w/Harbor View- downtown
17–24 Jul
Flat in Edgartown
4.94 out of 5 average rating, 174 reviewsThe Osprey - Short walk to Edgartown & beach
18–25 Apr
Flat in New Bedford
4.99 out of 5 average rating, 100 reviewsOne Bedroom in-law near beach with breakfast
19–26 Oct
Flat in Barnstable
4.99 out of 5 average rating, 231 reviewsYour dog will love it here and you will too.
19–26 Feb
Flat in Tisbury
4.83 out of 5 average rating, 162 reviewsQuaint Vineyard Escape
15–22 Nov
Family-friendly apartment rentals
Apartment in Mashpee
4.97 out of 5 average rating, 101 reviewsSleep 6 @ New Seabury w/ Pool Access, All Seasons!
8–15 Feb
Apartment in Oak Bluffs
4.95 out of 5 average rating, 21 reviewsLOCATION LOCATION!! Ocean- View TOP Floor Condo
22–29 Sep
Apartment in Oak Bluffs
5.0 out of 5 average rating, 6 reviewsOcean View Gem, Walk to it All, No Car Needed!
23–30 Sep
Apartment in Tisbury
4.91 out of 5 average rating, 45 reviewsSunny 2bedroom condo w pool, walk to town
25 Sep – 2 Oct
Apartment in Mattapoisett
4.97 out of 5 average rating, 31 reviewsBrand new! Whole apartment, huge tub, full kitchen
5–12 Nov
Apartment in Tisbury
4.98 out of 5 average rating, 44 reviewsShort Walk into Town - Nice Comfortable Reasonable
18–25 Sep
Apartment in Vineyard Haven
5.0 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
26 Dec – 2 Jan
Apartment in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
19–26 Apr
Quick stats about holiday rentals that are kid-friendly in Oak Bluffs
Total rentals
130 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
120 properties are a good fit for families
Total number of reviews
4.8T reviews
Nightly prices starting at
₹5,004 before taxes and fees
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