
Vacation rentals in Oak Bluffs
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Top-rated vacation rentals in Oak Bluffs
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Bluffs vacation rentals
Oak Bluffs house rentals

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

Walk to OB Town & Beach | Family & Dog Friendly

Juniper Point Cottage With Ocean View

Carolyn's Vineyard Haven

Sunny, Spacious Vineyard Retreat

Vineyard Haven Walk to Ferry

Valentine's Retreat Hot Tub Fire Pit Trails Beach

Close to Edgartown Village Center!
Oak Bluffs cottage rentals

Spectacular Beach- front home, includes linen

Quaint Cape Cod Cottage on a Private Beach!

One Bedroom Cottage in Vineyard Haven

“Cozy Cottage” on Great Bay

In town Cozy-Cottage-Glam w/ Fab backyard 2bd/2B

Martha's Vineyard Getaway Cottage

Charming Cottage

Island Charmer!
Oak Bluffs condo rentals

Heart of downtown, walk to ferry, bikeway & beach!

Short Walk into Town - Nice Comfortable Reasonable

1BR w/ Fireplace & Beach Access | Pool + Hot Tub

Relax....You're on Island Time......

Private 3bdrm Condo Tashmoo Woods

Sunny 2bedroom condo w pool, walk to town

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Martha’s Vineyard Condo * Near Ferry
Quick stats about vacation rentals in Oak Bluffs
Total rentals
770 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
25K reviews
Family-friendly rentals
540 properties are a good fit for families
Pet-friendly rentals
180 properties allow pets
Rentals with a pool
40 properties have a pool
Frequently Asked Questions
What types of vacation rentals are available in Oak Bluffs?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Oak Bluffs. From over 50 cottage rentals, over 30 condo rentals to over 480 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Where should I stay in Oak Bluffs?
Make yourself at home in Oak Bluffs by choosing from our most frequently booked neighborhoods. We have over 720 vacation rentals in West Chop, over 720 vacation rentals in East Chop, and over 720 vacation rentals in Eastville.
Are there vacation rentals with a dedicated workspace in Oak Bluffs?
Yes! Work meets play with ease at over 300 vacation rentals in Oak Bluffs featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Oak Bluffs?
Four-legged friends are welcome in Oak Bluffs. Choose from more than 180 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Oak Bluffs?
Experience the best of Oak Bluffs with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oak Bluffs have a bbq area?
Absolutely! We offer over 240 house rentals with a bbq area in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Bluffs have self check-in?
Absolutely! We offer over 160 house rentals with self check-in in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Are there Oak Bluffs house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Oak Bluffs, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Oak Bluffs have wifi?
Absolutely! We offer over 480 house rentals with wifi in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Bluffs have a gym?
Absolutely! We offer over 30 house rentals with a gym in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
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- Rentals with outdoor seating Oak Bluffs
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Point Judith Country Club
- Coast Guard Beach
- Oakland Beach
- Onset Beach
- Roger Williams Park Zoo
- Sandwich Glass Museum
- Lighthouse Beach
- Second Beach
- Horseneck Beach State Reservation
- Cahoon Hollow Beach
- Owen Park Beach
- Pinehills Golf Club
- Nickerson State Park
- South Shore Beach
- Island Park Beach
- Scusset Beach
- Inman Road Beach
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