Holiday rentals in Oak Bluffs

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Top-rated holiday rentals in Oak Bluffs

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!
1–8 Nov
£135 per night
4.94 out of 5 average rating, 299 reviews
Guest favourite
Guest suite in Oak Bluffs
Sea View Waterfront Beachfront Apartment
Prime location- right across the street from a sandy beach, a few minutes walk to the harbor, downtown, and transportation (boat, bus, etc). This beautiful street-level one-bedroom apartment sits across the street from the ocean, where you can take a dip and enjoy the beach. The apartment was recently redone and has a small bedroom with a queen size bed, small bathroom, full kitchen, and living room area with pull-out couch. Convenient to take the ferry into Oak Bluffs and walk to the apartment
25 Aug – 1 SeptIndividual Host,
£459 per night
4.99 out of 5 average rating, 101 reviews
Guest favourite
Home in Oak Bluffs
Sweet little post and beam
A 700 sq ft post& beam guest house that sleeps 2 people. Open kitchen, living, dining area with full bath. Stairs lead to a full second story bedroom- a queen size bed, half bath, separate seating area. Private back patio and outdoor shower. Cozy off season cottage as well- radiant heat and AC. Central location to everything you want to see! Easy bike to town/beach. Very quiet and spacious. Everyone says "so much nicer in person than in the photos". Come see for yourself!
18–25 AprIndividual Host,
£317 per night
4.97 out of 5 average rating, 229 reviews

Popular amenities for Oak Bluffs holiday rentals

Stay near Oak Bluffs's top sights

Inkwell Beach31 locals recommend
Lookout Tavern52 locals recommend
Nancy's Restaurant42 locals recommend
Jaws Bridge21 locals recommend
The Black Dog Tavern52 locals recommend
The Barn32 locals recommend

Other great holiday rentals in Oak Bluffs

Guest favourite
Cottage in Oak Bluffs
Charming water-front cottage on Martha's Vineyard!
4–11 FebIndividual Host,
£365 per night
4.93 out of 5 average rating, 132 reviews
Guest favourite
Flat in Oak Bluffs
Sunny Studio Apartment on Martha's Vineyard
24 Nov – 1 DecIndividual Host,
£199 per night
4.97 out of 5 average rating, 161 reviews
Guest favourite
Home in Oak Bluffs
Unique Luxury Yurt w/ Free kayaking
3–10 May
£407 per night
4.92 out of 5 average rating, 200 reviews
Guest favourite
Cottage in Oak Bluffs
Best location!!! Beach & Town 5min walk 113R
2–9 MayIndividual Host,
£217 per night
4.9 out of 5 average rating, 189 reviews
Guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4–11 NovIndividual Host,
£546 per night
4.93 out of 5 average rating, 164 reviews
Guest favourite
Guest suite in West Tisbury
Loft Guest Suite in Modern Barn House
2–9 FebIndividual Host,
£112 per night
4.94 out of 5 average rating, 101 reviews
Guest favourite
Home in Edgartown
Brand new gorgeous 2 bedroom guest house.
20–27 NovIndividual Host,
£155 per night
4.96 out of 5 average rating, 177 reviews
Guest favourite
Guest house in Oak Bluffs
Coastal Bungalow
17–24 Mar
£319 per night
5.0 out of 5 average rating, 48 reviews
Guest favourite
Flat in Oak Bluffs
Downtown Oak Bluffs, 2nd floor Harbor house.
12–19 JanIndividual Host,
£319 per night
4.92 out of 5 average rating, 62 reviews
Guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
1–8 Apr
£503 per night
4.92 out of 5 average rating, 12 reviews
Guest favourite
Guest suite in Oak Bluffs
Hart Suite- Warm & Cozy Get Away, Free EV Charging
5–12 AprProfessional Host,
£165 per night
4.88 out of 5 average rating, 56 reviews
Guest favourite
Home in Oak Bluffs
Airy and welcoming O.B apartment
22–29 Jun
£480 per night
5.0 out of 5 average rating, 10 reviews

Quick stats about holiday rentals in Oak Bluffs

Total rentals

680 properties

Rentals with a pool

80 properties have a pool

Pet-friendly rentals

150 properties allow pets

Family-friendly rentals

460 properties are a good fit for families

Total number of reviews

23K reviews

Nightly prices starting at

£24 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Dukes County
  5. Oak Bluffs