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!
27 Dec – 3 Jan
£144 per night
4.94 out of 5 average rating, 300 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
27 May – 3 JunIndividual Host,
£357 per night
4.99 out of 5 average rating, 101 reviews
Superhost
Home in Oak Bluffs
Waterview, Private, Walk to Beach, Mile to Town
Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Please view our entire listing and reviews for more about our unique property.
18–25 OctIndividual Host,
£438 per night
4.82 out of 5 average rating, 179 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
The Black Dog Tavern52 locals recommend
The Barn32 locals recommend
Linda Jean's Restaurant48 locals recommend

Other great holiday rentals in Oak Bluffs

Guest favourite
Flat in Oak Bluffs
Downtown Oak Bluffs, 2nd floor Harbor house.
16–23 OctIndividual Host,
£358 per night
4.92 out of 5 average rating, 62 reviews
Guest favourite
Apartment in Oak Bluffs
LOCATION LOCATION!! Ocean- View TOP Floor Condo
15–22 SeptIndividual Host,
£706 per night
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Oak Bluffs
Airy and welcoming O.B apartment
27 Aug – 3 Sept
£670 per night
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Oak Bluffs
#CozyBluffs #Oak Bluffs | walk to town/ferry/beach
6–13 JanIndividual Host,
£542 per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
11–18 DecIndividual Host,
£176 per night
4.98 out of 5 average rating, 64 reviews
Guest favourite
Flat in Oak Bluffs
Martha's Vineyard Chic Getaway
26 Aug – 2 SeptProfessional Host,
£602 per night
4.99 out of 5 average rating, 72 reviews
Guest favourite
Home in Oak Bluffs
Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course
10–17 Nov
£673 per night
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
4–11 Sept
£873 per night
4.92 out of 5 average rating, 12 reviews
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
10–17 Jun
£731 per night
5.0 out of 5 average rating, 45 reviews
Guest favourite
Home in Oak Bluffs
Vineyard Stroll
28 Oct – 4 NovIndividual Host,
£606 per night
4.93 out of 5 average rating, 70 reviews
Guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3–10 May
£619 per night
4.96 out of 5 average rating, 74 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs Cottage - Walk to Town & Beach
5–12 DecIndividual Host,
£544 per night
4.98 out of 5 average rating, 47 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