Oak Bluffs vacation rentals

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Top-rated vacation rentals in Oak Bluffs

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

Guest favorite

Cottage in Tisbury

4.96 out of 5 average rating, 209 reviews

Not Your Great Aunt's Island Cottage

CAR FERRY RESERVATIONS AVAILABLE - 7/7-7/13, 7/27-8/3, 8/24-31 In town, 1930's winterized cottage, lovingly updated by architect-owner. • Stylish informal decor, open floor plan, outdoor terrace • 2 blocks to Main Street/harbor/ferry/town beach/movie theater/playhouse • Central Air / Daikin Emura Zoned A/C • Close to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

Oct 20 – 27

€ 522 per night
Guest favorite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 301 reviews

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!

Nov 16 – 23

€ 142 per night
Guest favorite

Guest suite in Oak Bluffs

4.99 out of 5 average rating, 101 reviews

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

Oct 21 – 28

€ 436 per night

Popular amenities for Oak Bluffs vacation 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

Oak Bluffs home rentals

Guest favorite

Home in Oak Bluffs

4.94 out of 5 average rating, 116 reviews

The Lighthouse

Mar 23 – 30

€ 471 per night
Superhost

Home in Oak Bluffs

4.78 out of 5 average rating, 101 reviews

Cozy Vacation Getaway On Bike Path

Sep 5 – 12

€ 556 per night
Guest favorite

Home in Edgartown

4.96 out of 5 average rating, 181 reviews

Brand new gorgeous 2 bedroom guest house.

May 1 – 8

€ 338 per night
Guest favorite

Home in Tisbury

4.98 out of 5 average rating, 244 reviews

Vineyard Retreat: Just a mile from Tisbury center

Jun 1 – 8

€ 476 per night
Guest favorite

Home in Edgartown

4.92 out of 5 average rating, 140 reviews

✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path

May 22 – 29

€ 547 per night
Guest favorite

Home in West Tisbury

4.98 out of 5 average rating, 183 reviews

West Tisbury Escape, Long Point Beach

Nov 11 – 18

€ 390 per night
Guest favorite

Home in Edgartown

5.0 out of 5 average rating, 113 reviews

Close to Edgartown Village Center!

Oct 23 – 30

€ 570 per night
Guest favorite

Home in West Tisbury

4.97 out of 5 average rating, 119 reviews

Secluded Up Island Cottage

Sep 16 – 23

€ 412 per night
Guest favorite

Home in Edgartown

4.89 out of 5 average rating, 109 reviews

Edgartown Village: Walk to Everything

Dec 1 – 8

€ 500 per night
Superhost

Home in Edgartown

4.86 out of 5 average rating, 138 reviews

Martha's Vineyard Vacation Home

Apr 14 – 21

€ 296 per night
Superhost

Home in Aquinnah

4.98 out of 5 average rating, 124 reviews

Martha's Vineyard Oceanview Retreat

Apr 14 – 21

€ 632 per night
Guest favorite

Home in Woods Hole

4.92 out of 5 average rating, 107 reviews

Juniper Point Cottage With Ocean View

Nov 2 – 9

€ 478 per night

Oak Bluffs cottage rentals

Guest favorite

Cottage in Tisbury

4.98 out of 5 average rating, 309 reviews

Martha's Vineyard Getaway Cottage

Dec 9 – 16

€ 314 per night
Guest favorite

Cottage in Mashpee

4.95 out of 5 average rating, 300 reviews

★The Islander | Steps From Water, Fire Pit, AC★

Sep 5 – 12

€ 281 per night
Guest favorite

Cottage in Sandwich

4.95 out of 5 average rating, 155 reviews

Waterfront Lake Cottage, Private Beach, Wow View!

Jan 9 – 16

€ 421 per night
Superhost

Cottage in Fairhaven

4.79 out of 5 average rating, 277 reviews

On the Beach Cottage in Fairhaven

Dec 11 – 18

€ 287 per night
Guest favorite

Cottage in Falmouth

4.94 out of 5 average rating, 133 reviews

“Cozy Cottage” on Great Bay

Dec 21 – 28

€ 214 per night
Guest favorite

Cottage in Barnstable

4.99 out of 5 average rating, 120 reviews

Beach Glass Cottage - Pond Front

Nov 14 – 21

€ 362 per night
Superhost

Cottage in Barnstable

4.89 out of 5 average rating, 119 reviews

Osterville Charming Cottage in the Heart of Wianno

Jun 25 – Jul 2

€ 452 per night
Superhost

Cottage in Barnstable

4.91 out of 5 average rating, 140 reviews

Cape Cottage - Walk to Beach, Ferries, and Town!

Mar 11 – 18

€ 313 per night
Guest favorite

Cottage in Oak Bluffs

4.94 out of 5 average rating, 51 reviews

55 Farm Pond Road, Oak Bluffs

Jun 1 – 8

€ 431 per night
Guest favorite

Cottage in Tisbury

5.0 out of 5 average rating, 25 reviews

Classic Vineyard Cottage - Steps to Beach/Downtown

Apr 8 – 15

€ 508 per night
Guest favorite

Cottage in Edgartown

5.0 out of 5 average rating, 54 reviews

Stroll to Edgartown, AC, NEW Remodel, NEW Listing!

Dec 20 – 27

€ 620 per night
Guest favorite

Cottage in Tisbury

4.97 out of 5 average rating, 33 reviews

WATERFRONT Cottage, Downtown w/ Beach

Apr 19 – 26

€ 941 per night

Oak Bluffs condo rentals

Guest favorite

Condo in Oak Bluffs

4.95 out of 5 average rating, 21 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Jun 16 – 23

€ 831 per night
Guest favorite

Condo in Oak Bluffs

5.0 out of 5 average rating, 6 reviews

Ocean View Gem, Walk to it All, No Car Needed!

Sep 12 – 19

€ 993 per night
Guest favorite

Condo in Tisbury

4.91 out of 5 average rating, 45 reviews

Sunny 2bedroom condo w pool, walk to town

Nov 10 – 17

€ 429 per night
Guest favorite

Condo in Mashpee

5.0 out of 5 average rating, 54 reviews

The Cape Escape with Private Pool

Jun 5 – 12

€ 599 per night
Guest favorite

Condo in Tisbury

4.98 out of 5 average rating, 44 reviews

Short Walk into Town - Nice Comfortable Reasonable

Nov 26 – Dec 3

€ 500 per night
Superhost

Condo in Vineyard Haven

5.0 out of 5 average rating, 17 reviews

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

Oct 19 – 26

€ 355 per night
Superhost

Condo in Tisbury

4.76 out of 5 average rating, 17 reviews

Lovely studio above garage

Jun 9 – 16

€ 270 per night
Superhost

Condo in Tisbury

4.91 out of 5 average rating, 45 reviews

Private 3bdrm Condo Tashmoo Woods

Jan 9 – 16

€ 488 per night
Guest favorite

Condo in Mattapoisett

4.95 out of 5 average rating, 22 reviews

Brand new! Whole apartment, huge tub, full kitchen

Oct 19 – 26

€ 276 per night
Guest favorite

Condo in Mashpee

4.97 out of 5 average rating, 99 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Jun 24 – Jul 1

€ 434 per night
Guest favorite

Condo in Falmouth

4.97 out of 5 average rating, 34 reviews

Location, location! Historic Downtown Falmouth!

Sep 30 – Oct 7

€ 235 per night
Superhost

Condo in Barnstable

4.52 out of 5 average rating, 61 reviews

Oceanside Cottage Apt across Craigville beach

Sep 27 – Oct 4

€ 398 per night

Quick stats about vacation 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

€ 28 before taxes and fees

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 30 condo rentals, over 410 house rentals to over 50 cottage 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 630 vacation rentals in Eastville, over 630 vacation rentals in East Chop, and over 630 vacation rentals in West Chop.

  • Are there vacation rentals with a dedicated workspace in Oak Bluffs?

    Yes! Work meets play with ease at over 320 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 150 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cottage rentals in Oak Bluffs?

    Experience the best of Oak Bluffs with our cottage rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cottage rentals in Oak Bluffs have a bbq area?

    Absolutely! We offer over 30 cottage rentals with a bbq area in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Oak Bluffs have self check-in?

    Absolutely! We offer over 20 cottage rentals with self check-in in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Oak Bluffs have wifi?

    Absolutely! We offer over 50 cottage rentals with wifi 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 10 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 a gym?

    Absolutely! We offer over 20 house rentals with a gym in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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