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.

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Guest favorite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 307 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!

Dec 28 – Jan 4

G$28,791 GYD 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

Sep 1 – 8

G$94,881 GYD per night

Guest favorite

Home in Oak Bluffs

4.93 out of 5 average rating, 168 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and the outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, 6/21) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Mar 28 – Apr 4

G$128,569 GYD per night

Guest favorite

Apartment in Oak Bluffs

4.97 out of 5 average rating, 161 reviews

Sunny Studio Apartment on Martha's Vineyard

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

Jun 11 – 18

G$45,459 GYD per night

Guest favorite

Home in Edgartown

4.96 out of 5 average rating, 186 reviews

Brand new gorgeous 2 bedroom guest house.

This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

Dec 1 – 8

G$32,741 GYD per night

Superhost

Home in Oak Bluffs

4.91 out of 5 average rating, 126 reviews

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Nov 9 – 16

G$168,857 GYD per night

Guest favorite

Apartment in Tisbury

4.92 out of 5 average rating, 102 reviews

Harbor view apartment, a quick walk from the ferry

This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, the Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance! The new Martha's Vineyard Museum is a five minute walk, down the same street. My place is great for couples and solo adventurers.

May 3 – 10

G$35,801 GYD per night

Guest favorite

Home in Oak Bluffs

4.92 out of 5 average rating, 205 reviews

Unique Luxury Yurt w/ Free kayaking

Step into this unique yurt house! As soon as you walk in, you'll be greeted with a one-of-a-kind experience, from the textured concrete floors to the large circular skylight. Every detail is carefully planned, and you'll have the opportunity to unwind in a spacious private yard. Spend your evenings stargazing, take advantage of complimentary paddling, participate in our scheduled chicken feedings, do yoga in the roomy loft, and revel in the splendor of your exclusive island yurt!

Feb 2 – 9

G$56,352 GYD per night

Guest favorite

Home in Oak Bluffs

4.97 out of 5 average rating, 229 reviews

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!

Nov 24 – Dec 1

G$83,670 GYD per night

Guest favorite

Apartment in Oak Bluffs

4.88 out of 5 average rating, 146 reviews

WATERFRONT PENTHOUSE OAK BLUFFS

3rd fl Waterfront Oak Bluffs Harbor Penthouse- Sleeps 2 comfortably-3 in a pinch. (356sqft) . Queen bed & a reclining futon couch. With kitchenette & amazing harbor views, you cannot get closer to harbor, unless you fell in. Located above a seasonal restaurant, with 4 open air restaurants (2 on each side) Guests must bring they’re own LINENS and TOWELS. Bed is queen. There is a futon reclining couch that could be slept on, but I’d prefer not to have it used that way.

May 23 – 30

G$80,539 GYD per night

Guest favorite

Guest suite in Oak Bluffs

4.98 out of 5 average rating, 132 reviews

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

Nov 7 – 14

G$46,030 GYD per night

Guest favorite

Home in Oak Bluffs

4.9 out of 5 average rating, 101 reviews

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.

Jun 20 – 27

G$190,566 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oak Bluffs vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Oak Bluffs's top sights

Inkwell Beach31 locals recommend

Nancy's Restaurant42 locals recommend

Lookout Tavern52 locals recommend

The Black Dog Tavern52 locals recommend

The Barn32 locals recommend

Linda Jean's Restaurant48 locals recommend

Other great vacation rentals in Oak Bluffs

Superhost

Home in Oak Bluffs

4.82 out of 5 average rating, 179 reviews

Waterview, Private, Walk to Beach, Mile to Town

May 27 – Jun 3

G$118,978 GYD per night

Guest favorite

Home in Oak Bluffs

4.94 out of 5 average rating, 116 reviews

The Lighthouse

Sep 11 – 18

G$90,667 GYD per night

Guest favorite

Home in Oak Bluffs

4.78 out of 5 average rating, 217 reviews

Central location for your vacation

Oct 15 – 22

G$60,050 GYD per night

Superhost

Home in Oak Bluffs

4.79 out of 5 average rating, 103 reviews

Cozy Vacation Getaway On Bike Path

Nov 1 – 8

G$57,716 GYD per night

Guest favorite

Home in Edgartown

5.0 out of 5 average rating, 115 reviews

Close to Edgartown Village Center!

Nov 16 – 23

G$114,454 GYD per night

Guest favorite

Home in Tisbury

4.98 out of 5 average rating, 247 reviews

Vineyard Retreat: Just a mile from Tisbury center

Sep 17 – 24

G$78,143 GYD per night

Guest favorite

Home in West Tisbury

4.98 out of 5 average rating, 183 reviews

West Tisbury Escape, Long Point Beach

Nov 18 – 25

G$70,787 GYD per night

Guest favorite

Home in West Tisbury

4.98 out of 5 average rating, 121 reviews

Secluded Up Island Cottage

Feb 18 – 25

G$52,959 GYD per night

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Oak Bluffs cottage rentals

Guest favorite

Cottage in Tisbury

4.96 out of 5 average rating, 214 reviews

Not Your Great Aunt's Island Cottage

Dec 8 – 15

G$78,564 GYD per night

Guest favorite

Cottage in Tisbury

4.98 out of 5 average rating, 313 reviews

Martha's Vineyard Getaway Cottage

Dec 31 – Jan 7

G$57,548 GYD per night

Guest favorite

Cottage in Mashpee

4.95 out of 5 average rating, 302 reviews

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

Oct 22 – 29

G$41,704 GYD per night

Guest favorite

Cottage in Sandwich

4.95 out of 5 average rating, 157 reviews

Waterfront Lake Cottage, Private Beach, Wow View!

Sep 29 – Oct 6

G$77,734 GYD per night

Guest favorite

Cottage in Mashpee

4.9 out of 5 average rating, 183 reviews

Waterfront! Family Beach & Dock

Dec 9 – 16

G$45,497 GYD per night

Guest favorite

Cottage in Bourne

4.94 out of 5 average rating, 129 reviews

Seaglass Cottage

Mar 24 – 31

G$29,431 GYD per night

Guest favorite

Cottage in Falmouth

4.94 out of 5 average rating, 135 reviews

“Cozy Cottage” on Great Bay

Feb 16 – 23

G$39,163 GYD per night

Superhost

Cottage in Fairhaven

4.79 out of 5 average rating, 277 reviews

On the Beach Cottage in Fairhaven

Sep 16 – 23

G$54,264 GYD per night

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Oak Bluffs condo rentals

Guest favorite

Condo in Mashpee

4.97 out of 5 average rating, 101 reviews

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

Mar 7 – 14

G$32,307 GYD per night

Guest favorite

Condo in Oak Bluffs

5.0 out of 5 average rating, 20 reviews

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

May 5 – 12

G$147,309 GYD 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!

Oct 21 – 28

G$121,677 GYD per night

Superhost

Condo in Tisbury

4.91 out of 5 average rating, 45 reviews

Sunny 2bedroom condo w pool, walk to town

Mar 8 – 15

G$84,069 GYD per night

Guest favorite

Condo in Mattapoisett

4.97 out of 5 average rating, 29 reviews

Brand new! Whole apartment, huge tub, full kitchen

Oct 11 – 18

G$32,168 GYD per night

Guest favorite

Condo in Tisbury

4.98 out of 5 average rating, 44 reviews

Short Walk into Town - Nice Comfortable Reasonable

Jun 5 – 12

G$69,114 GYD per night

Superhost

Condo in Vineyard Haven

5.0 out of 5 average rating, 17 reviews

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

Feb 7 – 14

G$71,882 GYD per night

Superhost

Condo in Tisbury

4.91 out of 5 average rating, 45 reviews

Private 3bdrm Condo Tashmoo Woods

Apr 14 – 21

G$95,562 GYD per night

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Quick stats about vacation rentals in Oak Bluffs

Total rentals
690 properties
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
160 properties allow pets
Family-friendly rentals
480 properties are a good fit for families
Total number of reviews
22K reviews
Nightly prices starting at
G$2,084 GYD 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 420 house rentals, over 40 cottage rentals to over 30 condo 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 640 vacation rentals in West Chop, over 640 vacation rentals in East Chop, and over 640 vacation rentals in Eastville.
Are there vacation rentals with a dedicated workspace in Oak Bluffs?
Yes! Work meets play with ease at over 340 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 160 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 $10 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 260 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 170 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 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 wifi?
Absolutely! We offer over 420 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.

Oak Bluffs vacation rentals

Top-rated vacation rentals in Oak Bluffs

Vacation rentals for every style

Apartments

Cottages

Houses

Popular amenities for Oak Bluffs vacation rentals

Stay near Oak Bluffs's top sights

Other great vacation rentals in Oak Bluffs

Home in Oak Bluffs

Home in Oak Bluffs

Home in Oak Bluffs

Home in Oak Bluffs

Home in Edgartown

Home in Tisbury

Home in West Tisbury

Home in West Tisbury

Oak Bluffs cottage rentals

Cottage in Tisbury

Cottage in Tisbury

Cottage in Mashpee

Cottage in Sandwich

Cottage in Mashpee

Cottage in Bourne

Cottage in Falmouth

Cottage in Fairhaven

Oak Bluffs condo rentals

Condo in Mashpee

Condo in Oak Bluffs

Condo in Oak Bluffs

Condo in Tisbury

Condo in Mattapoisett

Condo in Tisbury

Condo in Vineyard Haven

Condo in Tisbury

Quick stats about vacation rentals in Oak Bluffs

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What types of vacation rentals are available in Oak Bluffs?

Where should I stay in Oak Bluffs?

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

Are there pet-friendly vacation rentals in Oak Bluffs?

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

Do house rentals in Oak Bluffs have a bbq area?

Do house rentals in Oak Bluffs have self check-in?

Are there Oak Bluffs house rentals on Airbnb with pools?

Do house rentals in Oak Bluffs have wifi?

Do house rentals in Oak Bluffs have a gym?

Destinations to explore