
Vacation rentals in Oak Bluffs
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Top-rated vacation rentals in Oak Bluffs
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Popular amenities for Oak Bluffs vacation rentals
House rentals in Oak Bluffs

Newly constructed home with AC , new furniture.
Again, we had a wonderful stay. The home was clean and has everything you need. Would definitely book again.

Brand new gorgeous 2 bedroom guest house.
Unfortunately we had to cancel our trip because the ferry was cancelled due to weather, but I had the opportunity to interact with Debra through messages prior to our trip. She is a very kind and gracious host. I hope to be able to stay at this location during future visits to Martha’s Vineyard.

The Mills Retreat- 3BR/2Bath - Beach pass included
This was a family Christmas getaway, and it was perfect.

The Lighthouse
Loved our stay at the vineyard. Heather's house was a perfect size and met all of our needs! We had one small problem with a toilet and it was taken care of right away. Thank you. Great place for a family. Love those dirt roads!

Spacious and immaculate custom home.
We had a fantastic family vacation in Falmouth and Anne’s house greatly exceeded all of our expectations! Comfortable, beautiful decorated and appointed with every amenity. We will be back!

Well-Appointed 3 Bedrm 4 Bathrm w/ 50+ 5* Reviews
Lisa is an incredible host! She was very responsive and easy to reach. The house was very clean and neat and well equipped to make your stay easy and enjoyable. You can really tell that she cares about the home and the comfort of her guests. The home is located in a very quiet lowkey neighborhood with easy access to town and everything you need either by bike or car. I would definitely stay there again.

Holiday in the sun!
Very quiet spot. Felt comfortable staying here. very good communication, very welcoming. Thank You Craig

Classic Downtown Property
Elizabeth is a wonderful host - responsive and friendly. The home is lovely and just a short walk from town. The living area has an open floor plan, with a well appointed kitchen and lots of comfortable living room furniture - a nice space for hanging out in the evenings. The beds are very comfortable and the bedrooms are quiet. The bathrooms were very clean and showers have great water pressure. There's a very thorough guest guide with everything you need to know about the house... heat, tv, garbage, etc... plus lots of helpful recommendations for restaurants, shopping and attractions. A great house whether you're traveling with family or friends - we felt very much at home.
Cottage rentals in Oak Bluffs

Spectacular Beach- front home, includes linen
Excellent stay. Plenty of room for the 5 of us. We rested well and were able to relax. We appreciated having laundry on site since we were on a 10-day trip. The beds were comfortable and we slept well. But that is a minor detail when you can watch the sunset over the peaceful water. Lisa communicated well and responded quickly. The house is easy to get to and stores are easy to travel to. Excellent location.

Seaside cottage
Comfortable place to stay, as described

Quaint Cape Cod Cottage on a Private Beach!
Wonderful place! Beautifully decorated. Fantastic location - easy walk to the beach. Very homey - hated to leave. Debora is a great host - very responsive to questions.

The Island Collection MV: Sandy Shores
Beautiful place in the perfect location. Jolanta was extremely responsive with all my questions and a pleasure to work with. Would go back again in a heart beat!

“Cozy Cottage” on Great Bay
The perfect cottage indeed! So homey and comfortable, I had everything I needed and more. The location could not have been better, the best Air BNB experience I have ever had. Doug and Robin are lovely hosts, very responsive and so friendly. I can’t wait to come back!

Osterville Charming Cottage in the Heart of Wianno
Great stay at Maria’s cute little cottage by the water. Beautiful private location, perfect for kids to play in the yard.

Martha's Vineyard Getaway Cottage
We had an amazing stay. Winter on the island is so different but still a magical place. We made a fire and just hung out while it snowed and had a fabulous Valentine’s Day. Marilyn is an awesome host - responsive, clear, and caring. One of the best stays we’ve had.

* Rustic Cape Cod Captain's Quarters Cottage
Wonderful place! Was completely accurate to what was shown on the listing, great place for a vacation. Super convenient to get to surrounding big towns, but the area itself was peaceful and quiet. 30 second walk to the water, and a beautiful view! Hosts were responsive and super helpful- even though we didn't stay at their place during "prime Cape Cod season", they were helpful in giving us suggestions on what we could still do during this time of year (many suggestions of which we used)! Will definitely look to stay here again in the future, maybe during the summer next time!
Condo rentals in Oak Bluffs

Short Walk into Town - Nice Comfortable Reasonable
Walkable to all local shops. Unit was clean and the kitchen was fully stocked with all items needed to prepare and enjoy a meal.

Relax....You're on Island Time......
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

Private 3bdrm Condo Tashmoo Woods
What a relaxing and wonderful stay! Barbara’s place was welcoming and even better than the pictures. The house has everything you need and the addition of the community pool was the cherry on top. The host was extremely responsive and helpful. We look forward to returning to Barbara‘s place the next time my family and I visit MV.

Sunny 2bedroom condo w pool, walk to town
We were very happy with this comfortable 2 bedroom condo. Very clean and furnished nicely. Easy walk into town for shopping and dining. We had a few questions, which Leah answered quickly and in a friendly manner. Would stay again. Thank you Leah!

LOCATION LOCATION!! Ocean- View TOP Floor Condo
Heather's place is beautiful! An amazing location with close proximity to the OB steamship authority station, a number of bus lines, and the beach! The view and location are unbeatable! Heather was also super responsive in terms of coordinating flexible check-in/check-out times which was very much appreciated. Overall, would definitely recommend to anyone visiting OB :)

Condo in Falmouth MA
Patrick’s place was absolutely perfect! We made great use of the kitchen with no problem whatsoever. We really appreciated the nearby trail to get some fresh air and enjoyed being close to a grocery store for cooking meals. Highly recommend this place if you want a quiet laidback place to rest and refit!

Martha’s Vineyard Condo * Near Ferry
Great location and a nice quaint spot for one or two ! Great value for the area as well

Summer @ Serenity By The Sea, Mashpee , MA
Our second visit. We love the place. Quiet but close to great beaches and the Popponesset Marketplace is 2 minutes walk away, with fish restaurants and small stores with necessities (including wine and beer!). A highlight of this visit was sitting on the patio in the morning and 3 times seeing an osprey dive to the pond and catch a fish.
Quick stats about vacation rentals in Oak Bluffs
Total rentals
720 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
24K reviews
Family-friendly rentals
500 properties are a good fit for families
Pet-friendly rentals
170 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 440 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 670 vacation rentals in East Chop, over 670 vacation rentals in West Chop, and over 670 vacation rentals in Eastville.
Are there vacation rentals with a dedicated workspace in Oak Bluffs?
Yes! Work meets play with ease at over 280 vacation rentals in Oak Bluffs featuring dedicated workspaces. Stay connected and productive in your home away from home.
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.
Are there pet-friendly vacation rentals in Oak Bluffs?
Four-legged friends are welcome in Oak Bluffs. Choose from more than 170 vacation rentals for guests traveling with pets.
Do house rentals in Oak Bluffs have a bbq area?
Absolutely! We offer over 250 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 440 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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- Cape Cod National Seashore
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Lighthouse Beach
- Onset Beach
- Scusset Beach
- Oakland Beach
- Goddard Memorial State Park
- Baker's Beach Club
- Corn Hill Beach
- The Breakers
- Nickerson State Park
- Kelly Beach
- North Kingston Town Beach
- Rocky Point Beach
- Island Park Beach
- The Aquidneck Club
- Easton's Beach
- Pawtucket Country Club
- Cherry and Webb Beach
- Brant Beach
- Barlows Landing Beach
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