Oak Bluffs Vacation Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Feb 28 - Mar 2
In two weeks
Mar 7 - Mar 9
In one month
Mar 21 - Mar 23
In two months
Apr 18 - Apr 20

Browse Select Oak Bluffs Vacation Homes

Cape Cod cottage
Exterior

Cape Cod cottage

9.6 out of 10, Exceptional, (95)
"House was very clean. Nicely decorated. Peaceful. Has everything you may need. Check in and check out was smooth. I even walked in to a nice little surprise. Highly recommend."
Cape Cod cottage
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Outdoor dining

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

10.0 out of 10, Exceptional, (22)
"Thank you Thomas and Julie, had a great week, so convenient and Welcoming. "
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Terrace/patio

Historic Oak Bluffs home, short walk to town, beach, and harbor.

9.6 out of 10, Exceptional, (28)
"We enjoy it all. "
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Gorgeous Spacious Victorian Cape Code Beach View Retreat
Beach nearby

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat
Large New Seabury Home with Heated Pool and Hot Tub
Interior

Large New Seabury Home with Heated Pool and Hot Tub

10.0 out of 10, Exceptional, (39)
"We stayed for a week over the Christmas holidays. The house easily accommodated our group of eight people and one dog. We enjoyed the easy walk to the National Wildlife Refuge and a quick drive for winter beach walks. We enjoyed spending time with a roaring fire and a few dips in the hot tub. Tori was very responsive to the couple of issues that arose. "
Large New Seabury Home with Heated Pool and Hot Tub
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Exterior

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

10.0 out of 10, Exceptional, (56)
"This house is the perfect destination for a group get together. It is an easy walk to the ferry so cars are not needed on the island. we had a great time and are looking forward to our next stay."
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
Smart TV, video games, DVD player, table tennis

Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches

10.0 out of 10, Exceptional, (89)
"My friends and I stayed at this wonderful property for my birthday celebration. We had a wonderful time. This is the best supplied Vrbo house I have ever stayed in and I have stayed in many. Korrie is a perfect host and her house is amazing. Great for a family with kids in that there are 2 separate fun areas for kids and grownups! We played ping pong and put puzzles together. The first floor bedroom is perfect for those who don't love stairs. I rate this house as 5/5 stars! Thank you...
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
Martha’s Vineyard 4BR Home-Katama Edgartown South Beach Area-open Mem Day wknd
Beach nearby, sun loungers, beach towels

Martha’s Vineyard 4BR Home-Katama Edgartown South Beach Area-open Mem Day wknd

9.8 out of 10, Exceptional, (49)
"We enjoyed our stay at this property. We didn’t spend a lot of time at the house but it certainly served its purpose. I think it would be a great place to stay in the summer with its proximity to the beach and bike path. The only minus was having to drive the long way around because of the horrible condition of the main dirt road. All that said, I would certainly stay there again!"
Martha’s Vineyard 4BR Home-Katama Edgartown South Beach Area-open Mem Day wknd
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Exterior

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

7.4 out of 10, Good, (3)
"We had a wonderful early-June weekend stay at this charming house minutes walk from town. Highlights were reading on the rocking chair on the deck and playing games in the screened-in porch. Everything looks just like in the listing - charming, warm, like staying at your grandpa's beach house. There were a few bumps - the listed dryer was in a locked shed, a faucet wasn't working - but our sense was this is a new listing and details are still being ironed out. None of that interfered with our...
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Walk To Town - Beautiful Edgartown House
Fridge, microwave, oven, stovetop

Walk To Town - Beautiful Edgartown House

9.8 out of 10, Exceptional, (52)
"We had a wonderful stay in this home. Perfectly appointed and you can’t beat the location. Especially loved the outdoor shower!"
Walk To Town - Beautiful Edgartown House
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel crib

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (74)
"Beautiful home and views"
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Ocean Views From Every Room, Beach 30 Seconds Away!
Exterior

Ocean Views From Every Room, Beach 30 Seconds Away!

10.0 out of 10, Exceptional, (101)
"Our three generation family has gathered together in California every Thanksgiving week for decades. This year, since our eldest granddaughter is an ob/gyn resident at Brown, we decided to save her a trip and stay on the Cape. We all loved our stay — watching the tides, cooking together. Some of us taking long walks, and visiting with longtime friends who live in the area. The perfect reunion."
Ocean Views From Every Room, Beach 30 Seconds Away!
Serene Waterfront Cottage with Private Dock, Walk to Beaches, Golf and Shops
Beach nearby, sun loungers, beach towels

Serene Waterfront Cottage with Private Dock, Walk to Beaches, Golf and Shops

10.0 out of 10, Exceptional, (7)
"The property is just fantastic!!! Beautiful, clean, the deck is amazing and the dock to drop a fishing line from is perfect. The location is amazing and close to anything you want to do!! The host was fantastic answering quickly to any questions we had!! Can’t wait to come back "
Serene Waterfront Cottage with Private Dock, Walk to Beaches, Golf and Shops
Cozy Cape home with outdoor shower and deck - minutes to beach
Terrace/patio

Cozy Cape home with outdoor shower and deck - minutes to beach

9.8 out of 10, Exceptional, (62)
"The housebwas beautiful! A girls weekend to experience tge Christmas Stroll. Thank you!!"
Cozy Cape home with outdoor shower and deck - minutes to beach
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Fridge, microwave, oven, stovetop

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (190)
"Once again, we enjoyed our family Christmas on the Cape in our favorite area. This house has everything you will need for a comfortable stay. The house is immaculate and completely stocked. The beds are extremely comfortable, there is plenty of room for our entire family to enjoy themselves and Roberta was so easy to communicate with if needed. We will definitely stay here again. "
The price is CA $256
CA $728 total
includes taxes & fees
Feb 24 - Feb 25
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Exterior

The Beach Estate, Panoramic Ocean Views, 5700 sqft

10.0 out of 10, Exceptional, (5)
"This house is spectacular and we cannot wait to rent again. There’s nothing to complain about except we didn’t rent it longer. "
The price is CA $1,107
CA $2,624 total
includes taxes & fees
Feb 27 - Feb 28
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
On the beach

Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

9.6 out of 10, Exceptional, (83)
"Wish it was warmer lol stayed and it snowed "
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana
Smart TV, fireplace, books

Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana

10.0 out of 10, Exceptional, (70)
"Loved the house. Enjoyed our walk to the beach "
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana
Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub
Exterior

Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub

10.0 out of 10, Exceptional, (94)
"Great location, even with the weather being awful we were able to utilize some of the amenities. "
Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
Outdoor dining

Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom

8.0 out of 10, Very good, (7)
"Cute property in a great location. The neighborhood felt very safe and it was a perfect spot for my family. House was clean and the space was great. "
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Oak Bluffs
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Oak Bluffs

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Dining

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

10.0 out of 10, Exceptional, (34)
"This is the second year in a row that we have stayed in this home. We just love it so much. It has everything you need which makes packing much easier. Owners are great. We hope to stay again."
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Cozy getaway in a central location w/ a full kitchen & furnished deck
Beach

Cozy getaway in a central location w/ a full kitchen & furnished deck

6.8 out of 10, (22)
"You can see by the photos that the home is outdated. However, this home shouldn't even be rented. I rent homes on VBRO all the time and this is my first bad experience. The doors didn't shut, including the two bathrooms. The larger bathroom we tried to avoid. The toliet moved, you could rock back and forth on it if you wanted too. They put a chain lock on the back of the door to hold it shut. A screw in the light switch, to make the switch work. The door in the smaller bathroom didn't shut...
Cozy getaway in a central location w/ a full kitchen & furnished deck
Make Lasting Memories In This Adorable Vineyard Cottage!
Exterior

Make Lasting Memories In This Adorable Vineyard Cottage!

9.8 out of 10, Exceptional, (140)
"This place is exactly as described and pictured on the website. Cute, clean, quiet cul de sac. All appliances in working order. Lori, the property manager was communicative, promptly and happily addressing all questions. I would definitely go back. :)"
Make Lasting Memories In This Adorable Vineyard Cottage!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.