Oak Bluffs Holiday Rentals

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Holiday Rentals in Oak Bluffs

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

8.4 out of 10, Very good, (33)
"Perfect escape for three actors coming from a project with an unexpected few days off. We booked last minute and were thrilled to be able to have some things so centrally located"
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Romantic seaside getaway with pool & tennis courts - dog-friendly

9.6 out of 10, Exceptional, (42)
"Nice inn with comfortable and clean units. Not spectacular, but it's one of the few affordable places on the island. Some people might be put off by the location, a mile south of Oaks Bluff. But it's got Noman's, a great restaurant with live music, and it's right on the bus line. Also you can walk 15 minutes to the beach. Units not soundproof, you can here some noise from your neighbors. Great pool and tennis courts."
Romantic seaside getaway with pool & tennis courts - dog-friendly

Luxury home with private pool & foosball - near 3 towns & many beaches

8.6 out of 10, Excellent, (36)
"I recently stayed in this lovely OB home with my family. It was me and 9 other people, and there was plenty of room for everyone. The photos are accurate. The pool was clean and heated. The house is located in a private, wooded area but conveniently located to OB, Edgartown, the airport and beaches. The interior/furniture were so cozy. The house came equipped with enough plates, dishes, pots, pans, utensil, towels, etc. It would be helpful if the house came with a book of instructions, so we'd...
Luxury home with private pool & foosball - near 3 towns & many beaches

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (304)
"will definitely go back again .. awesome place! "
The price is AU$260
includes taxes & fees
24 Nov - 25 Nov
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (154)
"Very clean property. Beach just across street. Great views."
InnSeason Resorts Captain's Quarters

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (195)
"I spent the weekend in this adorable cottage after waking up in 5 different states 5 days in a row for a work trip. The location is perfect and the sunrise and sunsets from the beach were some of the most vibrant and colorful I have ever seen. I’m sure this is an amazing place to vacation in the summer but the quiet and solitude of November was its own treasure. And I was able to visit Walden Pond on my way to Boston Airport—-just a quick 30 minute detour and well worth the visit. "
Steps to the Ocean! Perfect Location!!!

Cape Winds Resort by VRI Americas

3.5 star property
8.8 out of 10, Excellent, (423)
"The place was difficult to find during the night when we arrive. "
Cape Winds Resort by VRI Americas

Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

9.8 out of 10, Exceptional, (144)
"The house was very nice and the perfect layout for our gang. The check out pricess briught some grumbles from some family membersas well as the 10 AM check out. I explained its a lot of house to clean before a new group at 4PM. A relative that lives on the Cape said the other side of Sea Street is a bit shady, which is why I gave the 4 star for location. "
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (109)
"We came to visit Nantucket and Martha’s Vineyard and one of the best parts of our trip is this gem. It was the perfect size for 4 of us. Close to the beach and the seashell collecting was amazing. Lots of shops and restaurants close by. We had some questions and the owner was very responsive. We would stay here again!"
Steps to the beach with an ocean view,

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

10.0 out of 10, Exceptional, (72)
"The home and views were stunning! Clean, comfortable, and plenty of space for everyone. Easy communication with the host. We had a lovely stay!"
The price is AU$1,668
includes taxes & fees
14 Dec - 15 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Harbor-view home with seasonal hot tub, kayaks & fireplace - walk to beach

8.8 out of 10, Excellent, (13)
"We loved the hot tub and the space. Amazing kitchen. Could use a little bit more furniture, but looks like that's a work in progress. Very comfortable bedrooms and great access to things to do around the area. House is well equipped with everything you will need. "
Harbor-view home with seasonal hot tub, kayaks & fireplace - walk to beach

Quiet duplex by the beach, short walk to Falmouth Village, 1 GB Internet.

9.8 out of 10, Exceptional, (70)
"Between the beautifully landscaped yard and the proximity to the ocean, this is a fabulous place! We love walking to the ocean for our am and pm walks, The Shining Sea Bike trail is also very close and just a joy! Property owners were great to work with. Definitely will stay here next year. Thanks for a great stay!!! "
Quiet duplex by the beach, short walk to Falmouth Village, 1 GB Internet.

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower

9.4 out of 10, Exceptional, (38)
"We enjoyed the time spending there. That is mostly fit us well due to the circumstance for which we were there. My wife liked every minute of it and so did I; but I simply wish there were some coffee there, along with the coffee maker. So, I wouldn’t have to go out just for that, the first night we got there. "
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower

Walk to beach 3 bed 2 bath

7.4 out of 10, Good, (12)
"Rustic property. No one on site. Bring all your own stuff like toilet paper, trash bags, paper towels. Plenty of space but only one functioning window. Grandma vibe. Get details of where to go and how to get in before you get there. "
Walk to beach 3 bed 2 bath

Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK

9.0 out of 10, Wonderful, (53)
"Great location, clean, everything was as described in the listing. Upgraded furniture and linens would have yielded 5 stars."
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK

Wonderful waterfront getaway with furnished deck, pond access, kayaks & WiFi

9.4 out of 10, Exceptional, (29)
"We stayed here for a quick weekend away. The house was very clean and well-stocked. The location was perfect for a couple families to get together and enjoy the deck and lake. Close to the Mashpee Children’s Museum and not too far from beaches. Quick drive to local breweries. Communication with the property manager seemed to be through an automated bot type system but we didn’t have any issues so didn’t need to call anyone. Would stay again. "
Wonderful waterfront getaway with furnished deck, pond access, kayaks & WiFi

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

9.8 out of 10, Exceptional, (60)
"House was perfect. Wonderful location. Enjoyed stay so much."
Cozy Cape home with outdoor shower and deck - minutes to beach

Beautiful bright home with firepit, deck & backyard - walk to beach

9.6 out of 10, Exceptional, (50)
"Great space and location."
Beautiful bright home with firepit, deck & backyard - walk to beach

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

8.6 out of 10, Excellent, (79)
"Great location but the place was dirty. Need a better cleaning service. "
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Breathtaking Views with Private Dock & Pool!

9.2 out of 10, Wonderful, (21)
"Great location. Loved the deck overlooking the water, the dock, the kayaks and the pool right next to the house. We mostly stayed around the house and the bay. Local free beach was close by with no one there on cooler windy days. Host, Maria, was very responsive to questions we had."
Breathtaking Views with Private Dock & Pool!
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.
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Other types of properties in Oak Bluffs you may be interested in

Summercamp

3.5 star property
9.2 out of 10, Wonderful, (918)
"the staff went out of their way to help overcome the post office which took three visits to locate a package for me"
Summercamp

MV Surfside Hotel

2.5 star property
8.8 out of 10, Excellent, (805)
"We had an excellent stay! The staff made it very enjoyable and gave us recommendations when we needed to switch our plans around due to weather. We will definitely be back!"
MV Surfside Hotel

Morgan Hotel

2.5 star property
8.2 out of 10, Very good, (121)
"Nice location, charming Victorian. Walking distance to shopping and restaurants. No staff to be found. Water pitcher empty in front lobby. Lots of steep stairs to climb to get to room. Room small. No chair to sit on. TV on side of bed. It was convenient and quiet. "
The price is AU$307
includes taxes & fees
1 Dec - 2 Dec
Morgan Hotel
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find holiday rentals in Oak Bluffs?

Yes, there are holiday rentals in Oak Bluffs close to Flying Horses Carousel, or you can select a more secluded option if you're looking for a relaxing stay. The shops and waterfront are just a few reasons why tourists like Oak Bluffs. Allow lots of time to check out the beaches and wineries during your visit.

What are some of the best holiday rentals that Oak Bluffs has to offer?

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower: This holiday home rental outside of Oak Bluffs offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals will I find in Oak Bluffs?

Choose from 248 Expedia holiday rentals in Oak Bluffs for a memorable holiday.

What can I see and do in Oak Bluffs?

Ocean Park and Oak Bluffs Town Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Oak Bluffs Fishing Pier. Other places in town to visit include Circuit Avenue and Flying Horses Carousel.

What are holiday rentals like in Oak Bluffs?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Bluffs. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.