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
Fridge, microwave, oven, stovetop

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

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
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.6 out of 10, Exceptional, (78)
"This apartment was a great location to walk to the shops and restaurants in Oak Bluffs. We typically don't rent 1 bed/1 bath properties but we would rent this one again. It was very large and very clean and comfortable. The morning sun, coming in from over the ocean was beautiful each morning and we could sit out on the balcony with our coffee and people watch. We rented a car, only to explore the rest of the island and that, too, was a convenient walk, less than a block away. All in all,...
The price is AU$1,131
includes taxes & fees
31 Dec - 1 Jan 2025
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Terrace/patio

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.0 out of 10, (19)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
The Club at New Seabury
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (307)
"accommodation was good but cleanliness could have been better. Not bad but some areas needed more attention. Good restaurant and bar service on Thursday. No restaurant available on Saturday."
The price is AU$245
includes taxes & fees
30 Dec - 31 Dec
The Club at New Seabury
Steps to the Ocean! Perfect Location!!!
Beach nearby, sun-loungers

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (198)
"This cottage was perfect for me, my husband, and two adult daughters. It is exactly as advertised and the owner is very communicative and helpful recommending local restaurants, etc. We definitely would stay here again if we travel to the Cape. The beach is very close and we could see the water from the cottage. Great location! "
Steps to the Ocean! Perfect Location!!!
InnSeason Resorts Captain's Quarters
On the beach, white sand

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."
The price is AU$254
includes taxes & fees
2 Jan - 3 Jan 2025
InnSeason Resorts Captain's Quarters
New Coastal House, Steps to Keyes Beach, Main Street, Harbor; AC, Linens, Wi-Fi
Beach nearby, sun-loungers, beach towels

New Coastal House, Steps to Keyes Beach, Main Street, Harbor; AC, Linens, Wi-Fi

9.8 out of 10, Exceptional, (145)
"We just returned from our Vrbo stay in Hyannis. The property is perfectly located for a morning beach walk or any walk for that matter. Clean, good size bedrooms and very well equipped. One flaw, the heating situation is way off ! Upstairs bedrooms were boiling as well as the 2 downstairs bedrooms and the kitchen, living/ dining area were cool. This made sleeping almost impossible for everyone. If the heating was not a problem I would have given this rental 5 stars. "
New Coastal House, Steps to Keyes Beach, Main Street, Harbor; AC, Linens, Wi-Fi
Steps to the beach with an ocean view,
Beach nearby, sun-loungers, beach towels

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (112)
"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.
5 bedrooms, desk, iron/ironing board, travel cot

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$1,573
includes taxes & fees
22 Jan - 23 Jan 2025
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Harbor-view home with seasonal hot tub, kayaks & fireplace - walk to beach
Interior

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.
Exterior

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
TV, fireplace, books, stereo

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
Cape Winds Resort by VRI Americas
Children's play area - outdoor

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
Walk to beach 3 bed 2 bath
Interior

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
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. "
The price is AU$1,590
includes taxes & fees
31 Dec - 1 Jan 2025
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Fridge, microwave, oven, stovetop

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
Beach

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
Breathtaking Views with Private Dock & Pool!
Aerial view

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!
Beautiful bright home with firepit, deck & backyard - walk to beach
Fridge, microwave, oven, stovetop

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
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
Porch

Summercamp

3.5 star property
9.2 out of 10, Wonderful, (921)
"Easily accessible from the ferry "
Summercamp
MV Surfside Hotel
Room, 1 Queen Bed, Non Smoking | View from room

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
Interior

Morgan Hotel

2.5 star property
8.4 out of 10, Very good, (124)
"."
The price is AU$321
includes taxes & fees
1 Jan - 2 Jan 2025
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.

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?

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!: This holiday home rental outside of Oak Bluffs is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals will I find in Oak Bluffs?

Choose from 233 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 Oak Bluffs Harbor.

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.