Oak Bluffs Vacation Rentals

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Vacation Rentals in Oak Bluffs

Beach nearby, sun loungers
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, (168)
"The cottage was immaculate. Perfect for our needs. Including location… proximity to the beach, shops and restaurants. Great starting point for everything on the Cape as well as being not that far from Boston, Salem, Worcester and Fall River, everything we wanted to do…. Did I mention immaculate; super clean and fresh smelling. We above all appreciated the communication from the property manager/host. We have stayed with VRBO lots of times and this was the Best"
Steps to the Ocean! Perfect Location!!!
Beach
Steps to the beach with an ocean view,
10.0 out of 10, Exceptional, (96)
"Tom Loved your perfect cottage !!!"
Steps to the beach with an ocean view,
Property grounds
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
10.0 out of 10, Exceptional, (7)
"Beautiful home with a great view, right on the ocean. Was very quiet when we went (off season), but will definitely be renting again. Very clean, and had just about everything you would need!"
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
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Outdoor dining
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
10.0 out of 10, Exceptional, (157)
"Loved everything about this home! Perfect location. Fantastic views and decorated so beautifully. Would love to stay here again. Highly recommend!"
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Property grounds
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
10.0 out of 10, Exceptional, (11)
"All my wife's children and grandchildren gathered at this lovely home to celebrate her 70th birthday. The home and grounds/neighborhood are simply great and Thomas was a wonderful and responsive host. Since some folks stayed the whole visit and others were only with us for a long weekend, we were thrilled that the dining area accommodated our whole group when necessary, and the kitchen allowed many hands to make light work. The dining table doubled as a spot for the family to gather and...
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Property grounds
Tranquil Oasis: A Beautiful Water-Front Home
10.0 out of 10, Exceptional, (11)
"This house is very nice with lots of room and comfortable beds and furniture. It has everything you need and a beautiful view of the pond. The neighborhood is quiet, but close to a lot of good restaurants and stores. Definitely recommend!"
Tranquil Oasis: A Beautiful Water-Front Home
Fridge, microwave, oven, stovetop
Immaculate Home, 2 Acres, Short Walk To Beach!
10.0 out of 10, Exceptional, (4)
"The property was in a great location, not a long walk to a small beach. We had a group together for a memorial service, and were able to sleep 16. It was clean and pleasant. Some tips: - the seafood store down the road is amazing and cute - if you are a chef type, bring knives - 2 bathrooms for 16 ppl can get a little tight, so make sure your group is ready to share the space, etc. Overall, a great and affordable way to get a group of ppl together for a quiet gathering. Thanks!"
Immaculate Home, 2 Acres, Short Walk To Beach!
Iron/ironing board, WiFi, bed sheets
Romantic seaside getaway with pool & tennis courts - dog-friendly
9.8 out of 10, Exceptional, (36)
"Great location, lots of amenities - pool, fire pits, tennis courts, nearby restaurant. Communication for checking was excellent."
Romantic seaside getaway with pool & tennis courts - dog-friendly
Beach nearby, sun loungers, beach towels
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
9.8 out of 10, Exceptional, (123)
"Clean, well located, between beach and downtown. Responsive and friendly host."
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
Exterior
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
9.8 out of 10, Exceptional, (63)
"Property is in a great location, walking distance to the shore and a little longer walk or short drive will get you to town with a pub and a few places to eat. Martha’s Vineyard ferry parking is less than ten minutes away with a free shuttle bus that takes you to the ferry. Regina (owner) is right next door and is very friendly and accommodating!!"
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
Beach
Wonderful waterfront getaway with furnished deck, pond access, kayaks & WiFi
9.8 out of 10, Exceptional, (21)
"This beautiful home was clean and well maintained. It was spacious enough for our mid winter getaway with friends- plenty of room to spread out in the living room and the dining room table was big enough for our nightly board games."
Wonderful waterfront getaway with furnished deck, pond access, kayaks & WiFi
Property grounds
Cozy Cape home with outdoor shower and deck - minutes to beach
9.8 out of 10, Exceptional, (42)
"The cottage is in a quiet location, yet easily accessed off a main road. The place was clean and equipped with comfortable beds. Would recommend and stay here again."
Cozy Cape home with outdoor shower and deck - minutes to beach
Interior
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
9.6 out of 10, Exceptional, (70)
"The apartment was spotless! Open and airy. The host left excellent instructions, and a phone number if needed. We did and he responded immediately and problem resolved. I have only one suggestion. You need more than one mirror It’s located in the bathroom. Need another either in hall or bedroom I would recommend this apartment to anyone"
The price is CA $578
CA $946 total
includes taxes & fees
May 23 - May 24
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
On the beach, white sand
InnSeason Resorts Captain's Quarters
3.5 star property
9.6 out of 10, Exceptional, (143)
"Nice place in a great location"
InnSeason Resorts Captain's Quarters
Fridge, microwave, oven, stovetop
Beautiful bright home with firepit, deck & backyard - walk to beach
9.6 out of 10, Exceptional, (45)
"Very clean, welcoming"
Beautiful bright home with firepit, deck & backyard - walk to beach
Fridge, microwave, oven, stovetop
Sunny and Fun Family Cape Cod Vacation Home
9.6 out of 10, Exceptional, (5)
"Great location, space, and price was perfect."
Sunny and Fun Family Cape Cod Vacation Home
Interior
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
9.2 out of 10, Wonderful, (27)
"We really enjoyed our stay. There were a few issues. We couldn’t get in through the front door at all we had to go in through the garage. There were no potholders for cooking. Missing sugar for morning coffee. Napkins and tissues also unavailable. The only major concern that was an inconvenience neither of the bathrooms had heat. Thank you We will definitely be back again"
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Property grounds
Adorable waterfront home w/ boat access & a three-season sunroom
9.2 out of 10, Wonderful, (15)
"On the whole, we enjoyed our stay. Had informed Vacasa that we wouldn’t arrive in Falmouth until midnight 4/25 (as we picked up relatives at Logan Airport), but it hadn’t been forwarded: the sloping entry to the cottage was pitch-dark! In the morning we found garbage cans tipped over, & trash strewn all around the yard —the same thing happening the second night (both times we had to clean up a mess). We requested an hour’s leeway for departing 4/27, which was to have been relayed to local owner;...
Adorable waterfront home w/ boat access & a three-season sunroom
Aerial view
Breathtaking Views with Private Dock & Pool: Summer Special 40% off!
9.2 out of 10, Wonderful, (17)
"We had 3 family birthdays this week & for the 1st time in years we were all together. What made it extra special was this fantastic property & superb location. Maria was so easy to communicate with, it just made everything super smooth. When you get the weather here in the creeks and rivers it is an incredibly enjoyable place to stay, protected kayaking, peaceful yet close to the shops at Mashpee Commons for all the essentials. Thank you Maria."
Breathtaking Views with Private Dock & Pool: Summer Special 40% off!
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (281)
"Good "
The price is CA $335
CA $384 total
includes taxes & fees
May 19 - May 20
The Club at New Seabury
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See all available properties in Oak Bluffs
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.

Oak Bluffs Vacation Rental Travel Info

Number of vacation rentals
113
Popular accommodation
Oak Bluffs private vacation homes
Known landmarks
Inkwell Beach, Falmouth Heights Beach and Oak Bluffs Town Beach
International airport
Vineyard Haven, MA (MVY-Martha's Vineyard)

Other types of properties in Oak Bluffs you may be interested in

Porch
Summercamp
3.5 star property
9.2 out of 10, Wonderful, (589)
"Great location, clean, staff were very helpful and friendly."
The price is CA $279
CA $311 total
includes taxes & fees
May 19 - May 20
Summercamp
Room, 1 Queen Bed, Non Smoking | View from room
MV Surfside Hotel
2.5 star property
8.8 out of 10, Excellent, (738)
"Accessible "
The price is CA $334
CA $395 total
includes taxes & fees
May 19 - May 20
MV Surfside Hotel
Terrace/patio
Morgan Hotel
2.5 star property
8.4 out of 10, Very good, (113)
"Love the location in Oak bluff. Rates are reasonable. I would like to see a 2nd chair in the room for relaxation, watching tv, "
The price is CA $436
CA $486 total
includes taxes & fees
May 21 - May 22
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oak Bluffs. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Oak Bluffs?

Yes, you can find vacation rentals in Oak Bluffs near Oak Bluffs Fishing Pier, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Oak Bluffs?

Harbor-view home with seasonal hot tub, kayaks & fireplace - walk to beach: This vacation home rental outside of Oak Bluffs is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a spa tub.

How many vacation rentals will I find in Oak Bluffs?

Choose from 267 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

What can I see and do in Oak Bluffs?

Oak Bluffs Town Beach and Inkwell 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 vacation rentals like in Oak Bluffs?

Vacation rentals are private accommodations you can reserve for several days or longer in Oak Bluffs. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.

Recent reviews of Oak Bluffs properties
Expedia verified reviews