Oak Bluffs vacation rentals

We found 1,837 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
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Select from 265 houses, 25 condos, and other vacation rentals to find the perfect place for your stay in Oak Bluffs. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as parking and a hot tub. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

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    Enjoy full kitchens, laundry, pools, yards and more
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Explore the beachside setting in Oak Bluffs

Enjoy the wineries and other features of Oak Bluffs. This walkable and scenic city is known for its beaches, shopping and local tours. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Oak Bluffs

Are you looking for top things to see and do in the city? Venture out of your cozy vacation rental and experience everything that makes Oak Bluffs a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Shining Sea Bikeway (9.2 mi / 14.8 km)
  • Cape Cod Country Club (11.5 mi / 18.5 km)
  • Farm Neck Golf Club (1.2 mi / 2 km)
  • Falmouth Country Club (10 mi / 16.1 km)
  • Stand Up & Paddle Cape Cod (15.1 mi / 24.3 km)
  • Island Cove Adventures (2.8 mi / 4.5 km)

Exploring the natural landscape of Oak Bluffs

Whether you're looking for fun outdoor activities or just want to take in the scenery, Oak Bluffs is a great place to get outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Oak Bluffs Town Beach (0.4 mi / 0.7 km)
  • Inkwell Beach (0.5 mi / 0.7 km)
  • Lighthouse Beach (4.8 mi / 7.7 km)
  • Lambert's Cove Beach (5.6 mi / 9.1 km)
  • Menauhant Beach (6.4 mi / 10.3 km)
  • Falmouth Heights Beach (6.5 mi / 10.5 km)

Seasonal weather in Oak Bluffs

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 68°F.

Transportation to and around Oak Bluffs

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 5.2 mi (8.3 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Hyannis, MA (HYA-Barnstable Municipal), which is 20.5 mi (32.9 km) away.

Frequently asked questions

What is the best area to stay in Oak Bluffs when booking a vacation rental?

Among the most sought-after neighborhoods to get a vacation property in Oak Bluffs is Lagoon Heights. Find your perfect stay on Vrbo and experience this area just like a local.

What is the most popular type of vacation rental accommodation in Oak Bluffs?

The most desirable types of vacation rentals in Oak Bluffs are houses. After something a little different? Vrbo has a variety of options to match our guests' requirements, so you'll see vacation homes in all shapes and sizes. The ideal fit is waiting for you — snap up yours today.

How much does it cost to rent a vacation rental in Oak Bluffs?

The average price for a vacation rental in Oak Bluffs is determined by a number of factors, like length of stay, property type and season. Whether you're thinking about a sprawling villa with space for extended family or an apartment for just you and the kids, just add your dates of travel to find stays that offer great value.

How much does it cost to rent a beach house in Oak Bluffs?

The average price for a vacation rental near the beach in Oak Bluffs depends on when you're visiting the area and the style and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering your dates of travel. Then use our filters to choose the number of bedrooms and amenities that you require, like WiFi, air conditioning and a pool.

Are there pet-friendly vacation rentals in Oak Bluffs?

With 310 vacation rentals that welcome four-legged guests, your furry buddy can also come along on your Oak Bluffs vacation. Use the filter tool to browse our pet-friendly vacation rentals and find a vacation home that'll set tails wagging on Vrbo.

Can I rent a house with a pool in Oak Bluffs?

Pack your swimwear and inflatable unicorn, because there are 67 houses with a private pool in Oak Bluffs. Unwind at one of these terrific vacation rentals and every day can be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!

What are popular rental amenities in Oak Bluffs?

When it comes to rental amenities that guests are looking for in Oak Bluffs, tennis, a firepit and a chef are at the top of the list. With Vrbo vacation homes, you'll find options to fit your style and taste, whether you're going on a vacation with your partner, family members or even pets.

Are there large group vacation rentals in Oak Bluffs?

You'll find 62 vacation rentals in Oak Bluffs that can host 10 or more people. Whether you're organizing a get-together with extended family or a celebration like a birthday, there's ample space to get your group together under the same roof.

Are there vacation rentals in Oak Bluffs that welcome kids?

Bring the entire group together for a fun-packed adventure in Oak Bluffs at one of our 310 family-friendly vacation properties. These stays provide conveniences that are just perfect for getaways with children, such as full kitchens, living rooms and patios. Just click on the "Properties good for families" filter box and pick out your favorite.

What are the top attractions for families in Oak Bluffs?

Keeping the kids happy during your Oak Bluffs vacation is child's play with these top family-friendly attractions:

  • Inkwell Beach
  • Oak Bluffs Town Beach
  • Falmouth Heights Beach

Are there one-bedroom vacation rentals in Oak Bluffs?

There are 30 one-bedroom properties in Oak Bluffs to select from. A one-bedroom vacation rental is a great choice if it's only you and your partner or if you're traveling on your own. Add in more convenience, privacy and space compared to a hotel, and you've got the makings of a break to remember.

Can I find two-bedroom vacation rentals in Oak Bluffs?

Gather your loved ones and experience complete comfort and privacy in one of the 59 two-bedroom vacation rentals Oak Bluffs has to offer.

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