Oak Bluffs holiday rentals

We found 1,862 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
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Select from 264 houses, 25 flats and other holiday rentals to find the perfect place for your stay in Oak Bluffs. Holiday homes offer the best amenities for your family, friends or furry companion, such as parking and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Explore the beachside setting in Oak Bluffs

Enjoy the wineries and other features of Oak Bluffs. This walkable and scenic city is well known for its beaches, shopping and local tours. With a holiday 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 hoping to find attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Oak Bluffs a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Cape Cod Winery (8.6 mi / 13.8 km)
  • Falmouth Country Club (10 mi / 16.1 km)
  • Stand Up & Paddle Cape Cod (15.1 mi / 24.3 km)

Exploring the natural landscape of Oak Bluffs

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Oak Bluffs is a great place to get outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Oak Bluffs Town Beach (0.4 mi / 0.7 km)
  • Inkwell Beach (0.5 mi / 0.7 km)
  • Edgartown Beach (2.8 mi / 4.5 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)

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 20°C.

Transport 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 centre. 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 holiday home?

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

What is the most popular type of holiday home accommodation in Oak Bluffs?

The most desirable types of holiday homes in Oak Bluffs are houses. After something a little different? Stayz has a variety of options to match our guests' requirements, so you'll see holiday 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 holiday home in Oak Bluffs?

The average price for a holiday home 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 holiday home 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 Stayz 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 holiday homes in Oak Bluffs?

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

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 holiday homes and every day can be a pool day. Simply enter your travel dates into Stayz, then use the "pool" filter to find the perfect place for a splashing good time!

What are popular home amenities in Oak Bluffs?

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

Are there large group holiday homes in Oak Bluffs?

You'll find 62 holiday homes in Oak Bluffs that can host 10 or more people. Whether you're organising 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 holiday homes 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 holiday 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 favourite.

What are the top attractions for families in Oak Bluffs?

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

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

Are there one-bedroom holiday homes in Oak Bluffs?

There are 30 one-bedroom properties in Oak Bluffs to select from. A one-bedroom holiday home is a great choice if it's only you and your partner or if you're travelling 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 holiday homes in Oak Bluffs?

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

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