Oak Bluffs vacation rentals

We found 1,927 vacation rentals — enter your dates for availability

Select from 265 houses, 28 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.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Oak Bluffs

Find out more about Oak Bluffs

Why visit Oak Bluffs

  1. Beautiful Beaches: Relax at stunning beaches like Jetty Beach, perfect for sunbathing and swimming.
  2. Historic Lighthouses: Visit iconic lighthouses along the coastline that showcase the region's maritime heritage.
  3. Charming Downtown: Explore the family-friendly downtown area filled with quaint shops and local eateries.
  4. Outdoor Activities: Enjoy tennis, biking, and scenic walks that highlight Oak Bluffs' natural beauty.
  5. Cultural Experiences: Immerse yourself in the vibrant local culture through museums and community events.

Popular types of accommodation in Oak Bluffs

Discover the charm of Oak Bluffs with our diverse vacation rental options, including private homes, cozy cottages, and stylish apartments. Whether you're seeking a beachfront oasis, an Oak Bluffs condo, or a quaint Edgartown cottage within walking distance, we have the perfect spot for your getaway. Our transparent information and savings ensure you find accommodations that suit your needs, making your vacation memorable and hassle-free.

  • Houses: The top choice for many visitors, these spacious residences offer a home-like experience, ideal for families or groups.
  • Apartments: A popular option, offering convenient amenities and a cozy environment for couples or solo travelers.
  • Cottages: Charming and quaint, these rentals provide a cozy escape and a taste of local character.
  • Condos: These modern accommodations combine comfort and style, perfect for those seeking a bit more luxury.
  • Cabins: A favorite for nature enthusiasts, these rustic lodgings offer a peaceful retreat amidst the beautiful surroundings.**

Top attractions in Oak Bluffs

Oak Bluffs, Massachusetts, is the perfect destination for beach, outdoor, and scenic vacations. Explore its stunning beaches, visit local history museums, and admire historic lighthouses. Enjoy activities like lounging at Jetty Beach, playing tennis, and discovering the charming towns of Oak Bluffs and Tisbury. Whether you're seeking culture or adventure, Oak Bluffs offers a delightful blend of attractions for every traveler.

  1. Inkwell Beach: A beautiful stretch of sand located in Oak Bluffs, Inkwell Beach is perfect for sunbathing and swimming, offering a relaxed atmosphere and vibrant beach vibes.
  2. Oak Bluffs Harbor: This picturesque harbor showcases stunning scenery and a lively waterfront, making it a great spot for leisurely strolls and enjoying the beach ambiance.
  3. Martha's Vineyard Museum: Located 2 miles from Oak Bluffs, this museum immerses visitors in the rich culture and history of Martha's Vineyard, featuring intriguing exhibits and artifacts.

Things to do recommended for couples

For a romantic getaway in Oak Bluffs, indulge in a fun round of mini-golf at Island Cove Adventures, enjoy a concert at the Cape Cod Melody Tent, or relax at the luxurious Cape Cod Country Club. Each experience offers a unique vibe perfect for couples!

Things to do recommended for families

Your family will love the Flying Horses Carousel in Oak Bluffs for its charming atmosphere. For adventure, visit the Cape Codder Water Park, just 20 miles away. If you're seeking relaxation, explore the Fulling Mill Brook Preserve, located 10 miles from Oak Bluffs, perfect for unwinding together.

Things to do recommended for groups

Groups visiting Oak Bluffs can enjoy a movie at the Martha's Vineyard Film Center, play a round of golf at Farm Neck Golf Club, or shop and dine at Mashpee Commons for a delightful mix of culture, sports, and family-friendly fun.

What do I need to keep in mind when booking a vacation in Oak Bluffs

If you're planning a trip with a group, family, pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Oak Bluffs with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Oak Bluffs with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oak Bluffs: For many families, a vacation wouldn’t feel complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Oak Bluffs: If you’re in search of vacation rentals offering great deals for month-long stays, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search for the perfect getaway.

Where to stay in Oak Bluffs

Oak Bluffs, Massachusetts, offers a perfect blend of beach relaxation and scenic outdoor adventures. Visitors can explore the charming downtown area, known for its family-friendly atmosphere and friendly locals. Don't miss the breathtaking views along the coastline and the vibrant culture that makes vacationing in Oak Bluffs unforgettable. With plenty of excursions and exceptional spots to unwind, you'll find it easy to embrace the laid-back vibe of this delightful destination.

  • Falmouth: Located 7 miles from Oak Bluffs, Falmouth is a charming coastal town that offers a delightful blend of outdoor activities, stunning beaches, and scenic views. Renowned for its family-friendly beaches, Falmouth is perfect for those looking to soak up the sun or enjoy water sports. The area is also home to beautiful golf courses and private country clubs, making it a great spot for golf enthusiasts. Visitors can explore the picturesque coastline, engage in educational programs, or simply relax and enjoy the serene environment. Key highlights include the vibrant local beaches and the scenic Cape Cod area, providing an idyllic escape for nature lovers.
  • Edgartown: Just 5 miles from Oak Bluffs, Edgartown is a quaint village that exudes charm and history. Known for its stunning beaches and scenic landscapes, Edgartown is a top destination for outdoor enthusiasts. The area features several golf courses and even a ski field for those adventurous souls. The local landmarks, such as the beautiful beaches and serene lakes, offer the perfect backdrop for relaxation or family fun. Strolling through Edgartown’s historic streets, visitors can admire the classic New England architecture and enjoy delightful shops and restaurants, making it a must-visit destination.
  • Vineyard Haven: Only 2 miles from Oak Bluffs, Vineyard Haven is a vibrant town known for its beautiful beaches and cultural experiences. This charming town is a hub for education and the arts, featuring local theaters and educational venues. Vineyard Haven's beaches are perfect for families, offering calm waters and scenic views. With its close proximity to Oak Bluffs, visitors can easily explore the area's attractions, including lakes and picturesque parks. The lively atmosphere of Vineyard Haven, along with its rich cultural offerings, makes it an inviting spot for tourists seeking both relaxation and entertainment.

Best time to go to Oak Bluffs

If you're planning a trip to Oak Bluffs, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.1°F (1.7°C)Light RainMostly SunnyAverageModerately Low
February35.1°F (1.7°C)Light RainMostly CloudyAverageAverage
March38.8°F (3.8°C)Light RainMostly SunnyAverageModerately Low
April46.4°F (8.0°C)Light RainMostly SunnyAverageAverage
May54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
June63.0°F (17.2°C)Light RainMostly SunnyHighAverage
July71.1°F (21.7°C)Light RainMostly SunnyHighModerately High
August71.6°F (22.0°C)Light RainMostly SunnyHighModerately High
September66.6°F (19.2°C)Light RainMostly SunnyAverageModerately High
October58.5°F (14.7°C)Light RainMostly SunnyLowAverage
November48.9°F (9.4°C)Light RainMostly SunnyLowAverage
December41.4°F (5.2°C)Light RainMostly SunnyLowModerately Low

Booking with Vrbo is simple

Are you aiming to save on your next adventure? Being flexible with your travel dates can be a great way to take advantage of fluctuating prices. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash™ on the full booking amount. It's truly beneficial to be the organizer! Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash™ on qualifying stays. Sign up today and start reaping the rewards!

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board provides you with a dedicated area to plan new trips, pick up right where you left off, or manage and organize your travel plans. You can easily access the properties you've saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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)
  • 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)
  • Cape Cod Country Club (11.5 mi / 18.5 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 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:

  • Ocean Park (0.3 mi / 0.5 km)
  • 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)

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?
If you’re planning a trip to Oak Bluffs, Lagoon Heights is among the most sought-after neighborhoods to stay. No matter your style of travel, Vrbo is sure to have a vacation home here that’s perfect for you.
What is the most popular type of vacation rental accommodation in Oak Bluffs?
According to our research, cottages are the most desirable property type in Oak Bluffs. But that goes without saying, everyone’s idea of the perfect trip isn’t going to be the same. Vrbo has vacation homes with every shape, size and budget in mind, and we’ll help you find the perfect match.
How much does it cost to rent a vacation rental in Oak Bluffs?
The average price for a vacation rental in Oak Bluffs is based on several factors, like season, property type and length of stay. Whether you’re in search of a sprawling villa with space for the whole family or a comfy cabin just enough for two, just add your dates of travel to find stays with great value.
How much does it cost to rent a beach house in Oak Bluffs?
When you travel and the style and size of the property will influence the cost of your beachside vacation rental. Enter your Oak Bluffs travel dates to see all your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to select the features and amenities you need.
Are there pet-friendly vacation rentals in Oak Bluffs?
Yes. Choose from 325 stays that roll out the welcome mat in Oak Bluffs on Vrbo. Our furry friends need a break too, so simply use our search function for pet-friendly vacation rentals to find a perfect pad where your puppy can lap up the fun.
Can I rent a house with a pool in Oak Bluffs?
Add a new level of fun to your adventure by staying in one of the 70 houses with a private pool in Oak Bluffs. Use our search filter to find properties with pools on Vrbo, then spend leisurely days frolicking in a swimming pool that’s just for you.
What are popular rental amenities in Oak Bluffs?
When it comes to rental amenities that people are looking for in Oak Bluffs, a water view, an ocean view and a nearby waterfront are at the top of the list. With Vrbo vacation rentals, you’ll enjoy options to match your taste and style, whether you’re going on a vacation with your partner, your family or even pets.
Are there large group vacation rentals in Oak Bluffs?
Oak Bluffs has 64 vacation homes that can host 10 or more people. These stays come with all the space you need to enjoy good times with loved ones.
Are there vacation rentals in Oak Bluffs that welcome kids?
Oak Bluffs has 320 family-friendly vacation homes to pick from. And finding a stay that welcomes kids is a breeze with Vrbo’s “Properties good for families” filter. As well as having the entire place to yourselves, you can also look forward to conveniences and perks such as multiple bedrooms, full kitchens and private pools.
What are the top attractions for families in Oak Bluffs?
There are tons of awesome things to see and do with the family in Oak Bluffs, including:

  • East Chop Light
  • Cottage Museum
  • Farm Neck Golf Club

Are there one-bedroom vacation rentals in Oak Bluffs?
Yes, you can pick from 33 one-bedroom rentals in Oak Bluffs. Whether you’d like a cozy chalet or a condo, Vrbo’s one-bedroom rentals are ideal if you don’t require tons of space. One of the major perks of having your own place? You won’t need to share your adventure with strangers.
Can I find two-bedroom vacation rentals in Oak Bluffs?
Oak Bluffs has 63 two-bedroom vacation rentals to choose from. Book a vacation home with all the privacy and space you want at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Oak Bluffs?
Oak Bluffs has 106 vacation rentals with WiFi, so you’ll be able to stay connected while you’re on vacation. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to posting pics on social media, these Vrbo homes make it a cinch to get online.
How can I find vacation rentals with air conditioning in Oak Bluffs?
You’ll have your pick of 291 vacation homes with air conditioning in Oak Bluffs giving you that cooling breeze and extra element of comfort. Just enter your travel dates and then take advantage of our filter tool to help you locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Oak Bluffs?
The minimum age allowed can differ between properties on Vrbo, so be sure to look at the rules of the vacation rental in Oak Bluffs you want. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Oak Bluffs for?
How long you can book a vacation rental in Oak Bluffs depends on the property. Just enter your preferred dates to see a list of options offering extended stays. With many features such as air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you’re sure to find somewhere just right to call your home away from home in Oak Bluffs.
Does Vrbo offer discounts for vacation homes in Oak Bluffs?
Whether you’ve got your sights set on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some incredible deals and discounts on Vrbo. From weekend trips to extended vacations, we’ve got you covered for your next Oak Bluffs escape.

More Vacation Rentals ideas

People also search for