This West Falmouth apartment is located just off Route 28, offering a 2-minute walk to the Shining Sea Bikeway and a short drive to downtown Falmouth's shops and restaurants. This family-friendly vacation rental accommodates up to four guests in two bedrooms and features a full kitchen with a dishwasher, air conditioning, and access to a garden.
9.8 41 reviews
Oak Bluffs, MA
07/03 – 07/07
$7287/nighttotal: $29148 (4 )
Winnetu Oceanside Resort At South Beach
4 7
resort , Edgartown
Winnetu Oceanside Resort At South Beach in Edgartown offers an excellent location at South Beach, a renowned coastal landmark on the island. This resort provides home-like accommodations with thoughtfully designed spaces and bathroom amenities, ensuring guest contentment, and is located at South Beach, offering proximity to the island's coastline.
Oak Bluffs, MA
07/03 – 07/07
$5004/nighttotal: $20016 (4 )
Exclusive Ultra-luxury Vineyard Retreat
1 7
apartment , Oak Bluffs
This luxury vacation home in Oak Bluffs offers a peaceful retreat in a family-friendly area, conveniently located near local attractions. This 4-bedroom, 3.5-bathroom residence accommodates up to 8 guests and features a fully equipped kitchen, air conditioning, a private pool, hot tub, garden, and parking.
9.8 26 reviews
Oak Bluffs, MA
08/21 – 08/22
$1508/nightfor 1 night
The Seashell Cove - Martha's Vineyard
4 8
apartment , Edgartown
This Katama vacation home, located within two miles of Edgartown's Old Whaling Church, Vincent House Museum, and Edgartown Public Library, and three miles from Katama Plains Natural Heritage Area and Lighthouse Beach, offers convenient access to historic sites and natural beauty. This four-bedroom, four-bathroom house sleeps eight guests and features a fully equipped kitchen, a private patio, a garden, and a spa, providing ample space and amenities for a relaxing Edgartown getaway.
Oak Bluffs, MA
07/03 – 07/07
$3854/nighttotal: $15416 (4 )
Oak Bluffs Allure
1 7
apartment , Oak Bluffs
This bespoke estate in Oak Bluffs features a main residence and a separate guest home, offering a private oasis with a heated swimming pool and hot tub, all within convenient proximity to the island's attractions. This luxurious 4-bedroom, 4-bathroom villa accommodates up to 8 guests and boasts high-end finishes, top-tier appliances, and expansive grounds, providing a complete and private experience for your island getaway.
8.7 3 reviews
Oak Bluffs, MA
08/08 – 08/10
$1027/nighttotal: $2054 (2 )
Maushop With Scenic Views
1 4
cabin , Mashpee
The Maushop cottage is located in Mashpee, a short walk from a private beach and close to the Marketplace, Popponesset Inn, and Raw Bar. This charming cottage offers a peaceful escape with easy access to local attractions, making it ideal for exploring the area. The cottage has two bedrooms and one and a half bathrooms, comfortably accommodating up to four guests. The cottage comes fully equipped with linens, air conditioning, towels, beach chairs, and a barbecue for a convenient and enjoyable stay.
Oak Bluffs, MA
07/03 – 07/07
$2820/nighttotal: $11280 (4 )
Relax & Unwind: Poolside Martha’s Vineyard Stay
5 7
apartment , Oak Bluffs
This Vineyard Haven house rental is located 4 miles from Oak Bluffs and Vineyard Haven, and 5 miles from Edgartown, offering proximity to Inkwell Beach, Oak Bluffs Town Beach, and Manuel F. Correllus State Forest. This family-friendly house accommodates 10 guests with 5 bedrooms and 4 bathrooms, featuring a private heated outdoor pool, a garden, a terrace, a foosball table, a full kitchen with a dishwasher, and parking for up to six cars.
9.6 79 reviews
Oak Bluffs, MA
07/03 – 07/07
$1883/nighttotal: $7532 (4 )
Spacious, Old Vineyard Charm With Private Beach
5 7
apartment , Edgartown
This five-bedroom, four-bathroom Cape Cod house is located in the Katama neighborhood of Edgartown, a three-mile drive from Edgartown's historic district and a short walk or bike ride from South Beach. The 8-guest house features a private beach on Katama Bay, a newly renovated kitchen, expansive lawn with a Weber grill and outdoor shower, a private pier, and rooftop deck, ideal for swimming, kayaking, and sunset viewing.
8.9 27 reviews
Oak Bluffs, MA
08/08 – 08/10
$671/nighttotal: $1342 (2 )
Seaside Charm Near Beach & New Seabury Resort
1 4
apartment , Mashpee
Maushop By The Sea, a one-bedroom cottage in Mashpee's exclusive New Seabury resort community, is steps from a private beach and a short walk from Popponesset Marketplace with its renowned Raw Bar. This vacation rental offers a sunroom, full bathroom, kitchen with fridge, microwave, and dishwasher, washer/dryer, patio, and accommodates up to four guests, providing easy access to Mashpee Commons, Cape Cod Children's Museum, and ferries to Nantucket and Martha's Vineyard.
Oak Bluffs, MA
08/21 – 08/22
$3772/nightfor 1 night
4-bedroom House In Lovely Edgartown..centrally Located
4 8
apartment , Edgartown
This Edgartown house offers a central Martha's Vineyard location on a private 1/2 acre, situated 3.5 miles from State Beach and a short drive to Oak Bluffs and Vineyard Haven. This family-friendly home accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, featuring air conditioning, internet, and proximity to Edgartown's galleries, shops, restaurants, and the bike path.
Oak Bluffs, MA
07/03 – 07/07
$5446/nighttotal: $21784 (4 )
Beautiful Estate With Salt Water Pool & Pond With Kayaks
5 7
apartment , Oak Bluffs
This estate is located in Prestigious Fresh Pond Estates, Oak Bluffs, offering a private, wooded setting with a freshwater pond just 2 miles from Oak Bluffs center and 500 feet from a bike path. This 4500 square foot house accommodates up to 12 guests with 5 bedrooms and 3 bathrooms, featuring a heated saltwater pool, Jacuzzi, outdoor kitchen, and private 2-bedroom living quarters, ideal for multi-family stays.
Oak Bluffs, MA
07/03 – 07/07
$1674/nighttotal: $6696 (4 )
Mv Sea Glenn Flowers \Npleasant 4-bedroom 3-bathroom House With Ac In Oak Bluffs
4 7
apartment , Oak Bluffs
This four-bedroom house in Oak Bluffs is located 0.3 miles from Inkwell Beach and a short distance from the Woods Hole Ferry Terminal. This rental accommodates up to eight guests with four bedrooms and three bathrooms, featuring a microwave, dishwasher, and air conditioning, and is pet-friendly with parking and a garden.
Best Oak Bluffs, MA vacation rentals with a balcony
8.0 2 reviews
Oak Bluffs, MA
08/08 – 08/10
$467/nighttotal: $934 (2 )
4 Mi To Bristol Beach! Coastal Retreat W/ Pond
2 4
house , Falmouth
This East Falmouth Cape Cod cottage, a 4-mile drive from Bristol Beach and near South Cape Beach State Park, offers easy access to local attractions. The 700-square-foot house features two bedrooms, one bathroom, sleeps seven, and includes a fully equipped kitchen with a dishwasher, air conditioning, Wi-Fi, a private patio, and parking (extra charge).
Oak Bluffs, MA
07/03 – 07/07
$3227/nighttotal: $12908 (4 )
Relax & Unwind: Poolside Marthas Vineyard Stay
5 7
apartment , Oak Bluffs
This Oak Bluffs vacation home is situated a short drive from Martha's Vineyard Preservation Trust Historic Buildings, located 11 minutes away, offering convenient access to local attractions. This spacious 2930 square foot residence accommodates up to 10 guests with 5 bedrooms and 5 bathrooms, featuring a private swimming pool, a terrace with a fire pit, Wi-Fi, and a fully equipped kitchen.
9.8 5 reviews
Oak Bluffs, MA
08/08 – 08/10
$1050/nighttotal: $2100 (2 )
Autumn Escape By The Cape 4 Drm Home
4 4
house , Mashpee
This Mashpee vacation home, located 13 miles from the Sandwich Glass Museum and 14 miles from Heritage Museums & Gardens, offers convenient access to popular Cape Cod attractions. The 2,000-square-foot property features two bedrooms, two bathrooms, accommodates up to 17 guests, and includes amenities such as a fully equipped kitchen, free Wi-Fi, private parking, and a private garden.
Oak Bluffs, MA
08/08 – 08/10
$921/nighttotal: $1842 (2 )
Newly Built Bayview Home, Steps To Dock/launch On Great Pond - Small Dogs Ok
2 4
apartment , Falmouth
This East Falmouth condo is located in the city center, one house from Great Neck Pond with water views, and less than two miles from Falmouth Village. This 1120 square foot condo accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, a full kitchen, a balcony, and is located 100 feet from a public boat ramp and dock, and 1 mile from Bristol Beach.
Browse Family-Friendly Vacation Rentals in Oak Bluffs, MA
Family beach vacations in Oak Bluffs, MA are better in spacious rentals that offer plenty of room to spread out near the shore.
9.4 32 reviews
Oak Bluffs, MA
07/03 – 07/07
$1970/nighttotal: $7880 (4 )
Great Martha's Vineyard House: Everything You Need - Nothing You Don't!
3 7
apartment , Oak Bluffs
This modern Oak Bluffs vacation rental is conveniently located near Inkwell Beach and Cape Cod Beaches, offering easy access to the area's natural beauty. It has consistently received excellent ratings from past guests. This 3-bedroom, 2-bathroom home comfortably sleeps 9 guests and offers a spacious 1860 square feet of living space. The house includes a fully equipped kitchen, a wraparound deck, an outdoor shower, a jacuzzi, and a garden, perfect for enjoying the beautiful weather and outdoor activities.
9.6 14 reviews
Oak Bluffs, MA
08/08 – 08/10
$1199/nighttotal: $2398 (2 )
Falmouth Heights • 6br • Walk To Beach + Yard
1 4
apartment , Falmouth
This Falmouth Heights home, located in the Historic District, is steps from the Black Dog Café, three blocks from Heights Beach, and an eight-minute walk from the Island Queen Ferry. This spacious six-bedroom, two-bathroom house sleeps eleven guests and boasts a large yard with a 25-foot rope swing, plus amenities including beach chairs, umbrellas, and potentially youth bikes.
8.0 2 reviews
Oak Bluffs, MA
08/08 – 08/10
$4217/nighttotal: $8434 (2 )
Winnetu Oceanside Resort At South Beach
1 4
resort , Edgartown
Winnetu Oceanside Resort at South Beach is located near South Beach, a three-minute walk away, and 3.2 miles from Edgartown's Main Street, offering easy access to both beach and town. This Edgartown resort boasts seasonal heated pools, a fitness center, complimentary children's programs, tennis courts, and The Dunes restaurant with ocean views; various accommodations, including studios, cottages, and up to four-bedroom suites, are available.
9.7 14 reviews
Oak Bluffs, MA
08/08 – 08/10
$814/nighttotal: $1628 (2 )
Falmouth-near Downtown+beaches Less Than 5 Mins
1 4
apartment , Falmouth
This East Falmouth house, located 1.5 miles from Menauhant Beach, offers easy access to the beach and a quiet residential setting near Falmouth's attractions. The three-bedroom, two-bathroom home features a pull-out sofa bed, accommodating up to eight guests, and includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, parking, and internet access.
Frequently Asked Questions about vacation rentals in Oak Bluffs, MA
What are some interesting places to visit in or near Oak Bluffs, MA?
Oak Bluffs is full of charm! You can't miss the colorful gingerbread cottages in the historic district, and the Flying Horses Carousel is a must-see. For a bit of nature, head over to the Martha's Vineyard Island Wildlife Sanctuary. You can even take a ferry to Edgartown for a day trip, which is just a short hop away.
What are the best Airbnb and vacation rentals in Oak Bluffs, MA?
Which walking or cycling routes are the best in Oak Bluffs, MA?
The Oak Bluffs Harbor Walk is a great option for a stroll with beautiful views of the harbor. For a longer bike ride, check out the Martha's Vineyard Trail, which runs for 15 miles along the island's north shore. You can also rent a bike and explore the scenic backroads around town.
What are the most popular Airbnbs in Oak Bluffs, MA?
What sports or outdoor activites can visitors enjoy in and around Oak Bluffs, MA?
Oak Bluffs has plenty to offer outdoors! There are public beaches like Ocean Park and East Chop Beach for swimming, sunbathing, and surfing. You can also rent kayaks or paddleboards to explore the waters around the island. And don't forget to check out the Oak Bluffs Tennis Club for a game.
What are the best vacation rentals with a pool in Oak Bluffs, MA?
What amenities are commonly available in vacation rentals in Oak Bluffs, MA?
Vacation rentals in Oak Bluffs usually include all the essentials like kitchens, bathrooms, and bedrooms. Many also offer amenities like Wi-Fi, laundry facilities, and outdoor spaces with decks or patios. Some even have private pools or hot tubs!
What are the best rentals for families and kids in Oak Bluffs, MA?
What time of year is best to rent a vacation rental Oak Bluffs, MA?
Summer is definitely the most popular time to visit Oak Bluffs, but it can get crowded and expensive. If you prefer a quieter experience, consider visiting in the shoulder seasons, like spring or fall. The weather is still pleasant, and you'll find fewer crowds and lower prices.
What are the best rentals or Airbnbs with a jacuzzi in Oak Bluffs, MA?
What are the local dishes in Oak Bluffs, MA region?
Oak Bluffs is known for its fresh seafood, so you'll find plenty of clam chowder, lobster rolls, and fish tacos. Don't forget to try the local Martha's Vineyard blueberries, which are used in pies, muffins, and other delicious treats. You can also find a variety of other cuisines in the area, from Italian to Mexican.
Destinations nearby
Best Oak Bluffs, MA vacation rentals with parking
Oak Bluffs, MA
08/08 – 08/10
$1054/nighttotal: $2108 (2 )
Bella Luna
1 4
, Falmouth
10 1 review
Oak Bluffs, MA
08/08 – 08/10
$475/nighttotal: $950 (2 )
4 Mi To Bristol Beach! Coastal Retreat W/ Pond
2 4
cottage , Falmouth
This East Falmouth vacation home is conveniently located near several beaches (4-10 miles), Cape Cod Winery (2 miles), and downtown Falmouth (4 miles). This 700-square-foot cottage sleeps four guests in two bedrooms with a queen and full bed, one bathroom, and offers amenities including a furnished patio with a gas grill, a Smart TV, in-unit laundry, and driveway parking for up to four vehicles.
Choose the Right Vacation Rentals with a Pool in Oak Bluffs, MA
Complement your time by the water with a dip in the pool at these Oak Bluffs, MA vacation rentals with on-site swimming facilities.
10 2 reviews
Oak Bluffs, MA
07/03 – 07/07
$2753/nighttotal: $11012 (4 )
Views, Private Beach, & Pool!
6 7
apartment , West Tisbury
This stylish West Tisbury home, located in Upper Makonikey, is a five-minute walk from private association beaches and a ten-minute drive from the town center. This five-bedroom, three-bathroom house sleeps ten, features a private pool with Vineyard Sound views, a three-acre property, and proximity to a tennis court; enjoy outdoor entertaining on the large patio deck.
Top-Rated Oceanfront Vacation Rentals in Oak Bluffs, MA
Enjoy a relaxing beach getaway with these coastal and seaside vacation rentals in Oak Bluffs, MA. Book your next shoreside stay today.
8.0 1 review
Oak Bluffs, MA
08/08 – 08/10
$890/nighttotal: $1780 (2 )
Maushop By The Sea
1 4
house , Mashpee
Traveler-Approved Luxury Vacation Rentals in Oak Bluffs, MA
Indulge in a luxury vacation rental in Oak Bluffs, MA, where high-end design meets world-class 5-star comfort.
Oak Bluffs, MA
07/03 – 07/07
$1313/nighttotal: $5252 (4 )
The Belvedere
1 7
apartment , West Tisbury
Explore Vacation Rentals with Saunas in Oak Bluffs, MA
Elevate your wellness routine with a vacation rental featuring a sauna in Oak Bluffs, MA , ideal for a restorative end to your day.
10 2 reviews
Oak Bluffs, MA
08/08 – 08/10
$828/nighttotal: $1656 (2 )
Renovated One Bedroom Apartment Downtown Falmouth Minutes From The Beach