Vacation Rentals in Oak Bluffs, MA

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Oak Bluffs, MA vacation rentals
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846 Vacation rentals and Airbnb in Oak Bluffs, MA

Best family friendly Oak Bluffs, MA vacation rentals

Among the 846 accommodations in Oak Bluffs, MA, here are the 4 best family friendly rentals

Retreat To Martha's Vineyard With A Private Pool & Outdoor Living In Oak Bluffs\n - Oak Bluffs, MA
10 7 reviews
Oak Bluffs, MA
19/07 – 24/07
₹258399/nighttotal: ₹1291995 (5 )

Retreat To Martha's Vineyard With A Private Pool & Outdoor Living In Oak Bluffs\n

4 2
apartment , Oak Bluffs
This four-bedroom house in Oak Bluffs is a short distance from Lagoon Pond and within easy reach of Farm Neck Golf Club and Featherstone Center for the Arts. The surrounding area is peaceful and offers a secluded retreat with easy access to the island's natural beauty.
The property is ideal for families or groups of up to nine guests and features a spacious living room, an office, an exercise room, and an extensive entertainment area with a pool, decks, and patios. The house also has a fully equipped kitchen, central air conditioning, Wi-Fi, linens, a pool table, and a variety of games.
Autumn Escape By The Cape 4 Drm Home - Oak Bluffs, MA
9.8 5 reviews
Oak Bluffs, MA
08/08 – 10/08
₹100228/nighttotal: ₹200456 (2 )

Autumn Escape By The Cape 4 Drm Home

4 4
house , Mashpee
This Mashpee holiday home is situated approximately 21 kilometres from both the Sandwich Glass Museum and Heritage Museums & Gardens.
This two-bedroom, two-bathroom property offers 186 square metres of space, sleeping up to 17 guests and boasting a fully equipped kitchen, private garden, free Wi-Fi, and free on-site parking.
East Chop Oasis, Oak Bluffs, Ma - Oak Bluffs, MA
Oak Bluffs, MA
19/07 – 24/07
₹105817/nighttotal: ₹529085 (5 )

East Chop Oasis, Oak Bluffs, Ma

3 2
apartment , Oak Bluffs
This newly renovated three-bedroom flat is located in East Chop, Oak Bluffs, within a short walk of the town centre, shops, restaurants, and harbour, and is conveniently close to the ferry terminal.
This family-friendly property accommodates up to six guests, featuring air conditioning, Wi-Fi, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, off-street parking, and outdoor spaces including a covered porch and a private patio, with a ground-floor bedroom for accessibility.
Spacious Home In Central Location With Beautiful Patio, Pool Table, W/d, & Ac - Oak Bluffs, MA
10 5 reviews
Oak Bluffs, MA
19/07 – 24/07
₹175341/nighttotal: ₹876705 (5 )

Spacious Home In Central Location With Beautiful Patio, Pool Table, W/d, & Ac

5 2
apartment , Oak Bluffs
This five-bedroom rental property is located in a quiet neighbourhood of Oak Bluffs, a short walk from shops, restaurants, galleries, the harbour, and beaches, and adjacent to the public library with EV charging.
Spanning 216 square meters, this spacious house accommodates up to 12 guests with four bathrooms, a well-equipped kitchen featuring a Fridge, Microwave oven, and Dishwasher, and offers a private outdoor oasis with a pool, a garden, and a terrace, alongside a lower-level game room with a pool table for entertainment.

Best Oak Bluffs, MA vacation rentals with a pool

Among the 846 accommodations in Oak Bluffs, MA, here are the 2 best rentals with a pool

Beautiful Estate With Salt Water Pool  & Pond With Kayaks - Oak Bluffs, MA
Oak Bluffs, MA
19/07 – 24/07
₹469563/nighttotal: ₹2347815 (5 )

Beautiful Estate With Salt Water Pool & Pond With Kayaks

5 2
apartment , Oak Bluffs
This spacious five-bedroom residence, situated in the private Fresh Pond Estates of Oak Bluffs, offers direct access to a freshwater pond and is conveniently located 3.2 kilometres from Oak Bluffs centre, 152 metres from a bike path, and a five-minute drive from Edgartown and Vineyard Haven.
This family-friendly holiday home, covering 418 square metres and accommodating up to 12 guests, boasts a heated saltwater pool, Jacuzzi, outdoor kitchen, two fully equipped kitchens including a commercial-grade one, and ample outdoor space with a 21-metre deck perfect for enjoying the surroundings.
Winnetu Oceanside Resort At South Beach - Oak Bluffs, MA
8.0 2 reviews
Oak Bluffs, MA
08/08 – 10/08
₹402587/nighttotal: ₹805174 (2 )

Winnetu Oceanside Resort At South Beach

1 4
resort , Edgartown
Winnetu Oceanside Resort at South Beach is situated near South Beach in Edgartown, Massachusetts, a short 5.1 km walk from the beach and 5.1 km from Edgartown's Main Street.
The resort, offering studios to four-bedroom suites, some with kitchenettes, boasts seasonal heated pools, a health club, a children's program, tennis courts, The Dunes restaurant with ocean views, and arranges clambakes, lighthouse tours, and kayak trips.

Frequently asked questions about holiday rentals in Oak Bluffs, MA

  • What are some interesting places to visit in or near Oak Bluffs, MA?

    Oak Bluffs is known for its Victorian gingerbread houses, so a stroll down the streets is a must. You can also visit the Martha's Vineyard Museum for a glimpse into the island's history. If you're looking for something a bit further afield, the town of Edgartown is just a short drive away and offers a charming harbour and a variety of shops and restaurants.
  • 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 paved bike path that runs along the coast from Oak Bluffs to Edgartown is a popular choice for both walking and cycling. There are also some lovely trails through the woods at the State Forest, perfect for a leisurely stroll.
  • 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 is a great place for watersports, with plenty of opportunities for swimming, kayaking, and paddleboarding. You can also rent a boat and explore the surrounding waters. If you're looking for something on land, there are several golf courses nearby, as well as tennis courts and a public beach.
  • What are the best vacation rentals with a pool in Oak Bluffs, MA?

  • What other towns or cities can be easily accessed from Oak Bluffs, MA?

    Oak Bluffs is located on Martha's Vineyard, which is an island, so you'll need to take a ferry to get there. Once you're on the island, you can easily visit other towns like Edgartown, Vineyard Haven, and Aquinnah. The island is relatively small and can be explored by car or bicycle.
  • What are the best rentals for families and kids in Oak Bluffs, MA?

  • What amenities are commonly available in vacation rentals in Oak Bluffs, MA?

    Vacation rentals in Oak Bluffs often come with amenities like Wi-Fi, air conditioning, laundry facilities, and outdoor space. Some rentals also offer extra features like hot tubs, swimming pools, and private decks. It's always best to check the listing for specific details.
  • What are the best rentals or Airbnbs with a jacuzzi in Oak Bluffs, MA?

    The best vacation rentals or Airbnb with a jacuzzi in Oak Bluffs, MA are Historic 1800's House In Town/beach, Mermaid Cottage and Oak Bluffs Cottage Perfect Place To Honeymoon.

  • What time of year is best to rent a vacation rental Oak Bluffs, MA?

    Summer is the peak season in Oak Bluffs, so expect higher prices and larger crowds. If you're looking for a more relaxed experience, consider visiting in the shoulder seasons (spring or autumn) when the weather is still pleasant but the crowds are smaller.
  • What are the local dishes in Oak Bluffs, MA region?

    Fresh seafood is a must-try in Oak Bluffs. You can find everything from clam chowder and lobster rolls to grilled swordfish and oysters. The island is also known for its blueberry pie, a delicious treat that's perfect for a summer day.

Destinations nearby

Best Oak Bluffs, MA holiday rentals with a balcony

Cape House W/ Ac, Walk To Park, Ferries, Dining & Shops; Close To Rail Trail - Oak Bluffs, MA
Oak Bluffs, MA
08/08 – 10/08
₹63106/nighttotal: ₹126212 (2 )

Cape House W/ Ac, Walk To Park, Ferries, Dining & Shops; Close To Rail Trail

2 4
apartment , Falmouth
This Falmouth apartment is a short walk from Falmouth Marina Park, Falmouth Harbour, and ferries to Martha's Vineyard, with beaches and the town centre a short drive away.
This 79 square metre dwelling sleeps four people and features two bedrooms, one bathroom, a fully equipped kitchen, air conditioning, a garden, and an enclosed yard with an outdoor shower, offering easy access to local attractions and water-based activities.
Private House With Jetted Tub, Deck, Grill, Central Ac And Large Yard - Oak Bluffs, MA
Oak Bluffs, MA
19/07 – 24/07
₹160926/nighttotal: ₹804630 (5 )

Private House With Jetted Tub, Deck, Grill, Central Ac And Large Yard

4 2
apartment , Oak Bluffs
This Oak Bluffs residence is located near Inkwell Beach, providing easy access to attractions such as the Flying Horses Carousel and Island Cove Adventures.
This spacious four-bedroom, five-bathroom house spans 289 square meters, accommodating up to eight guests with amenities including a deck, garden, patio, gas grill, and an on-site tennis court.
Historic Cottage With Patio, Games, Walk To Beach & Dog-friendly Fenced Yard - Oak Bluffs, MA
Oak Bluffs, MA
19/07 – 24/07
₹70935/nighttotal: ₹354675 (5 )

Historic Cottage With Patio, Games, Walk To Beach & Dog-friendly Fenced Yard

3 2
apartment , Oak Bluffs
This historic 1897 cottage in Oak Bluffs offers a central location within 500 meters of the beaches, the Campground with its gingerbread houses, and downtown Circuit Avenue's shops and restaurants.
This 80 square meter holiday home accommodates up to 5 guests in 3 bedrooms and 2 bathrooms, featuring a well-equipped kitchen, air conditioning, WiFi, an enclosed patio, and a raised herb garden, with pets welcome.
Newly Remodeled Home W/ New Furniture, Large Yard & Great Porches - Oak Bluffs, MA
9.0 17 reviews
Oak Bluffs, MA
19/07 – 24/07
₹139221/nighttotal: ₹696105 (5 )

Newly Remodeled Home W/ New Furniture, Large Yard & Great Porches

1 2
apartment , Oak Bluffs
This recently refurbished flat in Oak Bluffs is located just over 1.6 kilometres west of the Steamship Authority Terminal, providing easy access to the town centre and several beaches including Inkwell Beach and Oak Bluffs Town Beach.
This residence accommodates up to eight guests with three bathrooms, features a modern kitchen with a fridge, microwave, and dishwasher, and offers air conditioning, free WiFi, a garden, and a terrace for enjoying the island atmosphere.

Best Oak Bluffs, MA holiday rentals with parking

Oak Bluffs Family Retreat - Private Roundabout, Walk To The Beach & Downtown Ob. - Oak Bluffs, MA
10 17 reviews
Oak Bluffs, MA
19/07 – 24/07
₹141259/nighttotal: ₹706295 (5 )

Oak Bluffs Family Retreat - Private Roundabout, Walk To The Beach & Downtown Ob.

3 2
apartment , Oak Bluffs
This charming house is located in Oak Bluffs, a short 1.6km walk from Martha's Vineyard Hospital and less than 1.6km from Oak Bluffs Public Library and Oak Bluffs Harbour. This accommodation has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
This three-bedroom, three-bathroom house offers 186 square metres of space, comfortably accommodating up to six guests. The house features a fully equipped kitchen, laundry facilities, air conditioning, a barbecue grill, and a comfortable living space with a TV and a sofa bed.
4 Mi To Bristol Beach! Coastal Retreat W/ Pond - Oak Bluffs, MA
10 1 review
Oak Bluffs, MA
08/08 – 10/08
₹45322/nighttotal: ₹90644 (2 )

4 Mi To Bristol Beach! Coastal Retreat W/ Pond

2 4
cottage , Falmouth
This East Falmouth holiday home is situated 3-16km from several beaches including Bristol Beach, Menauhant Beach, Old Silver Beach, and South Cape Beach State Park, and is also conveniently located 3km from Cape Cod Winery and 6km from Falmouth town centre.
The 65 square metre property sleeps four guests in two bedrooms and one bathroom, and boasts a fully equipped kitchen, patio with gas grill, laundry facilities, ample parking, and access to a pond, plus a Smart TV and board games.
< 1 Mi To Beaches: Home W/ Deck In Oak Bluffs - Oak Bluffs, MA
8.0 3 reviews
Oak Bluffs, MA
19/07 – 24/07
₹58026/nighttotal: ₹290130 (5 )

< 1 Mi To Beaches: Home W/ Deck In Oak Bluffs

2 2
house , Oak Bluffs
This Oak Bluffs holiday home is less than 1.6km from the beaches and a 15-minute walk from Oak Bluffs Town Beach, with Martha's Vineyard Airport 8km away.
The 102 square metre property offers two bedrooms, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, air conditioning, free Wi-Fi, parking, and a garden.
Brand New! Lovely Apartment-vineyard Haven - Oak Bluffs, MA
9.9 55 reviews
Oak Bluffs, MA
19/07 – 24/07
₹91621/nighttotal: ₹458105 (5 )

Brand New! Lovely Apartment-vineyard Haven

1 2
apartment , Tisbury
This apartment is conveniently located in Vineyard Haven, a short walk from Tisbury Town Hall and Lake Tashmoo, and within 15km of Island Cove Adventures and Vineyard Playhouse. The surrounding area offers a blend of historical charm and modern amenities, making it a great base for exploring the island. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The apartment offers one bedroom and one bathroom, comfortably accommodating up to four guests. It comes equipped with a fully equipped kitchen, a washing machine, a sofa bed, free Wi-Fi, a Smart TV, and a spa tub, providing all the comforts you need for a relaxing stay.
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