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Oak Bluffs, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Oak Bluffs, MA

Best Oak Bluffs, MA vacation rentals with a balcony

West Falmouth Family Retreat Near Chapoquoit Beach - Oak Bluffs, MA
No reviews

West Falmouth Family Retreat Near Chapoquoit Beach

house, Falmouth
This five-bedroom, three-bathroom family retreat is located in West Falmouth, 1.2 miles from Chapoquoit Beach.
The 1980 square foot vacation home accommodates up to 15 guests with air conditioning, a full kitchen, a garden, and private parking, and is close to the Sandwich Glass Museum and Heritage Museums & Gardens.
Modern Downtown Ob Condo, Stroll To Ferry & Beach - Oak Bluffs, MA
10 13 reviews

Modern Downtown Ob Condo, Stroll To Ferry & Beach

apartment, Oak Bluffs
This oceanfront condo in downtown Oak Bluffs offers scenic views and is a short walk from Circuit Avenue, Trinity Park Tabernacle, Oak Bluffs Harbor, and ferry access to Woods Hole Terminal.
This 660 square foot apartment sleeps up to 6 guests and features 2 bedrooms, 1 bathroom, air conditioning, a fireplace, a full kitchen, a washer/dryer, and Wi-Fi, with Inkwell Beach and family attractions nearby.
New Construction With Patio & Yard - Downtown & Beaches - Oak Bluffs, MA
No reviews

New Construction With Patio & Yard - Downtown & Beaches

apartment, Oak Bluffs
This Oak Bluffs residence is located a few blocks west of downtown, offering a one-mile walk to the Steamship Authority Terminal and proximity to Eastville Beach (0.5 miles) and Oak Bluffs Town Beach (1 mile).
This newly built four-bedroom home, featuring a loft and a 2060 square foot floor area, accommodates up to 10 guests with amenities including central air conditioning, a full kitchen with a dishwasher, and a private washer/dryer, complemented by a private patio and yard.
Sparkling Waterfront Gem, Spectacular Views, Private Beach, Great For Kayaks - Oak Bluffs, MA
10 76 reviews

Sparkling Waterfront Gem, Spectacular Views, Private Beach, Great For Kayaks

apartment, Tisbury
This waterfront vacation home is located in Vineyard Haven, just off Herring Creek Road, a mile from downtown Vineyard Haven, offering a peaceful escape with easy access to local attractions. The property has received excellent user ratings, indicating a high level of satisfaction among previous guests.
The house has three bedrooms and two bathrooms, accommodating up to six guests comfortably in its 2,400 square feet of space. Enjoy stunning lake and ocean views, private beach access, a fully equipped kitchen, and a variety of amenities for families, including a large parking lot, two-car garage, toys, games, and a second refrigerator.

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.

3-br Oak Bluffs Retreat Near Towns & Beaches - Oak Bluffs, MA
9.8 6 reviews

3-br Oak Bluffs Retreat Near Towns & Beaches

apartment, Oak Bluffs
This Oak Bluffs vacation home is located near Farm Neck Golf Club (1 mile) and within 3 miles of Oak Bluffs Public Library, Circuit Avenue, Trinity Park Tabernacle, and the Cottage Museum.
This 1810-square-foot house features three bedrooms, three bathrooms, and accommodates up to six guests, offering amenities such as a fully equipped kitchen, free Wi-Fi, a DVD player, air conditioning, and a peaceful garden with barbecue grills.
Condo In Falmouth With Access To The Secluded Flax Pond And A Built In Pool. - Oak Bluffs, MA
8.4 5 reviews

Condo In Falmouth With Access To The Secluded Flax Pond And A Built In Pool.

apartment, Falmouth
This East Falmouth condo is conveniently located near Cape Cod Winery (1.2 miles), Falmouth Country Club (within 3 miles), and the Waquoit Bay National Estuarine Research Reserve (within 3 miles).
This 950-square-foot, two-bedroom, one-bathroom apartment sleeps four and offers amenities including a swimming pool, parking, free WiFi, a fully equipped kitchen, and air conditioning.
Charming Falmouth Beach Bungalow Across From Water - Oak Bluffs, MA
10 1 review

Charming Falmouth Beach Bungalow Across From Water

apartment, Falmouth
This 3-bedroom vacation home is located in Falmouth's private Great Harbors community, offering direct access to Great Pond and Nantucket Sound, and is just minutes from Falmouth's beaches, downtown, and dining. This family-friendly rental includes access to community amenities like a pool and playground, and provides bikes, beach chairs, and an outdoor shower for guests.
East Chop Oasis, Oak Bluffs, Ma - Oak Bluffs, MA
No reviews

East Chop Oasis, Oak Bluffs, Ma

apartment, Oak Bluffs
This newly renovated 3-bedroom home is located in the East Chop district of Oak Bluffs, a short walk to town, beaches, shops, restaurants, and the harbor, offering convenient access to the ferry terminal.
This family-friendly house accommodates up to 8 guests with 3 bedrooms, features air conditioning, internet, parking, and a kitchen with a fridge, microwave, and dishwasher, plus a covered front porch and a private back patio with grilling and dining space.

Frequently Asked Questions about vacation rentals in Oak Bluffs, MA

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Best Oak Bluffs, MA vacation rentals with parking

Cape Getaway 4 Bedroom W/ Outdoor Shower, Ramp Access To Water, New Bathroom - Oak Bluffs, MA
8.4 13 reviews

Cape Getaway 4 Bedroom W/ Outdoor Shower, Ramp Access To Water, New Bathroom

apartment, Falmouth
This East Falmouth vacation home is located near beautiful Cape Cod beaches, within two miles of the Waquoit Bay National Estuarine Research Reserve and three miles from the Cape Cod Winery and Falmouth Country Club.
This 1,330-square-foot house boasts four bedrooms, three bathrooms, and sleeps ten, featuring a fully equipped kitchen, free Wi-Fi, a terrace, a garden, and on-site amenities including an arcade/game room and barbecue grills.
Beautiful 2bd Condo On Golf Course New Seabury - Oak Bluffs, MA
8.3 7 reviews

Beautiful 2bd Condo On Golf Course New Seabury

house, Mashpee
This renovated corner unit in Mashpee's Mews golf course community is conveniently located one mile from Mashpee's beaches and the Poppy Inn.
This two-bedroom, two-bathroom house offers guests a private setting with access to a community pool, parking, and accommodates up to four people, boasting a kitchen with a refrigerator and air conditioning.
Recently Renovated 3 Bedroom - Oak Bluffs, MA
10 3 reviews

Recently Renovated 3 Bedroom

apartment, Falmouth
This East Falmouth vacation rental is minutes from Mashpee Commons, downtown Falmouth, and the Martha's Vineyard ferry, offering easy access to beaches and attractions like Cape Codder Water Park and the Cape Cod Children's Museum.
This spacious 2,500-square-foot home features a 3-bedroom, 2-bathroom layout, sleeping up to 8 guests, with a private fenced backyard, lower-level games area, and amenities including Wi-Fi, air conditioning, and a fully equipped kitchen.
Spacious Colonial Home Close To Town With Ac, Porches, & W/d - Oak Bluffs, MA
9.4 6 reviews

Spacious Colonial Home Close To Town With Ac, Porches, & W/d

apartment, Oak Bluffs
This Oak Bluffs house is located within walking distance of the town, shops, restaurants, and the beach, and is also close to ferry transportation to Woods Hole.
This dog-friendly four-bedroom, two-bathroom home spans 1230 square feet and accommodates up to eight guests, featuring central air conditioning, an outdoor shower, and two parking spaces.

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.

Mansion House Inn And Spa - Oak Bluffs, MA
9.4 101 reviews

Mansion House Inn And Spa

manor house, Tisbury
Mansion House Inn and Spa is centrally located in Vineyard Haven, Massachusetts, less than 10 miles from Inkwell Beach and Vineyard Haven Terminal.
This manor house offers a full-service spa, indoor pool, fitness center, on-site restaurant, and bar, with rooms featuring air conditioning and minibars.
Winnetu Oceanside Resort At South Beach - Oak Bluffs, MA
8.0 2 reviews

Winnetu Oceanside Resort At South Beach

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.
Beautiful Estate With Salt Water Pool  & Pond With Kayaks - Oak Bluffs, MA
10 1 review

Beautiful Estate With Salt Water Pool & Pond With Kayaks

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.
Steps To The Beach In East Falmouth, Pet Friendly &  Clubhouse Heated Pool. - Oak Bluffs, MA
9.0 60 reviews

Steps To The Beach In East Falmouth, Pet Friendly & Clubhouse Heated Pool.

apartment, Falmouth
This Falmouth home is situated on Seacoast Shores, a peninsula with deep water access to Nantucket Sound, just 500 feet from the water and 3 blocks from a private association beach. It has earned a very good user rating, making it a popular choice for travelers.
The home features a spacious open floor plan with 1650 square feet of space, comfortably accommodating up to 8 guests. Amenities include a private swimming pool, jacuzzi, a fenced-in backyard, and access to a private association beach, perfect for enjoying the beautiful Falmouth weather and exploring the surrounding area.

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.

Kamp Kilowatt On Lake Tashmoo, Vineyard Haven, Ma - Oak Bluffs, MA
9.5 43 reviews

Kamp Kilowatt On Lake Tashmoo, Vineyard Haven, Ma

apartment, Tisbury
Soulas Marthas Vineyard - Oak Bluffs, MA
10 6 reviews

Soulas Marthas Vineyard

apartment, Oak Bluffs
14d Kennebec The Center Of Ob! No Car, No Problem! - Oak Bluffs, MA
9.9 28 reviews

14d Kennebec The Center Of Ob! No Car, No Problem!

apartment, Oak Bluffs
Waterfront Penthouse Oak Bluffs - Oak Bluffs, MA
9.8 170 reviews

Waterfront Penthouse Oak Bluffs

apartment, Oak Bluffs

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.

Fantastical Fishermens Cottage & Private Garden - Oak Bluffs, MA
9.1 30 reviews

Fantastical Fishermens Cottage & Private Garden

house, Oak Bluffs

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.

Mansion House Inn And Spa - Oak Bluffs, MA
9.4 101 reviews

Mansion House Inn And Spa

manor house, Tisbury
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