
Condo vacation rentals in Oak Bluffs
Find and book unique condos on Airbnb
Quick stats about condo rentals in Oak Bluffs

Total vacation rentals
Explore 30 vacation rentals in Oak Bluffs

Nightly prices starting at
Oak Bluffs vacation rentals start at G$29,258 GYD per night before taxes and fees

Verified guest reviews
Over 730 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
30 of Oak Bluffs vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oak Bluffs rentals

4.9 Average rating
Oak Bluffs stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated condo rentals in Oak Bluffs
Guests agree: these condos are highly rated for location, cleanliness, and more.

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Planning a family or couple's getaway to Martha's Vineyard? Then you'll love calling this delightful Oak Bluffs vacation rental your home-away-from-home. The quaint 2-bedroom, 2-bath condo offers beautiful beach views, cozy nautical decor, and a covered balcony perfect for socializing with a nice glass of wine. When it's time to explore the island, peruse the shops, restaurants, and lighthouses, or take a ride on the famous Flying Horses Carousel. A memorable Massachusetts vacation starts here!

Serenity on Martha's Vineyard
This 2BR, 2 Full Bath Condo with air condition (AC) and elevator access is located across the street from State Beach (AKA the "Ink Well") in Oak Bluffs. It's on the top floor, recently redecorated, with all the amenities for a wonderful vacation. Both bedrooms have Smart TVs & AC. Free Wi-Fi. Great location, within walking distance to the ferry, beach and downtown Oak Bluffs, restaurants and shops. Car not needed! Get ready to relax and unwind. It's the perfect location! Welcome to Serenity!

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach
Enjoy one of the most desirable locations on the Vineyard!! Enjoy AMAZING sunrises & gorgeous ocean views from this lovingly kept, super clean condo. Literally across the street from town beach, adjacent to Waban Park, a few blocks to Ocean Park, Flying Horses, Steamship Authority & downtown Circuit Avenue (restaurants, shops)! Bring a car (one unreserved parking spot) or walk over from the boat. Bike delivery & storage available. We hope to see you this summer in this fantastic summer condo!

Private 3bdrm Condo Tashmoo Woods
This 3 bedroom (3 king) 2 1/2 baths newly renovated condo is in a private setting with screened in porch. New kitchen, gas grill on deck, outdoor shower. -Access to the Tashmoo Woods Association pool, tennis courts and play ground. -Close to West Chop beaches. -Two miles from downtown Vineyard Haven. On bus route, but best to have a car. -The primary bedroom (king bed) is downstairs and the 2 upstairs bedrooms share a bath (shower only). Minimum rental 5 days, 1 week in summer.

Cape Esacpe at New Seabury
Relax with the whole family at this little Cape escape. This is a cozy 2 bedroom one bathroom condo. Walk to beaches, restaurants, bars, and shops. Visit The Popponesset Market place for food ,mini gold, and ice cream after your day at the beach. Also located directly across from The Popponesset Inn, a popular wedding venue, whether you are there for a wedding or just want to eat at the upscale restaurant, it's a beautiful place to visit. (Market place only open in summer season)

Ocean View Gem, Walk to it All, No Car Needed!
Lovely 2 BR/1 BA condo sleeps up to 4 guests. Amazing location with spectacular views! Experience island living at its finest. Martha’s Vineyard vacationers dream! Enjoy walking everywhere: Inkwell Beach, Circuit Avenue, Biscuits, OB ferry and harbor, Campground Cottages, Tabernacle, shops, restaurants and more! Have a front seat to Illumination fireworks, spectacular sunrises and romantic sunsets on the private balcony. No car needed; however, parking is available if required.

Short Walk into Town - Nice Comfortable Reasonable
Renovated modern ground floor unit in a two family house in Vineyard Haven. Only a short walk down the hill to the ferry terminal, and Main Street, with plenty of shops and restaurants, a supermarket, movie theatre, the famous Black Dog bakery and restaurant, the Martha's Vineyard museum, the beach and waterfront, the large Veterans Memorial park, and more. Public transportation to the other towns is easily accessible. A car is not necessary as it is with more remote locations.

Spectacular Martha's Vineyard Island Home!
This is our beautiful Hidden Cove home on Martha's Vineyard we call Shangri-La! Spectacular setting with a great peaceful view overlooking Sengekontacket Pond with the Ocean beyond. The property features a shared Pool, Tennis Courts & Dock. Our house is conveniently located midway between the Oak Bluffs & Edgartown town centers. When the presidents visit the Vineyard this is the area they come to relax (at the Farm Neck Golf Club which is right up the street).

Stunning. Walk to Beach, Town and Harbor 113B
Walk to all Oak Bluffs has to offer. 5-10 minutes to harbor, town, beach and restaraunts. Amazing location! This three unit property offers a shared patio and deck space along with all the amenities. It is private and well appointed. 2 flat screen Televisions, wifi, appliances, tile throughout, granite counters, outdoor shower, gas grill. This 400 square foot unit will provide you with an excellent home base to explore Oak Bluffs and Martha's Vineyard.

New Seabury Cape Condo | Pool & Beach Escape
Top 5% of Air Bnbs! Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

Lovely W Falmouth Home steps to bikeway & more!
Hello and welcome to our home in the heart of West Falmouth Village! Immerse yourself in the charm of this historic locale, just a stroll away from West Falmouth Harbor, the bike path, village store, renowned restaurants, and the sparkling Shining Sea Bike Path. -Child and pet friendly -Well stocked kitchen -Central Air & Heat throughout -Linens & bath and beach towels provided

Walk to Beach & Ferry: AC + Private Yard
Welcome to your perfect Cape Cod getaway in the heart of downtown Falmouth!. Step outside your door and take a short walk (less than a mile) to the soft sands of Surf Drive Beach and the Island Queen Ferry to Martha's Vineyard. The vibrant town center, with its wide variety of shops, cafes, bars, and restaurants, is just a stone's throw away, so you can leave your car behind.
Popular amenities for Oak Bluffs condo rentals
Weekly condo rentals

Island Inn - One Bedroom Suite - 10C - Oak Bluffs,

Island Inn - Cottage - 21E - Oak Bluffs, MA

Island Inn - Residential Suite - 38G - Oak Bluffs,

Island Inn - Studio Suite - 23F - Oak Bluffs, MA

Upscale Cape Cottage: Walk to Beach & Marketplace

Island Inn - Residential Suite - 30G - Oak Bluffs,

Private Ocean Overlook! Serene Cape Cod Escape

LOCATION LOCATION!! Ocean- View TOP Floor Condo
Pet-friendly condo rentals

Island Inn - Residential Suite - 33G - Dog-friendl

Island Inn - One Bedroom Suite - 8C - Dog-friendly

Island Inn - One Bedroom Suite - 15D - Dog-friendl

Island Inn - Residential Suite - 31G - Dog-friendl

Island Inn - Studio Suite - 3B - Dog-friendly - Oa

Island Inn - Residential Suite - 29G - Dog-friendl

Dog-Friendly Mashpee Condo with Pool access

Island Inn - Residential Suite - 36G - Dog-friendl
Condo rentals with a pool

Beautiful 2 Level Townhouse on Cape Cod !

2BR Condo in Cape Cod w/ Patio & Laundry

Falmouth MA, Cape Cod Getaway

Island Inn - Residential Suite - 35G - Oak Bluffs,

Cape Cod Townhouse w/ Patio & Kitchen

1BR Condo with Balcony in Mashpee, MA

Bright, Coastal Mashpee Condo Near the Commons

Two bedroom condo .on the water Falmouth, ma
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Portland Vacation rentals
- Providence Vacation rentals
- Atlantic City Vacation rentals
- Newport Vacation rentals
- York County Vacation rentals
- Cambridge Vacation rentals
- Bar Harbor Vacation rentals
- Apartment rentals Oak Bluffs
- Rentals with breakfast Oak Bluffs
- Rentals with outdoor seating Oak Bluffs
- Rentals with a fireplace Oak Bluffs
- Rentals with a hot tub Oak Bluffs
- Pet-friendly rentals Oak Bluffs
- Private suite rentals Oak Bluffs
- Family-friendly rentals Oak Bluffs
- Rentals with a patio Oak Bluffs
- Rentals with pools Oak Bluffs
- Hotel rooms Oak Bluffs
- Bed and breakfasts Oak Bluffs
- Beachfront rentals Oak Bluffs
- Waterfront rentals Oak Bluffs
- House rentals Oak Bluffs
- Boutique hotels Oak Bluffs
- Rentals with lake access Oak Bluffs
- Rentals with a fire pit Oak Bluffs
- Rentals with a kayak Oak Bluffs
- Rentals with a washer and dryer Oak Bluffs
- Rentals with beach access Oak Bluffs
- Condo rentals Dukes County
- Condo rentals Massachusetts
- Condo rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Matunuck State Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Duxbury Beach
- Bonnet Shores Beach
- Easton Beach
- Roger Williams Park Zoo
- Point Judith Lighthouse
- Sandy Neck Beach
- Pinehills Golf Club
- Second Beach
- Narragansett Town Beach
- New Silver Beach
- The Breakers
- Nauset Beach
- Coast Guard Beach
- Falmouth Heights Beach
- Skaket Beach
- Saquish Beach
- Race Point Beach





