
Condo vacation rentals in Oak Bluffs
Find and book unique condos on Airbnb
Top-rated condo rentals in Oak Bluffs
Guests agree: these condos are highly rated for location, cleanliness, and more.

Island Inn - Residential Suite - 29G - Dog-friendl
Your stay in this charming first-floor corner one and half-bedroom, one and half-bath unit is made comfortable with all the essentials. The cozy living and dining area features a TV for relaxing downtime, while WiFi keeps you connected with loved ones and helps you plan your island adventures. The kitchenette is equipped with an apartment-sized fridge, stove, microwave, and coffeemaker, along with silverware, plates, cups, cookware, and utensils—everything you need to enjoy a convenient and stre

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.

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
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

Stunning. Walk to Beach, Town and Harbor 113B

Short Walk into Town - Nice Comfortable Reasonable

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

Relax....You're on Island Time......

A Perfect. Walk to beach, harbor and Main Street

Serenity on Martha's Vineyard

Private 3bdrm Condo Tashmoo Woods

Sunny 2bedroom condo w pool, walk to town
Pet-friendly condo rentals

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

A Perfect. Walk to beach, harbor and Main Street

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

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

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

Dog-friendly, two-story condo with community pool

A Spectacular. Walk to beach, town and harbor 20

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

Surfside Resort Cape Cod, Falmouth MA

2BR Condo in Cape Cod w/ Patio & Laundry

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

Cape Cod Townhouse w/ Patio & Kitchen

Lovely lakefront studio/condo with pool

1BR Condo with Balcony in Mashpee, MA

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

Bright, Coastal Mashpee Condo Near the Commons
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 ﺩ.ﺇ514 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- The Hamptons Vacation rentals
- Rentals with a fireplace Oak Bluffs
- Rentals with pools Oak Bluffs
- Rentals with a patio Oak Bluffs
- Beachfront rentals Oak Bluffs
- Private suite rentals Oak Bluffs
- Rentals with a hot tub Oak Bluffs
- Pet-friendly rentals Oak Bluffs
- Rentals with a washer and dryer Oak Bluffs
- Boutique hotels Oak Bluffs
- Rentals with lake access Oak Bluffs
- Apartment rentals Oak Bluffs
- Rentals with a kayak Oak Bluffs
- House rentals Oak Bluffs
- Family-friendly rentals Oak Bluffs
- Hotel rooms Oak Bluffs
- Waterfront rentals Oak Bluffs
- Rentals with a fire pit Oak Bluffs
- Bed and breakfasts Oak Bluffs
- Rentals with breakfast Oak Bluffs
- Rentals with beach access Oak Bluffs
- Rentals with outdoor seating Oak Bluffs
- Condo rentals Dukes County
- Condo rentals Massachusetts
- Condo rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- East Matunuck State Beach
- Easton Beach
- Onset Beach
- Bonnet Shores Beach
- Roger Williams Park Zoo
- Second Beach
- Coast Guard Beach
- The Breakers
- New Silver Beach
- Pinehills Golf Club
- Sandy Neck Beach
- Point Judith Lighthouse
- Narragansett Town Beach
- South Shore Beach
- Nauset Beach
- Cahoon Hollow Beach
- Saquish Beach
- Nickerson State Park





