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

Island Inn - Residential Suite - 31G - Dog-friendl
Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comfortable with all the essentials. The cozy living and dining area features an electric fireplace with crystal glass stones, TV for relaxing downtime, while WiFi keeps you connected with loved ones and helps you plan your island adventures The kitchenette is equipped with a full-sized fridge, stove, microwave, dishwasher and coffeemaker, along with silverware, plates, cups, cookware, and utens

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!

LOCATION LOCATION!! Ocean- View TOP Floor Condo
LAST MIN opening in one of THE most desirable locations on the Vineyard! Enjoy AMAZING sunrises & SPECTACULAR ocean views from this family-run, premier top floor condo. Across street from popular town beach, short walk to Ocean Park, Waban Park, Flying Horses, Steamship Authority & downtown Circuit Ave (restaurants, shops). Bring a car (one unreserved parking spot available) or walk over from boat. Bike delivery & storage available. Linens, beach towels & chairs provided. Island Paradise! ☀️🏖️

Heart of VH, w/ac, pool & harborview
Enjoy your stay on Martha’s Vineyard in Causeway Harborview condos with this 2 bedroom/1 bathroom unit. - Views of the harbor from the unit - Pool & Laundry on-site - Parking on-site - Walk to ferry, restaurants, shops and beach - Bike to Oak Bluffs - All linens provided - Fully equipped kitchen with coffee and tea provided - Beach gear provided My goal is to provide guests with a 5-star experience, if there is anything that can improve your experience that isn’t listed, just ask!

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.

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).

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!
Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).

A Spectacular. Walk to beach, town and harbor 20
Hi! We are excited to share this newly completed space with you! It’s a fresh, clean and newly renovated townhouse style apartment. All spaces are private to the unit with exception to the parking area. We are steps to everything and have two other cottages on this property in addition to this duplex unit that have lots of great reviews. Please check my profile to help you comfortably make a choice

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
Popular amenities for Oak Bluffs condo rentals
Weekly condo rentals

Heart of downtown, walk to ferry, bikeway & beach!

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

A Perfect. Walk to beach, harbor and Main Street

Private 3bdrm Condo Tashmoo Woods

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Martha’s Vineyard Condo * Near Ferry

Island Inn - Residential Suite - 37G - Oak Bluffs,

A Spectacular. Walk to beach, town and harbor 20
Pet-friendly condo rentals

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

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

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

2BR dog-friendly 2-story condo with community pool

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

Falmouth MA, Cape Cod Getaway

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

Cape Cod Townhouse w/ Patio & Kitchen

Lovely lakefront studio/condo with pool

1BR Condo w/ Balcony in Mashpee, MA

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,
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 $209 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wifi availability
30 of Oak Bluffs vacation rentals include wifi 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!
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