Condo vacation rentals in Dukes County

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Top-rated condo rentals in Dukes County

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Top guest favorite

A clear view of a sandy beach meets the calm ocean, with several people enjoying the shore. A stone jetty extends into the water, while a few umbrellas provide shade at the water's edge. The sky is bright with a few scattered clouds.

Condo in Oak Bluffs

5 out of 5 average rating, 24 reviews

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 your 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!

A covered balcony is seen from the exterior, featuring a small bistro dining set. Adjacent to the balcony, a path leads to the beach, with unobstructed views of the ocean. Lush greenery and white gravel enhance the outdoor setting.

Condo in Oak Bluffs

4.91 out of 5 average rating, 22 reviews

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!

A wooden shelf is filled with various decorative items, including a white elephant figurine, a woven basket, and a vintage-style camera. A sign displaying the word 'BEACH' is prominently featured, alongside small collectibles reflecting a coastal theme.

Condo in Oak Bluffs

4.82 out of 5 average rating, 44 reviews

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!

Guest favorite

Condo in Edgartown

5 out of 5 average rating, 14 reviews

Walk to downtown Edgartown in a quiet neighborhood

This house is on a peaceful side street just a 15-min walk to Edgartown Village. It has 3 bedrooms, one bath, a well-equipped kitchen, porch and grill for summer cooking! This rental is a second-floor unit, the first floor is occupied by the owner. Both units are completely separate with private entrances and no shared spaces. Close to multiple popular beaches, the town library and playground, and just around the corner from the island's largest grocery store make this a great home base!

A private heated pool is surrounded by a concrete patio, with shade provided by a large umbrella. A dining table with several chairs is located nearby. Lush greenery and colorful flowers add a vibrant touch to the pool area, creating a relaxing outdoor space.

Condo in Mashpee

5 out of 5 average rating, 4 reviews

Capecation! 3-bedroom condo with heated pool

It's the perfect time for a Capecation! Our spacious 3-bedroom condo is perfect for a multigenerational family vacation or a girls weekend away. This rental comes with your own private heated pool (June thru September), two mountain bikes and a paddleboard for your use. We provide sheets, towels, beach chairs & family games. We are located about a mile from South Cape Beach and Popponesset Marketplace. It's about a 10 minutes to all the shops, restaurants and movie theatre at Mashpee Commons.

Guest favorite

A charming exterior of a two-story home is framed by a white picket fence. The light brown siding and decorative gable accentuate the inviting architecture. Lush greenery and flowering bushes are visible, complemented by a sunny blue sky.

Condo in Oak Bluffs

4.9 out of 5 average rating, 243 reviews

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 and best of all it's all brand new. This 400 square foot unit will provide you with an excellent home base to explore Oak Bluffs and Martha's Vineyard.

Guest favorite

A screened-in porch features a glass table surrounded by comfortable seating. Natural light filters through the windows, illuminating the space. The backdrop includes lush greenery, enhancing the tranquil outdoor setting.

Condo in Tisbury

4.91 out of 5 average rating, 47 reviews

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.

A welcoming entryway features hardwood floors and soft blue walls. Natural light enters through large glass doors leading to a staircase. A console table displays a framed artwork and decorative vases with fresh flowers, while a lamp provides a warm glow.

Condo in Oak Bluffs

4.77 out of 5 average rating, 13 reviews

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, Linda Jeans, 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.

Guest favorite

A modern kitchen features sleek white cabinetry and a spacious countertop. Natural light fills the area through a window, highlighting a gas stove and stainless steel appliances. A small door leads outside, while a patterned rug adds warmth to the floor.

Condo in Tisbury

4.98 out of 5 average rating, 50 reviews

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.

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Condo in Falmouth

5 out of 5 average rating, 4 reviews

InnSeason Resorts HarborWalk Studio

Walk out the door, cross the street and catch the Island Queen ferry to Martha's Vineyard. This resort is directly across from Falmouth Harbor, at the center of it all. Just minutes from the beach, you also have easy access to fishing and boating, and it's only a short walk to shopping, dining and more on bustling Main Street. When it's time to take a break, take your beach bag to the on-site tanning deck and enjoy the lovely harbor views.

Top guest favorite

The kitchen features modern wooden cabinetry with stainless steel appliances, including a refrigerator and oven. A granite countertop runs alongside a spacious sink, complemented by a stylish backsplash. Natural light floods the room through the window, creating a bright and functional cooking space.

Condo in Falmouth

4.95 out of 5 average rating, 43 reviews

Location, location! Historic Downtown Falmouth!

Completely renovated historic property with large relaxing backyard. Everything is at your fingertips! Steps to downtown Falmouth. Condo in historic "Consider Hatch" house. Stroll down Main Street for great restaurants, boutique shops, art galleries and more! Close to beaches, the 11 mile "Shining Sea" coastal bike path, bike rental shop, ferries to Martha’s Vineyard and more.