Condo holiday rentals in Oak Bluffs

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Top-rated condo rentals in Oak Bluffs

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Top Guest favourite

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!

Guest favourite

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!

Guest favourite

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 favourite

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.

Guest favourite

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 Hyannis

4.79 out of 5 average rating, 14 reviews

Charming Hyannis 3 Bed 2 Bath

Discover the allure of Cape Cod effortlessly in our spacious 3-bedroom, 2-bathroom Hyannis residence. Positioned centrally, mere steps from the Steamship Authority and the hospital, it promises both convenience and tranquility. Boasting ample room for family and friends, a well-equipped kitchen, and a cozy living area, this home provides a welcoming atmosphere. With the nearby ferry terminal at your disposal, embark on thrilling adventures to Martha's Vineyard and Nantucket.

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Condo in Barnstable

4.55 out of 5 average rating, 66 reviews

Oceanside Cottage Apt next to Craigville beach

Experience a perfect family retreat at this charming 2-bedroom, 1-bath cottage. Craigville Beach is 200 feet away. Whenever you're not playing the sand, venture and explore any attraction, restaurant, and shop in the Cape, since we are conveniently located in mid Cape We provide all the comforts of home here, including loaded kitchen, AC, WIFI, beach chairs, gas grill, and even beach toys for kids. So just come, enjoy, and relax! It is perfect place for beach lover!

Top Guest favourite

Condo in New Seabury

4.94 out of 5 average rating, 72 reviews

Summer @ Serenity By The Sea, Mashpee , MA

Enjoy our 1 br condo with the BEST view of all the condos, steps from Deans Pond! Walk to Popponesset Market Place, Popponesset Inn & Nantucket Sound. Stroll the beach, hike through conservations areas. Visit quaint shops, restaurants, antique stores! Enjoy morning coffee & evening cocktails on our private deck with that Spectacular View! Spa Rain shower bath, chef's kitchen. Egyptian Cotton Sheets!! NO: Pets-Smoking-Vaping-Parties NO Micro Fiber Sheets!

Guest favourite

Condo in Falmouth

4.73 out of 5 average rating, 15 reviews

Condo in Falmouth MA

The Condominium is just 10 minutes from Falmouth and Falmouth Heights, where you can enjoy the road race and 4th of July fireworks. It’s a quick 20-minute drive to the ferry to Martha's Vineyard and Nantucket, and only 5 minutes to the ocean. Guests can unwind in the stand-alone game room with arcade games or relax by the fire pit, take a swim in the pool, or explore the flax pond for kayaking and fishing. Perfect for both relaxation and adventure!

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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.

Guest favourite

Condo in West Falmouth

4.96 out of 5 average rating, 24 reviews

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

Top Guest favourite

Condo in New Seabury

4.97 out of 5 average rating, 133 reviews

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 only 5 minutes away by car or bike.