Oak Bluffs Vacation Rentals & Cottages - 124 Rentals Available

Welcome to the Flying Seahorse, an updated, antique beach cottage that is steps from Oak Bluffs Town Beach, has AC (upstairs, downstairs bedroom and living room), beach views from its balcony, a modern kitchen and ...

Beautiful four bedroom home within walking distance to the Oak Bluffs harbor and town. This home has a nice size first floor living room and separate eat in kitchen. The first floor also has a full bathroom with tub and ...

This grand Victorian jewel on Ocean Park has been completely renovated and transformed into a beautiful vacation home. Enjoy water and park views from inside this elegant home, the expansive wraparound porch and the sec...

A fully renovated four bedroom home with 3 1/2 baths, family room, landscaped lot and a private beach and dock. Dock can accommodate up to a 25 foot motor boat, located on The Lagoon and is accessible to Vineyard Soun...

Newly refurbished, stately 4262 sq ft. home with 4 bedrooms, 2. 5 baths situated within a five minute walk to the center of Oak Bluffs, beaches, and ride/jog to bike trail. Large fenced yard with shared tennis court ...

Waterview - located on the East Chop Vineyard Highlands overlooking Nantucket Sound, Oak Bluffs harbor, Sunset Lake, and 3 acre Washington Park, this charmingly original 1860's Vineyard cottage is an ideal family va...

Great Getaway Cottage with a short walk to Circuit Ave, the harbor, and the Lagoon . A back yard w/ picnic table, BBQ grill. About a mile walk or bike ride to Town. The house has hardwood and fir floors throughout and...

Come and relax on the front porch of this lovely Vineyard home. Located in the desirable East Chop area of Oak Bluffs. The first floor has a nice open space with dining area and living room. There is a nice kitchen with ...

Quietly nestled on quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The interior has open floor plan tha...

Amenities and Features include... Additional amenities include: beach chairs, coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outside shower - enclosed, vacuum, outdoor furniture, ...

East Chop Beauty, bike or walk to town and beach. This designer home features comfortable and elegant dĂŠcor, central A/C and large lovely yard and flagstone patio. Interior features a large open dining and living ar...

Classic vineyard cottage renovated, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. Main living level features a lovely kithcen very well stocked with dining and cook items, a lar...

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings including a 56' LED television. Summer...

Oak Bluffs retreat featuring three levels of luxury living, professionally decorated by one of the islands premier decorators This house is privately situated in an enclave of lovely homes. Bike paths at the entrance co...

A true Vineyard classic from 1890, this house retains its authentic charm yet has been thoughtfully renovated and serves the modern day vacationer well. The 8 bedrooms afford plenty of space to accomodate larger family ...

Classic, "Camp Ground" over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, galleries, etc. It offers double master bedrooms (1st and 2nd floo...

Large families looking for a true shore experience will enjoy this delightful, whimsical, large historic summer home with cottage details set on the edge of Harthaven Harbor. The home boasts spectacular views of Vineya...

Newly renovated 5 bedroom home just a mile and a half from the center of Oak Bluffs. New hard wood floors throughout as well as updated furnishings and decor. Dining area is extended by a nice sized sunny deck for outdoo...

This outstanding Oak Bluffs home is undergoing a complete face lift for the 2012 rental season and is sure to please. Spacious and perfect for extended families, featuring multiple attractively furnished living areas an...

Large families looking for a beachfront adventure will love this relaxed waterfront home. Spectacular views from every room and expansive patios stretch the shoreline. Central location offers a 5 minute drive to town, d...