Pet-friendly holiday rentals in Oak Bluffs

Lambert's Cove Retreat, Water view, Beach pass

Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

Secluded Up Island Cottage

Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

Beautiful private apartment walk to everything!

This is an incredible property! Renovated and spotless with all the amenities to make your stay feel like home, only better. Downtown Oak Bluffs and her beautiful beaches are within a five-minute walk. There is a local market and deli right next door where you can find anything you need in a pinch, and a great BBQ restaurant across the street. This second floor apartment has one bedroom with a queen-sized bed and a queen pullout couch. Smart TVs, full kitchen and laundry plus much more!

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home. Updated 7/25/2025 we do not have any more firewood on the property.

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

Charming Vacation Home in Oak Bluffs.

Escape to our stunning 4-bedroom home near Downtown Oak Bluffs and pristine beaches. Ideal for up to 8 guests, our open-concept layout and cozy bedrooms offer comfort and privacy. Experience a serene retreat with all the amenities you need for a perfect vacation. Book now for an unforgettable stay! Please note: the basement of the listed house is currently occupied. Enjoy the main house's 4 bedrooms, open-concept space, and ideal location near beaches.

The Little Ranch - A contemporary coastal retreat!

Welcome to the little ranch - a newly renovated contemporary coastal ranch that is outfitted to make your stay comfortable and easy. A mix of modern conveniences and comforts with the charm of Cape Cod is perfect for short and extended stays. The house is equipped with upgraded high speed internet and a work station for a reliable and peaceful work away-from-home experience.

Cape Cod Cotuit Cottage, 3 Bed Near Beaches

5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!

Cozy Vacation Getaway On Bike Path

CozyGetaway close to downtown. Dog friendly This 3 bed 1 bath home has an open diningroom-kitchen area. Relaxing outdoor space with outdoor shower. A/C and upgraded wifi 2023. The home is located on the bike path. There is a new bike path from VH ferry right to the home 1.5 miles away!