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.

Waterview, Private, Walk to Beach, Mile to Town

Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

**Vineyard Vacation Retreat** -3 BR

Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. 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.

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.

Single Occupancy Oak Bluffs Studio Apartment

Keep it simple in this peaceful studio apartment. We welcome one guest (and small dog) eager to explore all the Vineyard has to offer! Centrally located, you can easily explore Oak Bluffs or Vineyard Haven; each town is less than two miles from this natural oasis. Boasting a private entrance and stone patio, your own outdoor shower, and access to the fully fenced-in shared backyard, this apartment is perfect for one person and small dogs under 20 lbs.

3 beds, 3 baths 1.5 Miles to Downtown and Beaches!

Attractive Vineyard home located steps from Farm Neck Golf Course and Land Bank walking trails. 1.5 miles to downtown and beaches and right on the bike path! Open spaces with lots of light, cathedral ceilings, mahogany deck, covered porch and outdoor shower. Granite countertops with copper edging and stainless appliances. Walk to Farm Neck Golf Course and Café for breakfast, lunch, dinner or night cap. Bike to the beach or BBQ on the deck.

Arrowsmith Cottage-Oak Bluffs near Eastville Beach

Welcome to Arrowsmith Cottage! If you are considering bringing your pet, please note - one small dog will be considered, but please first contact me directly (scroll down on the cottage's listing page and click on the "Contact Host" button), and tell me a little bit about him/her, as pets require homeowner's written approval and guest’s agreement to the pet fee (generally $100 per stay) and homeowners’ pet rules.

Katama Barn

Selected dog friendly, Immaculate beach house this is the perfect property to bike to the beach and then to dinner in Edgartown. 1.2 miles from beach South Beach, and 1 mile from Edgartown's Main Street. Outdoor shower, large private yard.heated bathroom floors, a/c, heat, modern kitchen, brand new appliances/washer dryer, sleeping loft, and separate storage loft. Location, location, location.

Beautiful walk to Town, Inkwell and harbor!

Hi! This is a newer single family cottage. Two 50" smart tvs with Roku wifi, and state of the art appliances. We pride ourselves on the cleanest properties on island. This modern and newly 2021 constructed space is amazing. Glass shower doors, subway tile shower and all the amentities