Holiday rentals with a fire pit in Oak Bluffs

A private patio area features a stone surface with a seating arrangement that includes a cushioned bench and a small table. A fire-pit is positioned nearby, surrounded by gravel. Lush greenery from surrounding trees provides shade and enhances the serene atmosphere.

5 out of 5 average rating, 9 reviews

Diamond in The Bluffs - New Home, Private Backyard

A peaceful, serene dream Close to Oak Bluffs town, yet away from the noise. This 2025 custom built home is the perfect place for your relaxing MV getaway. Enjoy the fine touches of this lovely home, and the collection of art on display from many local artisans. Enjoy the sunshine in a hammock, the private patio, or the spacious backyard; or stay inside, soaking in the large deep soak tub. The house is just a 20 minute walk into town, or a 10 minute walk to the famous Lagoon swimming beach.

4.94 out of 5 average rating, 378 reviews

An inviting living area features a light-filled space with vaulted ceilings. A comfortable beige couch is complemented by decorative pillows. A dining table with four chairs sits adjacent to a modern kitchen, while glass doors lead to an outdoor area, enhancing the openness of the room.

Cottage in Mashpee

★The Islander | Steps From Water, Fire Pit, AC★

A pristine island getaway. This tastefully decorated cozy cottage is nestled in the Wild Life Sanctuary of Monomoscoy Island. The home is steps from the water with a small water access at the end of the road. The location is great for a family vacation, couples getaway or romantic retreat. You will be minutes from South Cape Beach, New Seabury and the Mashpee Commons. Relax on the large front porch that offers a fire pit and views of the water on either side. Stay with us on your next vacation!

5 out of 5 average rating, 126 reviews

A private garden patio is showcased, featuring a circular table surrounded by four chairs. Plush cushions in vibrant blue patterns adorn the seating. Nearby, two wooden lounge chairs offer additional relaxation options. Lush greenery and flowers provide a natural backdrop, enhancing the outdoor ambiance.

Flat in Edgartown

Private Garden Oasis -Outdoor Shower- Walk to town

* Private garden patio: string lights create chill evenings around the propane fire pit. Table & chairs, propane grill, & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC

5 out of 5 average rating, 9 reviews

Flat in Tisbury

Luxury Guest Suite w/ Private Patio • Near Town

This apartment was newly built just a few years ago & still feels brand new. Located above the garage of our main residence, it has a private side entrance completely separate from the main house for total privacy. Set at the end of a beautiful subdivision just 2 miles from downtown Vineyard Haven, guests enjoy a private patio w/ gardens & a gas fire pit. Inside features stylish Vineyard décor, crisp A/C, fully equipped kitchen, large bedroom w/ queen memory foam bed & a large walk-in shower.

5 out of 5 average rating, 18 reviews

Charming 3-Bedrm w/Loft.New Construct! Walk 2 town

A stylish place to stay, perfect for group trips. 15min walk from town and Inkwell beach. NEW construct, beautiful open layout home is just what you have been looking for. Every bedrm has its OWN full bath. The kitchen is modern and stylish. The open layout design, leads outside to the deck, to a peaceful yet fun backyard. As you sit on the mahogany deck, you will smell the tasty delights coming from the grill of the outdoor kitchen. This home is my home and I want to share it with you.

4.93 out of 5 average rating, 184 reviews

Home in Tisbury

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.

4.83 out of 5 average rating, 214 reviews

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!

Superhost

A dining area features a dark wooden table surrounded by six chairs, with a combination of woven and painted finishes. Above, a chandelier with multiple lights hangs elegantly. A decorative mirror with a sunburst design is mounted on the wall, reflecting the soft, natural light.

4.77 out of 5 average rating, 131 reviews

Beach home just 0.8 miles to Farm Neck Golf Club!

Our home is located in the heart of Oak Bluffs!! This 3-unit property is in a quiet neighborhood, within walking distance of public transportation (0.4 miles), a mile from the pond, and only 0.8 miles to Farm Neck Golf Course. It is a short bike or car ride to Circuit Ave and the Flying Horses (1.7 miles) - where you'll find all the famous restaurants, nightlife & bars - and 2.5 miles to State Beach. It has a well-equipped kitchen, laundry, outside shower, and an amazing backyard!

4.94 out of 5 average rating, 232 reviews

A gravel pathway winds through a lush forest, flanked by tall trees and dense greenery. Brightly colored signage can be seen attached to some trees. A narrow dirt path leads off to the right, inviting exploration.

Guest suite in Mashpee

Cottage on the Bay

Welcome to our charming Cape Cod cottage nestled on the tranquil shores of Popponessett Bay! This cozy space has been cherished by our family for generations, offering a quintessential Cape Cod experience. Located on a private point, our cottage provides stunning bay views and a serene atmosphere perfect for relaxation. Conveniently situated between Popponessett Market Place (2miles) and Mashpee Commons (2.6miles) you're close to shopping, dining, and entertainment options.

Tiny home in Mattapoisett

A welcoming living area features comfortable electric recliners and a small table, set against neutral-colored walls. A nautical-themed rug lies on the floor, while wall art and colorful flags add character. Natural light flows in through the window, which is adorned with blinds.

4.99 out of 5 average rating, 140 reviews

101 Steps to Beach/Island/Bike Path

Experience the Seaside Town of Mattapoisett. Location! Relax in this cozy cottage that is 101 steps from the front door to the Beach/Island/Bike Path. Enjoy this popular, sought after scenic Path for walking, biking, or a day at the Beach. The path is known for its picturesque coastal views. Walking distance to the Quaint Town, Shipyard Park, and many great restaurants. Ned's Point Lighthouse- 5min. Day trip to the Vineyard? Ferry- 14 min. Deals- 10% off 4 or more nights.

A bright living area features a large television mounted on a simple wooden stand, adjacent to a cozy armchair. An open kitchen is visible in the background, showcasing modern appliances and shelving. Warm wooden floors and neutral decor create a comfortable ambiance.

4.91 out of 5 average rating, 23 reviews

Newly renovated home in Oak Bluff near Farm Neck

Escape to this 3-bedroom home in Oak Bluffs, across from Farm Neck Golf Club. The Beach is just a 4-minute drive or 10-minute bike ride away, with the town center nearby for shopping and dining. Located on a quiet, private street, this home offers a spacious yard and a bright, open living space. Relax on the large deck with a grill—perfect for gatherings. With modern updates and ample outdoor space, this is your perfect Vineyard getaway. Book today!

A spacious, newly constructed home is showcased with a dark blue exterior and white accents. The façade features a prominent front porch with chairs and a large garage. A gravel driveway leads to the entrance, framed by a lush green lawn and trees.