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Spacious 4-Bedroom home with outdoor dining

The main floor greets you with an expansive living room, 65" television and pool table. The kitchen has granite countertops with a bar that seats four and large dining area with sliders to outdoor dining. The home includes the use of 2 kayaks that are housed at the association dock on Sengekontacket Pond, tennis/pickleball courts. It is located right off the bike path and includes the use of 2 bikes. Comfortably sleeps 8-10 in 4 bedrooms plus a Murphy bed. The is also a garage for storage.

Charming Oak Bluffs Retreat

Escape to this peaceful Oak Bluffs retreat featuring 4 bedrooms, 2 full modern baths, and an updated kitchen. The finished basement has two overflow rooms with beds (bedrooms 5 and 6 in the photos), a half bathroom, and a media and gaming area, offering plenty of space to unwind. The private outdoor yard offers a trellised deck, grill, kid-friendly tree platform and ample parking. This home is perfect for both relaxation and socializing and is centrally located between the island’s down towns.

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.

Oak Bluffs Renovated Retreat

Fully renovated for 2025, this 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis courts, and direct access to Sengekontacket Pond. Inside, a custom chef’s kitchen, new baths, and luxury furnishings set an upscale coastal tone. The main level flows from a sun-lit living room to dining area / deck, and powder room. The entire second floor is reserved for the primary suite. The walk-out lower level offers two guest bedrooms, a full bath, laundry, and a private patio.

Pinkletink Plantation

Your family will be close to everything when you stay at this centrally-located place. Less than a mile from the heart of Oak Bluffs and Circuit Ave., where you'll find all the famous restaurants, harbor & night life. A half mile from Eastville Beach (fabulous sunsets). Take a morning stroll around "the chop"-East Chop & walk or run a 5K. Less than 2.5 miles from Farm Neck Golf Club- & 2.5 miles to State Beach. It has a well equipped kitchen, laundry, outside shower, & back yard!

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

Stunning Open Concept Oak Bluffs Home

Stunning house in a beautiful community, sleeps 8 and has a huge living room ideal for watching the big screen TV or enjoying the fireplace. There’s tons of natural light throughout. Fully stocked kitchen. Three spacious bedrooms have space to spread out. There’s a twin sofa bed, a folding cot, and two deluxe queen air mattresses for extra guests. Guests can BBQ, eat outdoors, or take a hot outdoor shower. Property has tennis courts, trails, and is minutes walk to the lake.

Entire home newly renovated in August 2025

Step into your serene island getaway at 5 Pine Tree Lane, with 4 bedrooms (4 beds) and nestled in the heart of beautiful Martha’s Vineyard. This brand-new home blends modern comfort with Vineyard charm perfect for families, groups of friends, or couples looking for a relaxing escape. Walking distance to a neighborhood beach, year round ferry access (1mi) and shopping. This home was thoughtfully designed and offers everything you need for a peaceful and memorable experience.

Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

The Blue Lagoon, Oak Bluffs

Come enjoy this beautifully designed, brand new home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An outdoor patio with gas grill is the perfect spot to relax after a day at the beach. Just a few steps away is the lagoon where you can paddle board, kayak, dig clams, or just take in the amazing sunsets! Summer rentals are Saturday to Saturday. Please send a message if you have any questions.

Simone by the Sea

Come enjoy this beautifully designed, totally renovated home. This 3 level home features an open floor plan with a fully stocked kitchen, new appliances, Central HVAC, rooftop deck, EV charging station and much more. Spacious 3 bedrooms, 2 bathrooms is within walking distance to the heart of Downtown Oak Bluffs, OB Ferry and beaches. Comforts of home as well as all the beach accessories to enjoy your day in the sand.

Cozy Vineyard Cottage

Meticulously renovated in 2023. All the comforts of home in 500 well designed sq. ft.. Walking distance to one of the town beaches on Lagoon Pond. Upstairs a King size bed and half bath. Central location to Oak Buffs, Vineyard Haven and Edgartown, all less than 10 mins. away.