Holiday rentals in Edgartown South Beach

Guest suite in Oak Bluffs

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

Lovely 2 BR Oak Bluffs Apartment

*To returning guests: Airbnb has restructured their fees; so while our nightly price may look higher at first glance, it is our same pricing overall This private apartment is on the 1st floor of a family home with a personal entrance & parking; owners and their son live upstairs. There are no shared spaces. It is a mile from Oak Bluffs Center, a half mile from the Cottages and Farm Neck Golf Course, and across the street is a bike path. The bus stop is on the corner for easy island wide travel!

4.95 out of 5 average rating, 442 reviews

The exterior of a cape style home is presented, featuring a dark wood shingle facade and multiple gabled rooflines. A white front door is flanked by evergreen shrubs, while a stone path leads to the entrance. Lush green grass surrounds the property, complemented by a wooden fence.

4.92 out of 5 average rating, 106 reviews

Walk to EDG Wharf - Outdoor Shower, AC, and Grill

Just a short walk to Edgartown's shops & restaurants, this cape style home features open concept living, stainless steel appliances, bamboo floors, oversize 2 car garage, washer/dryer and outdoor shower! The master suite includes a sitting area, walk in closet & attached bath with walk-in shower, soaking tub & double vanity. Additional 3 BRs include queen/twin beds & 2 full baths. Kitchen sliders lead to outdoor brick patio with BBQ and dining area. Outdoors games and four bikes included.

Cottage in Chappaquiddick

A charming cottage features a shingle exterior surrounded by lush greenery. Large windows invite natural light, and a welcoming entryway is accentuated by steps leading to the front door. The tranquil wooded setting enhances the peaceful atmosphere of the property.

Chappy cottage close to ferry & walk to beach

Booking for '26 Season. Charming cottage is a 5-minute bike ride to the Chappy ferry & beach and a 10-15 minute walk to the Frances Preserve beach. Located in a quiet wooded setting, the property offers new furniture and beds; renovated kitchen with dishwasher and microwave; new bath w/ shower/tub; washer/dryer; hardwood; screen porch; deck & outdoor shower. Cable, wifi (200 megs), AC, ceiling fan, grill, deck furniture, beach chairs & umbrella. The rental season runs mid May through late Oct.

4.98 out of 5 average rating, 85 reviews

5.0 out of 5 average rating, 34 reviews

A two-story house is situated among trees with fresh green leaves. A wooden staircase leads to the entrance on the upper level, while a gravel driveway provides access to the home. The exterior features dark wood siding complemented by teal trim.

Home in Chappaquiddick

Chappy Beach House *DERBY DATES!*

Welcome to this charming 4-bedroom retreat tucked just off Chappaquiddick’s only paved road. Perfectly situated minutes from the Chappy Ferry, downtown Edgartown, and some of the island’s most pristine, uncrowded beaches. Features include AC, high-speed WiFi, a washer/dryer, and a gas grill for laid-back summer dinners. Whether you’re a longtime Vineyard lover or discovering Chappy for the first time, this home offers the ideal base to experience the island’s quiet beauty and classic charm.

4.96 out of 5 average rating, 140 reviews

An open living area features a light-colored sofa adorned with blue and white cushions. A flat-screen TV is mounted above a white brick fireplace. Large windows provide natural light, and a dining area with a table and chairs is visible in the background.

Home in Oak Bluffs

**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.

Cottage in Chappaquiddick

A cozy living area features a lightweight sofa adorned with colorful cushions, complemented by a pink upholstered chair. Large windows reveal ocean views, allowing natural light to fill the space. A small table holds fruit and a book, creating a welcoming setting.

Beachfront Cottage + Studio w. Town Access

Welcome to The Rudder Cottage! Fully renovated 1930's cottage on an ocean front compound, with a picturesque porch overlooking the outer harbor, full basement with washer/dryer and central air. An additional detached studio provides a third bedroom/work space. Stunning views of the Edgartown lighthouse and Cape Poge. Access to private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

5.0 out of 5 average rating, 35 reviews

An inviting living room features a light-colored sofa and a natural wood coffee table. Artwork and plants add warmth, while natural light fills the space through ample windows. A large television is mounted on the wall, providing entertainment options for guests.

4.98 out of 5 average rating, 82 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

LOCATION LOCATION ✅ Rated Top 5% of Homes ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood ✅ HotTub, Fire Pit, Trails at your door step, perfect for peaceful strolls or energetic hikes through lush landscapes. AND Flexibility, with Every detail curated for comfort and style, you'll feel at home the moment you step inside. Located with the island's natural beauty around you, unwind and reconnect with nature.

5.0 out of 5 average rating, 6 reviews

A contemporary home with a light-colored wooden exterior, framed by a manicured lawn and trees. The welcoming front porch features stairs leading to double doors, while a deck adorned with wooden railings invites relaxation amidst a lush natural setting.

Home in Chappaquiddick

Chappaquidick contemporary cottage with sauna

This unique place has a style all its own. Contemporary 3 bedroom 2 bathroom home in heart of chappaquidick island . Off the main road close to Mytoi garden , waque and dike bridge. Bike to the beach . And best of it all is the Outdoor shower . Just ferry ride To Edgartown to enjoy morning stroll or have dinner. Equipped with echelon cycling bike sauna and ping pong table. Enjoy bbq on deck .washing machine and dryer available for use All bed have linen and quilt blankets.

A charming two-story cottage features a shingled exterior with a pitched roof. The inviting front porch is supported by wooden pillars and surrounded by lush greenery. A white picket fence encloses the well-kept lawn, creating a warm curbside appeal.

5.0 out of 5 average rating, 29 reviews

Martha's Vineyard Cottage: Walk to Town and Beach

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

4.93 out of 5 average rating, 327 reviews

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

Home in Oak Bluffs

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

A classic Cape Cod home is presented, featuring a steeply pitched roof and natural wood siding. A spacious porch with white railings creates a welcoming entrance, surrounded by a gravel driveway and green grass. Mature trees are visible in the background, providing a sense of privacy.

4.88 out of 5 average rating, 104 reviews

Renovated picture perfect cape home on private lot

Rejuvenation and serenity await you at our newly renovated, thoughtfully appointed family home ideally located in the desirable Katama district just a few minutes by bike or car from gorgeous South Beach and charming Edgartown. Your escape begins when you turn off of Road To The Plains onto a quaint private drive flanked with nature. Right off the rustic stoned circle with sublime mature trees and parking for 8, you discover 4 Quail Path.