10 Luxury Martha's Vineyard Vacation Rentals for a Memorable Stay

Experience the beauty and serenity of Martha's Vineyard with these luxurious vacation rentals. Whether you're looking for a romantic getaway or a family escape, these 10 vacation homes offer an unforgettable experience.

⁠Chilmark Ocean View Estate with Pool

Elevate your Martha’s Vineyard vacation experience to presidential level with this Chilmark Estate. This special property, where the Obama family once vacationed, is available for your luxury stay. The property offers the ultimate in privacy and opulence, with stunning views of the Atlantic Ocean and Chilmark Pond. Enjoy the heated infinity pool, half-basketball court or take advantage of the property's private south shore beach that is accessible only by boat from Chilmark Pond.⁠ This property features 7 bedrooms and 5 ½ bathrooms and can sleep 16.

Historic Harbor Front Home With Dock⁠

This grand harbor front home on North Water Street in Edgartown has modern touches, sweeping views and a swimming dock with private beach.⁠ Beautiful waterfront views fill the windows of the living room, dining room, deck and primary suite of the main house as well as the deck and main living space in the guest house.⁠ The highly sought after location is the perfect distance from Edgartown Village, as well as Fuller Street and Lighthouse Beaches.⁠

This property features 6 bedrooms and 3 ½ bathrooms and can sleep 12.

Contemporary Coastal Waterfront West Tisbury Home

Exquisitely designed new contemporary coastal home with pool, set on a private freshwater pond that connects to a south shore barrier beach.⁠ The open floor plan takes full advantage of this spectacular property, surrounded by hundreds of acres of conservation land. Breathtaking sunrise and sunset views await you.⁠ This property features 3 bedrooms and 3 bathrooms and can sleep 7.

Meetinghouse Village Condo

This immaculate Meetinghouse Village end unit has been updated and is well maintained. You will have shared use of the pool and tennis courts and South Beach is just about 2 miles away. A nice floor plan with one bedroom and bathroom on the first and the second bedroom and bath on the second floor, plus a lower level with media room/lounge area and work space. Sliding glass doors open to a lovely private deck. This property features 2 bedrooms and 2 bathrooms and can sleep 4. *Owner prefers two week rentals or longer.

Newly Built Farmhouse in Oak Bluffs with Pool

Exclusive Listing - Gorgeous newly built Farmhouse Style home nestled in the Tower Ridge Neighborhood close to downtown Oak Bluffs with easy access to all other island towns as well. Upon entering the home you will see walls of windows looking out over the 18x36 pool and attached hot tub. Between the well appointed outside lounge area and the front door is the living room with gas fireplace. An open floor plan flows from living area to gourmet kitchen with breakfast bar and formal dining. This property features 4 bedrooms and 3 ½ bathrooms and can sleep 8.

Edgartown Luxury Retreat

This newly built Farmhouse Style Cape sits just on the cusp of Edgartown Village. Close enough to head into town for a bite to eat or shopping and just far enough away to enjoy some privacy.

As you enter the home you are greeted with natural light streaming through the windows and a beautifully appointed open flow kitchen with breakfast bar/prep island, dining area seating 8 and the living room lounge area with fireplace and television. This open floor plan creates a wonderful flow throughout the shared common space and extends to the back deck through wall-high glass sliding doors. Another fabulous feature is the passthrough bar window from the kitchen to the deck. With meticulous attention to detail and a prime location this is a wonderful home to enjoy your Martha’s Vineyard Summer Vacation. This property features 4 bedrooms and 4 ½ bathrooms and can sleep 10.

Edgartown Coastal Retreat

This beautifully maintained, newly built home offers gorgeous furnishings, and an open floor plan with gourmet kitchen overlooking the Edgartown Golf Course. This private residence is set back at the end of the road to offer privacy with easy access to Edgartown village. Upon arrival you are greeted by a large farmers porch. Once you enter the home you will find a bright, open living, dining and well appointed kitchen. A lovely bedroom with queen bed and shared full bath round out the first floor living space. A finished lower level offers separation for guests and families. Included with the lower level family room is a private gym area, complete with The Mirror, Peloton and free weights. The second floor is home to the Primary suite with ensuite bath, await your. In addition there is a lovely balcony that overlooks the golf course and two additional bedrooms. This property features 4 bedrooms and 4 bathrooms and can sleep 8.

Heart of Katama with Field Views

Short minutes to South Beach sits this impressive Katama home. Located down a quiet country lane, close to the Farm Institute and overlooking sprawling fields. With a private yard you could play football in. Enter into a large foyer with a cozy living room on the left and a spacious open dining room on the right. The kitchen is adjacent to the dining room and offers high end appliances along with a great breakfast bar/ prep island to sit and chat at while cooking dinner. Queen bedroom with shared full bath rounds out the first floor.

Head upstairs where you will find a lovely loft with t.v. and pull out sofa. Shared full bath for two bedrooms, one with two twin bunks and the other with a queen bed. The primary bedroom offers a king bed with ensuite bathroom. Plenty of space, close to the beach in a tranquil setting makes this a great summer rental option. This property features 4 bedrooms and 3 bathrooms and can sleep 10.

Waterfront Estate overlooking Eel Pond with Pool

Sophisticated waterfront estate with sweeping water views! Enjoy a formal living room with fireplace, sun room, den and music room with baby grand piano; formal dining room and Chef s kitchen all with beautiful ocean views. All bedrooms offer en suite baths. Main house: Primary bedroom with king bed + two twins, private bath located on 2nd floor. 3 additional bedrooms round out the 2nd floor- a second king suite with private bath, queen suite plus day bed, twin bunk suite. 5th bedroom suite located on the first floor in the main house and 6th bedroom is a queen suite with private bath is located on the 2nd floor of the carriage house. This property features 6 bedrooms and 6 ½ bathrooms and can sleep 12.

This elegant, in-town Waterfront Estate offers impressive sweeping views across Edgartown Harbor and a stunning setting from the harborside pool, patio and pool house. The main level features a formal Living Room with fireplace and opens up to a Sun Room/ Lounge with multiple seating areas framed by a wall of large glass windows overlooking vies across the pool and Edgartown Harbor. The Dining and Kitchen areas are adjoined with French doors. The fully-equipped Chef’s Kitchen has prep island, commercial grade appliances and lots of room to cook and entertain. All bedrooms have ensuite baths. The Primary bedroom along with a twin bedroom are located on the lower level. The Primary bedroom having French doors that open onto a bluestone patio with seating area, access to pool and views of the harbor. Upstairs bedrooms have french doors leading to a wraparound mahogany deck with breathtaking views of Edgartown Harbor and Chappy. The fifth bedroom makes up the entire third floor with built-in window seating to enjoy sweeping water views. The pool area is surrounded by bluestone with a pool house that allows for covered seating, wood burning fireplace, wet bar and half bath. Edgartown Village is just steps away from the front door. This property features 5 bedrooms and 6 ½ bathrooms and can sleep 10.