Martha’s Vineyard Luxury Rentals

Martha’s Vineyard, Massachusetts, is renowned for unparalleled ocean sounds with breathtaking sunrise and sunset vistas, as well as calm waters for any sailor’s delight. The variety of luxury rental homes available through Coldwell Banker Landmarks Real Estate will ensure that you and your loved ones enjoy all the Island's treasures, whatever your taste.  Whether you're searching for a luxurious waterfront home with ocean views, a contemporary estate in the hills of Tisbury, or a secluded mansion in the spectacular north end, there is certainly a rental option for everyone.

Whether you come for the Island's authentic beach culture, the myriad of signature shops and delicious top-rated restaurants, the gorgeous sandy coastlines, or one of many other reasons, there is always a great reason to be in Martha's Vineyard. What are you waiting for? Begin exploring, now.

If you would like to view one of these listings, please contact us or call 508-693-6866. To stay up to date on your favorite listings and searches, register with our site.

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Rental Price$8,400 to $16,800

Rental ID 116336

  • RTR Vacation Rental
  • Lease $8,400 to $16,800
  • Village Vineyard Haven
  • Bedrooms 6
  • Bathrooms 3

Built in 1758, this historic waterfront home was originally a tavern for sea-faring folk. Located less than 25 feet from the water, the home offers broad views of both inner and outer harbors, as well as Vineyard Sound. The stairway and boardwalk to the magnificent sandy beach include a deck and enclosed outdoor shower and provide access to the property s mooring. Inside this stunning vintage home, enjoy the library in the fireplaced living room while taking in views of the water. The formal dining room with fireplace and modern kitchen overlook the side terrace and garden. Ocean views from the master bedroom and the bath s vintage claw-foot tub complete the sea-side experience. This charmer includes a key to Hancock Beach, Chilmark s desirable gated south shore ocean beach.

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Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$6,000 to $16,000

Rental ID 135386

  • RTR Vacation Rental
  • Lease $6,000 to $16,000
  • Village Edgartown
  • Bedrooms 4
  • Bathrooms 5

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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$4,000 to $10,500

Rental ID 137364

  • RTR Vacation Rental
  • Lease $4,000 to $10,500
  • Village Vineyard Haven
  • Bedrooms 5
  • Bathrooms 4

The beautiful new home is conveniently located within walking distance to downtown Vineyard Haven. The Main house features four spacious bedrooms with 3 full baths and one half-bath. The first floor has a gourmet kitchen featuring Viking appliances that overlooks a large, comfortable family room with gas fireplace. The family room opens into a large dining area that seats up to 10 people with French doors opening to a deck and bluestone patio with additional outdoor seating. A second more formal gathering space is located in the living room which features a second gas fireplace, A lovely guest cottage is also located on the property and includes an open kitchen, 1 bedroom with French doors opening to the beautiful yard, 1.5 bath and a loft for extra space. This home is in walking distance to the library, shops and restaurants of Main Street Vineyard Haven and the Harbor.

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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$6,000 to $10,000

Rental ID 116941

  • RTR Vacation Rental
  • Lease $6,000 to $10,000
  • Village Vineyard Haven
  • Bedrooms 7
  • Bathrooms 6

This wonderful in-town property has just undergone a renovation and addition that seamlessly integrates the grace and patina of an 1840 s captain s house with the convenience and comfort of a modern family home. Great location one block from beaches, shopping and ferry and winter harbor views complete this spectacular home.

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Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$8,825 to $10,600

Rental ID 132137

  • RTR Vacation Rental
  • Lease $8,825 to $10,600
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Waterfront custom Farmhouse overlooking Crystal Lake toward East Chop Drive. There is a large manicured lawn and garden with a path to the lake and a row boat for your enjoyment. Sit on the expansive deck and use the 8 x15 hot tub/ dip pool, outdoor shower and enjoy the view, or grill on your brick patio (ALL WITH INCREDIBLE VIEWS). A very peaceful location, yet a five minute drive to Circuit Ave, East Chop Light, and the beaches of Oak Bluffs. Vineyard Haven and Oak Bluffs ferries are also a five minute drive. A great area for the kids to play and FAMILIES to get around very easily. Also lovely walking paths nearby for birdwatchers. This well-maintained, well-equipped house offers linens and towels, bicycles, and is loaded with amenities. The first floor offers a large modern kitchen, breakfast bar open to the dining room and a large living room all with views of a lovely yard, Crystal Lake, and Vineyard Sound oceanfront beyond. There is also a sun room, 2 bedrooms, and 1.5 baths on this floor.

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Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$4,000 to $12,000

Rental ID 134575

  • RTR Vacation Rental
  • Lease $4,000 to $12,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach! The house lies between West Tisbury (Alley’s General Store, 7A Foods, Farmer’s Market, Artisan’s Market, galleries, etc.) and Chilmark (Chilmark Store, Chilmark Tavern, Chilmark Community Center, etc.). It is also a short ride to Menemsha Village (fishing, fish markets, galleries, restaurants, and sunsets on the beach). This 1713 Mayhew farmhouse underwent a complete gut-renovation in 2017 and was reborn to honor its past while embracing today’s contemporary lifestyle. The house is fully air- conditioned and has Wi-Fi, high speed Internet and cable TV. A beautiful three-season porch was added to the back of the house. It is a relaxing place to sit, read, play a game, watch TV, or simply observe what is going on outside. The porch leads to a bluestone patio with a teak dining table with seating for 8 under a market umbrella along with a number of chairs to relax in and a gas grill. Adjacent to the patio is a large private outdoor shower. The house is surrounded by an expansive lawn bordered by stonewalls. The house is remarkably open on the first floor. The porch leads into a fully equipped cook’s kitchen with high-end appliances, quartz countertops and an island with seating. The dining room has a farmer’s table that seats up to 10 along with an additional sitting area by the fireplace. The library/media room is a cozy place to sit and talk, read by the fireplace, or binge watch that show you just never got to last year on a large flat screen TV. The final room downstairs is the first, of two, en suite master bedrooms (queen bed). It has a fireplace, flat screen TV, and a marble and tile bathroom. A French door leads from this bedroom to the bluestone patio. The central hallway contains a half bath and two stairways that lead to the second floor where you will find four additional bedrooms, (two queens, one twin and an en suite king), a full laundry and a large bathroom with an oversized tub/shower. The 2nd floor master bedroom (king bed) has a flat screen TV, an attached walk-in closet and en suite marble and tile bath. High quality linens and towels are provided throughout the house. The real bonus of this house is its key to Hancock Beach—located approximately 1.5 miles from the house down a private road. Hancock Beach is a premier private South Shore ocean beach adjacent to Chilmark Pond so that both can be enjoyed. Tenants can bring kayaks to the pond to explore this beautiful, unspoiled environment. Tenants also have access to Chilmark town beaches—Lucy Vincent and Squibnocket. Beach chairs, towels, umbrellas and coolers are all provided.

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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$35,000 to $60,000

Rental ID 116963

  • RTR Vacation Rental
  • Lease $35,000 to $60,000
  • Village Edgartown
  • Bedrooms 5
  • Bathrooms 6

Luxurious Edgartown waterfront estate with award-winning infinity pool surrounded by 150 acres of conservation land. This quintessential summer escape offers views, location and lifestyle. Deluxe amenities abound in this 8,000 sq ft custom built compound, the main house includes four bedrooms and five baths. A fully equipped gourmet kitchen with top of the line appliances and beautiful stone fireplace with sitting area add the perfect touch. Private guest quarters located above the garage includes separate bath, kitchen and living area. Elegant craftsmanship and attention to detail throughout the design of this home, everything state of the art. The bluestone patio, custom built stone gas grill, entertainment bar and sink and professionally landscaped grounds add to your summer outdoor entertaining. It s everything that you and your family could possible need for a spectacular Vineyard experience.

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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$5,000 to $13,000

Rental ID 116756

  • RTR Vacation Rental
  • Lease $5,000 to $13,000
  • Village Vineyard Haven
  • Bedrooms 7
  • Bathrooms 7

Sprawling, traditional Vineyard home and guesthouse located in West Chop. Very private, nicely landscaped setting, framed by trees and a great yard. Large outdoor porch, perfect for dining and relaxing. Comfortable, tastefully decorated home, fully equipped. Bright, airy open living space on main floor, second floor den with Bluray player. Every bedroom (main and guest) has full private bath.

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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$10,965 to $26,520

Rental ID 116998

  • RTR Vacation Rental
  • Lease $10,965 to $26,520
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 5

Located in one of the most exclusive associations on the Vineyard, this five bedrooms home offers some of the most stunning water views the island has to offer. This home includes spacious decks, vaulted ceilings, and all the amenities one expects in a premier property. Tenants have access to both the association and homeowners beaches.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$5,000 to $20,000

Rental ID 116755

  • RTR Vacation Rental
  • Lease $5,000 to $20,000
  • Village Edgartown
  • Bedrooms 6
  • Bathrooms 4

Masterfully renovated 1850’s Sea Captain’s home situated on a quiet tree lined street. Designer decorated Grecian Revival is within walking distance to the harbor, restaurants and beaches. Main level includes a large gourmet kitchen adjacent to a bright family with working fireplace. A living room, dining room (each with its own fireplace), wood paneled media room and office completes the first floor. There are four bedrooms and three baths on the second floor (two of these bedrooms have french doors that lead to a second floor balcony. On the third floor you will find a large sunny bedroom/play area along and bathroom. Separate from the main house is a detached one bedroom studio with full bath. This private compound located in the heart of Edgartown village is professionally landscaped with a heated pool and hot tub.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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