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 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$4,500 to $14,500

Rental ID 134310

  • RTR Vacation Rental
  • Lease $4,500 to $14,500
  • Village Edgartown
  • Bedrooms 4
  • Bathrooms 4

LARGE & DRAMATIC recently renovated custom designed and professionally decorated Tri-level contemporary home with open floor plan. Once inside, you will be captivated by the dramatic open spaces, soaring cathedral ceilings, and walls of glass. This extraordinary home is located on a beautifully landscaped property with a large backyard and 18x40 heated saltwater pool with a bluestone surround, with lounge chairs, as well as a FirePit. Ready for May 2017. With three levels, multiple gathering spaces, four bedrooms and four and half baths, it is perfect for accommodating two families. Of the four bedrooms, three are master suites with private bathrooms and the fourth has its own bathroom (just not ensuite). All of the bedrooms have large Flat Screen TVs. There are large wrap-around decks, offering great outdoor space. A 32’ high very large great room with vaulted ceilings is surrounded by expansive walls of glass and open to the dining area lending itself to superb entertaining. A beautiful marble fireplace creates a focal point from both the living room and dining room. A fabulous gourmet designed kitchen with quartz counter tops is fully equipped with top of the line stainless steel appliances and all the necessary kitchen essentials to create a great meal. There is also an additional first floor family room with a large flat screen TV and wall of glass that leads to another private deck. This first floor deck will lead to the new saltwater heated pool This large and luxurious home will fulfill every item on your must have list for a great Vineyard vacation. It is only a 5-minute drive to downtown Edgartown, as well as within walking distance to South Beach along a bike path. SPEND THE DAY AT THE BEACH, RETURN HOME AND ENJOY SWIMMING IN YOUR OWN REFRESHING HEATED SALT-WATER POOL. HAVE DINNER ON THE PATIO AND AFTER DARK, SIT AROUND THE FIRE PIT COOKING S MORES AND GAZING AT THE BEAUTIFUL STARLIT SKY.

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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$
$
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$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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 $10,000

Rental ID 126257

  • RTR Vacation Rental
  • Lease $4,000 to $10,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 3

This mid - century modern four bedroom with a 4 foot wading pool is not to be missed! Master offers air conditioning and private bath. Located just past Able s Hill perched on hill abutting conservation land you really feel away from it all.

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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$3,500 to $20,000

Rental ID 116456

  • RTR Vacation Rental
  • Lease $3,500 to $20,000
  • Village Oak Bluffs
  • Bedrooms 6
  • Bathrooms 3

Centrally located six bedroom Victorian home offers panoramic views of Ocean Park and the Vineyard Sound. Large, open spaces throughout home, huge kitchen, great for families. Convenient to Circuit Avenue shops and restaurants, just a short walk to the public beach. Central air conditioning.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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 $15,000

Rental ID 135386

  • RTR Vacation Rental
  • Lease $6,000 to $15,000
  • Village Edgartown
  • Bedrooms 4
  • Bathrooms 5

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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$7,500 to $13,000

Rental ID 118600

  • RTR Vacation Rental
  • Lease $7,500 to $13,000
  • Village West Tisbury
  • Bedrooms 5
  • Bathrooms 4

Stunning 1.5 landscaped acres, located in the Lower Makonikey area. Private beachfront, main house and guest house. 4 miles to downtown Vineyard Haven and 2.5 miles to up - island Cronings.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$4,000 to $10,000

Rental ID 134575

  • RTR Vacation Rental
  • Lease $4,000 to $10,000
  • 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.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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$10,000 to $20,000

Rental ID 116953

  • RTR Vacation Rental
  • Lease $10,000 to $20,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 4

This is a peaceful four bedroom Cape located directly on Chilmark Pond with a highly desirable Hancock Beach Association key. Tastefully decorated with all amenities. the first floor includes an open concept living room, dining cook s kitchen with an adjacent pantry laundry room. there two en suite bedrooms and a three season porch. All rooms overlook Chilmark Pond. Upstairs includes two en suite bedrooms and a tv room that leads a second floor deck with views of Chilmark Pond. This home offers all ingredients necessary to create a wonderful and relaxing up island vacation escape. It is conveniently located between West Tisbury and Chilmark village centers. Kick back and enjoy the best that Chilmark has to offer!

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$20,000 to $45,000

Rental ID 116578

  • RTR Vacation Rental
  • Lease $20,000 to $45,000
  • Village Edgartown
  • Bedrooms 6
  • Bathrooms 5

Elegant waterfront home on Eel Pond with private pool and carriage house suite. Spacious open interior with great attention to detail and full of amenities. Beautiful grounds and large patio area for outdoor entertaining. Located in desirable Edgartown, convenient to downtown area - boutique shopping, restaurants, galleries, cinema and harbor stroll.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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 $23,500

Rental ID 116541

  • RTR Vacation Rental
  • Lease $6,000 to $23,500
  • Village Edgartown
  • Bedrooms 4
  • Bathrooms 4

Located just two blocks from Edgartown Village this newly constructed sophisticated luxury retreat offers gracious style and comforts throughout. This 5200 square foot home features casual elegance and all of the finest amenities as well as a heated pool and blue stone patio for outdoor entertaining and enjoyment. There are four bedrooms, each with en-suite baths, the master separated by French doors for privacy and a den on the first floor which upon request can be converted into the fifth bedroom with a queen bed. You will find the media/game room hard to beat, with a large-screen TV and a pool table that has a Ping-Pong option. Perfect home for the family who wishes to have it all. Finishing touches are currently being completed and more photos to be posted soon.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details