Martha’s Vineyard Rentals with Air Conditioning

Find rentals with air conditioning in Martha's Vineyard. Let the experts at Landmark Real Estate to help you find your next vacation getaway or temporary home. Search through a variety of listings in beautiful towns on the Vineyard. Found something you love? Sign up with us to save your favorites and get updated with similar properties that match your criteria are posted. If you already have an account with, be sure to log in!

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Rental Price$3,000 to $5,005

Rental ID 135246

  • RTR Vacation Rental
  • Lease $3,000 to $5,005
  • Village Oak Bluffs
  • Bedrooms 3

Spacious, air conditioned 3BR home in private Sengekontacket Association with benefits of community docks, tennis courts and walking trails. Open and awash with natural light, pine flooring, delightful wood trim and beamed ceilings. Master suite and loft/study on 2nd floor has jetted tub, soaring ceilings and skylights. Fully equipped kitchen with granite counters, center island with additional bar seating, gas range and stainless appliances flows to dining room and inviting living room. Guest powder room adjacent to entry foyer. Sliding doors lead to upper deck with retractable awning. Finished lower level has 2 bedrooms each with sliding doors leading to lower deck. A shared full bathroom, game space, laundry room and unique curved outdoor shower also on lower level. Close to town and beaches - located on bike path and bus route.

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Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$1,500 to $4,000

Rental ID 135192

  • RTR Vacation Rental
  • Lease $1,500 to $4,000
  • Village West Tisbury
  • Bedrooms 4
  • Bathrooms 2

Live the sea-faring charm of Martha s Vineyard in this appealing, historic Sea Captain s home. Centrally located in West Tisbury village, this country farmhouse was home to members of the White House Staff when President Clinton made MV his "summer white house". The home features an elegant curved staircase in foyer and a "secret" back staircase leading from the kitchen to the master suite. There are 3-4 spacious bedrooms with air conditioners, desks, and sitting areas. There is a grand piano for your enjoyment. The living room has digital cable TV. Adjoining the living room is a separate dining room with a special farm "tavern" table constructed from a ship s starboard hatch cover, and charming country kitchen. Out of doors relax with a drink on the appealing front porch and watch the world go by. There is private rear patio and a charcoal grill. Walk to Alley s General store, café and deli - and you are steps away from the Famous Vineyard Farmers Market. The Sea Captain s home is located near two of most exquisite and unspoiled beaches. Relax at Lambert s Cove Beach or Long Point South Beach.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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Federal 30-year interest rate: 4.65% last updated on Sep 20, 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 $8,000

Rental ID 133995

  • RTR Vacation Rental
  • Lease $6,000 to $8,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

This brand new construction located just minutes from downtown Oak Bluffs is well appointed and comfortable. A first floor master outfitted with a king bed and is ADA compliant is perfect for grandparents or the nanny. Upstairs you will find three more bedrooms. A generous sized master with sitting area and en suite bath. Two additional bedrooms that share a lovely bath with double vanity and walk in shower. The living area is open concept with a 65 inch flat screen television and comfortable furnishings for movie night. The kitchen is well appointed with high end pots and pans as well as a kitchen-Aid mixer.

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Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$25,000 to $30,000

Rental ID 133977

  • RTR Vacation Rental
  • Lease $25,000 to $30,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

The house itself is spacious with elegant details, state of the art systems, and an attractive floor plan. Craftsmanship quality in this 5,400 square foot home is everywhere, from the kitchen, with its granite counters, center island with copper counter, custom cabinetry, and tile floors & backsplash. To the living areas and bedrooms, that include heart pine flooring, high-ceilings with exposed wood beams, wainscoting and moldings. And, the bathrooms, with their high-end fixtures, tile flooring and custom elements. The kitchen includes a Sub-Zero refrigerator, eight-burner, gas, Viking, stovetop, and two Bosch dishwashers. Heating/AC system includes a Viessmann boiler, forced hot air heat and air conditioning, and radiant heat in the lower level. Floor plan includes a number of bonus areas, table tennis room, media/TV room, wine cellar with brick floor and cedar paneling; two master suites, and an open main level that centers on the living room, which includes cathedral ceilings, fieldstone fireplace, and egress to exterior decking. Many rooms with water views. This beautiful home features all of the finest amenities as well as a heated pool for outdoor entertaining and enjoyment and just recently put tennis court.

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Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$4,500 to $11,500

Rental ID 132800

  • RTR Vacation Rental
  • Lease $4,500 to $11,500
  • Village Edgartown
  • Bedrooms 6
  • Bathrooms 4

New Updates For Summer 2017 - This In Town Victorian Farmhouse sits in the heart of Edgartown Village, with easy and convenient walking access to downtown. New for the 2017 summer season it will be getting a newly renovated kitchen, central air, and a new second floor bathroom. This in town Farmhouse offers all the comforts of a newly renovated home. On the first floor you will enjoy a media/ family room with a comfortable furnishings and a flat screen tv. A newly renovated eat in kitchen leads to a more formal dining area and parlor area. There is a lovely den with a daybed trundle for a fourth bedroom or reading area. On the second floor there are three en suite bedrooms. The master is grand with sitting area and large soaking tub in the master bath. Also located on property is a lovely 2 bedroom guest cottage with a full kitchen and bath If you enjoy in town living this is the home for you!

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Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$7,000 to $9,000

Rental ID 126309

  • RTR Vacation Rental
  • Lease $7,000 to $9,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 2

This contemporary home commands one of Martha s Vineyard s most spectacular 180 degree views overlooking the Elizabeth Islands and Vineyard Sound. You will experience breathtaking sunsets as you dine in or out. Situated high on one of Chilmark’s hills, this home is bright and airy with colorful appointments and artwork to be enjoyed. Open kitchen, living, dining and master bedroom is on the upper level with a wrap-around deck. On the first floor you will find family/TV room and remaining four bedrooms. This house offers a great up-island Vineyard experience with the charm of a nearby fishing village, access to Lucy Vincent Beach, hiking trails and much more.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$2,900 to $5,500

Rental ID 118274

  • RTR Vacation Rental
  • Lease $2,900 to $5,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 2

This five bedroom in-town Oak Bluffs home offers the perfect location to walk to town and beach. The living room opens out to the front wrap around porch which is great for people watching and family dinners. The first floor bedroom makes it easy for some family members and then upstairs includes four bedrooms that share a bathroom. The master bedroom looks out to street and distant ocean waterview from porch. Bring your coffee and newspaper and enjoy.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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$2,000 to $3,200

Rental ID 117809

  • RTR Vacation Rental
  • Lease $2,000 to $3,200
  • Village West Tisbury
  • Bedrooms 3
  • Bathrooms 2

Quiet Vineyard cottage, ranch style home, tucked into a well established West Tisbury neighborhood. Property has been TOTALLY, lovingly decorated, and renovated spring of 2013 inside and out. Great outdoor deck with plenty of sitting space relaxing or entertaining, beautifully landscaped yard. Open living, dining and kitchen, with cozy fireplace, 2 flat screen TV’s. Large Master bedroom, with attached Master bath, and built in office with large sofa chair that pulls out to a twin bed. Two more spacious bedrooms which share a bath, all on one floor…Come visit for a week or stay for the summer, you will love to call this your new summer home. Lamberts Cove Beach access.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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!

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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