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$1,800 to $4,800

Rental ID 116334

  • RTR Vacation Rental
  • Lease $1,800 to $4,800
  • Village Edgartown
  • Bedrooms 4
  • Bathrooms 3

Beautiful new home centrally located, only 3-4 miles to downtown Vineyard Haven, Oak Bluffs or Edgartown. Tastefully decorated, newly furnished interior. Open, airy living-dining-kitchen area with vaulted ceilings, beach stone fireplace. A cook s kitchen with gas stove and granite counter tops. Loft tv room with flat screen plasma tv. In addition, there s two master bedroom suites. A large deck and landscaped yard is perfect for outdoor entertaining or relaxing after a sunny day at the beach.

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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$3,300 to $5,500

Rental ID 135243

  • RTR Vacation Rental
  • Lease $3,300 to $5,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 5

Bright, open totally redesigned, restored and expanded summer cottage on a quiet street in an historic and lovely neighborhood. Less than 1/2 mile from town. Open space plan for maximum interaction for everyday or special gatherings. Private nooks for book reading. Numerous large windows throughout home for a light, airy feeling. Beautiful hardwood floors and ceramic tiles throughout. Top of the line appliances and granite countertops in the kitchen. Many extras. First floor master suite and laundry. Ceiling fans in each bedroom as well as central a/c. A newly finished basement with large flat screen TV, ping pong table, and an extra 1/2 bath to spread out and relax. Rocking chairs on wrap around porch.

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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$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.

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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 ID 134166

  • RTR Vacation Rental
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2
  • Half Baths 1

Brand New to the Rental Market for 2017! This four bedroom, two and a half bath home located in the heart East Chop is newly renovated. Beautiful kitchen, dining living space with french doors that lead to a large screened in porch for dining al fresco. Family room on the ground level for the kids to play and watch television. Four bedrooms, including master with newly renovated master bath. All of this and central air conditioning throughout!

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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 $3,250

Rental ID 134053

  • RTR Vacation Rental
  • Lease $2,000 to $3,250
  • Village Vineyard Haven
  • Bedrooms 2
  • Bathrooms 2

Unique Opportunity - leave your cares and car behind, hop the ferry for a relaxing stay at our Vineyard Haven Village home. This charming place offers privacy yet its historic lane, off Main Street is just a two minutes walk to the town beach, ferry and downtown. Our two bedroom, two bath, fireplaced home is beautifully appointed for your true Vineyard get-away. Just bring your dreams and suitcase because everything else is waiting for you, including kayaks, beach chairs and more! Stay for a week, or longer.

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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$7,000 to $14,500

Rental ID 126030

  • RTR Vacation Rental
  • Lease $7,000 to $14,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 5

The Weku House is a luxury, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha’s Vineyard. Originally built in the year 2000, this home was fully renovated in 2015. Elegantly decorated with designer furnishings and interior appointments, the meticulous attention-to-detail makes this home a unique vacation retreat. With a total of 5 bedrooms and 5 1/2 baths, the home features sleeping accommodations that include two master king suites with ensuite bathrooms, a bedroom with two twin beds, and another spacious queen-sized guest bedroom. Additionally featured is an attached 720 square foot private apartment. "The Apartment" at Weku House features a fully equipped kitchen with Bosch appliances, a queen-sized bedroom, private bathroom, in-unit washer and dryer and an open living and dining room. There is also a private deck with bistro seating. A most popular feature of the home is the spectacularly finished basement, which includes state-of-the-art entertainment come rain-or-shine. Features include: a fitness room, a Play Zone with PlayStation 4, and Wii gaming consoles, a 40 inch 4K high-definition TV and a multitude of board games. Also in the basement is a stunning custom designed bar area with icemaker, dishwasher, microwave and a Hi Def TV overlooking a customized pool table. A home theater with a 70 inch 4K high definition TV and surround sound complete this entertainment space. Add to all of this a 1.3-acre setting, a serene front porch with rocking chairs overlooking beautifully landscaped grounds and a rear deck with dining and seating areas surrounding a rectangular gas fire table, and a gas-powered outdoor grill. With great pride, we welcome you to The Weku House.

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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$2,500 to $6,000

Rental ID 119742

  • RTR Vacation Rental
  • Lease $2,500 to $6,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 2

Located on the North side of Chilmark, this contemporary getaway offers a wide open living space with vaulted ceilings, stylish furnishings, a spacious deck and a stunning widow’s watch with water views. Completely renovated in 2012, this home feels like new and features a brand new kitchen with top of the line appliances, luxury showers with multiple fixtures and central air conditioning. Set on over two acres of land, the property boasts multiple gardens, a private outdoor shower and a fire pit. There are several Land Bank properties within walking distance, including the historic hiking trails at Waskosim’s Rock Reservation. For beach goers, you get access to gorgeous Lucy Vincent beach and are a bike ride away from the beach at Great Rock Bight, a well-kept secret among locals. The Chilmark Flea is just around the corner for those looking for an authentic up island experience. Perfect for families, this is a great venue to recharge and reconnect amidst some of the island’s most beautiful scenery.

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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$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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$/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$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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$
%
$/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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