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$4,000 to $8,750

Rental ID 139449

  • RTR Vacation Rental
  • Lease $4,000 to $8,750
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Begin and end your Vineyard vacation search with this amazing home. If you are fit enough to climb a flight of stairs, it absolutely will not disappoint! Home boasts an upside-down design, specifically laid out to capture incredible WATER VIEWS from almost every room. It boasts 4 bedrooms (king, queen, queen, and two twins able to be kinged). Home also has two spacious living areas, many decks, both covered and uncovered, a four-person HOT TUB, and nice extras: use of beach chairs, beach towels, and brand new furnishings. Upscale appliances complete this open concept kitchen. Your only disappointment will be when you need to leave. Although this home is BRAND NEW to the rental market, we have been renting homes in Oak Bluffs for many years. We also build and sell them, and are experienced in providing vacationers with a wonderful experience. Walk to Eastville Beach and the Landbank Lagoon Beach (less than 1/8 mile), and bike to Vineyard Haven and Oak Bluffs from your vacation home. Or, if you prefer, step outside your door and hop on the Vineyard Transit Bus to anywhere....Farm Neck Golf, Aquinnah Cliffs and South Beach! Just bring your bathing suit and prepare to relax and enjoy!

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Federal 30-year interest rate: 4.63% last updated on Dec 13, 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$2,650 to $3,800

Rental ID 114932

  • RTR Vacation Rental
  • Lease $2,650 to $3,800
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 3

Spacious three bedroom, three and half bath home, only one mile from downtown Oak Bluffs. Bright, airy comfortably furnished interior with hardwood floors throughout. Open living and dining area with fully equipped kitchen. Nice yard with outdoor deck for entertaining or relaxing after a day on the Vineyard.

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Federal 30-year interest rate: 4.63% last updated on Dec 13, 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$9,500 to $9,500

Rental ID 116602

  • RTR Vacation Rental
  • Lease $9,500 to $9,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 4

Spectacular waterfront home on Sengekontacket Pond located in Farm Neck. Immaculate, open airy home with beautiful interior providing views of water on all three sides - Chappy, Edgartown and Farm Neck golf course. Private, shared Association dock & mooring as well as small beach. One minute drive to State Beach, ten minute walk to Farm Neck (pay to play golf and tennis). A great vacation getaway.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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 $4,000

Rental ID 116365

  • RTR Vacation Rental
  • Lease $2,500 to $4,000
  • Village West Tisbury
  • Bedrooms 5
  • Bathrooms 2

Custom designed home on two acres located on Seth s Pond within walking distance to Lambert s Cove Beach. This thoughtfully designed home has been furnished with comfort in mind. The bright and airy interior features 4 bedrooms, 2 full + 2 half baths, a fully equipped gourmet kitchen, large screened porch, second floor deck and enclosed outdoor shower.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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 $6,500

Rental ID 116299

  • RTR Vacation Rental
  • Lease $3,300 to $6,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 2

Large Victorian, beautifully furnished in wicker and mahogany with stone fireplace and large stained-glass window. Includes a gourmet kitchen and formal dining room. Enjoy outdoor relaxation time on the wraparound porch and large fenced in yard. This magnificent five bedroom home is bright and airy with lovely wood flooring throughout. Fantastic location surrounded by Oak Bluffs picturesque Victorians, and an easy stroll to town or beach.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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: 4.63% last updated on Dec 13, 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: 4.63% last updated on Dec 13, 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 116942

  • RTR Vacation Rental
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 2
  • Half Baths 1

Classic Victorian beach house with four bedrooms and Guest studio/office. Waterviews from porch, master bedroom and upstairs balcony. Private, fenced seating area, flower-filled garden with large picnic table. Great wrap around porch with rocking chairs and beach view. Also on the property is a newly remodeled garden guest cottage which includes a separate kitchen, washer, dryer, bathroom with shower, futon full bed and a garden table and chair. A perfect in-law or nanny suite. This property also has space for two cars in front of house & cottage.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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 $6,000

Rental ID 136665

  • RTR Vacation Rental
  • Lease $3,500 to $6,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Oak Bluffs is the front entry way. The Inkwell Beach is the living room with a large flat screen TV with surround a sound and a dining area, the kitchen area with an island cooking surface it is where all the action happens this flat screen today. . The family room downstairs is named Chilmark where you can play cards, games, or read your favorite book when you want to just “chill”, of course the kids can take over the room for their indoor activities. The bedroom on the main level is named West Tisbury with queen bed and access to the outdoor deck. A full bath is located next to the room with a bath and shower. On the second level you will find the master bedroom named Edgartown, it has king bed and a daybed for watching television or window gazing has an en suite bathroom that includes a shower and tub. Menemsha is the second bedroom and has a double bed next to a beautiful Jack and Jill bathroom with shower. . The Vineyard is the second master and has two queen beds and other exquisite decor.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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 $5,800

Rental ID 116745

  • RTR Vacation Rental
  • Lease $4,500 to $5,800
  • Village Edgartown
  • Bedrooms 5
  • Bathrooms 3

Freshly renovated, farmhouse-style home centrally located and easily accessible to Long Point and South beach. Open kitchen/dining area with new appliances and seating for 10 that opens onto an expansive deck and private yard. Two master bedrooms - one with full bath, walk-in closet, private deck and flat screen tv on main level, and a spacious second master upstairs with balcony, flat screen tv and gas fireplace. Large finished basement with projection tv home theater and separate game room. Also located on property is a lovely one bedroom guest apartment with a full kitchen and bath; private deck and AC.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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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