Martha’s Vineyard Rentals with Air Conditioning

Find rentals with air conditioning on Martha's Vineyard. Let the experts at Landmark Real Estate help you find your next vacation getaway or temporary home. Search through a variety of listings in beautiful towns on the Vineyard.

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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: 4.45% last updated on Jan 17, 2019
* 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 $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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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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 $9,000

Rental ID 116606

  • RTR Vacation Rental
  • Lease $4,000 to $9,000
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 3

Completely restored waterfront Cape, located next to the Vineyard Haven Yacht Club. Beautifully landscaped gardens and yard, private beach in front of property. Home includes central air, a screened-in dining porch, a farmers porch, as well as an outdoor shower. Ideal location close to town, shopping, restaurants and ferry. This home is fully equipped for a relaxing vacation on the Vineyard harbor waterfront.

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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$8,400 to $14,700

Rental ID 116336

  • RTR Vacation Rental
  • Lease $8,400 to $14,700
  • 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: 4.45% last updated on Jan 17, 2019
* 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 $6,250

Rental ID 139842

  • RTR Vacation Rental
  • Lease $2,000 to $6,250
  • Village West Tisbury
  • Bedrooms 3
  • Bathrooms 3

This newly-renovated 3+ bedroom/3 bath beach house is nestled on two private acres in West Tisbury. A right out of the driveway leads directly to the Long Point Conservation Area, home to one of the Vineyard’s most beautiful South shore beaches; a left will take you to the bike path that runs throughout the Island. The open floor plan of the modern kitchen, adjacent covered deck and dining room provides the perfect entertaining area, and the fully-equipped wet bar and professional pool table in the great room area allow for pastimes in the evening or on those rare rainy days. The second floor – with a private deck, second lounging/TV area, and two bedrooms with their own baths – allow vacationers to spread out in this 3200 square foot home. The third floor loft has four twin beds, perfect for extra guests and children. In addition to Long Point Beach and its adjacent kid-friendly pond, the West Tisbury location allows access to Lambert’s Cove, a private North shore beach great for families. Fully equipped with beach chairs, beach towels, coolers, bikes, kayaks, a canoe and fishing equipment, this home provides all one needs for a perfect Vineyard vacation.

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Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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 $6,300

Rental ID 139301

  • RTR Vacation Rental
  • Lease $4,000 to $6,300
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 1

After a day on one of Martha s Vineyard s varied beaches, come home to this lovely four-bedroom shingled Cape that overlooks Farm Pond, Harthaven, and Nantucket Sound. This 1900 vintage cottage (expanded and renovated in 2009, kitchen remodeled in 2017) is located in historic Oak Bluffs, near the victorian Camp Meeting Association gingerbread cottages, center of the long-standing Black community on Martha s Vineyard, and heart of the Vineyard s art district. Have the best of it all: walk to town, beach, nature trails, tennis, bike paths, Oak Bluffs ferry. Close to everything yet very quiet. Peaceful water views from almost every room with glorious, spacious upstairs porch. Very open, light interior, lots of windows, skylights. House is very cozy and inviting. Enjoy the living room with a custom Lew French beach stone fireplace, a window seat, and comfortable seating. There s a small den with a TV, a dining room with table for 6 or 8, a kitchen with good quality appliances and a table for 2. Laundry/powder room on first floor. Back deck with enclosed outdoor shower. Upstairs are 4 bedrooms (2 queens, 1 double, 1 with double-below/twin-above bunk) with vaulted ceilings and window unit air conditioners, a landing with a large skylight and French doors that open to a deck with spectacular 270-degree views of water and the surrounding landscape. Also full bath with tub and separate tiled shower on 2nd floor, 1/2 bath and brand new outdoor shower on 1st floor. 8x10 shed for bikes and equipment in back yard. Linens, towels, beach towels included (100% cotton). Wi-fi, cable TV provided. 1-2 blocks from the beach (with lifeguard), bike paths, public tennis courts, playground, and around the corner from Land Bank conservation walking/running paths. Less than a mile from Farm neck golf course. 10 minute walk to town, harbor, restaurants, shops, carousel.

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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 $4,800

Rental ID 138888

  • RTR Vacation Rental
  • Lease $3,500 to $4,800
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Set in a luxury community this modern 4 bedroom home is great for vacations. Located off the Edgartown-Vineyard Haven Road, the home is in a private community and is centrally located, only 5 miles from each of the down island’s 3 towns. There are private tennis courts and boat/kayak access to Sengekontacket pond. Scenic viewa abound and the private roads provide for safe bike riding, running and walking. Access to the island’s bicycle path network is just outside the entrance to Hidden Cove. The house sprawls over 3 levels. The recently modernized lower level contains 3 bedrooms, a full bathroom and washer/dryer. The main living level is a contiguous space of living room, media center, fireplace, full bathroom, dining area and kitchen. Brightly lit by 3 sliding glass doors that open out onto a deck facing Sengekontacket pond. The deck has a barbecue, lounges, plus table and chairs with umbrells for outdoor dining. The secluded upper level contains a master bedroom with ensuite bathroom. All in all a perfect base for a fantastic island vacation.

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$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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.

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%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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$3,700 to $5,200

Rental ID 135826

  • RTR Vacation Rental
  • Lease $3,700 to $5,200
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 4

Centrally located pristine four bedroom - four bath home near downtown Vineyard Haven and minutes from Oak Bluffs. Located down a paved road near the bike path, there is a tranquil and peaceful atmosphere at this immaculate home. This home has a fully stocked chef s kitchen overlooking a spacious family room and outdoor deck - perfect for indoor-outdoor summer living. The home boasts two living rooms and has an amazing amount of open space for family gatherings. There is a movie theater downstairs with plush seating and a popcorn machine for the whole family entertainment. Large master bedroom has en-suite bathroom and office nook.

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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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