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.

Questions about Martha's Vineyard vacation rentals?

Call Coldwell Banker Landmarks Real Estate: 508-693-6866

Save time & effort! Create an account to save your favorite listings & get notifications when similar properties become available.

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$5,200 to $6,000

Rental ID 124461

  • RTR Vacation Rental
  • Lease $5,200 to $6,000
  • Village Vineyard Haven
  • Bedrooms 5
  • Bathrooms 4

This spacious five bedroom, four bath main house is ideal for a large family to spread out in. The master offers window unit air conditioning and a private bath. Located on Mink Meadows Golf Course with access to private beach. Tons of outdoor living space with a large screened in porch on the backside of the house and a open deck on the front side of the house.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$6,300 to $11,095

Rental ID 141578

  • RTR Vacation Rental
  • Lease $6,300 to $11,095
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Endless views of the ocean, directly across from the water, and steps away from a sandy beach excellent for swimming. Gorgeously remodeled last summer (2018) and designed with a sophisticated California-meets-MV feel inside, our welcoming, centrally-air-conditioned, 4 bedroom house sleeps 10 and is a rarity in this area. Blonde wood wide plank flooring, new kitchen, new doors & windows, mattresses, and appliances including dishwasher, gas range, French door refrigerator with ice maker and a king size bed in a larger than usual (for OB) master BR. The house is airy and uncluttered, with a wide 3-sided wraparound porch, perfect for watching the annual fireworks, dining outside or watching the world go by. 4 well appointed bedrooms -- one downstairs and three upstairs (including a larger bedroom with a queen & 2 twins which is perfect for sharing). Second-story deck off the master bedroom offers views of the ocean, as well as Farm Pond. A second porch off the second & third upstairs bedrooms also has ocean views. Two sets of French doors from the kitchen and dining area open out to a larger portion of the deck and stunning ocean views. Updated bathrooms (glass-door subway tile walk-in shower downstairs, a deep soaking tub upstairs), wide porches to relax and dine on, and an open and connected feeling downstairs (a wood topped bar/island connects guests to the dining area and the kitchen, open french doors connect it all to the deck and the outdoor seating/dining). The house is set back from the road by a generous lawn, and is a very short distance (a few houses) to the bike path that runs along the island s edge & State Beach and into Edgartown, and within easy walking distance of both the Oak Bluffs ferry docking and the shops and restaurants in town and along the harbor, so you ll never have to search for a parking space to dine in-town in the high season. There s a large dining table inside & barbecue and additional outdoor seating/dining table on the porch, TV (televisions in the living room and the master BR). 1 king bed, 2 queen beds, 1 full sized bed, and 2 twin beds. Additionally, upon request/discussion, there is a back guest cottage aka "The Nest". The Nest has a good size upstairs bedroom (offering what is then a 5th BR); queen bed and a twin bed (sharing the same room), a deck off the bedroom that has water views (ocean and Farm Pond),

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$3,000 to $6,250

Rental ID 115846

  • RTR Vacation Rental
  • Lease $3,000 to $6,250
  • Village Vineyard Haven
  • Bedrooms 5
  • Bathrooms 4

This charming 5 bedroom/4.5 bath contemporary located in Mink Meadows with views of the 8th fairway is a great location for any golf enthusiast or vacationer that just wants a great home to relax and escape. A light filled open living room with beams & fireplace is a great spot to watch TV, relax with a book or watch the golfers go by. The large dining room with seating for 10 people and delightful eat-in kitchen is perfect for large or small family dinners or step outside into the expansive deck with comfortable outdoor furniture. Three bedrooms on the first floor, and the master bedroom and en suite bathroom provide a bath, shower, and dressing room area. Two bedrooms on the second floor each offer queen beds and a shared bathroom with shower. Key to private Mink Meadows beach available when booking this vacation home, and if lost $250 will be taken out of security. This Vineyard home is a perfect retreat for any small or large family.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$4,000 to $6,250

Rental ID 139842

  • RTR Vacation Rental
  • Lease $4,000 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$4,000 to $8,800

Rental ID 116606

  • RTR Vacation Rental
  • Lease $4,000 to $8,800
  • 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details