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$4,500 to $5,500

Rental ID 116745

  • RTR Vacation Rental
  • Lease $4,500 to $5,500
  • 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.

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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$2,740 to $8,825

Rental ID 113885

  • RTR Vacation Rental
  • Lease $2,740 to $8,825
  • Village Edgartown
  • Bedrooms 3
  • Bathrooms 2

Originally the boathouse for the Daggett house on Edgartown Harbor, this historic cottage was completely renovated in 2002, and in 2004 an addition was built. Located three blocks from downtown Edgartown, on a safe dead-end lane offers complete privacy. The original cottage is comprised of a gourmet kitchen with Italian tile, a wonderful dining room with a curved ceiling. Large stone patio overlooks Sheriff Meadow Bird Sanctuary. The addition includes a large living area with huge windows, entertainment center and a fully equipped wet bar. Upstairs, the beautiful master bedroom suite with full balcony offers a breathtaking panoramic view of Nantucket Sound and at night Cape Cod. Included is the key to Black Point Beach in Chilmark (30 min drive), a private and incredibly beautiful beach.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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$2,400 to $3,750

Rental ID 116679

  • RTR Vacation Rental
  • Lease $2,400 to $3,750
  • Village Edgartown
  • Bedrooms 3
  • Bathrooms 2

Three bedroom Cape in Katama, just a short walk (20 min.) into town, 1.5 miles to beaches and 0.5 mile to bike path. Beautifully decorated with upscale furnishings, gourmet kitchen with breakfast bar and full amenities. Open floor plan makes this a perfect home for family entertaining. It is bright and airy with a spacious living area. Additional sleeping available in the den (sofabed-queen). Other amenities include private wooded yard and large deck, outside shower, hardwood floors throughout.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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 $4,500

Rental ID 116671

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

Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the ambiance. The house offers 2,400 square feet of living space. The first floor is an open space plan with a living room and fireplace, a screened porch with a view of the large back yard, a fully equipped kitchen and a dining area. A double BR with ½ bath is off the living room. Upstairs, the king and queen bedrooms have a beautiful pond view. Additionally there is a twin-bedded room. Laundry facilities are conveniently located on the second floor in one of the 2 full baths. An adjacent old barn converted to a studio houses a living area and trundle twin beds (queen) for additional living space.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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

Rental Price$7,500 to $19,500

Rental ID 134281

  • RTR Vacation Rental
  • Lease $7,500 to $19,500
  • Village Edgartown
  • Bedrooms 5
  • Bathrooms 4

New construction just finished summer 2017! Coastal-inspired Gambrel with open layout and integrated outdoor living spaces, including a screened porch and farmer s porch, plus heated gunite pool with hot tub, and a large stone patio, redwood glider and hammock in the yard. The first floor includes open Living, Dining, and Kitchen Areas. The Living Area has vaulted ceilings and is anchored by a 16-foot tall, stone fireplace. There are built-in media center, plus French doors. The Dining area features see through gas fireplace. There are 9-foot ceilings a wall of glass windows, and a large dining table with high back comfortable chairs. The fully-equipped kitchen features large center prep bar, granite counters, high-end appliances. One end of the Kitchen opens to the Screened porch with Brazilian wood ceiling and floor to ceiling wood burning fireplace that overlooks the pool area. One of three Master Bedrooms Suites is on the first floor. It has a deluxe master bath with double granite vanity, soaking tub, double walk-in shower. The other two en suite Masters, are upstairs. The second floor has one other Bedroom, a shared bath, and a large, open TV/Family area with media center. There is a fully built-out, deluxe Lower Level with high ceilings, windows, and French doors that let in lots of light. The space features a Game/Media Area with pool table, ping pong, media center, plus gym are, and Kitchenette, casual Dining Area, a 4th king bedroom and a half bath. The outdoor space is centered around the 38x18-foot, heated gunite pool and hot tub for 6 and chaise lounge for 8. The pool is outfitted with swim jet and swim current system. The pool is surrounded by 1400 sq foot stone patio that has ample lounging, dining and seating areas for outdoor entertaining. A big bonus to the property is a garage outfitted with a universal electrical car charger. The property has professionally landscaped grounds and gardens, with trees providing privacy and luxurious outdoor setting. The is in a quiet residential neighborhood in Katama, a mile away from Edgartown Village and mile and a half from South Beach.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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$5,000 to $11,000

Rental ID 116756

  • RTR Vacation Rental
  • Lease $5,000 to $11,000
  • Village Vineyard Haven
  • Bedrooms 7
  • Bathrooms 7

Sprawling, traditional Vineyard home and guesthouse located in West Chop. Very private, nicely landscaped setting, framed by trees and a great yard. Large outdoor porch, perfect for dining and relaxing. Comfortable, tastefully decorated home, fully equipped. Bright, airy open living space on main floor, second floor den with Bluray player. Every bedroom (main and guest) has full private bath.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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

Rental Price$2,950 to $2,950

Rental ID 113603

  • RTR Vacation Rental
  • Lease $2,950 to $2,950
  • Village Vineyard Haven
  • Bedrooms 2
  • Bathrooms 3

Beautifully appointed condominium in Tashmoo Wood. Bright and airy with cathedral ceilings, gourmet kitchen and central air. The den could be used as an extra bedroom. Association tennis and pool. A great family vacation spot.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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

Rental Price$6,500 to $8,500

Rental ID 113579

  • RTR Vacation Rental
  • Lease $6,500 to $8,500
  • Village West Tisbury
  • Bedrooms 4
  • Bathrooms 4

Beautiful custom post and beam located in Deep Bottom Pond. Air-conditioned contemporary with cathedral ceilings and floor-to-ceiling windows facing the woods. Enjoy the spacious deck, hot tub and association tennis. Large, bright rooms and located close to the bike path. A basement sleeping room with sitting area, TV and private bath are perfect for extended family or nanny. New gunite pool and bluestone deck in a private wooded setting.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.32% last updated on Feb 8, 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