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Long-Term Vacation Rentals in Oak Bluffs

Rental homes are available for an extended stay of a month or more at a time. While some rentals by owner will be available for long-term stays during the summer or year-round, majority are available during the off-season (fall, winter and spring). Monthly prices may vary depending on the number in your party and length of stay.

Rentals are listed by location, sleeping capacity, and number of bedrooms.

# of Rentals: 18

Oak Bluffs

Island Escape with Water-Views; Lap Pool & Guest House
6BR
4 baths
Sleeps 15

Long term rentals considered! October - March $6,000/mo

Contact: Jack, Property ID: 39526

The Beach House: Historic Harthaven Gem on a Private Beach
5BR
3 ½ baths
Sleeps 12

32 day rental priced at $9,000 per week, $450 housecleaning fee, one free mid-month cleaning, $500 security fee. August-September. Late Fall not off...

Contact: Marion, Property ID: 31261

Glorious Sunsets On and Over the Water. Beautiful Home
4BR
3 ½ baths
Sleeps 12

Month-long rental available beginning in September into at least October. Rate is $6000-7500 weekly. No pets, smoking of subletting. Great Derby locat...

Contact: Richard, Property ID: 27817

Dempster Park of East Chop: Walk to Beach & Town!
4BR
3 baths
Sleeps 11

Long-term rentals available from October-Mid May. Please inquire. Monthy charge $5,000.00 plus utilities. Trash pick up will be the responsibiity of ...

Contact: Joan or Monica, Property ID: 34601

The “Summer Wind” House - Walk to the Beach!
5BR
3 baths
Sleeps 10

$20K per month off-season.

Contact: Wendy , Property ID: 35217

The Purple Door in Heart of OB/Close to Beaches & Town
3BR
2 ½ baths
Sleeps 10

Available Fall | Winter | Spring September through June monthly range $4,000.00 - $10,000.00

Contact: Maxey, Property ID: 39489

Spacious Oak Bluffs Farmhouse
4BR
2 ½ baths
Sleeps 8

Available as a long-term rental from approximately September-May (depending on bookings) for $3500/month.

Contact: Compass | MV Team, Property ID: 38312

Renovated Victorian Home - 2 Blocks to Beach, Town & Parks
4BR
2 baths
Sleeps 8

Available October thru May (2800-3200/month)

Contact: Greg Ehrman, Property ID: 19178

Classic waterfront Vict. cottage, walk to town; huge porch
4BR
2 baths
Sleeps 8

$6200 per month; discount for multiple months. Jan, Feb., March, April, available for a month or more. Great place to read, write, contemplate the cha...

Contact: Jamie, Property ID: 31304

Fun, Family, Vineyard Getaway
4BR
2 baths
Sleeps 8

If you are interested in long term rental please reach out to me. $5000 - $15000 monthly depending on month, I give a percentage off the market rate.

Contact: Steve, Property ID: 31476

Happy house 0.5mi Nancy’s & Jetty Beach: 1 2025 wk left!
3BR
2 baths
Sleeps 8

Long-term rental during winter months for $2,500/month

Contact: Emily, Property ID: 31215

NOBLE HOUSE: Charming Oasis Near Town & Beach
3BR
2 baths
Sleeps 8

Long-term rentals available from October - May. Please inquire for details and availability.

Contact: DiDi Noble, Property ID: 39654

Perfect! 7 houses from the Beach-Walk to Ferry & Town!
3BR
2 ½ baths
Sleeps 7

Our year ‘round house is fully heated and available off-season for monthly or weekly rentals. Monthly Off-season rentals: $5000-8000 Thanksgiving we...

Contact: Nancy, Property ID: 28831

Bright Modern House w/ AC-Sleeps 7 Walk to Beach & Shops
3BR
3 baths
Sleeps 6

Fall winter prices for 3-4 month stays range between $4000-$4,500 per month. We are only interested in inquiries for 8 week stays or more between Octo...

Contact: Jeanine, Property ID: 20575

Newly Renovated East Chop Home. Walk to beach and town!
3BR
2 baths
Sleeps 6

Winter rental available monthly beginning September 15th to May 15th. $3300 + utilities. Perfect for travelling nurses as we are close to the hospit...

Contact: Debra Moran, Property ID: 32946

Heated saltwater pool, stunning sunsets, 2 kayaks!
3BR
2 ½ baths
Sleeps 6

Available in September/October. $16,000 for 32 days.

Contact: Kim , Property ID: 34492

History and Heritage Awaits/Walk to Beach
3BR
1 ½ bath
Sleeps 6

Long term rental is available from Oct. 1 through May 1. Monthly rate during this period is $2,500. Tenant is responsible for heat, utilities, landsca...

Contact: Abby, Property ID: 38381

Wooded Haven, Martha's Vineyard Oasis
1BR
1 bath
Sleeps 3

Winter rental available $1800 per month for a 9-month lease, October to June. Near the hospital.

Contact: Julia, Property ID: 21977