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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).

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

# of Rentals: 16

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
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
Beachfront Oasis within Minutes from Downtown
4BR
1 ½ bath
Sleeps 8

April-October Summer 2025: Monthly price: $45,000- $60,000 Off Season 2025: Monthly price: $20,000- $30,000

Contact: Eric, Property ID: 39711
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
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
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