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Long-Term Vacation Rentals in Oak Bluffs

A long-term rental is considered to be an extended stay of more than 31 days. 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). Massachusetts Landlord Tenant Laws will apply.

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

# of Rentals: 5

Oak Bluffs

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

$20K per month off-season.

Contact: Wendy , ID: 35217

Oak Bluffs Rental
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, ID: 31304

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

April-October Summer 2026: Monthly price: $45,000- $60,000 Off Season 2026: Monthly price: $20,000- $30,000

Contact: Eric, ID: 39711

Historic Copeland District/ In Rental
Perfect! 7 houses from the Beach-Walk to Ferry & Town!
3BR
2 ½ baths
Sleeps 7

Monthly Off-season rentals: $5000-8000

Contact: Nancy, ID: 28831

Oak Bluffs on the Edgartown li Rental
Quiet, Clean, and Close to all 3 down-island towns
2BR
1 ½ bath
Sleeps 4

During summer 2026 you are welcome to rent the home for 9,000 per month

Contact: Stephanie, ID: 37184