38 Homes For Rent in Oak Bluffs, Massachusetts

Updated Victorian Cottage with views of downtown Oak Bluffs and the harbor.

7 BR Victorian Home in Oak Bluffs—Steps from Inkwell Beach

Great location-Beautiful home in Oak Bluffs

Charming 3 Bedroom Apartment in Oak Bluffs

Newly Built Guest House - 2024 Construction

Is chop waterfront retreat with stunning water views

Lovely 3 bedroom 2.5 bath, pet friendly home in the highlands of East Chop!

Downtown Oak Bluffs next to the beach! This 1 bedroom 1 bathroom apartment in great location!

Downtown Oak Bluffs! Right in front of the ferry!

Beautiful home with beautiful yard in Deer Park! Near the Airport!

Beautiful home overlooking the water and Ocean Park. AMAZING Location!

Stunning water views in Oak Bluffs!

Cute home very close to the center of Oak Bluffs town!

Beautiful home in Oak Bluffs with private pool! Pet Friendly!

Spacious 2-bedroom Apartment overlooking Circuit Ave! In the Center of Town!

Be in the middle of the action! Stay in Oak Bluffs center right on the beach!

On The Bluff with Water Views!

Beautiful 3-bedroom 2.5 bath nestled between Oak Bluffs and Vineyard Haven just off Barnes Rd. with outdoor shower and screened in porch.

Tucked in the waterfront community of Waterview Farms, gorgeous newly renovated mid-century beach cottage vacation oasis with private beach and dock.

Beach House meets coziness of an Adirondack Lodge. Spectacular custom home with water views over Sengekontacket.

Charming 3-Bedroom Vineyard Home: Perfectly situated within walking distance of downtown Oak Bluffs, beaches, restaurants, and shops.

Stunning four bedroom in desirable East Chop section of Oak Bluffs with a heated pool.

Ideal apartment for 2-4 guests with easy access to public transportation and bike paths

Perfect for family and friends retreat sleeps up to 8 people.

This Victorian Home has an ocean view and park view.