Oak Bluffs, Martha's Vineyard

Curated rentals in Oak Bluffs

4923 waterfront rentals·10 shores·Every listing on the water·Updated 2026-10-16

The Vineyard's 100 square miles cover six towns, each with its own character. Edgartown for captains' houses, Chilmark for cliffs, Oak Bluffs for gingerbread cottages, Aquinnah for red clay bluffs. Rentals concentrate in July-August; May and September are cheaper and quieter.

StateMA
Peak seasonJuly to August
Best forWaterfront stays
Featured3 rentals
The curated list · 3 rentals

Where we would stay in Oak Bluffs, Martha's Vineyard.

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Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
No. 01

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Apartment
2 bedroom sleeps 4 Beachfront

Beachfront location with direct access to Inkwell Beach.

Capricorn House
No. 02

Capricorn House

Oceanfront

Housed in a historic building, Capricorn House features accommodations with a terrace and free Wifi in Oak Bluffs, a 1-minute walk from Oak Bluffs Town Beach.

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
No. 03

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Oceanfront

Breezy Oak Bluffs Condo - Steps to Inkwell Beach! is located in Oak Bluffs, just a few steps from Oak Bluffs Town Beach and 5.9 miles from Edgartown Lighthouse.

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