Oak Bluffs Rentals By Owner

There are a lot of options in Oak Bluffs. If you plan on staying in the Oak Bluffs area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Oak Bluffs:

• In-Town Certified National Historic Oak Bluffs Property -
• Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
• Multiple Ensuites, Central Air, Perfect Location
• ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!
• Close to town, beautifully updated
• Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
• Historic Home in East Chop
• Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 !
• Private Family Home, Heated Pool, Hottub, 5 BR.4.5 bath, WiFi, AC. NO PETS.
• Beautiful Landscaped Grounds and Pond & Kayaks

There are many large, family-friendly vacation homes available in Oak Bluffs; however, here are the most popular family rentals listed on our site:

• Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
• Treeside Lodge
• The Island Inn on Martha's Vineyard
• Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town

Yes, there are 493 self-catering vacation homes in Oak Bluffs that have hot tubs, swimming pools, & other amenities.

There are more than 493 luxury villas and vacation homes in or near Oak Bluffs. Filter by price to compare find the most expensive places to stay on Cabinsincolorado.

Yes, there are 493 pet friendly vacation homes and places to stays that are available in or near Oak Bluffs that you may consider.