Oak Bluffs Massachusetts Vacation Rentals and Vacation Homes

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Marthas Vineyard Vacation Rentals Karen M Overtoom Real Estate
 508-693-7832 
Your Connection to all Martha's Vineyard Real Estate and Vacation Rentals! Browse our extensive rental inventory of Cozy Cottages to Waterfront Estates. Explore our MLS listings of Homes for Sale, or call us at 508-693-7832.   Click for 162 Vacation Rentals

 39 Rentals in Oak Bluffs

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Property 18328

OB504

  • OB504 Gothic Victorian located in the heart of Oak Bluffs where you are just steps to the beach
  • House in Oak Bluffs
  • 8 Bedroom(s), Sleeps 12
  • 2 Bathroom(s)
Property 32043

OB504

  • OB504 Oak Bluffs Downtown Victorian
  • House in Oak Bluffs
  • 8 Bedroom(s), Sleeps 12
  • 2 Bathroom(s)
  • Weekly Rates from $3,000
Property 21601

OB511

  • OB511- Oak Bluffs In-Town Vacation Home, Come Visit
  • House in Oak Bluffs
  • 7 Bedroom(s), Sleeps 14
  • 3 Bathroom(s)
Property 27271

OB527

  • OB527- What a spot!!! Oceanfront on Nantucket Sound.
  • House in Oak Bluffs
  • 6 Bedroom(s), Sleeps 11
  • 2 Bathroom(s)
  • Weekly Rates from $5,000
Property 27291

OB512

  • OB512- Waterfront Oak Bluffs home has a dock and beautiful views of Nantucket Sound
  • House in Oak Bluffs
  • 6 Bedroom(s), Sleeps 12
  • 3 Bathroom(s)
  • Weekly Rates from $8,000
Property 21789

Oak Bluffs

  • House Rental In Oak Bluffs Martha's Vineyard - Martha's Vineyard Waterfront w/ Private Beach, Car
  • House in Oak Bluffs
  • 5 Bedroom(s), Sleeps 10+
  • 3 Bathroom(s)
  • Weekly Rates from $2,000
Property 21798

OB507

  • OB507 Fabulous Waterfront Five Bedroom OakBluffs Estate
  • Condo in Oak Bluffs
  • 5 Bedroom(s), Sleeps 10
  • 2 Bathroom(s)
  • Weekly Rates from $5,000
Property 27261

OB505

  • OB505 Walk to the Oak Bluffs town from this charming East Chop home that sleeps 10
  • Cottage in Oak Bluffs
  • 5 Bedroom(s), Sleeps 10
  • 2 Bathroom(s)
  • Weekly Rates from $3,000
Property 27289

OB514

  • OB514- This Oak Bluffs is right around the corner from shopping, dining, tennis, and the beach!
  • House in Oak Bluffs
  • 5 Bedroom(s), Sleeps 10
  • 2 Bathroom(s)
Property 27290

OB513

  • OB513- In the heart of Oak Bluffs this spacious vacation home is with-in walking distance to Beach and tennis
  • House in Oak Bluffs
  • 5 Bedroom(s), Sleeps 12
  • 2 Bathroom(s)
  • Weekly Rates from $300
Property 53177

OB538

  • OB538 Meadow View Farm Community in Oak Bluffs
  • House in Oak Bluffs (Near Sengekontacket)
  • 5 Bedroom(s), Sleeps 11
  • 3.5 Bathroom(s)
  • Weekly Rates from $3,000
Property 18522

OB501

  • OB 501- Located in Waterview Farms with Private Beach on Sengekontacket Pond
  • House in Oak Bluffs (Near Sengekontacket Pond)
  • 4 Bedroom(s), Sleeps 8
  • 3 Bathroom(s)
Property 21600

OB508

  • OB508 Fabulous Waterfront Bungalow with Dock
  • House in Oak Bluffs
  • 4 Bedroom(s), Sleeps 8
  • 2 Bathroom(s)
Property 27260

OB516

  • OB516- Fabulous waterfront home with sandy beach and views across the Lagoon
  • House in Oak Bluffs
  • 4 Bedroom(s), Sleeps 8
  • 2 Bathroom(s)
  • Weekly Rates from $3,000
Property 27266

OB521

  • OB521 Located in a quiet neighborhood with association tennis, abutting bike path and close to Farm Neck Golf
  • House in Oak Bluffs
  • 4 Bedroom(s), Sleeps 8
  • 3 Bathroom(s)
  • Weekly Rates from $3,000
Property 27267

OB522

  • OB522 Centrally Located to Down-Island Towns, Farm Neck Golf, Beaches and Bike Path
  • House in Oak Bluffs
  • 4 Bedroom(s), Sleeps 8
  • 2 Bathroom(s)
  • Weekly Rates from $1,500
Property 27268

OB524

  • OB524- This beautiful home is centrally located to down island towns and beaches
  • House in Oak Bluffs
  • 4 Bedroom(s)
  • 2 Bathroom(s)
  • Weekly Rates from $1,500
Property 27270

OB526

  • OB526- Brand new, luxury, waterfront home with deep water dock and mooring and private beach.
  • House in Oak Bluffs
  • 4 Bedroom(s), Sleeps 8
  • 2 Bathroom(s)
  • Weekly Rates from $12,000
Property 27272

OB528

  • OB528 Unbelievable views of Nantucket Sound from this waterfront property.
  • House in Oak Bluffs
  • 4 Bedroom(s), Sleeps 10
  • 2 Bathroom(s)
  • Weekly Rates from $5,000
Property 27288

OB510

  • OB510- Charming,beautifully decorated & appointed new home close to beaches, shopping, restaurants and ferry. Visit this Oak Bluffs Vacation Rental
  • House in Oak Bluffs
  • 4 Bedroom(s), Sleeps 8
  • 2 Bathroom(s)
  • Weekly Rates from $1,500
Property 27293

VH415

  • VH415- Waterfront!! Private Cove, Ocean Beach--Perfect for two families. Secluded waterfront home on tranquil cove where Lake Tashmoo meets the sea.
  • House in Vineyard Haven (Near Oak Bluffs)
  • 4+ Bedroom(s), Sleeps 8
  • 3 Bathroom(s)
  • Weekly Rates from $5,000
Property 27299

VH421

  • VH421- Beautifully designed and maintained, four bedrooms, open living spaces located just outside of town.
  • House in Vineyard Haven (Near Oak Bluffs)
  • 4+ Bedroom(s), Sleeps 10+
  • 4 Bathroom(s)
  • Weekly Rates from $3,000
Property 32031

OB530

  • OB530 Oak Bluffs - Dramatic Waterview with Beach
  • Cottage in Oak Bluffs
  • 4 Bedroom(s), Sleeps 10
  • 2 Bathroom(s)
  • Weekly Rates from $3,000
Property 53174

OB533

  • OB533 East Chop Victorian Vacation Home
  • House in Oak Bluffs (Near East Chop)
  • 4 Bedroom(s), Sleeps 10
  • 4 Bathroom(s)
  • Weekly Rates from $3,000
Property 81436

OB541 - Conderella Cottage

  • OB541 - Cinderella Cottage - Martha's Vineyard Cottage Rental in the heart of Oak Bluffs this vacation rentals is very close to the beach.
  • Cottage in Oak Bluffs (Near Edgartown)
  • 4 Bedroom(s)
  • 3 Bathroom(s)


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