Vacation Rentals & Apartments in Oak Bluffs

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Luxury Oak Bluffs Home with 18 X 30' Pool

Oak Bluffs house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,143

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$1,966

Beautiful Oak Bluffs Home with Wonderful Waterviews

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,715

CLASSIC, VINTAGE,GINGERBREAD

Oak Bluffs house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$1,072

Cute Guest House Overlooking the Lagoon

Oak Bluffs house

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$1,429

Seaglass Cottage on East Chop

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$650

Clean, comfortable ranch with lots of amenities

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$545

Beautiful Four Bedroom Home Walking Distance to Downtown Oak Bluffs

Oak Bluffs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$575

Adorable Oak Bluffs Cottage Walking Distance to Town

Oak Bluffs house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$429

Beautiful Oak Bluffs home on Lagoon Pond with Pool!

Oak Bluffs house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$572

COME EXPERIENCE THE MAGIC OF THE VINEYARD

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$472

Victorian jewel on sought after Ocean Park in Oak Bluffs

Oak Bluffs house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$715

LUXURY WATERFRONT HOME- BEACH,DEEPWATER DOCK & MOORING

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$1,143

Renovated Oak Bluffs cottage steps from Ink Well Beach

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$715

Wonderful Four Bedroom Home in Oak Bluffs

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$643

NEW Modern & Charming Waterfront- The Harper House

Oak Bluffs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,548

Three Bedroom Oak Bluffs Home

Oak Bluffs house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$415

Classic East Chop Cottage

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$572

Cozy Oak Bluffs home close to beach & town.

Oak Bluffs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$629

Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

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Price per night from

$6,880

RENOVATED, ARCHITECTURALLY SIGNIFICANT BEACH COTTAGE

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$372

2+BR Renovated Gingerbread Cottage - Walk to All

Oak Bluffs house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$524

Modern Vineyard Home

Oak Bluffs house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

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Price per night from

$2,293

Waterfront Four Bedroom Sengenkontacket Pond Home

Oak Bluffs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$743

#CozyBluffs 1 BR House in Historic Oak Bluffs - walk to town and ferry

Oak Bluffs house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$802

Modern Private & Expansive Oasis - Pool & Hot Tub

Oak Bluffs house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$2,143

Beautiful Four Bedroom Cottage on East Chop

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$715

Three Bedroom Home Close to Oak Bluffs Harbor

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$429

East Wing of Captain's Mansion - Luxury, Waterfront, Town, & Beaches - 5 stars

Oak Bluffs house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$723

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Price per night from

$241

West Wing of Captain Morse House Waterfront, Town & Beach - Pets OK, - 5 stars

Oak Bluffs house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$699

Great rentals within 20 miles that match your search

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$1,639

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$631

High End-suite style cottage 5 min bike ride to amazing Craigville Beach.

Centerville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$344

3 bedroom 2 bath Fully remodeled home

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$316

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$844

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$371

Vineyard Haven Guest House - Sleeps 4, A/C, Walk to Town

Vineyard Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“great stay in Vineyard Haven” We enjoyed staying in David's guest house. It was clean, well situated (a short walk from downtown Vineyard Haven), and made for a relaxing few days on the Vineyard. David was easy to reach and very responsive to any of our needs. I would highly recommend you stay at the guesthouse.

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Price per night from

$264

Viewing 38 of 208
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