Vacation Rentals in Oak Bluffs, Massachusetts

50 Properties Available

BEAUTIFUL CUSTOM BUILT HOUSE WITH A POOL AND HOT TUB!!! Private vacation home
BEAUTIFUL CUSTOM BUILT HOUSE WITH A POOL AND HOT TUB!!!
$3048 / night
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Private Family Home, Heated Pool, Hottub, 5 BR.4.5 bath, WiFi, AC Private vacation home
Private Family Home, Heated Pool, Hottub, 5 BR.4.5 bath, WiFi, AC
$2737 / night
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Akwaaba House Martha's Vineyard Walk to Beach and Oak Bluffs Town & Harbor Private vacation home
Akwaaba House Martha's Vineyard Walk to Beach and Oak Bluffs Town & Harbor
$2533 / night
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Great Martha's Vineyard House: Everything You Need - Nothing You Don't! Private vacation home
Great Martha's Vineyard House: Everything You Need - Nothing You Don't!
$2144 / night
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Luxurious Sengekontacket Contemporary With Water Views Private vacation home
Luxurious Sengekontacket Contemporary With Water Views
$2036 / night
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Waterview Farm Contemporary Island Home Walk to Beach and Farm Neck Golf Club Private vacation home
Waterview Farm Contemporary Island Home Walk to Beach and Farm Neck Golf Club
$1852 / night
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Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs! Private vacation home
Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!
$1794 / night
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Charming Vacation Home in Oak Bluffs. Private vacation home
Charming Vacation Home in Oak Bluffs.
$1694 / night
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Modern Vineyard Home with Pool, Hot Tub and Pond Private vacation home
Modern Vineyard Home with Pool, Hot Tub and Pond
$1615 / night
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Historic, dog-friendly beach view house with fast WiFi, ocean view, & grill Private vacation home
Historic, dog-friendly beach view house with fast WiFi, ocean view, & grill
$1433 / night
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Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home. Private vacation home
Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home.
$1428 / night
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Charming home with walkable beach, large yard, deck, fire pit, and A/C Private vacation home
Charming home with walkable beach, large yard, deck, fire pit, and A/C
$1349 / night
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Indulge in the ultimate vacation experience at this exquisite custom log home. Private vacation home
Indulge in the ultimate vacation experience at this exquisite custom log home.
$1329 / night
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Fully Renovated Cottage and Guest House near downtown Oak Bluffs Private vacation home
Fully Renovated Cottage and Guest House near downtown Oak Bluffs
$1306 / night
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Last minute cancelation! August price reduced! Large, Renovated, Walk to Beach! Private vacation home
Last minute cancelation! August price reduced! Large, Renovated, Walk to Beach!
$1303 / night
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Oak Bluffs retreat with direct pond access Private vacation home
Oak Bluffs retreat with direct pond access
$1242 / night
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Spacious 5-bedroom house with AC and WiFi in brilliant Oak Bluffs Private vacation home
Spacious 5-bedroom house with AC and WiFi in brilliant Oak Bluffs
$1179 / night
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Charming Martha's Vineyard Cottage Minutes from the Beach Cottage
Charming Martha's Vineyard Cottage Minutes from the Beach
$1152 / night
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OB Cozy-Cottage-Glam off Circuit with Great Outdoor living Cottage
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living
$1145 / night
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Sea Glenn Flowers renovated pet friendly close to everything - Reduced Private vacation home
Sea Glenn Flowers renovated pet friendly close to everything - Reduced
$1127 / night
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Haydens Haven Marthas Vineyard \"What a breath of fresh air\" Apartment
Haydens Haven Marthas Vineyard \"What a breath of fresh air\"
$1118 / night
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Spacious Victorian, 5 minute walk to beach, town, and ferry in Oak Bluffs Private vacation home
Spacious Victorian, 5 minute walk to beach, town, and ferry in Oak Bluffs
$1101 / night
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Modern, luxury 5-bed, 4.5-bath w\/full basement! Now booking for 2024! Private vacation home
Modern, luxury 5-bed, 4.5-bath w\/full basement! Now booking for 2024!
$1100 / night
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Hideaway At Meadow View Farm\/Private Tennis Courts Private vacation home
Hideaway At Meadow View Farm\/Private Tennis Courts
$1021 / night
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Charming home with private hot tub, firepit, deck, grill, outdoor shower, AC Private vacation home
Charming home with private hot tub, firepit, deck, grill, outdoor shower, AC
$1017 / night
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Big Beach House - Ocean Views! Private vacation home
Big Beach House - Ocean Views!
$964 / night
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Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis Apartment
Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis
$894 / night
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Inca Gardens Apartment w Large Patio and Deck - Pets OK Apartment
Inca Gardens Apartment w Large Patio and Deck - Pets OK
$877 / night
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Welcome to The “SUMMER WIND” House! 5-Minutes to the Beach! Private vacation home
Welcome to The “SUMMER WIND” House! 5-Minutes to the Beach!
$850 / night
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Private Oak Bluffs Retreat w/AC • Fire Pit • Outdoor Living Private vacation home
Private Oak Bluffs Retreat w/AC • Fire Pit • Outdoor Living
$839 / night
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Lovely waterfront home with private, sandy beach and mooring on Lagoon Pond Private vacation home
Lovely waterfront home with private, sandy beach and mooring on Lagoon Pond
$821 / night
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The quintessential MV home. Now booking for 2024! Private vacation home
The quintessential MV home. Now booking for 2024!
$817 / night
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BEST LOCATION * Walk to Town\/Beaches * Fun and Relaxing Private vacation home
BEST LOCATION * Walk to Town\/Beaches * Fun and Relaxing
$814 / night
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Oak Bluffs Serenity: Luxurious Apartment nestled near Golf course, beaches. Apartment
Oak Bluffs Serenity: Luxurious Apartment nestled near Golf course, beaches.
$801 / night
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Spacious Waterview Condo - Steps To The Beach, Right Across The Street! Condo
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
$800 / night
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Magnificent Spacious Home Private vacation home
Magnificent Spacious Home
$798 / night
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New Oak Bluffs Home, Steps from the Lagoon Private vacation home
New Oak Bluffs Home, Steps from the Lagoon
$786 / night
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Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches! Private vacation home
Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!
$767 / night
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Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches Private vacation home
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches
$738 / night
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Air conditioned Oak Bluffs WATERVIEW Victorian. steps from beach. BIG porch. Private vacation home
Air conditioned Oak Bluffs WATERVIEW Victorian. steps from beach. BIG porch.
$698 / night
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Rustic circa 1870s home w\/outdoor shower, 3 decks & private grill - 1 dog OK Private vacation home
Rustic circa 1870s home w\/outdoor shower, 3 decks & private grill - 1 dog OK
$677 / night
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Beautiful Contemporary Farmhouse close to Oak Bluffs Private vacation home
Beautiful Contemporary Farmhouse close to Oak Bluffs
$677 / night
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Family Home Near Arts District & Inkwell Beach Private vacation home
Family Home Near Arts District & Inkwell Beach
$642 / night
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Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven Cottage
Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven
$638 / night
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Short walk to town! Private vacation home
Short walk to town!
$592 / night
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Private Waterfront, Beachfront, and 90' Dock. Views. Newly Renovated 3Bd 2.5Bath Private vacation home
Private Waterfront, Beachfront, and 90' Dock. Views. Newly Renovated 3Bd 2.5Bath
$590 / night
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Martha's Vineyard Beachfront Condo in Oak Bluffs Condo
Martha's Vineyard Beachfront Condo in Oak Bluffs
$575 / night
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Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere! Condo
Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!
$573 / night
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Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown Private vacation home
Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown
$571 / night
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Renovated Historic House \"The Legacy House\" Private vacation home
Renovated Historic House \"The Legacy House\"
$571 / night
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