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Oak Bluffs Rentals

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VRBO
6 Bedroom Oak Bluffs Victorian.
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
6 Bedrooms will comfortably allow your family to vacation in Oak Bluffs. A classic Victorian jewel, the house at 30 Samo ...
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VRBO
$Newly Renovated 3BR\/2BA - Walk to Restaurants$
From $877 per night (USD)
Expedia
Newly Renovated 3BR\/2BA - Walk to Restaurants
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our newly renovated cottage nestled in the peaceful town of Vineyard Haven. This delightful retreat features ...
From $877 per night (USD)
Expedia
From $503 per night (USD)
VRBO
Four bedroom 3 bathroom ranch located in Edgartown.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
*****Those summer vacation memories are waiting to be made here. Four bedroom 3 bathroom ranch located in Edgartown. M ...
From $503 per night (USD)
VRBO
$Gorgeous 7BR\/6BA Ocean views Walk to Beach & Town - 10% off two week stay!$
From $2376 per night (USD)
VRBO
Gorgeous 7BR\/6BA Ocean views Walk to Beach & Town - 10% off two week stay!
Bedrooms:
6
Bathrooms:
7
Sleeps:
10
Large Private Home formerly known as the SeaSpray Inn and featured on the reality television show "The Vineyard", this l ...
From $2376 per night (USD)
VRBO
From $1173 per night (USD)
VRBO
Looking for a relaxing getaway? Convenience & Privacy in Vineyard Haven
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This four bedroom home with two large living areas is great for two families or a group looking for a peaceful getaway. ...
From $1173 per night (USD)
VRBO
From $582 per night (USD)
Expedia
Six Bedroom Home with In-Law Suite
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Our home with AC is on a leafy dead end, quiet street, 4 minutes to downtown Oak Bluffs, 5 mins to Eastville Beach, 6 mi ...
From $582 per night (USD)
Expedia
From $1133 per night (USD)
VRBO
Oak Bluff's Victorian Walk to Town & Beaches
Bedrooms:
6
Bathrooms:
5
Sleeps:
13
About this space First floor has AC and hosts windowed living, dining, work space, kitchen and garden apartment that sle ...
From $1133 per night (USD)
VRBO
From $884 per night (USD)
Expedia
New 2024- 2 min from Circuit ave
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
**NEW FOR THE 2024 SEASON** Welcome to this beautifully renovated home, located within 2 minutes away (drive) from dow ...
From $884 per night (USD)
Expedia
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VRBO
Tisbury - Airy 4-bedroom with Peaceful Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
You'll have a great time at this quiet, clean, and comfortable place to stay. Walk to everywhere! Just minutes from the ...
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VRBO
$Luxurious Beachfront Haven w\/ Private Dock & Views$
From $1461 per night (USD)
VRBO
Luxurious Beachfront Haven w\/ Private Dock & Views
Bedrooms:
7
Bathrooms:
5
Sleeps:
12
Discover The Sandcastle: A luxurious beachfront retreat blending modern design with homely warmth. Five elegant bedrooms ...
From $1461 per night (USD)
VRBO
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VRBO
5 Minute Walk to Vineyard Haven Yacht Club and Town Beach at Owen Little Way!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Discover this spacious and conveniently located property which is just a 5 Minute Walk to Vineyard Haven Yacht Club an ...
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VRBO
From $694 per night (USD)
Expedia
Cute apartment in Edgartown - 2 min driving to center
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautiful apartment 2 min driving from Edgartown center, Bedroom, full kitchen, full bathroom, we provide pillows, bedsp ...
From $694 per night (USD)
Expedia
From $878 per night (USD)
VRBO
Cozy home in Edgartown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly renovated home with 3 bedrooms and 2 full bathrooms, spacious living room, full kitchen, washer and dryer, outdoor ...
From $878 per night (USD)
VRBO
From $3191 per night (USD)
VRBO
Beautiful Oak Bluffs Family Estate
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Perfectly located 1.5 acre beautiful Oak Bluffs getaway across the street from Farm Neck Golf Course and Sengekontacket ...
From $3191 per night (USD)
VRBO
$Charming cottage near the beach with a furnished deck, yard, & washer\/dryer$
From $530 per night (USD)
VRBO
Charming cottage near the beach with a furnished deck, yard, & washer\/dryer
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Birds of Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $530 per night (USD)
VRBO
$Entire Renovated Home w\/ JEEP Wrangler, Near Town, Private$
From $781 per night (USD)
Expedia
Entire Renovated Home w\/ JEEP Wrangler, Near Town, Private
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Spacious, modern, and privately situated home only 1.5 miles from downtown Vineyard Haven. Guests will have access to ou ...
From $781 per night (USD)
Expedia
From $1169 per night (USD)
VRBO
REDUCED! Oak Bluffs 5 bdrm 4 bath expansive contemporary home
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Nestled within a lovely private neighborhood in Oak Bluffs, this beautiful contemporary home unfolds with style and comf ...
From $1169 per night (USD)
VRBO
From $1853 per night (USD)
VRBO
Waterview Farm Contemporary Island Home Near Beach and Farm Neck Golf
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Six bedroom, five and a half bath contemporary island home located in Waterview Farm with direct access to the beach on ...
From $1853 per night (USD)
VRBO
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VRBO
Quaint and pristine home with private suites and baths.
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Welcome to our home! We are a husband & wife interior decorator/contractor team, who've tastefully renovated our entire ...
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VRBO
$LABOR DAY WEEKEND AVAILABLE! West Tisbury, Lambert's Cove Beach Access\n$
From $398 per night (USD)
Expedia
LABOR DAY WEEKEND AVAILABLE! West Tisbury, Lambert's Cove Beach Access\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Nestled in the woods of West Tisbury, this charming 2-bedroom +, 900 sq. ft. home, with additional sleeping loft, offers ...
From $398 per night (USD)
Expedia
From $981 per night (USD)
VRBO
Heart of Oak Bluffs - A Newly Renovated Gem, 5 Minute Walk to Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the perfect blend of location and luxury in this beautifully renovated charmer, centrally situated in Oak Bluff ...
From $981 per night (USD)
VRBO
From $584 per night (USD)
Expedia
Walking to the beach. Bars and Restaurants.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Walking distance to the beach. 5 minutes away from downtown, steamship, ice cream, and restaurants. Lovely backyard with ...
From $584 per night (USD)
Expedia
From $692 per night (USD)
VRBO
Private island house close to trails with kayak, jetted tub, and deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Lookout Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $692 per night (USD)
VRBO
From $734 per night (USD)
VRBO
Charming Cottage with Garden, Screened Porch, Outdoor Shower - Walk to Downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our charming whale-themed cottage in Vineyard Haven, Martha's Vineyard, MA. This cozy retreat features a spac ...
From $734 per night (USD)
VRBO
$Cozy History Resort\nLocated in the center of the city$
From $397 per night (USD)
VRBO
Cozy History Resort\nLocated in the center of the city
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Friendly and fun Environment. BBQ grills on the patio for those grill masters ready to whip up a mean steak. We have a b ...
From $397 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Harbor Landing Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Are you ready to come and enjoy the fun and beautiful island on a budget, then look no further. Come by our beautiful hi ...
From $397 per night (USD)
Expedia
From $509 per night (USD)
VRBO
Harbor Landing Resort
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Looking to visit the vineyard on a budget, look no further. We provide a friendly, fun, sociable, budget and cost effici ...
From $509 per night (USD)
VRBO
$Charming home near downtown & beach with patio, outdoor shower, grill, & W\/D$
From $876 per night (USD)
Expedia
Charming home near downtown & beach with patio, outdoor shower, grill, & W\/D
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Blissful Island Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $876 per night (USD)
Expedia
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VRBO
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
2 Decks, hot tub and close to everything. Has all new stainless appliances, wi-fi, cable, grill, about one mile walk t ...
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VRBO
From $510 per night (USD)
Expedia
Harbor Landing Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Looking to have a good time on the Vineyard, but on a budget? Look no further. We provide a Fun, Energetic,Social and co ...
From $510 per night (USD)
Expedia
From $638 per night (USD)
VRBO
Private island house with close beach access and water view from deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Soundmeadow House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $638 per night (USD)
VRBO
From $427 per night (USD)
Expedia
1 Bedroom, Sleeps 4; perfect small family vacation home
Bedrooms:
3
Bathrooms:
1
Sleeps:
4
Close to town and beach, but far enough away for peaceful quiet. 1 Bedroom; 3.5 bath; outdoor shower; front and side por ...
From $427 per night (USD)
Expedia
$5 min walk to the BEACH ON MARTHA'S VINEYARD. Beautiful, new, modern, 1BED\/1BATH$
From $192 per night (USD)
VRBO
5 min walk to the BEACH ON MARTHA'S VINEYARD. Beautiful, new, modern, 1BED\/1BATH
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
LONG TERM SUMMER RENTAL! Lower level, NY style beach apartment on Martha's Vineyard, 2 min walk to the beach, 2 min dri ...
From $192 per night (USD)
VRBO
From $363 per night (USD)
VRBO
Martha’s Vineyard 15 minute walk to Oak Bluffs Beach and Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
15 minute walk to Oak Bluffs town and beach. 2 queen beds. 5 minute walk to the bus. 5 minute walk to library. 1 bedroom ...
From $363 per night (USD)
VRBO
From $418 per night (USD)
VRBO
Guest House In Edgartown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax with the whole family at this peaceful place to stay. Experience island living at this one-bedroom, one-bathroom g ...
From $418 per night (USD)
VRBO
From $900 per night (USD)
VRBO
Cozy Oak Bluffs Cottage walk to town Pet Friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This modest single-family home was newly renovated in 2023. It is a single-level house just west of downtown Oak Bluffs. ...
From $900 per night (USD)
VRBO
From $766 per night (USD)
VRBO
charming bungalow -- walk to beach & downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
A quintessential island vacation spot in this charming Vineyard Haven bungalow -- formerly owned by a legendary local se ...
From $766 per night (USD)
VRBO
$Lagoon Waterfront 3 Bedroom Private Sandy Beach Oak Bluffs Martha's Vineyard \n$
From $1604 per night (USD)
Expedia
Lagoon Waterfront 3 Bedroom Private Sandy Beach Oak Bluffs Martha's Vineyard \n
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This three-bedroom idyllic vacation home offers the perfect escape for a truly memorable summer vacation on Martha's Vin ...
From $1604 per night (USD)
Expedia
From $554 per night (USD)
VRBO
Classic home with screened porch - walk to town, beaches & Lake Tashmoo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Fish Bowl Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $554 per night (USD)
VRBO
From $502 per night (USD)
Expedia
Garden Gem: Cozy Island Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Escape to Garden Gem! Nestled near Morning Glory Farm, minutes from town and trails that lead to local beaches. Our home ...
From $502 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Garden Gem: Cozy Guest House in Edgartown, Marthas Vineyard
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Escape to Garden Gem! Nestled near Morning Glory Farm, minutes from town and trails that lead to local beaches. Take a b ...
From $305 per night (USD)
VRBO
$Beautiful and Modern 4Bdrm, 3Ba Colonial w\/ a large yard in Historic Oak Bluffs!$
From $1436 per night (USD)
VRBO
Beautiful and Modern 4Bdrm, 3Ba Colonial w\/ a large yard in Historic Oak Bluffs!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This two-story, well-appointed Colonial boasts plenty of parking and an expansive backyard in a quaint neighborhood at t ...
From $1436 per night (USD)
VRBO
$Charming home with deck, W\/D, & amazing location$
From $637 per night (USD)
VRBO
Charming home with deck, W\/D, & amazing location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oak Bluffs Darling Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $637 per night (USD)
VRBO
$Charming condo near ferry with roof top deck, AC, W\/D, & central location$
From $622 per night (USD)
Expedia
Charming condo near ferry with roof top deck, AC, W\/D, & central location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Harbor View Heights Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $622 per night (USD)
Expedia
$Welcome to \Suzy's Place\ Best Location! Walk Everywhere. Newly built in 2024.$
From $435 per night (USD)
VRBO
Welcome to \"Suzy's Place\" Best Location! Walk Everywhere. Newly built in 2024.
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
"Suzy's Place" is arguably the best location on the island. Your cozy getaway awaits in Oak Bluffs at this beautiful new ...
From $435 per night (USD)
VRBO
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Expedia
Cozy Family Cottage Circuit Ave OB Walk to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Stay comfortably in Oak Bluffs at this 4-bedroom cottage. With 2 full beds a twin beds, this quaint property is perfect ...
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Expedia
From $224 per night (USD)
VRBO
Charming studio with amazing location near town & beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Sankofa Studio Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $224 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Brand New Guest house
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in Oak Bluffs, enjoy what this 2-bedroom apartment has to offer. With a washing machine, WiFi, AC, iron, hair dr ...
From $510 per night (USD)
Expedia
$Updated 3-bedroom in gorgeous Oak Bluffs w\/ waterviews and expansive front porch$
From $482 per night (USD)
VRBO
Updated 3-bedroom in gorgeous Oak Bluffs w\/ waterviews and expansive front porch
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Get ready to relax in this 3-bedroom cottage in Oak Bluffs. Nestled in a peaceful neighborhood, this beautiful property ...
From $482 per night (USD)
VRBO
From $722 per night (USD)
Expedia
Luxurious 5BR Retreat : Steps from the Waterfront
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to a unique contemporary style home! Just steps from the town landing, enjoy access to Sengekontacket Pond and N ...
From $722 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Updated house close to town and beach with patio, AC, and games
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Sankofa House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $487 per night (USD)
VRBO
$Spacious home in central location with beautiful patio, pool table, W\/D, & AC$
From $880 per night (USD)
Expedia
Spacious home in central location with beautiful patio, pool table, W\/D, & AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Bird Street Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $880 per night (USD)
Expedia
$A \Close to All\ Oak Bluffs Oasis!$
From $590 per night (USD)
VRBO
A \"Close to All\" Oak Bluffs Oasis!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Nestled at the end of a cul-de-sac, this home is the ideal spot for a peaceful island retreat. It sits on over a1/2 acre ...
From $590 per night (USD)
VRBO
From $882 per night (USD)
Expedia
Charming 2-bedroom house in iconic West Chop area with AC, WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Down a quiet private lane you will find this newly renovated cottage with everything one could want for a vacation on Ma ...
From $882 per night (USD)
Expedia
From $439 per night (USD)
VRBO
BRAND NEW 1-bedroom Owner's Suite in wonderful Oak Bluffs with Air Conditioning
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Get ready to relax in this 1-bedroom Owner's Suite in Oak Bluffs. This brand new property features a cozy bedroom with a ...
From $439 per night (USD)
VRBO
From $660 per night (USD)
Expedia
House with guest studio close to town and beach with grill, games, AC & patio
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Sankofa Martha's Vineyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $660 per night (USD)
Expedia
From $4140 per night (USD)
VRBO
Beautiful Estate with salt water pool & pond with kayaks
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
WELCOME TO PARADISE!!! we sanitize!!!!! We have implemented a system so you are able to check in and out without any per ...
From $4140 per night (USD)
VRBO
$Centrally located Island getaway with bike path access, patio, W\/D, & games$
From $330 per night (USD)
Expedia
Centrally located Island getaway with bike path access, patio, W\/D, & games
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Cozy Island Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $330 per night (USD)
Expedia
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VRBO
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Book your next East Coast escape at this Vineyard Haven vacation rental! Conveniently located near downtown Oak Bluffs, ...
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VRBO
From $1201 per night (USD)
Expedia
Modern Cottage Walk To Town & Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy one of Oak Bluffs’ newest accommodations perched at the peak of the Highlands boasting just a 10 minute walk to to ...
From $1201 per night (USD)
Expedia
$Charming Cottage on Harbor on Martha's Vineyard\n\n$
Click For Pricing
VRBO
Charming Cottage on Harbor on Martha's Vineyard\n\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Sit on the front porch of our cottage on the harbor in Oak Bluffs on Martha's Vineyard and take in all the bustling town ...
Click For Pricing
VRBO

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Oak Bluffs Rentals

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Results: 561 Rentals