Vacation Rentals By Owner In Oak Bluffs, MA

Showing 200 Of 221 Vacation Rentals

Exceptional(13)

$631.67

/ Nightly

Private Vacation Home

Water View 1 mi from Oak Bluffs 10 min Walk to Beach

Oak Bluffs, Massachusetts, United States

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Sleeps

Exceptional(92)

$561.48

/ Nightly

Private Vacation Home

Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(159)

$798.94

/ Nightly

Apartment

In-Town Certified National Historic Oak Bluffs Property -

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$884.83

/ Nightly

Private Vacation Home

New to the rental market! Air conditioned family home, 1 mile from Circuit Ave

Oak Bluffs, Massachusetts, United States

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Sleeps

Exceptional(2)

$613.64

/ Nightly

Private Vacation Home

Walk to Beach Spacious Retreat

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(10)

$1786.09

/ Nightly

Private Vacation Home

Oceanview East Chop Beach House - 4 Bed/2 Bath - 5 min walk to beach

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(54)

$537.6

/ Nightly

Private Vacation Home

Location, Charm, & Steps to Town/Beach -- Central AC, 100% Renewable Energy

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(2)

$468.02

/ Nightly

Private Vacation Home

Oak Bluffs home conveniently located.

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(24)

$866.57

/ Nightly

Private Vacation Home

Charming Island House-Close to Ginger Bread Cottages, Beaches, Shops...

Oak Bluffs, Massachusetts, United States

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Exceptional(9)

$503.99

/ Nightly

Private Vacation Home

Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car prkng

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(37)

$536.8

/ Nightly

Private Vacation Home

CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(7)

$2225.86

/ Nightly

Private Vacation Home

Relaxing Beach Front Home

Oaks Bluff, Massachusetts, United States

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Bath

Sleeps

Exceptional(11)

$1167.27

/ Nightly

Private Vacation Home

AMENITIES GALORE IN OAK BLUFFS PRIVATE COMMUNITY, DOCK, TENNIS, CENTRAL AC

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(100)

$981.13

/ Nightly

Private Vacation Home

Spacious Oak Bluffs Retreat | Walk to Town | Central Air | Ensuite bedrooms

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(12)

$714.88

/ Nightly

Private Vacation Home

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(15)

$1479.87

/ Nightly

Cottage

Gingerbread cottage with stunning Oak Bluffs Harbor View

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(44)

$908.96

/ Nightly

Private Vacation Home

OB Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(33)

$571.43

/ Nightly

Private Vacation Home

Spacious family house, short walk to the Lagoon & close to Oak Bluffs center

Oak Bluffs, Massachusetts, United States

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Sleeps

Exceptional(61)

$2099.77

/ Nightly

Private Vacation Home

The Carousel House - Ocean Park - Featured in New York Times

Oak Bluffs, Massachusetts, United States

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Sleeps

Exceptional(38)

$490.37

/ Nightly

Private Vacation Home

Updated Oak Bluffs home! Close to everything! Walk to town!

OAK BLUFFS, Massachusetts, United States

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Rent a place that suits your needs

Private vacation home

View 171 Private vacation home

Most popular vacation rentals in Oak Bluffs

Exceptional(38)

$720.24

/ Nightly

Private vacation home

Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(38)

$798.94

/ Nightly

Apartment

In-Town Certified National Historic Oak Bluffs Property -

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(38)

$769.99

/ Nightly

Private vacation home

Historic Home in East Chop

Oak Bluffs, Massachusetts, United States

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Exceptional(38)

$740.20

/ Nightly

Private vacation home

A \"Close to All\" Oak Bluffs Oasis!

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(38)

$740.02

/ Nightly

Private vacation home

Welcome to \"Suzy's Place\" Best Location! Walk Everywhere. Newly built in 2024.

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(38)

$729.57

/ Nightly

Private vacation home

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(38)

$711.53

/ Nightly

Cottage

The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(38)

$686.15

/ Nightly

Condo

A BRILLANT WAY Central Location To Beach/Shops/Restaurants/Arcade/Family Bowling

Oak Bluffs, Massachusetts, United States

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Exceptional(38)

$695.90

/ Nightly

Apartment

Downtown Oasis, Walk to Beach: Vineyard Vacation Houses Welcomes You!

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(38)

$803.87

/ Nightly

Private vacation home

Hideaway At Meadow View Farm/Private Tennis Courts with Spacious Bedrooms

Oak Bluffs, Massachusetts, United States

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Bath

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Vacation Rentals By Owner In Oak Bluffs, MA

$631.67

$561.48

$798.94

$884.83

$613.64

$1786.09

$537.6

$468.02

$866.57

$503.99

$536.8

$2225.86

$1167.27

$981.13

$714.88

$1479.87

$908.96

$571.43

$2099.77

$490.37

Rent a place that suits your needs

Most popular vacation rentals in Oak Bluffs

$720.24

$798.94

$769.99

$740.20

$740.02

$729.57

$711.53

$686.15

$695.90

$803.87

Most Popular Cities in Massachusetts