Home Vacation Rentals By Owner In Oak Bluffs, MA

Showing 40 Of 221 Vacation Rentals
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Exceptional(18)

$1440.09

/ Nightly
Private Vacation Home

Oceanfront Home - Walk to Everything

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(10)

$880.2

/ Nightly
Private Vacation Home

Centrally located Oak Bluffs property next to Bike Path

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(24)

$1032.11

/ Nightly
Private Vacation Home

Beautiful Oak Bluffs Home, Steps from the Lagoon

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(19)

$966.77

/ Nightly
Private Vacation Home

Oak Bluffs Retreat, Walk to Town, Harbor, Ferries

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(159)

$466.16

/ Nightly
Cottage

Make Lasting Memories In This Adorable Vineyard Cottage!

Oak Bluffs, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(3)

$307.55

/ Nightly
Apartment

Martha’s Vineyard studio

Oak Bluffs, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(8)

$803.87

/ Nightly
Private Vacation Home

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

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$933.81

/ Nightly
Private Vacation Home

Walk to Beach! Oak Bluffs Home & Studio

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(11)

$1606.25

/ Nightly
Cottage

OB Cozy-Cottage-Glam off Circuit with Great Outdoor living

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(1)

$841.22

/ Nightly
Private Vacation Home

Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(26)

$424.47

/ Nightly
Apartment

The Nest, Comfortable, Cozy and Convenient

Oak Bluffs, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(33)

$908.12

/ Nightly
Private Vacation Home

Private Oak Bluffs Retreat w/AC • Fire Pit • Outdoor Living

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(7)

$3270.58

/ Nightly
Private Vacation Home

101 Ocean Ave. On the corner of Inkwell beach and Ocean park.

Oak Bluffs, Massachusetts, United States

Bed 7

Bed

Bath 5

Bath

Sleep 14

Sleeps
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$663.5

/ Nightly
Cottage

Charming 3-bedroom Cottage with AC in Oak Bluffs - Sleeps 8

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(7)

$851.78

/ Nightly
Apartment

Inca Gardens Apartment w Large Patio and Deck - Pets OK

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(57)

$606.53

/ Nightly
Private Vacation Home

Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(10)

$574.14

/ Nightly
Cottage

Family cottage in Oak Bluffs. Close to town

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(1)

$1818.48

/ Nightly
Condo

Condo facing Kennebec with AC in charming Oak Bluffs, WiFi, TV, 2 Queen beds

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$3731.9

/ Nightly
Condo

Cozy 4-bedroom condo in perfect Oak Bluffs with AC, on Circuit Ave, WiFi!

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps
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$3645.89

/ Nightly
Condo

2 BR, 1-bath condo, Facing Circuit Ave. 2nd floor. AC, WiFi. TV. No kitchen

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Home Most popular vacation rentals in Oak Bluffs

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$720.24

/ Nightly
Private vacation home

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

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$798.94

/ Nightly
Apartment

In-Town Certified National Historic Oak Bluffs Property -

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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$769.99

/ Nightly
Private vacation home

Historic Home in East Chop

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$740.20

/ Nightly
Private vacation home

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

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$740.02

/ Nightly
Private vacation home

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

Oak Bluffs, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 5

Sleeps
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$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

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$711.53

/ Nightly
Cottage

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

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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$686.15

/ Nightly
Condo

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

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$695.90

/ Nightly
Apartment

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

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$803.87

/ Nightly
Private vacation home

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

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps

Most Popular Cities in Massachusetts