Home Vacation Rentals By Owner In Oak Bluffs, MA

Showing 120 Of 221 Vacation Rentals
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Exceptional(9)

$1337.29

/ Nightly
Private Vacation Home

Charming home with private hot tub, firepit, deck, grill, outdoor shower, AC

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(1)

Select Dates for Price
Private Vacation Home

Enchanting bungalow with golf nearby, full kitchen, central AC, & washer/dryer

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(3)

$1058.28

/ Nightly
Private Vacation Home

House with guest studio close to town and beach with grill, games, AC & patio

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(9)

$997.43

/ Nightly
Private Vacation Home

Private island house with close beach access and water view from deck

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$321.82

/ Nightly
Private Vacation Home

Stylish island retreat with sunny interiors, wraparound deck, firepit & AC

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(5)

$629.93

/ Nightly
Apartment

Private suite with roof deck, near golf, bus stop, shops, and trails

Oak Bluffs, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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$1235.74

/ Nightly
Private Vacation Home

Charming home near downtown & beach with patio, outdoor shower, grill, & W/D

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$1079.29

/ Nightly
Private Vacation Home

Serene private home w/ large deck & yard on conservation land

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps
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Exceptional(5)

$517.66

/ Nightly
Private Vacation Home

Quaint, ranch style home in Oak Bluffs with central air

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(2)

$434.4

/ Nightly
Private Vacation Home

Bright old-world cottage with two porches & large yard - walk to town & beaches

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(2)

$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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$708.2

/ Nightly
Private Vacation Home

Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(5)

$1044.33

/ Nightly
Private Vacation Home

Enchanting home with tennis, firepit, golf nearby & washer/dryer

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 7

Sleeps
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Exceptional(7)

$993.94

/ Nightly
Private Vacation Home

Spacious colonial home close to town with AC, porches, & W/D

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(2)

Select Dates for Price
Private Vacation Home

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(14)

$395.58

/ Nightly
Private Vacation Home

Coastal home with outdoor shower, grill, fireplace, central AC, & W/D

Oak Bluffs, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(1)

$1630.22

/ Nightly
Private Vacation Home

Private house with jetted tub, deck, grill, central AC and large yard

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(2)

$819.26

/ Nightly
Private Vacation Home

Cozy island cottage near local attractions with breezy yard & inviting interior

Oak Bluffs, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(2)

$1062.33

/ Nightly
Private Vacation Home

Spacious island home near Farm Neck Golf Course, the beach and town

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(1)

$580.12

/ Nightly
Private Vacation Home

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Oak Bluffs, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Home Most popular vacation rentals in Oak Bluffs

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Exceptional(1)

$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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Exceptional(1)

$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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Exceptional(1)

$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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Exceptional(1)

$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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Exceptional(1)

$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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Exceptional(1)

$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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Exceptional(1)

$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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Exceptional(1)

$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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Exceptional(1)

$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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Exceptional(1)

$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