Vacation Home Rentals By Owner In Oak Bluffs, MA

Showing 20 Of 172 Vacation Rentals

Exceptional(2)

$1159.31

/ Nightly

Private Vacation Home

Sengekontacket Contemporary With Water Views

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(10)

$1077.91

/ Nightly

Private Vacation Home

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs, Massachusetts, United States

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Sleeps

Exceptional(1)

$1079.29

/ Nightly

Private Vacation Home

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

Oak Bluffs, Massachusetts, United States

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Sleeps

Exceptional(3)

$1084.38

/ Nightly

Private Vacation Home

Newly renovated home in Oak Bluffs. Walk to private beach on the Lagoon.

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(10)

$1084.61

/ Nightly

Private Vacation Home

Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(2)

$1115.14

/ Nightly

Private Vacation Home

Modern Farmhouse in OB, walk to Beach and Restaurants

Oak Bluffs, Massachusetts, United States

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Exceptional(13)

$1118.11

/ Nightly

Private Vacation Home

Lovely waterfront home with private, sandy beach and mooring on Lagoon Pond

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(5)

$1119.05

/ Nightly

Private Vacation Home

Spacious home in central location with beautiful patio, pool table, W/D, & AC

Oak Bluffs, Massachusetts, United States

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Exceptional(8)

$1122.27

/ Nightly

Private Vacation Home

Secluded Escape- Central AC & Wireless Internet Access.

Oak Bluffs, Massachusetts, United States

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Sleeps

$1130.97

/ Nightly

Private Vacation Home

A quiet Oak Bluffs retreat steps from Circuit Avenue and Inkwell Beach.

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(19)

$1132.64

/ Nightly

Private Vacation Home

The Island Collection MV: Experience a Luxury Getaway by the Lagoon

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(4)

$1235.72

/ Nightly

Private Vacation Home

Welcome to The “SUMMER WIND” House! 5-Minutes to the Beach!

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1325.4

/ Nightly

Private Vacation Home

Walk to town 3-bedroom Oak Bluffs- Pet friendly with fenced in yard

OAK BLUFFS, Massachusetts, United States

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Bath

Sleeps

$1250.8

/ Nightly

Private Vacation Home

East Chop Escape - Water Views, Roof Deck & Minutes to Oak Bluffs

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1242.55

/ Nightly

Private Vacation Home

Oak Bluffs retreat with direct pond access

Oak Bluffs, Massachusetts, United States

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Exceptional(6)

$1236.52

/ Nightly

Private Vacation Home

Walking to the beach. Bars and Restaurants.

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1235.74

/ Nightly

Private Vacation Home

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

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1211.57

/ Nightly

Private Vacation Home

The Cottage - Part of a waterfront compound in Oak Bluffs, Martha's Vineyard

Oak Bluffs, Massachusetts, United States

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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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Sleeps

Exceptional(9)

$1209.1

/ Nightly

Private Vacation Home

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

Oak Bluffs, Massachusetts, United States

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Bath

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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(9)

$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

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Exceptional(9)

$798.94

/ Nightly

Apartment

In-Town Certified National Historic Oak Bluffs Property -

Oak Bluffs, Massachusetts, United States

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Exceptional(9)

$769.99

/ Nightly

Private vacation home

Historic Home in East Chop

Oak Bluffs, Massachusetts, United States

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Exceptional(9)

$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(9)

$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(9)

$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(9)

$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(9)

$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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Bath

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Exceptional(9)

$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(9)

$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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Vacation Home Rentals By Owner In Oak Bluffs, MA

$1159.31

$1077.91

$1079.29

$1084.38

$1084.61

$1115.14

$1118.11

$1119.05

$1122.27

$1130.97

$1132.64

$1235.72

$1325.4

$1250.8

$1242.55

$1236.52

$1235.74

$1211.57

$1167.27

$1209.1

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