Vacation Rentals By Owner In Oak Bluffs, MA

Showing 100 Of 221 Vacation Rentals

Exceptional(4)

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Private Vacation Home

1 Bedroom, Sleeps 4; perfect small family vacation home

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$644.51

/ Nightly

Cottage

Cozy vineyard cottage close to downtown with outdoor living space and amentiies.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(37)

$634.45

/ Nightly

Condo

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(86)

$489.25

/ Nightly

Private Vacation Home

Comfortable Island Home, Easy Access to Beaches and Town

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(45)

$1205.24

/ Nightly

Cottage

Completely renovated, air conditioned cottage close to the beach. Dog friendly.

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(6)

$1282.32

/ Nightly

Private Vacation Home

Walking to the beach. Bars and Restaurants.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$446.58

/ Nightly

Private Vacation Home

Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(3)

$3749.77

/ Nightly

Private Vacation Home

Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$712.28

/ Nightly

Private Vacation Home

Beautiful Contemporary Farmhouse close to Oak Bluffs

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(18)

$1411.63

/ Nightly

Private Vacation Home

Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(13)

$606.64

/ Nightly

Private Vacation Home

Oak Bluffs Retreat - The perfect getaway!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$2066.45

/ Nightly

Private Vacation Home

Beautiful Custom Home In Oak Bluffs

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$1115.14

/ Nightly

Private Vacation Home

Modern Farmhouse in OB, walk to Beach and Restaurants

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(10)

$1283.71

/ Nightly

Private Vacation Home

Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$805.31

/ Nightly

Private Vacation Home

Charming home away from home near lagoon pond w/ boat launch

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(8)

$407.8

/ Nightly

Private Vacation Home

Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$634.79

/ Nightly

Private Vacation Home

New Construction with Patio & Yard - Downtown & Beaches

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$369.6

/ Nightly

Private Vacation Home

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$1058.89

/ Nightly

Private Vacation Home

Newly remodeled home w/ new furniture, large yard & great porches

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$361.92

/ Nightly

Private Vacation Home

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 170 Private vacation home

Most popular vacation rentals in Oak Bluffs

Exceptional(7)

$705.03

/ Nightly

Private vacation home

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$769.99

/ Nightly

Private vacation home

Historic Home in East Chop

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$740.20

/ Nightly

Private vacation home

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$719.41

/ Nightly

Private vacation home

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$712.28

/ Nightly

Private vacation home

Beautiful Contemporary Farmhouse close to Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$711.53

/ Nightly

Cottage

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$686.15

/ Nightly

Condo

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$663.50

/ Nightly

Private vacation home

COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$666.64

/ Nightly

Private vacation home

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$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

Sleeps

Vacation Rentals By Owner In Oak Bluffs, MA

$644.51

$634.45

$489.25

$1205.24

$1282.32

$446.58

$3749.77

$712.28

$1411.63

$606.64

$2066.45

$1115.14

$1283.71

$805.31

$407.8

$634.79

$369.6

$1058.89

$361.92

Rent a place that suits your needs

Most popular vacation rentals in Oak Bluffs

$705.03

$769.99

$740.20

$719.41

$712.28

$711.53

$686.15

$663.50

$666.64

$803.87

Most Popular Cities in Massachusetts