Vacation rentals in Oak Bluffs, MA

Best vacation rentals and Airbnb offers in Oak Bluffs, MA

New Seabury Escape

Holiday Home, Oak Bluffs

New Seabury Escape is a holiday home in Oak Bluffs, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About New Seabury Escape

New Seabury Escape is a holiday home in Oak Bluffs, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, ourdoor pool, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,723.

From$382/night

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The CAVU Mansion on Bellevue

Holiday Home, Oak Bluffs

The CAVU Mansion on Bellevue is a holiday home in Oak Bluffs. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About The CAVU Mansion on Bellevue

The CAVU Mansion on Bellevue is a holiday home in Oak Bluffs. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,423.

From$698/night

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Island Getaway

Holiday Home, Oak Bluffs

Island Getaway is a holiday home in Oak Bluffs. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Island Getaway

Island Getaway is a holiday home in Oak Bluffs. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: ac, air conditioning, heating, and garden.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,077.

From$362/night

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Quintessential Vineyard Vacation Home

Holiday Home, Oak Bluffs

Quintessential Vineyard Vacation Home is a holiday home in Oak Bluffs, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Quintessential Vineyard Vacation Home

Quintessential Vineyard Vacation Home is a holiday home in Oak Bluffs, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,794.

From$399/night

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Vacation rentals with a pool in Oak Bluffs, MA

Add a pool to the search when you want an easy place to cool off between outings.

EXPLORE NEW SEABURY'S YEAR ROUND CHARM - Views + Beach+ Pool+ Deck.

Holiday Home, Oak Bluffs

EXPLORE NEW SEABURY'S YEAR ROUND CHARM - Views + Beach+ Pool+ Deck. is a holiday home in Oak Bluffs, with pool access, easy beach access, and outdoor space. This stay gives travelers a…

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About EXPLORE NEW SEABURY'S YEAR ROUND CHARM - Views + Beach+ Pool+ Deck.

EXPLORE NEW SEABURY'S YEAR ROUND CHARM - Views + Beach+ Pool+ Deck. is a holiday home in Oak Bluffs, with pool access, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,426.

From$489/night

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Golf course-front townhouse with private heated pool & poolside patio

Condo, Oak Bluffs

Golf course-front townhouse with private heated pool & poolside patio is a condo in Oak Bluffs, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable…

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About Golf course-front townhouse with private heated pool & poolside patio

Golf course-front townhouse with private heated pool & poolside patio is a condo in Oak Bluffs, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,799.

From$543/night

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Car Ferry ticket for Aug 28 & Sept 4 weeks, late Summer escape with less crowds!

Holiday Home, Oak Bluffs

Car Ferry ticket for Aug 28 & Sept 4 weeks, late Summer escape with less crowds! is a holiday home in Oak Bluffs, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Car Ferry ticket for Aug 28 & Sept 4 weeks, late Summer escape with less crowds!

Car Ferry ticket for Aug 28 & Sept 4 weeks, late Summer escape with less crowds! is a holiday home in Oak Bluffs, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,139.

From$734/night

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Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available.

Holiday Home, Oak Bluffs

Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available. is a holiday home in Oak Bluffs, with pool access, kitchen access, and a quieter setting. This stay gives…

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About Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available.

Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available. is a holiday home in Oak Bluffs, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,846.

From$835/night

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Vacation rentals with parking in Oak Bluffs, MA

Find vacation rentals that make arriving by car easier.

WATER View Falmouth Gateway 3BR Family Retreat - \"WALK to BEACH\"

Holiday Home, Oak Bluffs

WATER View Falmouth Gateway 3BR Family Retreat - \"WALK to BEACH\" is a holiday home in Oak Bluffs, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About WATER View Falmouth Gateway 3BR Family Retreat - \"WALK to BEACH\"

WATER View Falmouth Gateway 3BR Family Retreat - \"WALK to BEACH\" is a holiday home in Oak Bluffs, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,266.

From$467/night

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Brick Ranch On Cul-de-Sac with Central Air/Heat In Quiet Neighborhood Oak Bluffs

Holiday Home, Oak Bluffs

Brick Ranch On Cul-de-Sac with Central Air/Heat In Quiet Neighborhood Oak Bluffs is a holiday home in Oak Bluffs, with parking, kitchen access, and a quieter setting. This stay gives…

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About Brick Ranch On Cul-de-Sac with Central Air/Heat In Quiet Neighborhood Oak Bluffs

Brick Ranch On Cul-de-Sac with Central Air/Heat In Quiet Neighborhood Oak Bluffs is a holiday home in Oak Bluffs, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,741.

From$534/night

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

Holiday Home, Oak Bluffs

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach! is a holiday home in Oak Bluffs, with easy beach access, parking, and kitchen access. This stay gives…

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

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach! is a holiday home in Oak Bluffs, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,925.

From$846/night

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Oak Bluffs Rental - Walk to the Beach

Holiday Home, Oak Bluffs

Oak Bluffs Rental - Walk to the Beach is a holiday home in Oak Bluffs, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Oak Bluffs Rental - Walk to the Beach

Oak Bluffs Rental - Walk to the Beach is a holiday home in Oak Bluffs, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,996.

From$857/night

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Pet-friendly vacation rentals in Oak Bluffs, MA

Bring your pet along with stays that welcome four-legged travelers.

2-story home near the beach with large lawn, deck, W/D, streaming, & partial AC

Holiday Home, Oak Bluffs

2-story home near the beach with large lawn, deck, W/D, streaming, & partial AC is a holiday home in Oak Bluffs, with pet-friendly space, easy beach access, and outdoor space. This stay…

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About 2-story home near the beach with large lawn, deck, W/D, streaming, & partial AC

2-story home near the beach with large lawn, deck, W/D, streaming, & partial AC is a holiday home in Oak Bluffs, with pet-friendly space, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,225.

From$318/night

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Great Vacation Place Just Steps From The Beach

Holiday Home, Oak Bluffs

Great Vacation Place Just Steps From The Beach is a holiday home in Oak Bluffs, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Great Vacation Place Just Steps From The Beach

Great Vacation Place Just Steps From The Beach is a holiday home in Oak Bluffs, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,672.

From$382/night

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Great location! walk to restaurants, shops, ferries; close to beach & bike trail

Holiday Home, Oak Bluffs

Great location! walk to restaurants, shops, ferries; close to beach & bike trail is a holiday home in Oak Bluffs, with easy beach access and kitchen access. This stay gives travelers a…

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About Great location! walk to restaurants, shops, ferries; close to beach & bike trail

Great location! walk to restaurants, shops, ferries; close to beach & bike trail is a holiday home in Oak Bluffs, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,864.

From$409/night

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0.8 miles to Circuit Avenue in Downtown Oak Bluffs

Holiday Home, Oak Bluffs

0.8 miles to Circuit Avenue in Downtown Oak Bluffs is a holiday home in Oak Bluffs, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 0.8 miles to Circuit Avenue in Downtown Oak Bluffs

0.8 miles to Circuit Avenue in Downtown Oak Bluffs is a holiday home in Oak Bluffs, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,579.

From$797/night

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Vacation rentals with a kitchen in Oak Bluffs, MA

Compare stays with kitchen access for longer trips and easier meals.

Walk to Falmouth Heights Beach

Holiday Home, Oak Bluffs

Walk to Falmouth Heights Beach is a holiday home in Oak Bluffs, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Walk to Falmouth Heights Beach

Walk to Falmouth Heights Beach is a holiday home in Oak Bluffs, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,660.

From$380/night

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Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

Holiday Home, Oak Bluffs

Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access! is a holiday home in Oak Bluffs, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

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About Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access! is a holiday home in Oak Bluffs, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,524.

From$503/night

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Charming Recently Renovated 3-Bedroom Retreat

Holiday Home, Oak Bluffs

Charming Recently Renovated 3-Bedroom Retreat is a holiday home in Oak Bluffs, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming Recently Renovated 3-Bedroom Retreat

Charming Recently Renovated 3-Bedroom Retreat is a holiday home in Oak Bluffs, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,033.

From$719/night

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Chic Oak Bluffs Renovated 3-BR with Hot Tub, Large Yard, and Short Walk to Town

Holiday Home, Oak Bluffs

Chic Oak Bluffs Renovated 3-BR with Hot Tub, Large Yard, and Short Walk to Town is a holiday home in Oak Bluffs, with kitchen access and room for a group. This stay gives travelers a…

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About Chic Oak Bluffs Renovated 3-BR with Hot Tub, Large Yard, and Short Walk to Town

Chic Oak Bluffs Renovated 3-BR with Hot Tub, Large Yard, and Short Walk to Town is a holiday home in Oak Bluffs, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,230.

From$890/night

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Family-friendly vacation rentals in Oak Bluffs, MA

Plan a trip with stays that give families more room to spread out.

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

Cottage, Oak Bluffs

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace is a cottage in Oak Bluffs, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace is a cottage in Oak Bluffs, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,016.

From$288/night

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Cozy Cottage 1/2 mile to Woods Hole village

Cottage, Oak Bluffs

Cozy Cottage 1/2 mile to Woods Hole village is a cottage in Oak Bluffs, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Cottage 1/2 mile to Woods Hole village

Cozy Cottage 1/2 mile to Woods Hole village is a cottage in Oak Bluffs, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,463.

From$352/night

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Private cottage nestled in center of the Vineyard

Holiday Home, Oak Bluffs

Private cottage nestled in center of the Vineyard is a holiday home in Oak Bluffs, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Private cottage nestled in center of the Vineyard

Private cottage nestled in center of the Vineyard is a holiday home in Oak Bluffs, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,788.

From$398/night

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Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!

Condo, Oak Bluffs

Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere! is a condo in Oak Bluffs, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

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About Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!

Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere! is a condo in Oak Bluffs, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,192.

From$885/night

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