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Homes For Rent in Oak Bluffs, Massachusetts

37 Homes For Rent in Oak Bluffs, Massachusetts

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$3,500-$6,000/Week

Charming 3 Bedroom Apartment in Oak Bluffs

Oak Bluffs > Central | ID: 90Wa

3
2
Sleeps: 6

Charming 3 Bedroom Apartment in Oak Bluffs

$3,500-$6,000/Week

$5,000-$7,500/Week

Brand New Guest House in Oak Bluffs

Oak Bluffs | ID: 11Jes

2
1
Sleeps: 4

Newly Built Guest House - 2024 Construction

$5,000-$7,500/Week

$5,000-$12,000/Week

East Chop Waterfront Retreat

Oak Bluffs > East Chop | ID: 27PM

3
2
Sleeps: 6

Is chop waterfront retreat with stunning water views

$5,000-$12,000/Week

$2,200-$4,500/Week

Pet Friendly Home in East Chop!

Oak Bluffs > East Chop | ID: 3COR

3
2
Sleeps: 6

Lovely 3 bedroom 2.5 bath, pet friendly home in the highlands of East Chop!

$2,200-$4,500/Week

$5,500-$6,000/Week

Adorable Treehouse House in Oak Bluffs!

Oak Bluffs > Central | ID: 67ALP

4
2
Sleeps: 8

Home in Oak Bluffs!

$5,500-$6,000/Week

$3,500-$3,500/Week

One Bedroom Apartment in Downtown Oak Bluffs...

Oak Bluffs > In Town | ID: 101AOC

1
1
Sleeps: 4

Downtown Oak Bluffs next to the beach! This 1 bedroom 1 bathroom apartment in great location!

$3,500/Week

$15,000-$25,000/Week

Perfect Home with Water Views in Downtown Oak...

Oak Bluffs > In Town | ID: 10SEA

5
5
Sleeps: 10

Downtown Oak Bluffs! Right in front of the ferry!

$15,000-$25,000/Week

$6,300-$6,300/Week

Beautiful home in Deer Run!

Oak Bluffs > Central | ID: 24DEE

3
2
Sleeps: 6

Beautiful home with beautiful yard in Deer Park! Near the Airport!

$6,300/Week

$13,500-$13,500/Week

Beautiful Spacious Home in Ocean Park, Downtown...

Oak Bluffs > In Town | ID: 101OCE

7
4
Sleeps: 14

Beautiful home overlooking the water and Ocean Park. AMAZING Location!

$13,500/Week

$3,500-$9,450/Week

Stuning home on the water in Oak Bluffs!

Oak Bluffs | ID: 80BEL

3
2
Sleeps: 8

Stunning water views in Oak Bluffs!

$3,500-$9,450/Week

$3,850-$7,980/Week

Cute home in Oak Bluffs!

Oak Bluffs > In Town | ID: 73WIN

3
2
Sleeps: 6

Cute home very close to the center of Oak Bluffs town!

$3,850-$7,980/Week

$9,500-$17,700/Week

Oak Bluffs home with Private Pool!

Oak Bluffs > Central | ID: 56HEA

4
3
Sleeps: 11

Beautiful home in Oak Bluffs with private pool! Pet Friendly!

$9,500-$17,700/Week

$2,282-$3,955/Week

Apartment on Circuit Ave, Downtown Oak Bluffs!

Oak Bluffs > In Town | ID: 47CIR

2
1
Sleeps: 8

Spacious 2-bedroom Apartment overlooking Circuit Ave! In the Center of Town!

$2,282-$3,955/Week

$9,500-$13,500/Week

Beachfront Downtown Oak Bluffs!

Oak Bluffs > In Town | ID: 4CONI

4
2
Sleeps: 9

Be in the middle of the action! Stay in Oak Bluffs center right on the beach!

$9,500-$13,500/Week

$5,500-$6,500/Week

Charming Oak Bluffs Pet Friendly Remodel!

Oak Bluffs | ID: 26BRI

3
3
Sleeps: 6

Pet Friendly in Oak Bluffs!

$5,500-$6,500/Week

$9,500-$12,500/Week

Home in East Chop, Oak Bluffs with Waterviews!

Oak Bluffs > East Chop | ID: 10TEM

4
2
Sleeps: 8

On The Bluff with Water Views!

$9,500-$12,500/Week

$5,500-$6,500/Week

Amazing Home in Oak Bluffs near Lagoon!

Oak Bluffs > Central | ID: 50PON

3
2
Sleeps: 6

Beautiful 3-bedroom 2.5 bath nestled between Oak Bluffs and Vineyard Haven just off Barnes Rd. with outdoor shower and screened in porch.

$5,500-$6,500/Week

$3,500-$10,000/Week

Beautiful Lagoon Waterfront Home in Oak Bluffs!

Oak Bluffs > Central | ID: 13HUB

3
2
Sleeps: 7

Stunning Views! Oak Bluffs! Private Beach!

$3,500-$10,000/Week

$2,660-$6,510/Week

Waterview Farms Association Oak Bluffs Beach...

Oak Bluffs > Central | ID: 18TERS

4
2
Sleeps: 6

Tucked in the waterfront community of Waterview Farms, gorgeous newly renovated mid-century beach cottage vacation oasis with private beach and dock.

$2,660-$6,510/Week

$15,000-$16,000/Week

Family Retreat in Private Setting

Oak Bluffs | ID: 40PUL

5
2
Sleeps: 10

Beach House meets coziness of an Adirondack Lodge. Spectacular custom home with water views over Sengekontacket.

$15,000-$16,000/Week

$3,300-$6,200/Week

Walk to Downtown OB: 3-Bedroom Charming Home

Oak Bluffs > In Town | ID: 171CIR

3
2
Sleeps: 9

Charming 3-Bedroom Vineyard Home: Perfectly situated within walking distance of downtown Oak Bluffs, beaches, restaurants, and shops.

$3,300-$6,200/Week

$12,000-$22,000/Week

New Construction Oak Bluffs 4 Bedroom, Pool,...

Oak Bluffs > East Chop | ID: 6CLA

4
3
Sleeps: 8

Stunning four bedroom in desirable East Chop section of Oak Bluffs with a heated pool.

$12,000-$22,000/Week

$2,500-$7,700/Week

2 BR Apartment in Oak Bluffs

Oak Bluffs | ID: 1061

2
1
Sleeps: 4

Ideal apartment for 2-4 guests with easy access to public transportation and bike paths

$2,500-$7,700/Week

$5,000-$15,000/Week

Beautiful Home w Pool Extensively Landscaped...

Oak Bluffs | ID: 1057

4
2
Sleeps: 8

Perfect for family and friends retreat sleeps up to 8 people.

$5,000-$15,000/Week

$10,000-$19,000/Week

7 BD Beautiful home in downtown Oak Bluffs

Oak Bluffs | ID: 1058

7
4
Sleeps: 14

This Victorian Home has an ocean view and park view.

$10,000-$19,000/Week

37 Homes For Rent in Oak Bluffs, Massachusetts

Charming 3 Bedroom Apartment in Oak Bluffs

Brand New Guest House in Oak Bluffs

East Chop Waterfront Retreat

Pet Friendly Home in East Chop!

Adorable Treehouse House in Oak Bluffs!

One Bedroom Apartment in Downtown Oak Bluffs...

Perfect Home with Water Views in Downtown Oak...

Beautiful home in Deer Run!

Beautiful Spacious Home in Ocean Park, Downtown...

Stuning home on the water in Oak Bluffs!

Cute home in Oak Bluffs!

Oak Bluffs home with Private Pool!

Apartment on Circuit Ave, Downtown Oak Bluffs!

Beachfront Downtown Oak Bluffs!

Charming Oak Bluffs Pet Friendly Remodel!

Home in East Chop, Oak Bluffs with Waterviews!

Amazing Home in Oak Bluffs near Lagoon!

Beautiful Lagoon Waterfront Home in Oak Bluffs!

Waterview Farms Association Oak Bluffs Beach...

Family Retreat in Private Setting

Walk to Downtown OB: 3-Bedroom Charming Home

New Construction Oak Bluffs 4 Bedroom, Pool,...

2 BR Apartment in Oak Bluffs

Beautiful Home w Pool Extensively Landscaped...

7 BD Beautiful home in downtown Oak Bluffs

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