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Oak Bluffs House Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
333 rentals in Oak Bluffs.
Close to town, beautifully updated- September & October availability 2023, vacation rental in Oak Bluffs
Close to town, beautifully updated- September & October availability 2023, vacation rental in Oak Bluffs
Close to town, beautifully updated- September & October availability 2023, vacation rental in Oak Bluffs

Close to town, beautifully updated- September & October availability 2023

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Modern 4 bed/3.5 bath Farmhouse with private HEATED POOL and AC on bike path, vacation rental in Oak Bluffs
Modern 4 bed/3.5 bath Farmhouse with private HEATED POOL and AC on bike path, vacation rental in Oak Bluffs
Modern 4 bed/3.5 bath Farmhouse with private HEATED POOL and AC on bike path, vacation rental in Oak Bluffs

Modern 4 bed/3.5 bath Farmhouse with private HEATED POOL and AC on bike path

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs, vacation rental in Oak Bluffs
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs, vacation rental in Oak Bluffs
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs, vacation rental in Oak Bluffs

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven, vacation rental in Oak Bluffs
Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven, vacation rental in Oak Bluffs
Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven, vacation rental in Oak Bluffs

Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!, vacation rental in Oak Bluffs
Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!, vacation rental in Oak Bluffs
Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!, vacation rental in Oak Bluffs

Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches, vacation rental in Oak Bluffs
Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches, vacation rental in Oak Bluffs
Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches, vacation rental in Oak Bluffs

Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path, vacation rental in Oak Bluffs
Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path, vacation rental in Oak Bluffs
Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path, vacation rental in Oak Bluffs

Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Oak bluffs cottage, Perfect for.  Honeymoon! Summer rentals fill up early !, vacation rental in Oak Bluffs
Oak bluffs cottage, Perfect for.  Honeymoon! Summer rentals fill up early !, vacation rental in Oak Bluffs
Oak bluffs cottage, Perfect for.  Honeymoon! Summer rentals fill up early !, vacation rental in Oak Bluffs

Oak bluffs cottage, Perfect for. Honeymoon! Summer rentals fill up early !

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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Cozy, exceptional view, quiet, high speed WIFI,  close to all island attractions, vacation rental in Oak Bluffs
Cozy, exceptional view, quiet, high speed WIFI,  close to all island attractions, vacation rental in Oak Bluffs
Cozy, exceptional view, quiet, high speed WIFI,  close to all island attractions, vacation rental in Oak Bluffs

Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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New Construction with Patio & Yard - Walk to the Ferry, Downtown & Beaches, vacation rental in Oak Bluffs
New Construction with Patio & Yard - Walk to the Ferry, Downtown & Beaches, vacation rental in Oak Bluffs
New Construction with Patio & Yard - Walk to the Ferry, Downtown & Beaches, vacation rental in Oak Bluffs

New Construction with Patio & Yard - Walk to the Ferry, Downtown & Beaches

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!, vacation rental in Oak Bluffs
ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!, vacation rental in Oak Bluffs
ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!, vacation rental in Oak Bluffs

ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Luxury Loft Historic Center Oak Bluffs, vacation rental in Oak Bluffs
Luxury Loft Historic Center Oak Bluffs, vacation rental in Oak Bluffs
Luxury Loft Historic Center Oak Bluffs, vacation rental in Oak Bluffs

Luxury Loft Historic Center Oak Bluffs

Rental Home
6 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps, Vacation Rental House
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Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer, vacation rental in Oak Bluffs
Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer, vacation rental in Oak Bluffs
Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer, vacation rental in Oak Bluffs

Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Multiple Ensuites, Central Air, Perfect Location, vacation rental in Oak Bluffs
Multiple Ensuites, Central Air, Perfect Location, vacation rental in Oak Bluffs
Multiple Ensuites, Central Air, Perfect Location, vacation rental in Oak Bluffs

Multiple Ensuites, Central Air, Perfect Location

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Cozy cottage 3/4 mile from Oak Bluffs harbor, vacation rental in Oak Bluffs
Cozy cottage 3/4 mile from Oak Bluffs harbor, vacation rental in Oak Bluffs
Cozy cottage 3/4 mile from Oak Bluffs harbor, vacation rental in Oak Bluffs

Cozy cottage 3/4 mile from Oak Bluffs harbor

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Location & Charm -- Central AC, vacation rental in Oak Bluffs
Location & Charm -- Central AC, vacation rental in Oak Bluffs
Location & Charm -- Central AC, vacation rental in Oak Bluffs

Location & Charm -- Central AC

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Comfortable Island Home, Easy Access to Beaches and Town, vacation rental in Oak Bluffs
Comfortable Island Home, Easy Access to Beaches and Town, vacation rental in Oak Bluffs
Comfortable Island Home, Easy Access to Beaches and Town, vacation rental in Oak Bluffs

Comfortable Island Home, Easy Access to Beaches and Town

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps, Vacation Rental House
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New Carriage House, Swimming, Boating, Kayaking, just steps from your door..., vacation rental in Oak Bluffs
New Carriage House, Swimming, Boating, Kayaking, just steps from your door..., vacation rental in Oak Bluffs
New Carriage House, Swimming, Boating, Kayaking, just steps from your door..., vacation rental in Oak Bluffs

New Carriage House, Swimming, Boating, Kayaking, just steps from your door...

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Vacation Rental House
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Adorable Oak Bluffs Cottage Walking Distance to Town, vacation rental in Oak Bluffs
Adorable Oak Bluffs Cottage Walking Distance to Town, vacation rental in Oak Bluffs
Adorable Oak Bluffs Cottage Walking Distance to Town, vacation rental in Oak Bluffs

Adorable Oak Bluffs Cottage Walking Distance to Town

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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Great location, happy house 0.5 mile Nancy’s & Jetty Beach., vacation rental in Oak Bluffs
Great location, happy house 0.5 mile Nancy’s & Jetty Beach., vacation rental in Oak Bluffs
Great location, happy house 0.5 mile Nancy’s & Jetty Beach., vacation rental in Oak Bluffs

Great location, happy house 0.5 mile Nancy’s & Jetty Beach.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Historic Oak Bluffs home, short walk to town, beach, and harbor., vacation rental in Oak Bluffs
Historic Oak Bluffs home, short walk to town, beach, and harbor., vacation rental in Oak Bluffs
Historic Oak Bluffs home, short walk to town, beach, and harbor., vacation rental in Oak Bluffs

Historic Oak Bluffs home, short walk to town, beach, and harbor.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard, vacation rental in Oak Bluffs
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard, vacation rental in Oak Bluffs
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard, vacation rental in Oak Bluffs

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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Classic Oak Bluffs Beach House | Excellent Harbor Views | Near Shops & Dining, vacation rental in Oak Bluffs
Classic Oak Bluffs Beach House | Excellent Harbor Views | Near Shops & Dining, vacation rental in Oak Bluffs
Classic Oak Bluffs Beach House | Excellent Harbor Views | Near Shops & Dining, vacation rental in Oak Bluffs

Classic Oak Bluffs Beach House | Excellent Harbor Views | Near Shops & Dining

Rental Home
5 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps, Vacation Rental House
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1-Bedroom cottage, 200ft from the beach, vacation rental in Oak Bluffs
1-Bedroom cottage, 200ft from the beach, vacation rental in Oak Bluffs
1-Bedroom cottage, 200ft from the beach, vacation rental in Oak Bluffs

1-Bedroom cottage, 200ft from the beach

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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,Artist Guest House on beautiful estate open concept King Sized Bunk Beds, vacation rental in Oak Bluffs
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds, vacation rental in Oak Bluffs
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds, vacation rental in Oak Bluffs

,Artist Guest House on beautiful estate open concept King Sized Bunk Beds

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Vacation Rental House
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Sweet Get Away Suite, Private Beach &Tennis, vacation rental in Oak Bluffs
Sweet Get Away Suite, Private Beach &Tennis, vacation rental in Oak Bluffs
Sweet Get Away Suite, Private Beach &Tennis, vacation rental in Oak Bluffs

Sweet Get Away Suite, Private Beach &Tennis

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Vacation Rental House
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#CozyBluffs 1 BR House in Historic Oak Bluffs - walk to town and ferry, vacation rental in Oak Bluffs
#CozyBluffs 1 BR House in Historic Oak Bluffs - walk to town and ferry, vacation rental in Oak Bluffs
#CozyBluffs 1 BR House in Historic Oak Bluffs - walk to town and ferry, vacation rental in Oak Bluffs

#CozyBluffs 1 BR House in Historic Oak Bluffs - walk to town and ferry

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, Vacation Rental House
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Oak Bluffs Waterfront Cottage, vacation rental in Oak Bluffs
Oak Bluffs Waterfront Cottage, vacation rental in Oak Bluffs
Oak Bluffs Waterfront Cottage, vacation rental in Oak Bluffs

Oak Bluffs Waterfront Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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Oak Bluffs Rental - Walk to the Beach, vacation rental in Oak Bluffs
Oak Bluffs Rental - Walk to the Beach, vacation rental in Oak Bluffs
Oak Bluffs Rental - Walk to the Beach, vacation rental in Oak Bluffs

Oak Bluffs Rental - Walk to the Beach

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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2+BR Renovated Gingerbread Cottage - Walk to All, vacation rental in Oak Bluffs
2+BR Renovated Gingerbread Cottage - Walk to All, vacation rental in Oak Bluffs
2+BR Renovated Gingerbread Cottage - Walk to All, vacation rental in Oak Bluffs

2+BR Renovated Gingerbread Cottage - Walk to All

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Vineyard Charming Retreat near beaches and center, vacation rental in Oak Bluffs
Vineyard Charming Retreat near beaches and center, vacation rental in Oak Bluffs
Vineyard Charming Retreat near beaches and center, vacation rental in Oak Bluffs

Vineyard Charming Retreat near beaches and center

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach, vacation rental in Oak Bluffs
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach, vacation rental in Oak Bluffs
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach, vacation rental in Oak Bluffs

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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GingerBread Cottage at Oak Bluffs, vacation rental in Oak Bluffs
GingerBread Cottage at Oak Bluffs, vacation rental in Oak Bluffs
GingerBread Cottage at Oak Bluffs, vacation rental in Oak Bluffs

GingerBread Cottage at Oak Bluffs

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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Three Bedroom Oak Bluffs Home, vacation rental in Oak Bluffs
Three Bedroom Oak Bluffs Home, vacation rental in Oak Bluffs
Three Bedroom Oak Bluffs Home, vacation rental in Oak Bluffs

Three Bedroom Oak Bluffs Home

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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In-town Oak Bluffs House, vacation rental in Oak Bluffs
In-town Oak Bluffs House, vacation rental in Oak Bluffs
In-town Oak Bluffs House, vacation rental in Oak Bluffs

In-town Oak Bluffs House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town, vacation rental in Oak Bluffs
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town, vacation rental in Oak Bluffs
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town, vacation rental in Oak Bluffs

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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Oak Bluffs Cape Not too Far from Town, vacation rental in Oak Bluffs
Oak Bluffs Cape Not too Far from Town, vacation rental in Oak Bluffs
Oak Bluffs Cape Not too Far from Town, vacation rental in Oak Bluffs

Oak Bluffs Cape Not too Far from Town

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, Vacation Rental House
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East Chop Custom Built 3 Bedroom Cottage, vacation rental in Oak Bluffs
East Chop Custom Built 3 Bedroom Cottage, vacation rental in Oak Bluffs
East Chop Custom Built 3 Bedroom Cottage, vacation rental in Oak Bluffs

East Chop Custom Built 3 Bedroom Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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COZY,CUTE COTTAGE NEAR TOWN & BEACH., vacation rental in Oak Bluffs
COZY,CUTE COTTAGE NEAR TOWN & BEACH., vacation rental in Oak Bluffs
COZY,CUTE COTTAGE NEAR TOWN & BEACH., vacation rental in Oak Bluffs

COZY,CUTE COTTAGE NEAR TOWN & BEACH.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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Sweet Little Post&Beam, vacation rental in Oak Bluffs
Sweet Little Post&Beam, vacation rental in Oak Bluffs
Sweet Little Post&Beam, vacation rental in Oak Bluffs

Sweet Little Post&Beam

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, Vacation Rental House
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New Oak Bluffs Home Close to Town, vacation rental in Oak Bluffs
New Oak Bluffs Home Close to Town, vacation rental in Oak Bluffs
New Oak Bluffs Home Close to Town, vacation rental in Oak Bluffs

New Oak Bluffs Home Close to Town

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Nice home  w outdoor patio bar , dining table, comfortable furniture   See photo, vacation rental in Oak Bluffs
Nice home  w outdoor patio bar , dining table, comfortable furniture   See photo, vacation rental in Oak Bluffs
Nice home  w outdoor patio bar , dining table, comfortable furniture   See photo, vacation rental in Oak Bluffs

Nice home w outdoor patio bar , dining table, comfortable furniture See photo

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Vacation Rental House
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Family home located near everything needed for  the perfect vacation., vacation rental in Oak Bluffs
Family home located near everything needed for  the perfect vacation., vacation rental in Oak Bluffs
Family home located near everything needed for  the perfect vacation., vacation rental in Oak Bluffs

Family home located near everything needed for the perfect vacation.

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps, Vacation Rental House
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Enjoy Sea Breezes from third floor roof deck!, vacation rental in Oak Bluffs
Enjoy Sea Breezes from third floor roof deck!, vacation rental in Oak Bluffs
Enjoy Sea Breezes from third floor roof deck!, vacation rental in Oak Bluffs

Enjoy Sea Breezes from third floor roof deck!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, Vacation Rental House
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Beautiful Four Bedroom Cottage on East Chop, vacation rental in Oak Bluffs
Beautiful Four Bedroom Cottage on East Chop, vacation rental in Oak Bluffs
Beautiful Four Bedroom Cottage on East Chop, vacation rental in Oak Bluffs

Beautiful Four Bedroom Cottage on East Chop

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Gorgeous A-Frame Cabin On the Chop with Amazing Views/Walk to Town and Ferry, vacation rental in Oak Bluffs
Gorgeous A-Frame Cabin On the Chop with Amazing Views/Walk to Town and Ferry, vacation rental in Oak Bluffs
Gorgeous A-Frame Cabin On the Chop with Amazing Views/Walk to Town and Ferry, vacation rental in Oak Bluffs

Gorgeous A-Frame Cabin On the Chop with Amazing Views/Walk to Town and Ferry

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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New to the rental market! Air conditioned family home, 1 mile from Circuit Ave, vacation rental in Oak Bluffs
New to the rental market! Air conditioned family home, 1 mile from Circuit Ave, vacation rental in Oak Bluffs
New to the rental market! Air conditioned family home, 1 mile from Circuit Ave, vacation rental in Oak Bluffs

New to the rental market! Air conditioned family home, 1 mile from Circuit Ave

Rental Home
4 bedrooms
0 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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OB Cozy-Cottage-Glam off Circuit with Great Outdoor living, vacation rental in Oak Bluffs
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living, vacation rental in Oak Bluffs
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living, vacation rental in Oak Bluffs

OB Cozy-Cottage-Glam off Circuit with Great Outdoor living

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Guest House with two Sweet Suites, vacation rental in Oak Bluffs
Guest House with two Sweet Suites, vacation rental in Oak Bluffs
Guest House with two Sweet Suites, vacation rental in Oak Bluffs

Guest House with two Sweet Suites

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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Classic Cottage In Oak Bluffs, vacation rental in Oak Bluffs
Classic Cottage In Oak Bluffs, vacation rental in Oak Bluffs
Classic Cottage In Oak Bluffs, vacation rental in Oak Bluffs

Classic Cottage In Oak Bluffs

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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