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Oak Bluffs Vacation Rentals

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260 rentals in Oak Bluffs.
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Arrowsmith Cottage - Near Eastville Point Beach, Oak Bluffs, Martha's Vineyard, vacation rental in Oak Bluffs
Arrowsmith Cottage - Near Eastville Point Beach, Oak Bluffs, Martha's Vineyard, vacation rental in Oak Bluffs
Arrowsmith Cottage - Near Eastville Point Beach, Oak Bluffs, Martha's Vineyard, vacation rental in Oak Bluffs

Arrowsmith Cottage - Near Eastville Point Beach, Oak Bluffs, Martha's Vineyard

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Perfect for Family, Friends, or a Romantic Getaway, vacation rental in Oak Bluffs
Perfect for Family, Friends, or a Romantic Getaway, vacation rental in Oak Bluffs
Perfect for Family, Friends, or a Romantic Getaway, vacation rental in Oak Bluffs

Perfect for Family, Friends, or a Romantic Getaway

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br, vacation rental in Oak Bluffs
Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br, vacation rental in Oak Bluffs
Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br, vacation rental in Oak Bluffs

Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br

Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Your 'Vineyard Dream' Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town, vacation rental in Oak Bluffs
Your 'Vineyard Dream' Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town, vacation rental in Oak Bluffs
Your 'Vineyard Dream' Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town, vacation rental in Oak Bluffs

Your 'Vineyard Dream' Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
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Cozy, exceptional view, quiet, comfortable, yet close to all island attractions, vacation rental in Oak Bluffs
Cozy, exceptional view, quiet, comfortable, yet close to all island attractions, vacation rental in Oak Bluffs
Cozy, exceptional view, quiet, comfortable, yet close to all island attractions, vacation rental in Oak Bluffs

Cozy, exceptional view, quiet, comfortable, yet close to all island attractions

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Make Lasting Memories In This Adorable Vineyard Cottage!, vacation rental in Oak Bluffs
Make Lasting Memories In This Adorable Vineyard Cottage!, vacation rental in Oak Bluffs
Make Lasting Memories In This Adorable Vineyard Cottage!, vacation rental in Oak Bluffs

Make Lasting Memories In This Adorable Vineyard Cottage!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable cottage w/ access to a shared pool, tennis courts, & picnic area, vacation rental in Oak Bluffs
Adorable cottage w/ access to a shared pool, tennis courts, & picnic area, vacation rental in Oak Bluffs
Adorable cottage w/ access to a shared pool, tennis courts, & picnic area, vacation rental in Oak Bluffs

Adorable cottage w/ access to a shared pool, tennis courts, & picnic area

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to Downtown & Beach ❤️ Firepit & s'mores, stocked groceries, experiences!, vacation rental in Oak Bluffs
Walk to Downtown & Beach ❤️ Firepit & s'mores, stocked groceries, experiences!, vacation rental in Oak Bluffs
Walk to Downtown & Beach ❤️ Firepit & s'mores, stocked groceries, experiences!, vacation rental in Oak Bluffs

Walk to Downtown & Beach ❤️ Firepit & s'mores, stocked groceries, experiences!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Cottage Located In Heart Of Oak Bluffs, vacation rental in Oak Bluffs
Charming Cottage Located In Heart Of Oak Bluffs, vacation rental in Oak Bluffs
Charming Cottage Located In Heart Of Oak Bluffs, vacation rental in Oak Bluffs

Charming Cottage Located In Heart Of Oak Bluffs

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Historic Renovated Home in East Chop, vacation rental in Oak Bluffs
Historic Renovated Home in East Chop, vacation rental in Oak Bluffs
Historic Renovated Home in East Chop, vacation rental in Oak Bluffs

Historic Renovated Home in East Chop

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Martha's Vineyard Beachfront Condo in Oak Bluffs, vacation rental in Oak Bluffs
Martha's Vineyard Beachfront Condo in Oak Bluffs, vacation rental in Oak Bluffs
Martha's Vineyard Beachfront Condo in Oak Bluffs, vacation rental in Oak Bluffs

Martha's Vineyard Beachfront Condo in Oak Bluffs

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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'The Carousel House' - Ocean Park - Featured in New York Times

Rental Home
7 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Family-friendly, Island Retreat With Luxurious Amenities, vacation rental in Oak Bluffs
Family-friendly, Island Retreat With Luxurious Amenities, vacation rental in Oak Bluffs
Family-friendly, Island Retreat With Luxurious Amenities, vacation rental in Oak Bluffs

Family-friendly, Island Retreat With Luxurious Amenities

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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The Oak bluffs cottage, Martha’s Vineyard Island., vacation rental in Oak Bluffs
The Oak bluffs cottage, Martha’s Vineyard Island., vacation rental in Oak Bluffs
The Oak bluffs cottage, Martha’s Vineyard Island., vacation rental in Oak Bluffs

The Oak bluffs cottage, Martha’s Vineyard Island.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfortable townhouse close to town & the beach w/ shared outdoor pool & tennis, vacation rental in Oak Bluffs
Comfortable townhouse close to town & the beach w/ shared outdoor pool & tennis, vacation rental in Oak Bluffs
Comfortable townhouse close to town & the beach w/ shared outdoor pool & tennis, vacation rental in Oak Bluffs

Comfortable townhouse close to town & the beach w/ shared outdoor pool & tennis

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New construction w/ patio & yard - walk to the ferry, downtown & beaches!, vacation rental in Oak Bluffs
New construction w/ patio & yard - walk to the ferry, downtown & beaches!, vacation rental in Oak Bluffs
New construction w/ patio & yard - walk to the ferry, downtown & beaches!, vacation rental in Oak Bluffs

New construction w/ patio & yard - walk to the ferry, downtown & beaches!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming Artsy Apartment, vacation rental in Oak Bluffs
Charming Artsy Apartment, vacation rental in Oak Bluffs
Charming Artsy Apartment, vacation rental in Oak Bluffs

Charming Artsy Apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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
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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
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Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town, vacation rental in Oak Bluffs
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town, vacation rental in Oak Bluffs
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town, vacation rental in Oak Bluffs

Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Stylish townhouse 1/2 mile from the beach - tennis courts & shared pool onsite!, vacation rental in Oak Bluffs
Stylish townhouse 1/2 mile from the beach - tennis courts & shared pool onsite!, vacation rental in Oak Bluffs
Stylish townhouse 1/2 mile from the beach - tennis courts & shared pool onsite!, vacation rental in Oak Bluffs

Stylish townhouse 1/2 mile from the beach - tennis courts & shared pool onsite!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Come experience a Winter getaway on the Vineyard!, vacation rental in Oak Bluffs
Come experience a Winter getaway on the Vineyard!, vacation rental in Oak Bluffs
Come experience a Winter getaway on the Vineyard!, vacation rental in Oak Bluffs

Come experience a Winter getaway on the Vineyard!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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NEW Oak Bluffs apartment, walk to town and beaches!, vacation rental in Oak Bluffs
NEW Oak Bluffs apartment, walk to town and beaches!, vacation rental in Oak Bluffs
NEW Oak Bluffs apartment, walk to town and beaches!, vacation rental in Oak Bluffs

NEW Oak Bluffs apartment, walk to town and beaches!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area, vacation rental in Oak Bluffs
Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area, vacation rental in Oak Bluffs
Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area, vacation rental in Oak Bluffs

Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mid-week turnovers...Great for those who don't have a Monday-Friday workweek, vacation rental in Oak Bluffs
Mid-week turnovers...Great for those who don't have a Monday-Friday workweek, vacation rental in Oak Bluffs
Mid-week turnovers...Great for those who don't have a Monday-Friday workweek, vacation rental in Oak Bluffs

Mid-week turnovers...Great for those who don't have a Monday-Friday workweek

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Waterfront, Private Beach, Private 90' Dock, Views Views Views, vacation rental in Oak Bluffs
Private Waterfront, Private Beach, Private 90' Dock, Views Views Views, vacation rental in Oak Bluffs
Private Waterfront, Private Beach, Private 90' Dock, Views Views Views, vacation rental in Oak Bluffs

Private Waterfront, Private Beach, Private 90' Dock, Views Views Views

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Sunny coastal retreat w/ shared pool & tennis - 1/2 mile to beach, vacation rental in Oak Bluffs
Sunny coastal retreat w/ shared pool & tennis - 1/2 mile to beach, vacation rental in Oak Bluffs
Sunny coastal retreat w/ shared pool & tennis - 1/2 mile to beach, vacation rental in Oak Bluffs

Sunny coastal retreat w/ shared pool & tennis - 1/2 mile to beach

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming townhouse w/ deck, shared pool & on-site tennis - walk to the beach!, vacation rental in Oak Bluffs
Charming townhouse w/ deck, shared pool & on-site tennis - walk to the beach!, vacation rental in Oak Bluffs
Charming townhouse w/ deck, shared pool & on-site tennis - walk to the beach!, vacation rental in Oak Bluffs

Charming townhouse w/ deck, shared pool & on-site tennis - walk to the beach!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom, vacation rental in Oak Bluffs
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom, vacation rental in Oak Bluffs
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom, vacation rental in Oak Bluffs

Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy condo with shared pool & tennis - close to beaches, golf, & parks!, vacation rental in Oak Bluffs
Cozy condo with shared pool & tennis - close to beaches, golf, & parks!, vacation rental in Oak Bluffs
Cozy condo with shared pool & tennis - close to beaches, golf, & parks!, vacation rental in Oak Bluffs

Cozy condo with shared pool & tennis - close to beaches, golf, & parks!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Dog-friendly seaside cottage w/access to a shared pool, tennis courts, & more, vacation rental in Oak Bluffs
Dog-friendly seaside cottage w/access to a shared pool, tennis courts, & more, vacation rental in Oak Bluffs
Dog-friendly seaside cottage w/access to a shared pool, tennis courts, & more, vacation rental in Oak Bluffs

Dog-friendly seaside cottage w/access to a shared pool, tennis courts, & more

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dog-friendly condo with shared pool - explore the parks & hit the beach, vacation rental in Oak Bluffs
Dog-friendly condo with shared pool - explore the parks & hit the beach, vacation rental in Oak Bluffs
Dog-friendly condo with shared pool - explore the parks & hit the beach, vacation rental in Oak Bluffs

Dog-friendly condo with shared pool - explore the parks & hit the beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ob Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfortable condo with shared tennis courts & pool - close to beaches, vacation rental in Oak Bluffs
Comfortable condo with shared tennis courts & pool - close to beaches, vacation rental in Oak Bluffs
Comfortable condo with shared tennis courts & pool - close to beaches, vacation rental in Oak Bluffs

Comfortable condo with shared tennis courts & pool - close to beaches

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful small home with fabulous private patio and  yard, vacation rental in Oak Bluffs
Beautiful small home with fabulous private patio and  yard, vacation rental in Oak Bluffs
Beautiful small home with fabulous private patio and  yard, vacation rental in Oak Bluffs

Beautiful small home with fabulous private patio and yard

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Premium Cleaned | Dog-friendly townhouse w/ shared pool, tennis & more - easy wa, vacation rental in Oak Bluffs
Premium Cleaned | Dog-friendly townhouse w/ shared pool, tennis & more - easy wa, vacation rental in Oak Bluffs
Premium Cleaned | Dog-friendly townhouse w/ shared pool, tennis & more - easy wa, vacation rental in Oak Bluffs

Premium Cleaned | Dog-friendly townhouse w/ shared pool, tennis & more - easy wa

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Waterview Condo - Steps To The Beach, Right Across The Street!, vacation rental in Oak Bluffs
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!, vacation rental in Oak Bluffs
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!, vacation rental in Oak Bluffs

Spacious Waterview Condo - Steps To The Beach, Right Across The Street!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Central location for your vacation

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min., vacation rental in Oak Bluffs
New Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min., vacation rental in Oak Bluffs
New Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min., vacation rental in Oak Bluffs

New Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach., vacation rental in Oak Bluffs
CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach., vacation rental in Oak Bluffs
CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach., vacation rental in Oak Bluffs

CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS, vacation rental in Oak Bluffs
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS, vacation rental in Oak Bluffs
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS, vacation rental in Oak Bluffs

CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Recently renovated, close to town, still booking summer 2020, vacation rental in Oak Bluffs
Recently renovated, close to town, still booking summer 2020, vacation rental in Oak Bluffs
Recently renovated, close to town, still booking summer 2020, vacation rental in Oak Bluffs

Recently renovated, close to town, still booking summer 2020

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Romantic seaside getaway w/ shared pool and community tennis courts - dogs OK!, vacation rental in Oak Bluffs
Romantic seaside getaway w/ shared pool and community tennis courts - dogs OK!, vacation rental in Oak Bluffs
Romantic seaside getaway w/ shared pool and community tennis courts - dogs OK!, vacation rental in Oak Bluffs

Romantic seaside getaway w/ shared pool and community tennis courts - dogs OK!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine, vacation rental in Oak Bluffs
Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine, vacation rental in Oak Bluffs
Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine, vacation rental in Oak Bluffs

Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine

Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Cozy seaside escape with onsite tennis, communal pool, and prime location, vacation rental in Oak Bluffs
Cozy seaside escape with onsite tennis, communal pool, and prime location, vacation rental in Oak Bluffs
Cozy seaside escape with onsite tennis, communal pool, and prime location, vacation rental in Oak Bluffs

Cozy seaside escape with onsite tennis, communal pool, and prime location

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect Family Home- Amazing Oak Bluffs, vacation rental in Oak Bluffs
Perfect Family Home- Amazing Oak Bluffs, vacation rental in Oak Bluffs
Perfect Family Home- Amazing Oak Bluffs, vacation rental in Oak Bluffs

Perfect Family Home- Amazing Oak Bluffs

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Pristine Retreat - Spectacular outdoor space - New Blue Stone Patio and Fire Pit, vacation rental in Oak Bluffs
Pristine Retreat - Spectacular outdoor space - New Blue Stone Patio and Fire Pit, vacation rental in Oak Bluffs
Pristine Retreat - Spectacular outdoor space - New Blue Stone Patio and Fire Pit, vacation rental in Oak Bluffs

Pristine Retreat - Spectacular outdoor space - New Blue Stone Patio and Fire Pit

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Oak Bluffs! Renovated and close to everything!, vacation rental in Oak Bluffs
Oak Bluffs! Renovated and close to everything!, vacation rental in Oak Bluffs
Oak Bluffs! Renovated and close to everything!, vacation rental in Oak Bluffs

Oak Bluffs! Renovated and close to everything!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Meadow View Farms, OB.  4+ BR.  Great location., vacation rental in Oak Bluffs
Meadow View Farms, OB.  4+ BR.  Great location., vacation rental in Oak Bluffs
Meadow View Farms, OB.  4+ BR.  Great location., vacation rental in Oak Bluffs

Meadow View Farms, OB. 4+ BR. Great location.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Frequently Asked Questions about Oak Bluffs