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Oak Bluffs Holiday Apartments

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

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

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

Perfect for Family, Friends, or a Romantic Getaway

Holiday Rental House
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, holiday rental in Oak Bluffs
Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br, holiday rental in Oak Bluffs
Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br, holiday rental in Oak Bluffs

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

Holiday Rental House
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, holiday rental in Oak Bluffs
Your 'Vineyard Dream' Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town, holiday rental in Oak Bluffs
Your 'Vineyard Dream' Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town, holiday rental in Oak Bluffs

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy, exceptional view, quiet, comfortable, yet close to all island attractions, holiday rental in Oak Bluffs
Cozy, exceptional view, quiet, comfortable, yet close to all island attractions, holiday rental in Oak Bluffs
Cozy, exceptional view, quiet, comfortable, yet close to all island attractions, holiday rental in Oak Bluffs

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

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

Make Lasting Memories In This Adorable Vineyard Cottage!

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

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

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

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Cottage Located In Heart Of Oak Bluffs, holiday rental in Oak Bluffs
Charming Cottage Located In Heart Of Oak Bluffs, holiday rental in Oak Bluffs
Charming Cottage Located In Heart Of Oak Bluffs, holiday rental in Oak Bluffs

Charming Cottage Located In Heart Of Oak Bluffs

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

Historic Renovated Home in East Chop

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

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

Family-friendly, Island Retreat With Luxurious Amenities

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

The Oak bluffs cottage, Martha’s Vineyard Island.

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

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

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

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming Artsy Apartment, holiday rental in Oak Bluffs
Charming Artsy Apartment, holiday rental in Oak Bluffs
Charming Artsy Apartment, holiday 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, holiday rental in Oak Bluffs
Location & Charm -- Central AC, holiday rental in Oak Bluffs
Location & Charm -- Central AC, holiday rental in Oak Bluffs

Location & Charm -- Central AC

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

Comfortable Island Home, Easy Access to Beaches and Town

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town, holiday rental in Oak Bluffs
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town, holiday rental in Oak Bluffs
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town, holiday rental in Oak Bluffs

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

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

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

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

Come experience a Winter getaway on the Vineyard!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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NEW Oak Bluffs apartment, walk to town and beaches!, holiday rental in Oak Bluffs
NEW Oak Bluffs apartment, walk to town and beaches!, holiday rental in Oak Bluffs
NEW Oak Bluffs apartment, walk to town and beaches!, holiday 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, holiday rental in Oak Bluffs
Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area, holiday rental in Oak Bluffs
Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area, holiday 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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Private Waterfront, Private Beach, Private 90' Dock, Views Views Views, holiday rental in Oak Bluffs
Private Waterfront, Private Beach, Private 90' Dock, Views Views Views, holiday rental in Oak Bluffs
Private Waterfront, Private Beach, Private 90' Dock, Views Views Views, holiday rental in Oak Bluffs

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Mid-week turnovers...Great for those who don't have a Monday-Friday workweek, holiday rental in Oak Bluffs
Mid-week turnovers...Great for those who don't have a Monday-Friday workweek, holiday rental in Oak Bluffs
Mid-week turnovers...Great for those who don't have a Monday-Friday workweek, holiday 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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Sunny coastal retreat w/ shared pool & tennis - 1/2 mile to beach, holiday rental in Oak Bluffs
Sunny coastal retreat w/ shared pool & tennis - 1/2 mile to beach, holiday rental in Oak Bluffs
Sunny coastal retreat w/ shared pool & tennis - 1/2 mile to beach, holiday rental in Oak Bluffs

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

Holiday Rental House
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!, holiday rental in Oak Bluffs
Charming townhouse w/ deck, shared pool & on-site tennis - walk to the beach!, holiday rental in Oak Bluffs
Charming townhouse w/ deck, shared pool & on-site tennis - walk to the beach!, holiday rental in Oak Bluffs

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

Holiday Rental House
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, holiday rental in Oak Bluffs
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom, holiday rental in Oak Bluffs
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom, holiday rental in Oak Bluffs

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy condo with shared pool & tennis - close to beaches, golf, & parks!, holiday rental in Oak Bluffs
Cozy condo with shared pool & tennis - close to beaches, golf, & parks!, holiday rental in Oak Bluffs
Cozy condo with shared pool & tennis - close to beaches, golf, & parks!, holiday 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
More info
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Dog-friendly seaside cottage w/access to a shared pool, tennis courts, & more, holiday rental in Oak Bluffs
Dog-friendly seaside cottage w/access to a shared pool, tennis courts, & more, holiday rental in Oak Bluffs
Dog-friendly seaside cottage w/access to a shared pool, tennis courts, & more, holiday 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, holiday rental in Oak Bluffs
Dog-friendly condo with shared pool - explore the parks & hit the beach, holiday rental in Oak Bluffs
Dog-friendly condo with shared pool - explore the parks & hit the beach, holiday 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.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfortable condo with shared tennis courts & pool - close to beaches, holiday rental in Oak Bluffs
Comfortable condo with shared tennis courts & pool - close to beaches, holiday rental in Oak Bluffs
Comfortable condo with shared tennis courts & pool - close to beaches, holiday 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, holiday rental in Oak Bluffs
Beautiful small home with fabulous private patio and  yard, holiday rental in Oak Bluffs
Beautiful small home with fabulous private patio and  yard, holiday rental in Oak Bluffs

Beautiful small home with fabulous private patio and yard

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

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Central location for your vacation

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spacious Waterview Condo - Steps To The Beach, Right Across The Street!, holiday rental in Oak Bluffs
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!, holiday rental in Oak Bluffs
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!, holiday 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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New Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min., holiday rental in Oak Bluffs
New Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min., holiday rental in Oak Bluffs
New Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min., holiday rental in Oak Bluffs

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

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

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

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

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

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

Recently renovated, close to town, still booking summer 2020

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Romantic seaside getaway w/ shared pool and community tennis courts - dogs OK!, holiday rental in Oak Bluffs
Romantic seaside getaway w/ shared pool and community tennis courts - dogs OK!, holiday rental in Oak Bluffs
Romantic seaside getaway w/ shared pool and community tennis courts - dogs OK!, holiday 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, holiday rental in Oak Bluffs
Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine, holiday rental in Oak Bluffs
Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine, holiday rental in Oak Bluffs

Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Cozy seaside escape with onsite tennis, communal pool, and prime location, holiday rental in Oak Bluffs
Cozy seaside escape with onsite tennis, communal pool, and prime location, holiday rental in Oak Bluffs
Cozy seaside escape with onsite tennis, communal pool, and prime location, holiday 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, holiday rental in Oak Bluffs
Perfect Family Home- Amazing Oak Bluffs, holiday rental in Oak Bluffs
Perfect Family Home- Amazing Oak Bluffs, holiday rental in Oak Bluffs

Perfect Family Home- Amazing Oak Bluffs

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

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Oak Bluffs! Renovated and close to everything!, holiday rental in Oak Bluffs
Oak Bluffs! Renovated and close to everything!, holiday rental in Oak Bluffs
Oak Bluffs! Renovated and close to everything!, holiday rental in Oak Bluffs

Oak Bluffs! Renovated and close to everything!

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

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

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