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Oak Bluffs Luxury Holiday Homes

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259 rentals in Oak Bluffs.
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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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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 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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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 House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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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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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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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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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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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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Save time - get the best Oak Bluffs rentals sent straight to your email!
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 House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Make Lasting Memories In This Adorable Vineyard Cottage!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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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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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Location & Charm -- Central AC
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Oak bluffs cottage, Martha’s Vineyard Island.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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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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Comfortable Island Home, Easy Access to Beaches and Town
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Charming Artsy Apartment
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family-friendly, Island Retreat With Luxurious Amenities
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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NEW Oak Bluffs apartment, walk to town and beaches!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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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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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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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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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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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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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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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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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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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Come experience a Winter getaway on the Vineyard!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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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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Comfortable condo with shared tennis courts & pool - close to beaches
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Central location for your vacation
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 House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Family Home- Amazing Oak Bluffs
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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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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Martha's Vineyard Beachfront Condo in Oak Bluffs
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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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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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Recently renovated, close to town, still booking summer 2020
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful small home with fabulous private patio and yard
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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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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4 Bedroom Home Family Friendly in Desirable Area
Holiday Rental House
4 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 House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Family Friendly, Air Conditioned Oasis
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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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