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Oak Bluffs, MA Holiday Rentals, Apartments and Villas
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Massachusetts (MA)
Martha's Vineyard
Oak Bluffs, MA Holiday Rentals, Apartments and Villas
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260 rentals
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Arrowsmith Cottage - Near Eastville Point Beach, Oak Bluffs, Martha's Vineyard
46 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Perfect for Family, Friends, or a Romantic Getaway
72 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
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Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br
52 reviews
Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 16
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Your 'Vineyard Dream' Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town
71 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!
36 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Cozy, exceptional view, quiet, comfortable, yet close to all island attractions
49 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Make Lasting Memories In This Adorable Vineyard Cottage!
96 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match:
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Adorable cottage w/ access to a shared pool, tennis courts, & picnic area
45 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Walk to Downtown & Beach ❤️ Firepit & s'mores, stocked groceries, experiences!
29 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Charming Cottage Located In Heart Of Oak Bluffs
26 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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Historic Renovated Home in East Chop
34 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Martha's Vineyard Beachfront Condo in Oak Bluffs
35 reviews
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match:
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'The Carousel House' - Ocean Park - Featured in New York Times
36 reviews
Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 12
Match:
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Family-friendly, Island Retreat With Luxurious Amenities
32 reviews
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
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The Oak bluffs cottage, Martha’s Vineyard Island.
42 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Comfortable townhouse close to town & the beach w/ shared outdoor pool & tennis
31 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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New construction w/ patio & yard - walk to the ferry, downtown & beaches!
51 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Charming Artsy Apartment
23 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Location & Charm -- Central AC
26 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Comfortable Island Home, Easy Access to Beaches and Town
40 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
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Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town
35 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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Stylish townhouse 1/2 mile from the beach - tennis courts & shared pool onsite!
24 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Come experience a Winter getaway on the Vineyard!
33 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match:
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NEW Oak Bluffs apartment, walk to town and beaches!
16 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match:
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Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area
29 reviews
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
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Private Waterfront, Private Beach, Private 90' Dock, Views Views Views
19 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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Mid-week turnovers...Great for those who don't have a Monday-Friday workweek
18 reviews
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Sunny coastal retreat w/ shared pool & tennis - 1/2 mile to beach
23 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match:
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Charming townhouse w/ deck, shared pool & on-site tennis - walk to the beach!
34 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
20 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match:
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Cozy condo with shared pool & tennis - close to beaches, golf, & parks!
36 reviews
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
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Dog-friendly seaside cottage w/access to a shared pool, tennis courts, & more
29 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match:
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Dog-friendly condo with shared pool - explore the parks & hit the beach
39 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Ob Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.
25 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match:
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Comfortable condo with shared tennis courts & pool - close to beaches
44 reviews
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
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Beautiful small home with fabulous private patio and yard
18 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match:
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Premium Cleaned | Dog-friendly townhouse w/ shared pool, tennis & more - easy wa
17 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Central location for your vacation
30 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
55 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match:
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New Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min.
13 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match:
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CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach.
35 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match:
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CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
24 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match:
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Recently renovated, close to town, still booking summer 2020
17 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Romantic seaside getaway w/ shared pool and community tennis courts - dogs OK!
24 reviews
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match:
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Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine
16 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match:
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Cozy seaside escape with onsite tennis, communal pool, and prime location
23 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match:
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Perfect Family Home- Amazing Oak Bluffs
12 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match:
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Pristine Retreat - Spectacular outdoor space - New Blue Stone Patio and Fire Pit
21 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Oak Bluffs! Renovated and close to everything!
23 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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Meadow View Farms, OB. 4+ BR. Great location.
20 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match:
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Frequently Asked Questions about Oak Bluffs
Do any holiday rentals in Oak Bluffs have a pool?
Yes, here are some popular holiday rentals in Oak Bluffs that have a pool:\n
\n
Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!
\n
Family Retreat Home with Inground Pool
\n
Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br
\n
\n
See all holiday rentals with a pool in Oak Bluffs on Tripadvisor
Do any holiday rentals in Oak Bluffs have internet access?
Yes, here are some popular holiday rentals in Oak Bluffs that have internet access:\n
\n
ENJOY WATERVIEWS OF SENGENKONTACKET POND FROM THE WONDERFUL DECK
\n
CLASSIC AND CHARMING COTTAGE WALKING DISTANCE TO THE BEACH AND TOWN
\n
CLASSIC, VINTAGE,GINGERBREAD
\n
\n
See all holiday rentals in Oak Bluffs on Tripadvisor
What are the best pet friendly rentals in Oak Bluffs?
The best pet friendly rentals in Oak Bluffs are:\n
\n
Clean, comfortable ranch with lots of amenities
\n
Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!
\n
Ocean, lake, harbor & parkview Vineyard cottage w/AC
\n
\n
See all pet friendly holiday rentals in Oak Bluffs on Tripadvisor
What are some great rentals in Oak Bluffs that are kid friendly?
Some of the most popular kid friendly rentals in Oak Bluffs are:\n
\n
Oak Bluffs Contemporary Summer Home
\n
Charming 3br Getaway in Oak Bluffs
\n
Clean, comfortable ranch with lots of amenities
\n
\n
See all kid friendly holiday rentals in Oak Bluffs on Tripadvisor