Oak Bluffs Holiday Rentals
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240 rentals in Oak Bluffs.
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New construction w/ patio & yard - walk to the ferry, downtown & beaches!
4 bedrooms
3 bathrooms
Sleeps 10
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Classic Oak Bluffs Beach House | Excellent Harbor Views | Near Shops & Dining
5 bedrooms
1 bathroom
Sleeps 8
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THOMS - New Modern Farmhouse Design, Great Location!, Wrap Around Farmers Porch
4 bedrooms
3 bathrooms
Sleeps 8
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Walk to Lagoon from this Cute Cottage
4 bedrooms
2 bathrooms
Sleeps 8
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THORB - Contemporary 5 Bedroom 4 Bath, Multiple Living Spaces, Walk to Oak Bluff
4 bedrooms
4 bathrooms
Sleeps 8
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New Four Bedroom in-town Oak Bluffs Home
4 bedrooms
3 bathrooms
Sleeps 8
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Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br
3 bedrooms
5 bathrooms
Sleeps 17
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In-Town Historic Property on Martha's Vineyard
2 bedrooms
1 bathroom
Sleeps 5
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Perfect for Family, Friends, or a Romantic Getaway
4 bedrooms
2 bathrooms
Sleeps 7
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Make Lasting Memories In This Adorable Vineyard Cottage!
1 bedroom
1 bathroom
Sleeps 4
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Your 'Vineyard Dream' Vacation (OAK BLUFFS)-Sunny Open Floor Plan Close to Town
4 bedrooms
2 bathrooms
Sleeps 8
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Adorable cottage w/ access to a shared pool, tennis courts, & picnic area
2 bedrooms
2 bathrooms
Sleeps 6
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'The Carousel House' - Ocean Park - Featured in New York Times
7 bedrooms
3 bathrooms
Sleeps 12
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Cozy, exceptional view, quiet, comfortable, yet close to all island attractions
3 bedrooms
3 bathrooms
Sleeps 8
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Walk to Downtown & Beach ❤️ Firepit & s'mores, stocked groceries, experiences!
3 bedrooms
3 bathrooms
Sleeps 6
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Charming Cottage Located In Heart Of Oak Bluffs
2 bedrooms
3 bathrooms
Sleeps 4
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Historic Renovated Home in East Chop
4 bedrooms
2 bathrooms
Sleeps 8
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Charming Artsy Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Arrowsmith Cottage - Near Eastville Point Beach, Oak Bluffs, Martha's Vineyard
2 bedrooms
2 bathrooms
Sleeps 4
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Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town
3 bedrooms
2 bathrooms
Sleeps 7
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Comfortable Island Home, Easy Access to Beaches and Town
2 bedrooms
1 bathroom
Sleeps 8
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Location & Charm -- Central AC
4 bedrooms
2 bathrooms
Sleeps 8
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Lovely retreat 1/2 mile from the beach - shared pool, 3 tennis courts, & WiFi
1 bedroom
2 bathrooms
Sleeps 6
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Perfect Family Home- Amazing Oak Bluffs
3 bedrooms
4 bathrooms
Sleeps 10
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Ob Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.
4 bedrooms
2 bathrooms
Sleeps 8
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Dog-friendly seaside cottage w/access to a shared pool, tennis courts, & more
1 bedroom
1 bathroom
Sleeps 4
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Comfortable townhouse close to town & the beach w/ shared outdoor pool & tennis
2 bedrooms
2 bathrooms
Sleeps 6
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Dog-friendly condo with shared pool - explore the parks & hit the beach
1 bedroom
1 bathroom
Sleeps 4
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Sunny coastal retreat w/ shared pool & tennis - 1/2 mile to beach
2 bedrooms
2 bathrooms
Sleeps 4
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Oak Bluffs! Renovated and close to everything!
2 bedrooms
2 bathrooms
Sleeps 5
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Stylish townhouse 1/2 mile from the beach - tennis courts & shared pool onsite!
2 bedrooms
2 bathrooms
Sleeps 6
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Cozy seaside escape with onsite tennis, communal pool, and prime location
1 bedroom
1 bathroom
Sleeps 4
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NEW Oak Bluffs apartment, walk to town and beaches!
2 bedrooms
2 bathrooms
Sleeps 4
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Seaside suite w/tennis courts and a shared pool, perfect for romantic getaways!
0 bedrooms
1 bathroom
Sleeps 4
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ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!
4 bedrooms
2 bathrooms
Sleeps 7
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Charming townhouse w/ deck, shared pool & on-site tennis - walk to the beach!
2 bedrooms
2 bathrooms
Sleeps 6
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Luxury home w/pool & foosball-near 3 towns & many beaches
5 bedrooms
5 bathrooms
Sleeps 10
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BEST LOCATION * Walk to Town/Beaches * Fun and Relaxing
3 bedrooms
2 bathrooms
Sleeps 6
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Cozy townhouse w/ shared pool, tennis & great location close to the beach!
2 bedrooms
2 bathrooms
Sleeps 6
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Premium Cleaned | Dog-friendly townhouse w/ shared pool, tennis & more - easy wa
2 bedrooms
2 bathrooms
Sleeps 6
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New Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min.
4 bedrooms
3 bathrooms
Sleeps 9
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The Oak bluffs cottage, Martha’s Vineyard Island.
2 bedrooms
1 bathroom
Sleeps 4
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Sunny, dog-friendly suite with tennis, shared pool - close to golf & beach
1 bedroom
2 bathrooms
Sleeps 6
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Cozy, dog-friendly condo by the sea with a shared pool, tennis, picnic area
0 bedrooms
1 bathroom
Sleeps 4
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Comfortable, dog-friendly condo with shared pool & tennis - perfect location!
2 bedrooms
1 bathroom
Sleeps 6
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Cozy condo with shared pool & tennis - close to beaches, golf, & parks!
0 bedrooms
1 bathroom
Sleeps 4
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Romantic seaside getaway w/ shared pool and community tennis courts - dogs OK!
0 bedrooms
1 bathroom
Sleeps 4
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Newly renovated home w/ deck & amazing location near town/beach - 1 dog OK!
3 bedrooms
2 bathrooms
Sleeps 6
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Comfortable condo with shared tennis courts & pool - close to beaches
0 bedrooms
1 bathroom
Sleeps 4
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Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine
5 bedrooms
3 bathrooms
Sleeps 9
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Frequently Asked Questions about Oak Bluffs
- Yes, here are some popular holiday rentals in Oak Bluffs that have a pool:
- Heated Pool, AC, WiFi, Sleeps 22, 2 mi to beach!
- Private Family Home, Heated Backyard Pool,Outdoor Shower, AC,Pet Friendly, 5 br
- Spectacular Martha's Vineyard Island Home!
- Yes, here are some popular holiday rentals in Oak Bluffs that have internet access:
- ENJOY WATERVIEWS OF SENGENKONTACKET POND FROM THE WONDERFUL DECK
- CLASSIC AND CHARMING COTTAGE WALKING DISTANCE TO THE BEACH AND TOWN
- QUINTESSENTIAL VINEYARD SUMMER HOME
- Some of the most popular kid friendly rentals in Oak Bluffs are:
- Summer Vacation Rental
- In-Town Historic Property on Martha's Vineyard
- Oak Bluffs Contemporary Summer Home