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Holiday Rentals in Oak Bluffs

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240 rentals in Oak Bluffs.
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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!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Classic Oak Bluffs Beach House | Excellent Harbor Views | Near Shops & Dining, holiday rental in Oak Bluffs

Classic Oak Bluffs Beach House | Excellent Harbor Views | Near Shops & Dining

5 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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THOMS - New Modern Farmhouse Design, Great Location!, Wrap Around  Farmers Porch, holiday rental in Oak Bluffs

THOMS - New Modern Farmhouse Design, Great Location!, Wrap Around Farmers Porch

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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THORB - Contemporary 5 Bedroom 4 Bath, Multiple Living Spaces, Walk to Oak Bluff, holiday rental in Oak Bluffs

THORB - Contemporary 5 Bedroom 4 Bath, Multiple Living Spaces, Walk to Oak Bluff

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Walk to Lagoon from this Cute Cottage, holiday rental in Oak Bluffs

Walk to Lagoon from this Cute Cottage

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Four Bedroom in-town Oak Bluffs Home, holiday rental in Oak Bluffs

New Four Bedroom in-town Oak Bluffs Home

4 bedrooms
3 bathrooms
Sleeps 8
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

3 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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In-Town Historic Property on Martha's Vineyard, holiday rental in Oak Bluffs

In-Town Historic Property on Martha's Vineyard

2 bedrooms
1 bathroom
Sleeps 5
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

4 bedrooms
2 bathrooms
Sleeps 7
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!

1 bedroom
1 bathroom
Sleeps 4
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

4 bedrooms
2 bathrooms
Sleeps 8
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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'The Carousel House' - Ocean Park - Featured in New York Times, holiday rental in Oak Bluffs

'The Carousel House' - Ocean Park - Featured in New York Times

7 bedrooms
3 bathrooms
Sleeps 12
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

3 bedrooms
3 bathrooms
Sleeps 8
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!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Historic Renovated Home in East Chop, holiday rental in Oak Bluffs

Historic Renovated Home in East Chop

4 bedrooms
2 bathrooms
Sleeps 8
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

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Charming Artsy Apartment, holiday rental in Oak Bluffs

Charming Artsy Apartment

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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

2 bedrooms
2 bathrooms
Sleeps 4
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

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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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

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Location & Charm -- Central AC, holiday rental in Oak Bluffs

Location & Charm -- Central AC

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Family Home- Amazing Oak Bluffs, holiday rental in Oak Bluffs

Perfect Family Home- Amazing Oak Bluffs

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Lovely retreat 1/2 mile from the beach - shared pool, 3 tennis courts, & WiFi, holiday rental in Oak Bluffs

Lovely retreat 1/2 mile from the beach - shared pool, 3 tennis courts, & WiFi

1 bedroom
2 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 in Oak Bluffs

Ob Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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

1 bedroom
1 bathroom
Sleeps 4
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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!, holiday rental in Oak Bluffs

ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Oak Bluffs! Renovated and close to everything!, holiday rental in Oak Bluffs

Oak Bluffs! Renovated and close to everything!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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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!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Seaside suite w/tennis courts and a shared pool, perfect for romantic getaways!, holiday rental in Oak Bluffs

Seaside suite w/tennis courts and a shared pool, perfect for romantic getaways!

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Luxury home w/pool & foosball-near 3 towns & many beaches, holiday rental in Oak Bluffs

Luxury home w/pool & foosball-near 3 towns & many beaches

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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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!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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BEST LOCATION * Walk to Town/Beaches * Fun and Relaxing, holiday rental in Oak Bluffs

BEST LOCATION * Walk to Town/Beaches * Fun and Relaxing

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy townhouse w/ shared pool, tennis & great location close to the beach!, holiday rental in Oak Bluffs

Cozy townhouse w/ shared pool, tennis & great location close to the beach!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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.

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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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.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sunny, dog-friendly suite with tennis, shared pool - close to golf & beach, holiday rental in Oak Bluffs

Sunny, dog-friendly suite with tennis, shared pool - close to golf & beach

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Comfortable, dog-friendly condo with shared pool & tennis - perfect location!, holiday rental in Oak Bluffs

Comfortable, dog-friendly condo with shared pool & tennis - perfect location!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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!

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Newly renovated home w/ deck & amazing location near town/beach - 1 dog OK!, holiday rental in Oak Bluffs

Newly renovated home w/ deck & amazing location near town/beach - 1 dog OK!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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!

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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