Oak Bluffs, Massachusetts

Vacation Rentals in Oak Bluffs, Massachusetts

Discover 73 vacation rental properties in Oak Bluffs. From 1 to 6 bedrooms. Average $508/night. 100% have pools.

73 verified listings Book securely on VRBO Prices updated March 2026

73 properties available

Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!

1 bath
PoolA/CWiFiBalcony
$249/night
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Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions

Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions

4 beds 2 baths
PoolA/CWiFiBalcony
$549/night
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Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

1 bed 1 bath
PoolA/CWiFiBalcony
$422/night
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Comfortable condo with tennis courts & pool - close to beaches

Comfortable condo with tennis courts & pool - close to beaches

1 bath
PoolA/CWiFiBalcony
$312/night
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Sweet Little Post&Beam

Sweet Little Post&Beam

1 bed 1 bath
PoolA/CWiFiBalcony
$381/night
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Arrowsmith Cottage Oak Bluffs 1 mi to beach. July 13-20 ferry tickets available

Arrowsmith Cottage Oak Bluffs 1 mi to beach. July 13-20 ferry tickets available

2 beds 1 bath
PoolA/CWiFiBalcony
$386/night
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East Chop Tree Tops

East Chop Tree Tops

3 beds 2 baths
PoolA/CWiFiBalcony
$395/night
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Charming salt box in quiet woodsy neighborhood - centrally located!

Charming salt box in quiet woodsy neighborhood - centrally located!

3 beds 2 baths
PoolA/CWiFiBalcony
$392/night
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Cute condo with pool & tennis - close to golf & the beach

Cute condo with pool & tennis - close to golf & the beach

2 beds 1 bath
PoolA/CWiFiBalcony
$324/night
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Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

5 beds 2 baths
PoolA/CWiFiBalcony
$936/night
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THE PARK ESTATE! Your Martha's Vineyard Getaway!

THE PARK ESTATE! Your Martha's Vineyard Getaway!

6 beds 4 baths
PoolA/CWiFiBalcony
$5,870/night
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Cozy studio with free WiFi, private deck & kitchenette - walk to downtown

Cozy studio with free WiFi, private deck & kitchenette - walk to downtown

1 bath
PoolA/CWiFiBalcony
$173/night
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In-Town Certified National Historic Oak Bluffs Property -

In-Town Certified National Historic Oak Bluffs Property -

2 beds 1 bath
PoolA/CWiFiBalcony
$278/night
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Oak Bluffs! Close to everything! Updated in 2023! Booking fast!!!

Oak Bluffs! Close to everything! Updated in 2023! Booking fast!!!

2 beds 1 bath
PoolA/CWiFiBalcony
$208/night
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Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!

Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!

2 beds 1 bath
PoolA/CWiFiBalcony
$561/night
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Coastal condo with pool & tennis courts near golf, beaches & town

Coastal condo with pool & tennis courts near golf, beaches & town

1 bath
PoolA/CWiFiBalcony
$262/night
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Charming Home with High-Speed WiFi, Washer/Dryer, Furnished Deck, & Gas Grill

Charming Home with High-Speed WiFi, Washer/Dryer, Furnished Deck, & Gas Grill

4 beds 2 baths
PoolA/CWiFiBalcony
$277/night
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Historic Oak Bluffs home, short walk to town, beach, and harbor.

Historic Oak Bluffs home, short walk to town, beach, and harbor.

3 beds 1 bath
PoolA/CWiFiBalcony
$277/night
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Central location for your vacation

Central location for your vacation

2 beds 2 baths
PoolA/CWiFiBalcony
$281/night
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Cozy Beach Cottage

Cozy Beach Cottage

2 beds
PoolA/CWiFiBalcony
$301/night
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Spacious 1 Bedroom Apt - 3 min Walk to the Beach!

Spacious 1 Bedroom Apt - 3 min Walk to the Beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$272/night
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Rustic circa 1870s home w/outdoor shower, 3 decks & private grill - 1 dog OK

Rustic circa 1870s home w/outdoor shower, 3 decks & private grill - 1 dog OK

3 beds 1 bath
PoolA/CWiFiBalcony
$305/night
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Cozy seaside escape with on-site tennis, pool & prime location

Cozy seaside escape with on-site tennis, pool & prime location

1 bed 1 bath
PoolA/CWiFiBalcony
$343/night
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Beautiful Beachfront Condo with Spectacular View in the Heart of Oak Bluffs!

Beautiful Beachfront Condo with Spectacular View in the Heart of Oak Bluffs!

2 beds 2 baths
PoolA/CWiFiBalcony
$611/night
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Comfortable Island Home, Easy Access to Beaches and Town

Comfortable Island Home, Easy Access to Beaches and Town

2 beds 1 bath
PoolA/CWiFiBalcony
$302/night
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Renovated townhome with pool & 3 tennis courts - golfing & beaches nearby

Renovated townhome with pool & 3 tennis courts - golfing & beaches nearby

2 beds 2 baths
PoolA/CWiFiBalcony
$436/night
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CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

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

5 beds 2 baths
PoolA/CWiFiBalcony
$704/night
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Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach

Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach

4 beds 2 baths
PoolA/CWiFiBalcony
$333/night
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Dog-friendly first-floor seaside cottage with pool & tennis courts

Dog-friendly first-floor seaside cottage with pool & tennis courts

1 bed 1 bath
PoolA/CWiFiBalcony
$334/night
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Quaint,,,Quiet..up island feel yet a short walk to to , x ,, z wn and harbor

Quaint,,,Quiet..up island feel yet a short walk to to , x ,, z wn and harbor

3 beds 2 baths
PoolA/CWiFiBalcony
$352/night
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Luxury home with private pool & foosball - near 3 towns & many beaches

Luxury home with private pool & foosball - near 3 towns & many beaches

5 beds 4 baths
PoolA/CWiFiBalcony
$809/night
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Private Waterfront, Beachfront, and 90' Dock. Views. Newly Renovated 3Bd 2.5Bath

Private Waterfront, Beachfront, and 90' Dock. Views. Newly Renovated 3Bd 2.5Bath

3 beds 2 baths
PoolA/CWiFiBalcony
$594/night
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Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven

Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven

3 beds 1 bath
PoolA/CWiFiBalcony
$325/night
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Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

1 bed 1 bath
PoolA/CWiFiBalcony
$396/night
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Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

2 beds 2 baths
PoolA/CWiFiBalcony
$264/night
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Sunny, dog-friendly suite with tennis & pool - close to golf & beach

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

1 bed 1 bath
PoolA/CWiFiBalcony
$384/night
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Sweet Get Away Suite, Private Beach &Tennis

Sweet Get Away Suite, Private Beach &Tennis

1 bed
PoolA/CWiFiBalcony
$376/night
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Waterfront Home in Oak Bluffs - Walk to Town and Beach

Waterfront Home in Oak Bluffs - Walk to Town and Beach

4 beds 2 baths
PoolA/CWiFiBalcony
$959/night
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COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.

COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.

3 beds 2 baths
PoolA/CWiFiBalcony
$671/night
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Historic Home with Gorgeous Antiques & Mondern Conveniences

Historic Home with Gorgeous Antiques & Mondern Conveniences

4 beds 2 baths
PoolA/CWiFiBalcony
$363/night
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Walk to Beach, Downtown Shops, Dining & Attractions

Walk to Beach, Downtown Shops, Dining & Attractions

3 beds 2 baths
PoolA/CWiFiBalcony
$400/night
View Details → Book on VRBO
Private Beach Waterfront Oak-Bluffs Family Cottage

Private Beach Waterfront Oak-Bluffs Family Cottage

4 beds 2 baths
PoolA/CWiFiBalcony
$526/night
View Details → Book on VRBO
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches

Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches

2 beds 1 bath
PoolA/CWiFiBalcony
$269/night
View Details → Book on VRBO
Contemporary dog-friendly studio with beach access, pool & tennis courts

Contemporary dog-friendly studio with beach access, pool & tennis courts

1 bath
PoolA/CWiFiBalcony
$277/night
View Details → Book on VRBO
Comfy studio near the beach with pool & tennis court - dog-friendly

Comfy studio near the beach with pool & tennis court - dog-friendly

1 bath
PoolA/CWiFiBalcony
$276/night
View Details → Book on VRBO
Dog-friendly condo with pool & tennis - close to golf & beach

Dog-friendly condo with pool & tennis - close to golf & beach

1 bath
PoolA/CWiFiBalcony
$281/night
View Details → Book on VRBO
Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer

Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer

4 beds 2 baths
PoolA/CWiFiBalcony
$284/night
View Details → Book on VRBO
Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

4 beds 2 baths
PoolA/CWiFiBalcony
$265/night
View Details → Book on VRBO

Showing 48 of 73 properties

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