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Oak Bluffs House Rentals

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Bedrooms

Bathrooms

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Property type

Distinctive Features

Distance from

5 km
234 rentals in Oak Bluffs.
Close to town, beautifully updated, holiday rental in Oak Bluffs
Close to town, beautifully updated, holiday rental in Oak Bluffs
Close to town, beautifully updated, holiday rental in Oak Bluffs

Close to town, beautifully updated

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path, holiday rental in Oak Bluffs
Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path, holiday rental in Oak Bluffs
Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path, holiday rental in Oak Bluffs

Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 10
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Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs, holiday rental in Oak Bluffs
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs, holiday rental in Oak Bluffs
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs, holiday rental in Oak Bluffs

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

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!, holiday rental in Oak Bluffs
Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!, holiday rental in Oak Bluffs
Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!, holiday rental in Oak Bluffs

Perfect for Family, Friends, or a Romantic Getaway - Newly Renovated!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
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Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches, holiday rental in Oak Bluffs
Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches, holiday rental in Oak Bluffs
Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches, holiday rental in Oak Bluffs

Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path, holiday rental in Oak Bluffs
Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path, holiday rental in Oak Bluffs
Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path, holiday rental in Oak Bluffs

Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Please let us know in advance which ferry you’re on and arrival time., holiday rental in Oak Bluffs
Please let us know in advance which ferry you’re on and arrival time., holiday rental in Oak Bluffs
Please let us know in advance which ferry you’re on and arrival time., holiday rental in Oak Bluffs

Please let us know in advance which ferry you’re on and arrival time.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Holiday Rental House
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Cozy, exceptional view, quiet, high speed WIFI,  close to all island attractions, holiday rental in Oak Bluffs
Cozy, exceptional view, quiet, high speed WIFI,  close to all island attractions, holiday rental in Oak Bluffs
Cozy, exceptional view, quiet, high speed WIFI,  close to all island attractions, holiday rental in Oak Bluffs

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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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!, holiday rental in Oak Bluffs
Make Lasting Memories In This Adorable Vineyard Cottage!, holiday rental in Oak Bluffs

Make Lasting Memories In This Adorable Vineyard Cottage!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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New Construction with Patio & Yard - Downtown & Beaches, holiday rental in Oak Bluffs
New Construction with Patio & Yard - Downtown & Beaches, holiday rental in Oak Bluffs
New Construction with Patio & Yard - Downtown & Beaches, holiday rental in Oak Bluffs

New Construction with Patio & Yard - Downtown & Beaches

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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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!, holiday rental in Oak Bluffs
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!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Luxury Loft Historic Center Oak Bluffs, holiday rental in Oak Bluffs
Luxury Loft Historic Center Oak Bluffs, holiday rental in Oak Bluffs
Luxury Loft Historic Center Oak Bluffs, holiday rental in Oak Bluffs

Luxury Loft Historic Center Oak Bluffs

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 13
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Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer, holiday rental in Oak Bluffs
Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer, holiday rental in Oak Bluffs
Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer, holiday rental in Oak Bluffs

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

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
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Multiple Ensuites, Central Air, Perfect Location, holiday rental in Oak Bluffs
Multiple Ensuites, Central Air, Perfect Location, holiday rental in Oak Bluffs
Multiple Ensuites, Central Air, Perfect Location, holiday rental in Oak Bluffs

Multiple Ensuites, Central Air, Perfect Location

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Cozy cottage 3/4 mile from Oak Bluffs harbor, holiday rental in Oak Bluffs
Cozy cottage 3/4 mile from Oak Bluffs harbor, holiday rental in Oak Bluffs
Cozy cottage 3/4 mile from Oak Bluffs harbor, holiday rental in Oak Bluffs

Cozy cottage 3/4 mile from Oak Bluffs harbor

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Location & Charm -- Central AC, 100% Renewable Energy, holiday rental in Oak Bluffs
Location & Charm -- Central AC, 100% Renewable Energy, holiday rental in Oak Bluffs
Location & Charm -- Central AC, 100% Renewable Energy, holiday rental in Oak Bluffs

Location & Charm -- Central AC, 100% Renewable Energy

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
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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, holiday rental in Oak Bluffs
Comfortable Island Home, Easy Access to Beaches and Town, holiday rental in Oak Bluffs

Comfortable Island Home, Easy Access to Beaches and Town

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps, Holiday Rental House
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Carriage House, Swimming, Boating, Kayaking, just steps from your door..., holiday rental in Oak Bluffs
Carriage House, Swimming, Boating, Kayaking, just steps from your door..., holiday rental in Oak Bluffs
Carriage House, Swimming, Boating, Kayaking, just steps from your door..., holiday rental in Oak Bluffs

Carriage House, Swimming, Boating, Kayaking, just steps from your door...

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Great location, happy house 0.5 mile Nancy’s & Jetty Beach., holiday rental in Oak Bluffs
Great location, happy house 0.5 mile Nancy’s & Jetty Beach., holiday rental in Oak Bluffs
Great location, happy house 0.5 mile Nancy’s & Jetty Beach., holiday rental in Oak Bluffs

Great location, happy house 0.5 mile Nancy’s & Jetty Beach.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Historic Oak Bluffs home, short walk to town, beach, and harbor., holiday rental in Oak Bluffs
Historic Oak Bluffs home, short walk to town, beach, and harbor., holiday rental in Oak Bluffs
Historic Oak Bluffs home, short walk to town, beach, and harbor., holiday rental in Oak Bluffs

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard, holiday rental in Oak Bluffs
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard, holiday rental in Oak Bluffs
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard, holiday rental in Oak Bluffs

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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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, holiday rental in Oak Bluffs
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

Holiday Rental House
5 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps, Holiday Rental House
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,Artist Guest House on beautiful estate open concept King Sized Bunk Beds, holiday rental in Oak Bluffs
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds, holiday rental in Oak Bluffs
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds, holiday rental in Oak Bluffs

,Artist Guest House on beautiful estate open concept King Sized Bunk Beds

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Holiday Rental House
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Sweet Get Away Suite, Private Beach &Tennis, holiday rental in Oak Bluffs
Sweet Get Away Suite, Private Beach &Tennis, holiday rental in Oak Bluffs
Sweet Get Away Suite, Private Beach &Tennis, holiday rental in Oak Bluffs

Sweet Get Away Suite, Private Beach &Tennis

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Holiday Rental House
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Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell, holiday rental in Oak Bluffs
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell, holiday rental in Oak Bluffs
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell, holiday rental in Oak Bluffs

Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Holiday Rental House
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GingerBread Cottage at Oak Bluffs, holiday rental in Oak Bluffs
GingerBread Cottage at Oak Bluffs, holiday rental in Oak Bluffs
GingerBread Cottage at Oak Bluffs, holiday rental in Oak Bluffs

GingerBread Cottage at Oak Bluffs

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Holiday Rental House
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Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town, holiday rental in Oak Bluffs
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town, holiday rental in Oak Bluffs
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town, holiday rental in Oak Bluffs

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Holiday Rental House
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Sweet Little Post&Beam, holiday rental in Oak Bluffs
Sweet Little Post&Beam, holiday rental in Oak Bluffs
Sweet Little Post&Beam, holiday rental in Oak Bluffs

Sweet Little Post&Beam

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
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Family home located near everything needed for  the perfect vacation., holiday rental in Oak Bluffs
Family home located near everything needed for  the perfect vacation., holiday rental in Oak Bluffs
Family home located near everything needed for  the perfect vacation., holiday rental in Oak Bluffs

Family home located near everything needed for the perfect vacation.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps, Holiday Rental House
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New to the rental market! Air conditioned family home, 1 mile from Circuit Ave, holiday rental in Oak Bluffs
New to the rental market! Air conditioned family home, 1 mile from Circuit Ave, holiday rental in Oak Bluffs
New to the rental market! Air conditioned family home, 1 mile from Circuit Ave, holiday rental in Oak Bluffs

New to the rental market! Air conditioned family home, 1 mile from Circuit Ave

Holiday Rental House
4 bedrooms
0 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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OB Cozy-Cottage-Glam off Circuit with Great Outdoor living, holiday rental in Oak Bluffs
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living, holiday rental in Oak Bluffs
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living, holiday rental in Oak Bluffs

OB Cozy-Cottage-Glam off Circuit with Great Outdoor living

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!, holiday rental in Oak Bluffs
#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!, holiday rental in Oak Bluffs
#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!, holiday rental in Oak Bluffs

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, Holiday Rental House
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2025 NOW OPEN! Updated Oak Bluffs home! Close to everything!, holiday rental in Oak Bluffs
2025 NOW OPEN! Updated Oak Bluffs home! Close to everything!, holiday rental in Oak Bluffs
2025 NOW OPEN! Updated Oak Bluffs home! Close to everything!, holiday rental in Oak Bluffs

2025 NOW OPEN! Updated Oak Bluffs home! Close to everything!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Rustic circa 1870s home w/outdoor shower, 3 decks & private grill - 1 dog OK, holiday rental in Oak Bluffs
Rustic circa 1870s home w/outdoor shower, 3 decks & private grill - 1 dog OK, holiday rental in Oak Bluffs
Rustic circa 1870s home w/outdoor shower, 3 decks & private grill - 1 dog OK, holiday rental in Oak Bluffs

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Cozy Beach Cottage, holiday rental in Oak Bluffs
Cozy Beach Cottage, holiday rental in Oak Bluffs
Cozy Beach Cottage, holiday rental in Oak Bluffs

Cozy Beach Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
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Delilah & Joseph Pierce House, holiday rental in Oak Bluffs
Delilah & Joseph Pierce House, holiday rental in Oak Bluffs
Delilah & Joseph Pierce House, holiday rental in Oak Bluffs

Delilah & Joseph Pierce House

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches, holiday rental in Oak Bluffs
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches, holiday rental in Oak Bluffs
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches, holiday rental in Oak Bluffs

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Oak Bluffs Retreat - The perfect getaway!, holiday rental in Oak Bluffs
Oak Bluffs Retreat - The perfect getaway!, holiday rental in Oak Bluffs
Oak Bluffs Retreat - The perfect getaway!, holiday rental in Oak Bluffs

Oak Bluffs Retreat - The perfect getaway!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C, holiday rental in Oak Bluffs
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C, holiday rental in Oak Bluffs
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C, holiday rental in Oak Bluffs

Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Serene Sengekontacket Pond Getaway, holiday rental in Oak Bluffs
Serene Sengekontacket Pond Getaway, holiday rental in Oak Bluffs
Serene Sengekontacket Pond Getaway, holiday rental in Oak Bluffs

Serene Sengekontacket Pond Getaway

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage, holiday rental in Oak Bluffs
Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage, holiday rental in Oak Bluffs
Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage, holiday rental in Oak Bluffs

Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Carriage House on the Chop, holiday rental in Oak Bluffs
Beautiful Carriage House on the Chop, holiday rental in Oak Bluffs
Beautiful Carriage House on the Chop, holiday rental in Oak Bluffs

Beautiful Carriage House on the Chop

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Brick Ranch on Cul-de-sac, with Fireplace and Central Air Conditioning !, holiday rental in Oak Bluffs
Brick Ranch on Cul-de-sac, with Fireplace and Central Air Conditioning !, holiday rental in Oak Bluffs
Brick Ranch on Cul-de-sac, with Fireplace and Central Air Conditioning !, holiday rental in Oak Bluffs

Brick Ranch on Cul-de-sac, with Fireplace and Central Air Conditioning !

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
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Convenient In-Town (Oak Bluffs) Location, holiday rental in Oak Bluffs
Convenient In-Town (Oak Bluffs) Location, holiday rental in Oak Bluffs
Convenient In-Town (Oak Bluffs) Location, holiday rental in Oak Bluffs

Convenient In-Town (Oak Bluffs) Location

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car, holiday rental in Oak Bluffs
Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car, holiday rental in Oak Bluffs
Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car, holiday rental in Oak Bluffs

Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
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Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs, holiday rental in Oak Bluffs
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs, holiday rental in Oak Bluffs
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs, holiday rental in Oak Bluffs

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat, holiday rental in Oak Bluffs
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat, holiday rental in Oak Bluffs
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat, holiday rental in Oak Bluffs

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Holiday Rental House
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Peaceful Summer Oasis, holiday rental in Oak Bluffs
Peaceful Summer Oasis, holiday rental in Oak Bluffs
Peaceful Summer Oasis, holiday rental in Oak Bluffs

Peaceful Summer Oasis

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Oak Bluffs Martha Vineyard, holiday rental in Oak Bluffs
Oak Bluffs Martha Vineyard, holiday rental in Oak Bluffs
Oak Bluffs Martha Vineyard, holiday rental in Oak Bluffs

Oak Bluffs Martha Vineyard

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
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Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path., holiday rental in Oak Bluffs
Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path., holiday rental in Oak Bluffs
Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path., holiday rental in Oak Bluffs

Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Holiday Rental House
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