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South Orleans Vacation Rentals

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20 rentals in South Orleans.
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Family Friendly - 3 levels, on a secluded Acre. Linens provided. Light & Bright!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Beautiful home w/ entertainment - near golf courses & Pleasant Bay

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Cape Cod Comfortable House Awaits!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Topside BoatHouse on Pleasant Bay

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Luxurious Dream Home Just a Walk Away From Pleasant Bay Beach

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Harwich Cape Escape: Minutes from Everything!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Comfortable, Pet-Friendly Orleans Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Gorgeous Waterfront Property

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Expansive Home by Orleans Town Landing

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Spacious Harwich Home Near Round Cove

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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New To VRBO! Just renovated, family perfect, central A/C, WIFI, pet friendly!  C

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Topside MainHouse

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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Immaculate home that is a Short Distance to Pleasant Bay!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Orleans Home on the Water

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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9 Woodridge Road 99912

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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17729: Newly Renovated, Across from Round Cove on Pleasant Bay, Next Door to Weq

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Spacious 4BR Home with Pool and Peak Views!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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East Dennis Gem with Access to private beach!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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18824: Beautiful Home in Fantastic Location Close to Pleasant Bay & Chatham/Orle

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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17733: Immaculate Home + Fantastic Location - Walk to Jackknife Beach, Wequasset

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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