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

Family Friendly - 3 levels, on a secluded Acre. Linens provided. Light & Bright!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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Beautiful home w/ entertainment - near golf courses & Pleasant Bay, holiday rental in South Orleans
Beautiful home w/ entertainment - near golf courses & Pleasant Bay, holiday rental in South Orleans
Beautiful home w/ entertainment - near golf courses & Pleasant Bay, holiday rental in South Orleans

Beautiful home w/ entertainment - near golf courses & Pleasant Bay

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cape Cod Comfortable House Awaits!, holiday rental in South Orleans
Cape Cod Comfortable House Awaits!, holiday rental in South Orleans
Cape Cod Comfortable House Awaits!, holiday rental in South Orleans

Cape Cod Comfortable House Awaits!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Topside BoatHouse on Pleasant Bay, holiday rental in South Orleans
Topside BoatHouse on Pleasant Bay, holiday rental in South Orleans
Topside BoatHouse on Pleasant Bay, holiday rental in South Orleans

Topside BoatHouse on Pleasant Bay

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxurious Dream Home Just a Walk Away From Pleasant Bay Beach, holiday rental in South Orleans
Luxurious Dream Home Just a Walk Away From Pleasant Bay Beach, holiday rental in South Orleans
Luxurious Dream Home Just a Walk Away From Pleasant Bay Beach, holiday rental in South Orleans

Luxurious Dream Home Just a Walk Away From Pleasant Bay Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Harwich Cape Escape: Minutes from Everything!, holiday rental in South Orleans
Harwich Cape Escape: Minutes from Everything!, holiday rental in South Orleans
Harwich Cape Escape: Minutes from Everything!, holiday rental in South Orleans

Harwich Cape Escape: Minutes from Everything!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Comfortable, Pet-Friendly Orleans Home, holiday rental in South Orleans
Comfortable, Pet-Friendly Orleans Home, holiday rental in South Orleans
Comfortable, Pet-Friendly Orleans Home, holiday rental in South Orleans

Comfortable, Pet-Friendly Orleans Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Waterfront Property, holiday rental in South Orleans
Gorgeous Waterfront Property, holiday rental in South Orleans
Gorgeous Waterfront Property, holiday rental in South Orleans

Gorgeous Waterfront Property

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Expansive Home by Orleans Town Landing, holiday rental in South Orleans
Expansive Home by Orleans Town Landing, holiday rental in South Orleans
Expansive Home by Orleans Town Landing, holiday rental in South Orleans

Expansive Home by Orleans Town Landing

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Harwich Home Near Round Cove, holiday rental in South Orleans
Spacious Harwich Home Near Round Cove, holiday rental in South Orleans
Spacious Harwich Home Near Round Cove, holiday rental in South Orleans

Spacious Harwich Home Near Round Cove

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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New To VRBO! Just renovated, family perfect, central A/C, WIFI, pet friendly!  C, holiday rental in South Orleans
New To VRBO! Just renovated, family perfect, central A/C, WIFI, pet friendly!  C, holiday rental in South Orleans
New To VRBO! Just renovated, family perfect, central A/C, WIFI, pet friendly!  C, holiday rental in South Orleans

New To VRBO! Just renovated, family perfect, central A/C, WIFI, pet friendly!  C

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Immaculate home that is a Short Distance to Pleasant Bay!, holiday rental in South Orleans
Immaculate home that is a Short Distance to Pleasant Bay!, holiday rental in South Orleans
Immaculate home that is a Short Distance to Pleasant Bay!, holiday rental in South Orleans

Immaculate home that is a Short Distance to Pleasant Bay!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Topside MainHouse, holiday rental in South Orleans
Topside MainHouse, holiday rental in South Orleans
Topside MainHouse, holiday rental in South Orleans

Topside MainHouse

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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9 Woodridge Road 99912, holiday rental in South Orleans
9 Woodridge Road 99912, holiday rental in South Orleans
9 Woodridge Road 99912, holiday rental in South Orleans

9 Woodridge Road 99912

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Orleans Home on the Water, holiday rental in South Orleans
Private Orleans Home on the Water, holiday rental in South Orleans
Private Orleans Home on the Water, holiday rental in South Orleans

Private Orleans Home on the Water

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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17729: Newly Renovated, Across from Round Cove on Pleasant Bay, Next Door to Weq, holiday rental in South Orleans
17729: Newly Renovated, Across from Round Cove on Pleasant Bay, Next Door to Weq, holiday rental in South Orleans
17729: Newly Renovated, Across from Round Cove on Pleasant Bay, Next Door to Weq, holiday rental in South Orleans

17729: Newly Renovated, Across from Round Cove on Pleasant Bay, Next Door to Weq

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious 4BR Home with Pool and Peak Views!, holiday rental in South Orleans
Spacious 4BR Home with Pool and Peak Views!, holiday rental in South Orleans
Spacious 4BR Home with Pool and Peak Views!, holiday rental in South Orleans

Spacious 4BR Home with Pool and Peak Views!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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East Dennis Gem with Access to private beach!, holiday rental in South Orleans
East Dennis Gem with Access to private beach!, holiday rental in South Orleans
East Dennis Gem with Access to private beach!, holiday rental in South Orleans

East Dennis Gem with Access to private beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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18824: Beautiful Home in Fantastic Location Close to Pleasant Bay & Chatham/Orle, holiday rental in South Orleans
18824: Beautiful Home in Fantastic Location Close to Pleasant Bay & Chatham/Orle, holiday rental in South Orleans
18824: Beautiful Home in Fantastic Location Close to Pleasant Bay & Chatham/Orle, holiday rental in South Orleans

18824: Beautiful Home in Fantastic Location Close to Pleasant Bay & Chatham/Orle

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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17733: Immaculate Home + Fantastic Location - Walk to Jackknife Beach, Wequasset, holiday rental in South Orleans
17733: Immaculate Home + Fantastic Location - Walk to Jackknife Beach, Wequasset, holiday rental in South Orleans
17733: Immaculate Home + Fantastic Location - Walk to Jackknife Beach, Wequasset, holiday rental in South Orleans

17733: Immaculate Home + Fantastic Location - Walk to Jackknife Beach, Wequasset

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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