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Holiday Apartments in South Orleans

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51 rentals in South Orleans.
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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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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!

4 bedrooms
4 bathrooms
Sleeps 10
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Topside BoatHouse on Pleasant Bay, holiday rental in South Orleans

Topside BoatHouse on Pleasant Bay

2 bedrooms
1 bathroom
Sleeps 4
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Gorgeous Waterfront Property, holiday rental in South Orleans

Gorgeous Waterfront Property

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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52 Forest Way 18423, holiday rental in South Orleans

52 Forest Way 18423

5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Topside MainHouse, holiday rental in South Orleans

Topside MainHouse

3 bedrooms
4 bathrooms
Sleeps 8
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9 Woodridge Road 99912, holiday rental in South Orleans

9 Woodridge Road 99912

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pleasant Bay Gem | All-New Beds & Linens, Game Room & Big Deck | Near Beaches, holiday rental in South Orleans

Pleasant Bay Gem | All-New Beds & Linens, Game Room & Big Deck | Near Beaches

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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2 Cove Road Harwich Cape Cod ~  Cozy Cove, holiday rental in South Orleans

2 Cove Road Harwich Cape Cod ~ Cozy Cove

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Highly Rated Cottage in Orleans, Cape Cod, holiday rental in South Orleans

Highly Rated Cottage in Orleans, Cape Cod

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to Crystal Lake; private Tennis Court; Basketball Hoop, holiday rental in South Orleans

Walk to Crystal Lake; private Tennis Court; Basketball Hoop

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach, holiday rental in South Orleans

Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach

7 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps
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Quaint Cape Near Beaches And Centrally Located, holiday rental in South Orleans

Quaint Cape Near Beaches And Centrally Located

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Orleans Pilgrim Lake Waterfront Home, holiday rental in South Orleans

Beautiful Orleans Pilgrim Lake Waterfront Home

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, holiday rental in South Orleans

CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE

2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Learn To Sail This Summer At Your Vacation Home!, holiday rental in South Orleans

Learn To Sail This Summer At Your Vacation Home!

6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Enchanting Waterfront Escape on Pleasant Bay, holiday rental in South Orleans

Enchanting Waterfront Escape on Pleasant Bay

4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, holiday rental in South Orleans

Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming, Renovated 1870s Home with Private Beach, holiday rental in South Orleans

Charming, Renovated 1870s Home with Private Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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#526: Luxury waterfront, private sunbathing beach. 9-seat movie theater - GAME R, holiday rental in South Orleans

#526: Luxury waterfront, private sunbathing beach. 9-seat movie theater - GAME R

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Water Views, Central AC, Sleeps 12, 3 Floors of Living Space: 058-O, holiday rental in South Orleans

Water Views, Central AC, Sleeps 12, 3 Floors of Living Space: 058-O

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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New listing! Stylish Orleans home w/ spacious deck - near bay & ocean beaches!, holiday rental in South Orleans

New listing! Stylish Orleans home w/ spacious deck - near bay & ocean beaches!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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22 Uncle Vicks Way 18401, holiday rental in South Orleans

22 Uncle Vicks Way 18401

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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#515: Private beach just 10 feet from Crystal Lake! Brand new renovation!, holiday rental in South Orleans

#515: Private beach just 10 feet from Crystal Lake! Brand new renovation!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pleasant Bay Retreat, holiday rental in South Orleans

Pleasant Bay Retreat

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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10 Shorewood Drive 18402, holiday rental in South Orleans

10 Shorewood Drive 18402

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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#524: Newly Furnished, Large Yard, Outdoor Shower, Central A/C, Dog Friendly!, holiday rental in South Orleans

#524: Newly Furnished, Large Yard, Outdoor Shower, Central A/C, Dog Friendly!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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27 Pond Road 22347, holiday rental in South Orleans

27 Pond Road 22347

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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25 Oak Lane 18523, holiday rental in South Orleans

25 Oak Lane 18523

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Conveniently located home in beautiful Orleans, Cape Cod - Available throughout the year, holiday rental in South Orleans

Conveniently located home in beautiful Orleans, Cape Cod - Available throughout the year

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Quanset Harbor Club Location, holiday rental in South Orleans

Quanset Harbor Club Location

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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17 Blue Heron Way 121865, holiday rental in South Orleans

17 Blue Heron Way 121865

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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16 PRIMROSE LANE 123468, holiday rental in South Orleans

16 PRIMROSE LANE 123468

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Peaceful Views and Lakefront Living on Crystal Lake, holiday rental in South Orleans

Peaceful Views and Lakefront Living on Crystal Lake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Cape Cod vacation home with brand new pool, holiday rental in South Orleans

Beautiful Cape Cod vacation home with brand new pool

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Jack Knife Point Associates 130468, holiday rental in South Orleans

Jack Knife Point Associates 130468

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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West-Facing Pure Waterfront Home in Orleans, Overlooking Arey's Pond, holiday rental in South Orleans

West-Facing Pure Waterfront Home in Orleans, Overlooking Arey's Pond

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Townhouse Condo in Cape Cod, MA, holiday rental in South Orleans

Lakefront Townhouse Condo in Cape Cod, MA

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Pet friendly Barley Neck Home, holiday rental in South Orleans

Pet friendly Barley Neck Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy riverfront house w/views & entertainment-great for families!, holiday rental in South Orleans

Cozy riverfront house w/views & entertainment-great for families!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Lake House for 2 Families, holiday rental in South Orleans

Perfect Lake House for 2 Families

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Delightful South Orleans Cottage, holiday rental in South Orleans

Delightful South Orleans Cottage

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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California Contemporary, Walk to Beach, 1.3 Wooded Acres, holiday rental in South Orleans

California Contemporary, Walk to Beach, 1.3 Wooded Acres

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Peaceful Paradise in Orleans, holiday rental in South Orleans

Peaceful Paradise in Orleans

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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#806: Private Trail to Deeded Freshwater Pond! Bring Your Kayaks, Bikes, and Dog, holiday rental in South Orleans

#806: Private Trail to Deeded Freshwater Pond! Bring Your Kayaks, Bikes, and Dog

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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East Orleans Water View Getaway, holiday rental in South Orleans

East Orleans Water View Getaway

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New Listing! Gorgeous Wooded Haven w/ Decks & Hot Tub — Access Secluded Bay, holiday rental in South Orleans

New Listing! Gorgeous Wooded Haven w/ Decks & Hot Tub — Access Secluded Bay

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Classic Cape Cod Home | Backyard, Patio & Outdoor Fireplace | Near Beaches, holiday rental in South Orleans

Classic Cape Cod Home | Backyard, Patio & Outdoor Fireplace | Near Beaches

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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#541: Exceptional Pond-Front, Newly-Renovated Home w/ Spacious Deck & Yard! Game, holiday rental in South Orleans

#541: Exceptional Pond-Front, Newly-Renovated Home w/ Spacious Deck & Yard! Game

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Brewster Poolside Retreat, holiday rental in South Orleans

Brewster Poolside Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about South Orleans


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