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Orleans Family & Kid Friendly Rentals

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391 rentals in Orleans.
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Charming Post & Beam Near State Park and Pond, vacation rental in Orleans
Charming Post & Beam Near State Park and Pond, vacation rental in Orleans
Charming Post & Beam Near State Park and Pond, vacation rental in Orleans

Charming Post & Beam Near State Park and Pond

Rental Home
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps, Kid friendly
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Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12, vacation rental in Orleans
Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12, vacation rental in Orleans
Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12, vacation rental in Orleans

Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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East Orleans - walk to Nauset Beach, vacation rental in Orleans
East Orleans - walk to Nauset Beach, vacation rental in Orleans
East Orleans - walk to Nauset Beach, vacation rental in Orleans

East Orleans - walk to Nauset Beach

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Highly Rated Cottage in Orleans, Cape Cod, vacation rental in Orleans
Highly Rated Cottage in Orleans, Cape Cod, vacation rental in Orleans
Highly Rated Cottage in Orleans, Cape Cod, vacation rental in Orleans

Highly Rated Cottage in Orleans, Cape Cod

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Waterfront. Private beach. Pool. Estate has it all!!, vacation rental in Orleans
Waterfront. Private beach. Pool. Estate has it all!!, vacation rental in Orleans
Waterfront. Private beach. Pool. Estate has it all!!, vacation rental in Orleans

Waterfront. Private beach. Pool. Estate has it all!!

Rental Home
9 bedrooms
7 bathrooms
Sleeps 19
Match: Sleeps, Kid friendly
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Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach, vacation rental in Orleans
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach, vacation rental in Orleans
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach, vacation rental in Orleans

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

Rental Home
7 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps, Kid friendly
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Executive Waterfront Luxury Home  6000 Sqft; Heated Pool;, vacation rental in Orleans
Executive Waterfront Luxury Home  6000 Sqft; Heated Pool;, vacation rental in Orleans
Executive Waterfront Luxury Home  6000 Sqft; Heated Pool;, vacation rental in Orleans

Executive Waterfront Luxury Home 6000 Sqft; Heated Pool;

Rental Home
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps, Kid friendly
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Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond, vacation rental in Orleans
Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond, vacation rental in Orleans
Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond, vacation rental in Orleans

Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Walk to Crystal Lake; private Pickleball/Tennis Court; Basketball Hoop, vacation rental in Orleans
Walk to Crystal Lake; private Pickleball/Tennis Court; Basketball Hoop, vacation rental in Orleans
Walk to Crystal Lake; private Pickleball/Tennis Court; Basketball Hoop, vacation rental in Orleans

Walk to Crystal Lake; private Pickleball/Tennis Court; Basketball Hoop

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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15504: 1 minute drive to Rock Harbor and 2 minutes to Orleans Town Center!, vacation rental in Orleans
15504: 1 minute drive to Rock Harbor and 2 minutes to Orleans Town Center!, vacation rental in Orleans
15504: 1 minute drive to Rock Harbor and 2 minutes to Orleans Town Center!, vacation rental in Orleans

15504: 1 minute drive to Rock Harbor and 2 minutes to Orleans Town Center!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
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Quaint Cape Near Beaches And Centrally Located, vacation rental in Orleans
Quaint Cape Near Beaches And Centrally Located, vacation rental in Orleans
Quaint Cape Near Beaches And Centrally Located, vacation rental in Orleans

Quaint Cape Near Beaches And Centrally Located

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Booking now Summer 2022!, vacation rental in Orleans
Booking now Summer 2022!, vacation rental in Orleans
Booking now Summer 2022!, vacation rental in Orleans

Booking now Summer 2022!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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5 BR/4 bath w/heated pool .2 miles to Nauset Beach, vacation rental in Orleans
5 BR/4 bath w/heated pool .2 miles to Nauset Beach, vacation rental in Orleans
5 BR/4 bath w/heated pool .2 miles to Nauset Beach, vacation rental in Orleans

5 BR/4 bath w/heated pool .2 miles to Nauset Beach

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Your perfect Cape Cod Getaway!  Fully renovated cottage minutes from the beach!, vacation rental in Orleans
Your perfect Cape Cod Getaway!  Fully renovated cottage minutes from the beach!, vacation rental in Orleans
Your perfect Cape Cod Getaway!  Fully renovated cottage minutes from the beach!, vacation rental in Orleans

Your perfect Cape Cod Getaway! Fully renovated cottage minutes from the beach!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Luxury 8 Bedroom Home  w/ Pool - 4 minutes to the beach!, vacation rental in Orleans
Luxury 8 Bedroom Home  w/ Pool - 4 minutes to the beach!, vacation rental in Orleans
Luxury 8 Bedroom Home  w/ Pool - 4 minutes to the beach!, vacation rental in Orleans

Luxury 8 Bedroom Home w/ Pool - 4 minutes to the beach!

Rental Home
8 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps, Kid friendly
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Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream, vacation rental in Orleans
Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream, vacation rental in Orleans
Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream, vacation rental in Orleans

Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches, vacation rental in Orleans
Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches, vacation rental in Orleans
Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches, vacation rental in Orleans

Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging, vacation rental in Orleans
Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging, vacation rental in Orleans
Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging, vacation rental in Orleans

Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket, vacation rental in Orleans
Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket, vacation rental in Orleans
Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket, vacation rental in Orleans

Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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15515: Private beach just 10 feet from Crystal Lake! Brand new renovation!, vacation rental in Orleans
15515: Private beach just 10 feet from Crystal Lake! Brand new renovation!, vacation rental in Orleans
15515: Private beach just 10 feet from Crystal Lake! Brand new renovation!, vacation rental in Orleans

15515: Private beach just 10 feet from Crystal Lake! Brand new renovation!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood, vacation rental in Orleans
Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood, vacation rental in Orleans
Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood, vacation rental in Orleans

Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, vacation rental in Orleans
CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, vacation rental in Orleans
CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, vacation rental in Orleans

CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE

Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Spacious 5 bedroom home with Heated pool - Perfect for multiple families, vacation rental in Orleans
Spacious 5 bedroom home with Heated pool - Perfect for multiple families, vacation rental in Orleans
Spacious 5 bedroom home with Heated pool - Perfect for multiple families, vacation rental in Orleans

Spacious 5 bedroom home with Heated pool - Perfect for multiple families

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Well-appointed Cottage Getaway!, vacation rental in Orleans
Well-appointed Cottage Getaway!, vacation rental in Orleans
Well-appointed Cottage Getaway!, vacation rental in Orleans

Well-appointed Cottage Getaway!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Walk to Skaket Beach, vacation rental in Orleans
Walk to Skaket Beach, vacation rental in Orleans
Walk to Skaket Beach, vacation rental in Orleans

Walk to Skaket Beach

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Rock Harbor Retreat - ***Accepting RESERVATIONS for SUMMER 2023***, vacation rental in Orleans
Rock Harbor Retreat - ***Accepting RESERVATIONS for SUMMER 2023***, vacation rental in Orleans
Rock Harbor Retreat - ***Accepting RESERVATIONS for SUMMER 2023***, vacation rental in Orleans

Rock Harbor Retreat - ***Accepting RESERVATIONS for SUMMER 2023***

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Charming Family-Friendly Home On Beach Rd.  Close To Nauset Beach & Village Ctr., vacation rental in Orleans
Charming Family-Friendly Home On Beach Rd.  Close To Nauset Beach & Village Ctr., vacation rental in Orleans
Charming Family-Friendly Home On Beach Rd.  Close To Nauset Beach & Village Ctr., vacation rental in Orleans

Charming Family-Friendly Home On Beach Rd. Close To Nauset Beach & Village Ctr.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Your perch to the Cape's best ocean view with private Nauset access for 8!, vacation rental in Orleans
Your perch to the Cape's best ocean view with private Nauset access for 8!, vacation rental in Orleans
Your perch to the Cape's best ocean view with private Nauset access for 8!, vacation rental in Orleans

Your perch to the Cape's best ocean view with private Nauset access for 8!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Newly Renovated, 3BR Steps To Pleasant Bay, Close To Nauset Beach, vacation rental in Orleans
Newly Renovated, 3BR Steps To Pleasant Bay, Close To Nauset Beach, vacation rental in Orleans
Newly Renovated, 3BR Steps To Pleasant Bay, Close To Nauset Beach, vacation rental in Orleans

Newly Renovated, 3BR Steps To Pleasant Bay, Close To Nauset Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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15526: Luxury Secluded Waterfront w/ Private 9-Seat Movie Theater & 1500 sq ft, vacation rental in Orleans
15526: Luxury Secluded Waterfront w/ Private 9-Seat Movie Theater & 1500 sq ft, vacation rental in Orleans
15526: Luxury Secluded Waterfront w/ Private 9-Seat Movie Theater & 1500 sq ft, vacation rental in Orleans

15526: Luxury Secluded Waterfront w/ Private 9-Seat Movie Theater & 1500 sq ft

Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps, Kid friendly
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Salty Dog Cottage In East Orleans With Access To Town Cove, vacation rental in Orleans
Salty Dog Cottage In East Orleans With Access To Town Cove, vacation rental in Orleans
Salty Dog Cottage In East Orleans With Access To Town Cove, vacation rental in Orleans

Salty Dog Cottage In East Orleans With Access To Town Cove

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Family Vacation Dream! Firepit, Outdoor Kitchen & Central AC, vacation rental in Orleans
Family Vacation Dream! Firepit, Outdoor Kitchen & Central AC, vacation rental in Orleans
Family Vacation Dream! Firepit, Outdoor Kitchen & Central AC, vacation rental in Orleans

Family Vacation Dream! Firepit, Outdoor Kitchen & Central AC

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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6 1/2 Min Walk to Nauset Beach, Saltwater Heated Pool & Hot Tub, vacation rental in Orleans
6 1/2 Min Walk to Nauset Beach, Saltwater Heated Pool & Hot Tub, vacation rental in Orleans
6 1/2 Min Walk to Nauset Beach, Saltwater Heated Pool & Hot Tub, vacation rental in Orleans

6 1/2 Min Walk to Nauset Beach, Saltwater Heated Pool & Hot Tub

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O, vacation rental in Orleans
Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O, vacation rental in Orleans
Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O, vacation rental in Orleans

Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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15519: Private beach access, Screened in dining, Wrap around porch! Dogs, vacation rental in Orleans
15519: Private beach access, Screened in dining, Wrap around porch! Dogs, vacation rental in Orleans
15519: Private beach access, Screened in dining, Wrap around porch! Dogs, vacation rental in Orleans

15519: Private beach access, Screened in dining, Wrap around porch! Dogs

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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15502: Completely Renovated, Walk to Water & Preservation Land!, vacation rental in Orleans
15502: Completely Renovated, Walk to Water & Preservation Land!, vacation rental in Orleans
15502: Completely Renovated, Walk to Water & Preservation Land!, vacation rental in Orleans

15502: Completely Renovated, Walk to Water & Preservation Land!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, vacation rental in Orleans
Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, vacation rental in Orleans
Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, vacation rental in Orleans

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Quaint & Immaculate on Town Cove in East Orleans, vacation rental in Orleans
Quaint & Immaculate on Town Cove in East Orleans, vacation rental in Orleans
Quaint & Immaculate on Town Cove in East Orleans, vacation rental in Orleans

Quaint & Immaculate on Town Cove in East Orleans

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD, vacation rental in Orleans
SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD, vacation rental in Orleans
SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD, vacation rental in Orleans

SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Delightfully Located Home Near Scenic Pah Wah Pond, vacation rental in Orleans
Delightfully Located Home Near Scenic Pah Wah Pond, vacation rental in Orleans
Delightfully Located Home Near Scenic Pah Wah Pond, vacation rental in Orleans

Delightfully Located Home Near Scenic Pah Wah Pond

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Under large renovation with added bath for 2023, vacation rental in Orleans
Under large renovation with added bath for 2023, vacation rental in Orleans
Under large renovation with added bath for 2023, vacation rental in Orleans

Under large renovation with added bath for 2023

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Central AC, Spacious, 5-level, beautiful home, near lakes and beach, vacation rental in Orleans
Central AC, Spacious, 5-level, beautiful home, near lakes and beach, vacation rental in Orleans
Central AC, Spacious, 5-level, beautiful home, near lakes and beach, vacation rental in Orleans

Central AC, Spacious, 5-level, beautiful home, near lakes and beach

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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15527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!, vacation rental in Orleans
15527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!, vacation rental in Orleans
15527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!, vacation rental in Orleans

15527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Charming Cottage w/ Deck - Walk to Skaket Beach!, vacation rental in Orleans
Charming Cottage w/ Deck - Walk to Skaket Beach!, vacation rental in Orleans
Charming Cottage w/ Deck - Walk to Skaket Beach!, vacation rental in Orleans

Charming Cottage w/ Deck - Walk to Skaket Beach!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Private, Recently Updated Home A Short Walk Down Private Path to Skaket Beach, vacation rental in Orleans
Private, Recently Updated Home A Short Walk Down Private Path to Skaket Beach, vacation rental in Orleans
Private, Recently Updated Home A Short Walk Down Private Path to Skaket Beach, vacation rental in Orleans

Private, Recently Updated Home A Short Walk Down Private Path to Skaket Beach

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Enchanting Waterfront Summer Escape on Pleasant Bay, vacation rental in Orleans
Enchanting Waterfront Summer Escape on Pleasant Bay, vacation rental in Orleans
Enchanting Waterfront Summer Escape on Pleasant Bay, vacation rental in Orleans

Enchanting Waterfront Summer Escape on Pleasant Bay

Rental Home
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps, Kid friendly
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Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O, vacation rental in Orleans
Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O, vacation rental in Orleans
Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O, vacation rental in Orleans

Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O

Rental Home
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps, Kid friendly
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15505: Walk to Nauset Beach! Private yard & large private patio!, vacation rental in Orleans
15505: Walk to Nauset Beach! Private yard & large private patio!, vacation rental in Orleans
15505: Walk to Nauset Beach! Private yard & large private patio!, vacation rental in Orleans

15505: Walk to Nauset Beach! Private yard & large private patio!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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15529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!, vacation rental in Orleans
15529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!, vacation rental in Orleans
15529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!, vacation rental in Orleans

15529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24, vacation rental in Orleans
Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24, vacation rental in Orleans
Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24, vacation rental in Orleans

Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24

Rental Home
10 bedrooms
11 bathrooms
Sleeps 24
Match: Sleeps, Kid friendly
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