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Osceola Holiday Rentals

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50 rentals in Osceola.
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Historic 1880s Home, holiday rental in Osceola

Historic 1880s Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Lake Home with a View, holiday rental in Osceola

Secluded Lake Home with a View

3 bedrooms
4 bathrooms
Sleeps 8
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Lake life is Calling, holiday rental in Osceola

Lake life is Calling

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Dr. Combacker’s Historic 1880s Home, holiday rental in Osceola

Dr. Combacker’s Historic 1880s Home

3 bedrooms
2 bathrooms
Sleeps 8
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Cozy Mother-in-Law Apartment—Dr. Combacker’s Legacy, holiday rental in Osceola

Cozy Mother-in-Law Apartment—Dr. Combacker’s Legacy

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage Home On Lake Mckusick, 1 Mile From Historic Downtown Stillwater, holiday rental in Osceola

Cottage Home On Lake Mckusick, 1 Mile From Historic Downtown Stillwater

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Private Northwoods Retreat, holiday rental in Osceola

Private Northwoods Retreat

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Stillwater's 3rd Street Inn, holiday rental in Osceola

Stillwater's 3rd Street Inn

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful cabin getaway on Green Lake, holiday rental in Osceola

Beautiful cabin getaway on Green Lake

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Extraordinary Home on the River Bluff Directly Across from Stillwater, Minn., holiday rental in Osceola

Extraordinary Home on the River Bluff Directly Across from Stillwater, Minn.

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Cozy Cabin on Cedar Lake, holiday rental in Osceola

Cozy Cabin on Cedar Lake

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful, private vacation home rental on the point in Lindstrom, MN, holiday rental in Osceola

Beautiful, private vacation home rental on the point in Lindstrom, MN

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Riverview In Downtown Stillwater: Porches, Decks & Yard Overlooking Main Street, holiday rental in Osceola

Riverview In Downtown Stillwater: Porches, Decks & Yard Overlooking Main Street

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Taylors Falls River Cottage, holiday rental in Osceola

Taylors Falls River Cottage

3 bedrooms
1 bathroom
Sleeps 8
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Also see Main Street Hideaway 1 for additional pics & booking availability, holiday rental in Osceola

Also see Main Street Hideaway 1 for additional pics & booking availability

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Great Two Bedroom Apartment in Historic Downtown Stillwater, holiday rental in Osceola

Great Two Bedroom Apartment in Historic Downtown Stillwater

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Hamptons style Lake house on Sunset point. With water on both east and west!, holiday rental in Osceola

Hamptons style Lake house on Sunset point. With water on both east and west!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beach House #1 with a Private Beach on the St. Croix River, holiday rental in Osceola

Beach House #1 with a Private Beach on the St. Croix River

4 bedrooms
2 bathrooms
Sleeps 12
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Sunset Point cottage escape, holiday rental in Osceola

Sunset Point cottage escape

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Rustic Lodge With A Beach Charm On The St. Croix River, holiday rental in Osceola

Rustic Lodge With A Beach Charm On The St. Croix River

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Blocks to Downtown. Charming 3 Bed, Entire House, holiday rental in Osceola

Blocks to Downtown. Charming 3 Bed, Entire House

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Nature Lover's Log Cabin Retreat, holiday rental in Osceola

Nature Lover's Log Cabin Retreat

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Peaceful Wooded Getaway, holiday rental in Osceola

Peaceful Wooded Getaway

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Relive the Summers of Your Youth on Beautiful Deer Lake Wi, holiday rental in Osceola

Relive the Summers of Your Youth on Beautiful Deer Lake Wi

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous Lake Home Getaway W/ Hot Tub, holiday rental in Osceola

Gorgeous Lake Home Getaway W/ Hot Tub

4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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The Artist's Loft in scenic St Croix Falls, WI, holiday rental in Osceola

The Artist's Loft in scenic St Croix Falls, WI

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Romantic getaway! With gorgeous views from the newly added Hot Tub!, holiday rental in Osceola

Romantic getaway! With gorgeous views from the newly added Hot Tub!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ti Voglio Bene Bed & Breakfast - Greaton Suite, holiday rental in Osceola

Ti Voglio Bene Bed & Breakfast - Greaton Suite

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxury Northwoods Lakehome - Bone Lake, Wisconsin, Polk Co. Lic. #76778, holiday rental in Osceola

Luxury Northwoods Lakehome - Bone Lake, Wisconsin, Polk Co. Lic. #76778

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEWLY REMODELED!  Getaway on Balsam Lake, WI, holiday rental in Osceola

NEWLY REMODELED! Getaway on Balsam Lake, WI

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Historic Stillwater Home, Downtown, Walkable, Colonial Revival Design, holiday rental in Osceola

Historic Stillwater Home, Downtown, Walkable, Colonial Revival Design

6 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Ever wanted to vacation at an exclusive 980 acre estate!?, holiday rental in Osceola

Ever wanted to vacation at an exclusive 980 acre estate!?

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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AMERY ALE WORKS BAR(N) HOME, holiday rental in Osceola

AMERY ALE WORKS BAR(N) HOME

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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980 acre private estate, holiday rental in Osceola

980 acre private estate

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Adorable Cottage on Forest Lake - Great for Families!, holiday rental in Osceola

Adorable Cottage on Forest Lake - Great for Families!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Lake House Getaway just 30 min from the Twin Cities!, holiday rental in Osceola

Spacious Lake House Getaway just 30 min from the Twin Cities!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Romantic Copper Room at historic 123 S Washington, holiday rental in Osceola

Romantic Copper Room at historic 123 S Washington

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing Location, Great Fishing  Sunfish, Crappies, Pike, Muskie!, holiday rental in Osceola

Amazing Location, Great Fishing Sunfish, Crappies, Pike, Muskie!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A River Runs Near it, downtown Stillwater, holiday rental in Osceola

A River Runs Near it, downtown Stillwater

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Near State Parks, Stillwater, and Taylors Falls, holiday rental in Osceola

Near State Parks, Stillwater, and Taylors Falls

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Ti Voglio Bene Bed & Breakfast - Simonton Suite, holiday rental in Osceola

Ti Voglio Bene Bed & Breakfast - Simonton Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rendezvous Retreats, Inc., holiday rental in Osceola

Rendezvous Retreats, Inc.

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Charming 1940 Family Cottage on the St. Croix River, holiday rental in Osceola

Charming 1940 Family Cottage on the St. Croix River

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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The Historic Lumber Mill House, holiday rental in Osceola

The Historic Lumber Mill House

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Large Pet-Friendly Hugo Home w/Hot Tub & Game Room, holiday rental in Osceola

Large Pet-Friendly Hugo Home w/Hot Tub & Game Room

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cabin w/ Dock & Porch Across from Balsam Lake, holiday rental in Osceola

Cabin w/ Dock & Porch Across from Balsam Lake

6 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Ti Voglio Bene Bed & Breakfast - Wade Suite, holiday rental in Osceola

Ti Voglio Bene Bed & Breakfast - Wade Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vitae Woodland Retreat, holiday rental in Osceola

Vitae Woodland Retreat

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Quiet Farmhouse Retreat w/Fire Pit - Pets Welcome!, holiday rental in Osceola

Quiet Farmhouse Retreat w/Fire Pit - Pets Welcome!

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Big Rock Creek, holiday rental in Osceola

Big Rock Creek

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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