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Osceola Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
48 rentals in Osceola.
Cozy Mother-in-Law Apartment, holiday rental in Osceola
Cozy Mother-in-Law Apartment, holiday rental in Osceola
Cozy Mother-in-Law Apartment, holiday rental in Osceola

Cozy Mother-in-Law Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic 1880s Home, holiday rental in Osceola
Historic 1880s Home, holiday rental in Osceola
Historic 1880s Home, holiday rental in Osceola

Historic 1880s Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Osceola Vacation Rental - Dogs Welcome!, holiday rental in Osceola
Lakefront Osceola Vacation Rental - Dogs Welcome!, holiday rental in Osceola
Lakefront Osceola Vacation Rental - Dogs Welcome!, holiday rental in Osceola

Lakefront Osceola Vacation Rental - Dogs Welcome!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Beauty w Modern Updates Near Taylor's Falls, holiday rental in Osceola
Historic Beauty w Modern Updates Near Taylor's Falls, holiday rental in Osceola
Historic Beauty w Modern Updates Near Taylor's Falls, holiday rental in Osceola

Historic Beauty w Modern Updates Near Taylor's Falls

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Lake Osceola Retreat 100-Acre Private Lake Home, holiday rental in Osceola
Lake Osceola Retreat 100-Acre Private Lake Home, holiday rental in Osceola
Lake Osceola Retreat 100-Acre Private Lake Home, holiday rental in Osceola

Lake Osceola Retreat 100-Acre Private Lake Home

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Lakefront Home with 6-person Hot Tub, holiday rental in Osceola
Lakefront Home with 6-person Hot Tub, holiday rental in Osceola
Lakefront Home with 6-person Hot Tub, holiday rental in Osceola

Lakefront Home with 6-person Hot Tub

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Walking Distance to the St. Croix River & Downtown, holiday rental in Osceola
Walking Distance to the St. Croix River & Downtown, holiday rental in Osceola
Walking Distance to the St. Croix River & Downtown, holiday rental in Osceola

Walking Distance to the St. Croix River & Downtown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy cabin for getaway! On a beautiful lake, 1 mile from Trollhaugen, holiday rental in Osceola
Cozy cabin for getaway! On a beautiful lake, 1 mile from Trollhaugen, holiday rental in Osceola
Cozy cabin for getaway! On a beautiful lake, 1 mile from Trollhaugen, holiday rental in Osceola

Cozy cabin for getaway! On a beautiful lake, 1 mile from Trollhaugen

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The following properties within 20 miles of Osceola match all your filters:
The perfect valley getaway, holiday rental in Osceola
The perfect valley getaway, holiday rental in Osceola
The perfect valley getaway, holiday rental in Osceola

The perfect valley getaway

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 4BD/3BA Custom Home-12 Acres - Sauna, Jet Tub, Theater, 3 Gas Fireplaces, holiday rental in Osceola
Luxury 4BD/3BA Custom Home-12 Acres - Sauna, Jet Tub, Theater, 3 Gas Fireplaces, holiday rental in Osceola
Luxury 4BD/3BA Custom Home-12 Acres - Sauna, Jet Tub, Theater, 3 Gas Fireplaces, holiday rental in Osceola

Luxury 4BD/3BA Custom Home-12 Acres - Sauna, Jet Tub, Theater, 3 Gas Fireplaces

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Relax and be Glad at the Lake!, holiday rental in Osceola
Relax and be Glad at the Lake!, holiday rental in Osceola
Relax and be Glad at the Lake!, holiday rental in Osceola

Relax and be Glad at the Lake!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Artist's Loft located 8 miles from Wild Mountain, holiday rental in Osceola
The Artist's Loft located 8 miles from Wild Mountain, holiday rental in Osceola
The Artist's Loft located 8 miles from Wild Mountain, holiday rental in Osceola

The Artist's Loft located 8 miles from Wild Mountain

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Peaceful Vintage Retreat on Pristine St Croix River near Marine-on-St-Croix, holiday rental in Osceola
Peaceful Vintage Retreat on Pristine St Croix River near Marine-on-St-Croix, holiday rental in Osceola
Peaceful Vintage Retreat on Pristine St Croix River near Marine-on-St-Croix, holiday rental in Osceola

Peaceful Vintage Retreat on Pristine St Croix River near Marine-on-St-Croix

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lodge at Lotus Lake, holiday rental in Osceola
Lodge at Lotus Lake, holiday rental in Osceola
Lodge at Lotus Lake, holiday rental in Osceola

Lodge at Lotus Lake

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Wannigan Point Cabin #4, holiday rental in Osceola
Wannigan Point Cabin #4, holiday rental in Osceola
Wannigan Point Cabin #4, holiday rental in Osceola

Wannigan Point Cabin #4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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, holiday rental in Osceola
Romantic Copper ROOM at historic 123 S Washington, holiday rental in Osceola

Romantic Copper ROOM at historic 123 S Washington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wannigan Point Cabin #2, holiday rental in Osceola
Wannigan Point Cabin #2, holiday rental in Osceola
Wannigan Point Cabin #2, holiday rental in Osceola

Wannigan Point Cabin #2

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Wannigan Point Cabin #3, holiday rental in Osceola
Wannigan Point Cabin #3, holiday rental in Osceola
Wannigan Point Cabin #3, holiday rental in Osceola

Wannigan Point Cabin #3

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Wannigan Point Cabin #1, holiday rental in Osceola
Wannigan Point Cabin #1, holiday rental in Osceola
Wannigan Point Cabin #1, holiday rental in Osceola

Wannigan Point Cabin #1

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Peacock Suite at historic 123 South Washington, holiday rental in Osceola
Peacock Suite at historic 123 South Washington, holiday rental in Osceola
Peacock Suite at historic 123 South Washington, holiday rental in Osceola

Peacock Suite at historic 123 South Washington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Nordic Harbor Haus, holiday rental in Osceola
Nordic Harbor Haus, holiday rental in Osceola
Nordic Harbor Haus, holiday rental in Osceola

Nordic Harbor Haus

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunset Point cottage escape, holiday rental in Osceola
Sunset Point cottage escape, holiday rental in Osceola
Sunset Point cottage escape, holiday rental in Osceola

Sunset Point cottage escape

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pet-Friendly St Croix Falls Remote Retreat!, holiday rental in Osceola
Pet-Friendly St Croix Falls Remote Retreat!, holiday rental in Osceola
Pet-Friendly St Croix Falls Remote Retreat!, holiday rental in Osceola

Pet-Friendly St Croix Falls Remote Retreat!

Holiday Rental House
5 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hamptons style Lake house on Sunset point. With water on both the east and west!, holiday rental in Osceola
Hamptons style Lake house on Sunset point. With water on both the east and west!, holiday rental in Osceola
Hamptons style Lake house on Sunset point. With water on both the east and west!, holiday rental in Osceola

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quiet Waterfront Round Lake Home w/ Hot Tub, holiday rental in Osceola
Quiet Waterfront Round Lake Home w/ Hot Tub, holiday rental in Osceola
Quiet Waterfront Round Lake Home w/ Hot Tub, holiday rental in Osceola

Quiet Waterfront Round Lake Home w/ Hot Tub

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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St. Croix River Summer House in Scandia, Waterfront Access & Stunning Views., holiday rental in Osceola
St. Croix River Summer House in Scandia, Waterfront Access & Stunning Views., holiday rental in Osceola
St. Croix River Summer House in Scandia, Waterfront Access & Stunning Views., holiday rental in Osceola

St. Croix River Summer House in Scandia, Waterfront Access & Stunning Views.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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St. Croix River Home in the Heart of Taylors Falls, holiday rental in Osceola
St. Croix River Home in the Heart of Taylors Falls, holiday rental in Osceola
St. Croix River Home in the Heart of Taylors Falls, holiday rental in Osceola

St. Croix River Home in the Heart of Taylors Falls

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Charming Taylors Falls Home w/ Deck, Fire Pit, holiday rental in Osceola
Charming Taylors Falls Home w/ Deck, Fire Pit, holiday rental in Osceola
Charming Taylors Falls Home w/ Deck, Fire Pit, holiday rental in Osceola

Charming Taylors Falls Home w/ Deck, Fire Pit

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Secluded in-town get-away close to Interstate Park. 45 min from Mpls/St Paul, holiday rental in Osceola
Secluded in-town get-away close to Interstate Park. 45 min from Mpls/St Paul, holiday rental in Osceola
Secluded in-town get-away close to Interstate Park. 45 min from Mpls/St Paul, holiday rental in Osceola

Secluded in-town get-away close to Interstate Park. 45 min from Mpls/St Paul

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Winter Riverside Retreat Near Skiing, holiday rental in Osceola
Cozy Winter Riverside Retreat Near Skiing, holiday rental in Osceola
Cozy Winter Riverside Retreat Near Skiing, holiday rental in Osceola

Cozy Winter Riverside Retreat Near Skiing

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront Retreat on South Center Lake, holiday rental in Osceola
Lakefront Retreat on South Center Lake, holiday rental in Osceola
Lakefront Retreat on South Center Lake, holiday rental in Osceola

Lakefront Retreat on South Center Lake

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Lovely spacious 6 BR home in St. Croix River valley, holiday rental in Osceola
Lovely spacious 6 BR home in St. Croix River valley, holiday rental in Osceola
Lovely spacious 6 BR home in St. Croix River valley, holiday rental in Osceola

Lovely spacious 6 BR home in St. Croix River valley

Holiday Rental House
8 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Scandia Forest Lodge - Near State Parks, Stillwater, and Taylors Falls, holiday rental in Osceola
Scandia Forest Lodge - Near State Parks, Stillwater, and Taylors Falls, holiday rental in Osceola
Scandia Forest Lodge - Near State Parks, Stillwater, and Taylors Falls, holiday rental in Osceola

Scandia Forest Lodge - Near State Parks, Stillwater, and Taylors Falls

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Nordic Harbor Inn - Tranquil Maple - Room 2, holiday rental in Osceola
Nordic Harbor Inn - Tranquil Maple - Room 2, holiday rental in Osceola
Nordic Harbor Inn - Tranquil Maple - Room 2, holiday rental in Osceola

Nordic Harbor Inn - Tranquil Maple - Room 2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wannigan Point Cabin #5, holiday rental in Osceola
Wannigan Point Cabin #5, holiday rental in Osceola
Wannigan Point Cabin #5, holiday rental in Osceola

Wannigan Point Cabin #5

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Swedish Log Cabin with Loft in Peaceful Scandia - Enjoy the hygge Lifestyle, holiday rental in Osceola
Cozy Swedish Log Cabin with Loft in Peaceful Scandia - Enjoy the hygge Lifestyle, holiday rental in Osceola
Cozy Swedish Log Cabin with Loft in Peaceful Scandia - Enjoy the hygge Lifestyle, holiday rental in Osceola

Cozy Swedish Log Cabin with Loft in Peaceful Scandia - Enjoy the hygge Lifestyle

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Haven located within 45min of the Twin Cities and right on the lake!, holiday rental in Osceola
Sunset Haven located within 45min of the Twin Cities and right on the lake!, holiday rental in Osceola
Sunset Haven located within 45min of the Twin Cities and right on the lake!, holiday rental in Osceola

Sunset Haven located within 45min of the Twin Cities and right on the lake!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Nordic Harbor Inn - Acorn Oak - Room 1, holiday rental in Osceola
Nordic Harbor Inn - Acorn Oak - Room 1, holiday rental in Osceola
Nordic Harbor Inn - Acorn Oak - Room 1, holiday rental in Osceola

Nordic Harbor Inn - Acorn Oak - Room 1

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wannigan Point Resort!, holiday rental in Osceola
Wannigan Point Resort!, holiday rental in Osceola
Wannigan Point Resort!, holiday rental in Osceola

Wannigan Point Resort!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 28
Match: Sleeps
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Nordic Harbor Inn - Silver Birch - Room 6, holiday rental in Osceola
Nordic Harbor Inn - Silver Birch - Room 6, holiday rental in Osceola
Nordic Harbor Inn - Silver Birch - Room 6, holiday rental in Osceola

Nordic Harbor Inn - Silver Birch - Room 6

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Scandinavian Retreat, holiday rental in Osceola
Scandinavian Retreat, holiday rental in Osceola
Scandinavian Retreat, holiday rental in Osceola

Scandinavian Retreat

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nordic Harbor Inn - Arctic Pine - Room 3, holiday rental in Osceola
Nordic Harbor Inn - Arctic Pine - Room 3, holiday rental in Osceola
Nordic Harbor Inn - Arctic Pine - Room 3, holiday rental in Osceola

Nordic Harbor Inn - Arctic Pine - Room 3

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Nordic Harbor Inn-Nordic Spruce - Room 4, holiday rental in Osceola
Nordic Harbor Inn-Nordic Spruce - Room 4, holiday rental in Osceola
Nordic Harbor Inn-Nordic Spruce - Room 4, holiday rental in Osceola

Nordic Harbor Inn-Nordic Spruce - Room 4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Home in Taylors Falls w/ Patio & Fire Pit, holiday rental in Osceola
Historic Home in Taylors Falls w/ Patio & Fire Pit, holiday rental in Osceola
Historic Home in Taylors Falls w/ Patio & Fire Pit, holiday rental in Osceola

Historic Home in Taylors Falls w/ Patio & Fire Pit

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Grove Cottage walkable Taylors Falls retreat-  close to Minneapolis/ St. Paul!, holiday rental in Osceola
Grove Cottage walkable Taylors Falls retreat-  close to Minneapolis/ St. Paul!, holiday rental in Osceola
Grove Cottage walkable Taylors Falls retreat-  close to Minneapolis/ St. Paul!, holiday rental in Osceola

Grove Cottage walkable Taylors Falls retreat- close to Minneapolis/ St. Paul!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious Secluded Lakehouse, holiday rental in Osceola
Spacious Secluded Lakehouse, holiday rental in Osceola
Spacious Secluded Lakehouse, holiday rental in Osceola

Spacious Secluded Lakehouse

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Gatsby’s Getaway-Unique stay near downtown, holiday rental in Osceola
Gatsby’s Getaway-Unique stay near downtown, holiday rental in Osceola
Gatsby’s Getaway-Unique stay near downtown, holiday rental in Osceola

Gatsby’s Getaway-Unique stay near downtown

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Nordic Harbor Inn - Cedar Shadows - Room 5, holiday rental in Osceola
Nordic Harbor Inn - Cedar Shadows - Room 5, holiday rental in Osceola
Nordic Harbor Inn - Cedar Shadows - Room 5, holiday rental in Osceola

Nordic Harbor Inn - Cedar Shadows - Room 5

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-48 of 48
Frequently Asked Questions about Osceola