Vacation rentals in Osceola, WI

33 available vacation rental offers

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Best vacation rentals and Airbnb offers in Osceola, WI

Classic Home - Osceola, WI

Classic Home

Holiday Home, Osceola

Classic Home is a holiday home in Osceola, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Classic Home

Classic Home is a holiday home in Osceola, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,107.

From$158/night
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Wannigan Point Cabin #1 - Osceola, WI

Wannigan Point Cabin #1

Cabin, Osceola

Wannigan Point Cabin #1 is a cabin in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Wannigan Point Cabin #1

Wannigan Point Cabin #1 is a cabin in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,284.

From$183/night
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Wannigan Point Cabin #3 - Osceola, WI

Wannigan Point Cabin #3

Cabin, Osceola

Wannigan Point Cabin #3 is a cabin in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Wannigan Point Cabin #3

Wannigan Point Cabin #3 is a cabin in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,289.

From$184/night
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Wannigan Point Cabin #5 - Osceola, WI

Wannigan Point Cabin #5

Cabin, Osceola

Wannigan Point Cabin #5 is a cabin in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Wannigan Point Cabin #5

Wannigan Point Cabin #5 is a cabin in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,289.

From$184/night
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Vacation rentals with parking in Osceola, WI

Find vacation rentals that make arriving by car easier.

Nordic Harbor | Room 5 | Cedar Shadows - Osceola, WI

Nordic Harbor | Room 5 | Cedar Shadows

Holiday Home, Osceola

Nordic Harbor · Room 5 · Cedar Shadows is a holiday home in Osceola, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor · Room 5 · Cedar Shadows is a holiday home in Osceola, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,741.

From$249/night
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Long Lake Retreat Centuria - Osceola, WI

Long Lake Retreat Centuria

Holiday Home, Osceola

Long Lake Retreat Centuria is a holiday home in Osceola, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Long Lake Retreat Centuria

Long Lake Retreat Centuria is a holiday home in Osceola, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,163.

From$309/night
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Nordic Harbor | Room 3 | Arctic Pine - Suite - Osceola, WI

Nordic Harbor | Room 3 | Arctic Pine - Suite

Apartment, Osceola

Nordic Harbor · Room 3 · Arctic Pine - Suite is a apartment in Osceola, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Nordic Harbor | Room 3 | Arctic Pine - Suite

Nordic Harbor · Room 3 · Arctic Pine - Suite is a apartment in Osceola, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,527.

From$361/night
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Nordic Harbor | Room 6 | Silver Birch - Suite - Osceola, WI

Nordic Harbor | Room 6 | Silver Birch - Suite

Holiday Home, Osceola

Nordic Harbor · Room 6 · Silver Birch - Suite is a holiday home in Osceola, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Nordic Harbor | Room 6 | Silver Birch - Suite

Nordic Harbor · Room 6 · Silver Birch - Suite is a holiday home in Osceola, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,527.

From$361/night
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Pet-friendly vacation rentals in Osceola, WI

Bring your pet along with stays that welcome four-legged travelers.

Even Tide on Deer Lake Just steps Lake with kaykas & canoes & private dock - Osceola, WI

Even Tide on Deer Lake Just steps Lake with kaykas & canoes & private dock

Holiday Home, Osceola

Even Tide on Deer Lake Just steps Lake with kaykas & canoes & private dock is a holiday home in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Even Tide on Deer Lake Just steps Lake with kaykas & canoes & private dock

Even Tide on Deer Lake Just steps Lake with kaykas & canoes & private dock is a holiday home in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,726.

From$247/night
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Charming Underhill 2-bedroom cabin in lovely Center City with lake access. - Osceola, WI

Charming Underhill 2-bedroom cabin in lovely Center City with lake access.

Cabin, Osceola

Charming Underhill 2-bedroom cabin in lovely Center City with lake access. is a cabin in Osceola, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Charming Underhill 2-bedroom cabin in lovely Center City with lake access.

Charming Underhill 2-bedroom cabin in lovely Center City with lake access. is a cabin in Osceola, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,926.

From$275/night
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Lakefront Osceola Vacation Rental - Dogs Welcome! - Osceola, WI

Lakefront Osceola Vacation Rental - Dogs Welcome!

Holiday Home, Osceola

Lakefront Osceola Vacation Rental - Dogs Welcome! is a holiday home in Osceola, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Lakefront Osceola Vacation Rental - Dogs Welcome!

Lakefront Osceola Vacation Rental - Dogs Welcome! is a holiday home in Osceola, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,335.

From$535/night
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St. Croix Valley Inn - Osceola, WI

St. Croix Valley Inn

Holiday Home, Osceola

St. Croix Valley Inn is a holiday home in Osceola, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About St. Croix Valley Inn

St. Croix Valley Inn is a holiday home in Osceola, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,032.

From$913/night
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Vacation rentals with a kitchen in Osceola, WI

Compare stays with kitchen access for longer trips and easier meals.

Lakefront Osceola Vacation Rental - Dogs Welcome! - Osceola, WI

Lakefront Osceola Vacation Rental - Dogs Welcome!

Cabin, Osceola

Lakefront Osceola Vacation Rental - Dogs Welcome! is a cabin in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Lakefront Osceola Vacation Rental - Dogs Welcome!

Lakefront Osceola Vacation Rental - Dogs Welcome! is a cabin in Osceola, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,927.

From$561/night
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Chic Boho-Luxe Getaway Near the St. Croix River - Near Trollhaugen & Wild Mt. - Osceola, WI

Chic Boho-Luxe Getaway Near the St. Croix River - Near Trollhaugen & Wild Mt.

Holiday Home, Osceola

Chic Boho-Luxe Getaway Near the St. Croix River - Near Trollhaugen & Wild Mt. is a holiday home in Osceola, with kitchen access. This stay gives travelers a comfortable base for exploring…

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About Chic Boho-Luxe Getaway Near the St. Croix River - Near Trollhaugen & Wild Mt.

Chic Boho-Luxe Getaway Near the St. Croix River - Near Trollhaugen & Wild Mt. is a holiday home in Osceola, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,950.

From$564/night
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Lakefront Osceola Vacation Rental - Dogs Welcome! - Osceola, WI

Lakefront Osceola Vacation Rental - Dogs Welcome!

Cottage, Osceola

Lakefront Osceola Vacation Rental - Dogs Welcome! is a cottage in Osceola, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Lakefront Osceola Vacation Rental - Dogs Welcome!

Lakefront Osceola Vacation Rental - Dogs Welcome! is a cottage in Osceola, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,498.

From$583/night
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MINNeSTAY* St. Croix Valley Inn - Osceola, WI

MINNeSTAY* St. Croix Valley Inn

Holiday Home, Osceola

MINNeSTAY* St. Croix Valley Inn is a holiday home in Osceola, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About MINNeSTAY* St. Croix Valley Inn

MINNeSTAY* St. Croix Valley Inn is a holiday home in Osceola, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,945.

From$1,135/night
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Family-friendly vacation rentals in Osceola, WI

Plan a trip with stays that give families more room to spread out.

River Song Cottage ~ quiet retreat 2 bedroom - Q, T/F bunk + T trundle - Osceola, WI

River Song Cottage ~ quiet retreat 2 bedroom - Q, T/F bunk + T trundle

Holiday Home, Osceola

River Song Cottage ~ quiet retreat 2 bedroom - Q, T/F bunk + T trundle is a holiday home in Osceola, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers…

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About River Song Cottage ~ quiet retreat 2 bedroom - Q, T/F bunk + T trundle

River Song Cottage ~ quiet retreat 2 bedroom - Q, T/F bunk + T trundle is a holiday home in Osceola, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,788.

From$255/night
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Creekside Family Tent Great to Create New Memories in Saint Croix Falls, Wisconsin - Osceola, WI

Creekside Family Tent Great to Create New Memories in Saint Croix Falls, Wisconsin

Holiday Home, Osceola

Creekside Family Tent Great to Create New Memories in Saint Croix Falls, Wisconsin is a holiday home in Osceola, with room for a group. This stay gives travelers a comfortable base for…

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About Creekside Family Tent Great to Create New Memories in Saint Croix Falls, Wisconsin

Creekside Family Tent Great to Create New Memories in Saint Croix Falls, Wisconsin is a holiday home in Osceola, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: fireplace, ac, air conditioning, family friendly, and kids toys.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,881.

From$269/night
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Lakefront Cabin w/ Private Dock, Kayaks + Firepit - Osceola, WI

Lakefront Cabin w/ Private Dock, Kayaks + Firepit

Cabin, Osceola

Lakefront Cabin w/ Private Dock, Kayaks + Firepit is a cabin in Osceola, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Lakefront Cabin w/ Private Dock, Kayaks + Firepit

Lakefront Cabin w/ Private Dock, Kayaks + Firepit is a cabin in Osceola, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,474.

From$353/night
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Taylors Falls family adventures - Osceola, WI

Taylors Falls family adventures

Holiday Home, Osceola

Taylors Falls family adventures is a holiday home in Osceola, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Taylors Falls family adventures

Taylors Falls family adventures is a holiday home in Osceola, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,148.

From$450/night
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