Vacation rentals in Dickinson County, IA

Best vacation rentals and Airbnb offers in Dickinson County, IA

Charming 2-bedroom guest country farmhouse with WiFi, AC in rural Milford.

Country House, Dickinson County

Charming 2-bedroom guest country farmhouse with WiFi, AC in rural Milford. is a country house in Dickinson County, with parking, kitchen access, and room for a group. This stay gives…

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About Charming 2-bedroom guest country farmhouse with WiFi, AC in rural Milford.

Charming 2-bedroom guest country farmhouse with WiFi, AC in rural Milford. is a country house in Dickinson County, with parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,195.

From$171/night

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Cute little cottage in the best location.

Cottage, Dickinson County

Cute little cottage in the best location. is a cottage in Dickinson County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cute little cottage in the best location.

Cute little cottage in the best location. is a cottage in Dickinson County, with 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,493.

From$213/night

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Cozy Waterfront Cabin on Big Spirit Lake

Cabin, Dickinson County

Cozy Waterfront Cabin on Big Spirit Lake is a cabin in Dickinson County, with easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Waterfront Cabin on Big Spirit Lake

Cozy Waterfront Cabin on Big Spirit Lake is a cabin in Dickinson County, with easy beach 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, ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,523.

From$218/night

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127 Hwy 71 AT Bunk House

Apartment, Dickinson County

127 Hwy 71 AT Bunk House is a apartment in Dickinson County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About 127 Hwy 71 AT Bunk House

127 Hwy 71 AT Bunk House is a apartment in Dickinson County, with 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, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,807.

From$219/night

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Vacation rentals with a pool in Dickinson County, IA

Add a pool to the search when you want an easy place to cool off between outings.

Your Okoboji Getaway: 3BR, 2.5 BA Bridges Bay Resort Cabin w/Resort amenities!

Cabin, Dickinson County

Your Okoboji Getaway: 3BR, 2.5 BA Bridges Bay Resort Cabin w/Resort amenities! is a cabin in Dickinson County, with pool access, easy beach access, and room for a group. This stay gives…

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About Your Okoboji Getaway: 3BR, 2.5 BA Bridges Bay Resort Cabin w/Resort amenities!

Your Okoboji Getaway: 3BR, 2.5 BA Bridges Bay Resort Cabin w/Resort amenities! is a cabin in Dickinson County, with pool access, easy beach 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,839.

From$406/night

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Cabin 233 at Bridges Bay Resort sleeps up to 7 - comes with 6 daily pool passes

Cabin, Dickinson County

Cabin 233 at Bridges Bay Resort sleeps up to 7 - comes with 6 daily pool passes is a cabin in Dickinson County, with pool access, easy beach access, and room for a group. This stay gives…

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About Cabin 233 at Bridges Bay Resort sleeps up to 7 - comes with 6 daily pool passes

Cabin 233 at Bridges Bay Resort sleeps up to 7 - comes with 6 daily pool passes is a cabin in Dickinson County, with pool access, easy beach 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,930.

From$419/night

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Bridges Bay Resort Coronado Building 302

Apartment, Dickinson County

Bridges Bay Resort Coronado Building 302 is a apartment in Dickinson County, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the…

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About Bridges Bay Resort Coronado Building 302

Bridges Bay Resort Coronado Building 302 is a apartment in Dickinson County, with pool access, easy beach access, 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, pool, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,689.

From$449/night

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3-bedroom Cabin 13 in Bridges Bay, with on site eating and in/outdoor pool.

Cabin, Dickinson County

3-bedroom Cabin 13 in Bridges Bay, with on site eating and in/outdoor pool. is a cabin in Dickinson County, with pool access, easy beach access, and room for a group. This stay gives…

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About 3-bedroom Cabin 13 in Bridges Bay, with on site eating and in/outdoor pool.

3-bedroom Cabin 13 in Bridges Bay, with on site eating and in/outdoor pool. is a cabin in Dickinson County, with pool access, easy beach 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,201.

From$457/night

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Vacation rentals with parking in Dickinson County, IA

Find vacation rentals that make arriving by car easier.

Okoboji Sweet Retreat

Holiday Home, Dickinson County

Okoboji Sweet Retreat is a holiday home in Dickinson County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Okoboji Sweet Retreat

Okoboji Sweet Retreat is a holiday home in Dickinson County, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,260.

From$323/night

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Cozy 3 bedroom Cabin- Close to splash pad

Holiday Home, Dickinson County

Cozy 3 bedroom Cabin- Close to splash pad is a holiday home in Dickinson County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 3 bedroom Cabin- Close to splash pad

Cozy 3 bedroom Cabin- Close to splash pad is a holiday home in Dickinson County, with parking, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,310.

From$330/night

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Amazing 2-BR townhome, Sleeps 6

Holiday Home, Dickinson County

Amazing 2-BR townhome, Sleeps 6 is a holiday home in Dickinson County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Amazing 2-BR townhome, Sleeps 6

Amazing 2-BR townhome, Sleeps 6 is a holiday home in Dickinson County, with parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,682.

From$383/night

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2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.

Apartment, Dickinson County

2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps. is a apartment in Dickinson County, with parking, kitchen access, and room for a group.…

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About 2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.

2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps. is a apartment in Dickinson County, with parking, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,814.

From$402/night

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Pet-friendly vacation rentals in Dickinson County, IA

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

Loft Oasis:Fam+Pet,Friendly,Big Spirit Lake

Guest House, Dickinson County

Loft Oasis:Fam+Pet,Friendly,Big Spirit Lake is a guest house in Dickinson County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Loft Oasis:Fam+Pet,Friendly,Big Spirit Lake

Loft Oasis:Fam+Pet,Friendly,Big Spirit Lake is a guest house in Dickinson County, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,765.

From$252/night

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FamFriendly|Full Kitchen|Near Big Spirit Lake

Holiday Home, Dickinson County

FamFriendly · Full Kitchen · Near Big Spirit Lake is a holiday home in Dickinson County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About FamFriendly|Full Kitchen|Near Big Spirit Lake

FamFriendly · Full Kitchen · Near Big Spirit Lake is a holiday home in Dickinson County, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,547.

From$364/night

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Cozy 3-bedroom cabin on East Lake Okoboji with WiFi, AC

Cabin, Dickinson County

Cozy 3-bedroom cabin on East Lake Okoboji with WiFi, AC is a cabin in Dickinson County, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 3-bedroom cabin on East Lake Okoboji with WiFi, AC

Cozy 3-bedroom cabin on East Lake Okoboji with WiFi, AC is a cabin in Dickinson County, with pet-friendly space 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,604.

From$372/night

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Arnolds Park - prime location - walk everywhere - Historic 1940's cottage.

Cottage, Dickinson County

Arnolds Park - prime location - walk everywhere - Historic 1940's cottage. is a cottage in Dickinson County, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Arnolds Park - prime location - walk everywhere - Historic 1940's cottage.

Arnolds Park - prime location - walk everywhere - Historic 1940's cottage. is a cottage in Dickinson County, with 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,095.

From$442/night

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Vacation rentals with a kitchen in Dickinson County, IA

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

This lake getaway on the `Narrows` off East Lake offers easy access to boating, fishing, & nightlife

Holiday Home, Dickinson County

This lake getaway on the `Narrows` off East Lake offers easy access to boating, fishing, & nightlife is a holiday home in Dickinson County, with pet-friendly space, parking, and kitchen…

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About This lake getaway on the `Narrows` off East Lake offers easy access to boating, fishing, & nightlife

This lake getaway on the `Narrows` off East Lake offers easy access to boating, fishing, & nightlife is a holiday home in Dickinson County, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,867.

From$410/night

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Sleeps 7|Newly Built 3BD 2BTH| Kid+Pet Friendly

Holiday Home, Dickinson County

Sleeps 7 · Newly Built 3BD 2BTH · Kid+Pet Friendly is a holiday home in Dickinson County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Sleeps 7|Newly Built 3BD 2BTH| Kid+Pet Friendly

Sleeps 7 · Newly Built 3BD 2BTH · Kid+Pet Friendly is a holiday home in Dickinson County, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,867.

From$410/night

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The Monarch Cove House off West Lake Okoboji

Holiday Home, Dickinson County

The Monarch Cove House off West Lake Okoboji is a holiday home in Dickinson County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About The Monarch Cove House off West Lake Okoboji

The Monarch Cove House off West Lake Okoboji is a holiday home in Dickinson County, with 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,248.

From$464/night

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Entire Top Floor Only: Okoboji Oasis/ Private Entrance

Apartment, Dickinson County

Entire Top Floor Only: Okoboji Oasis/ Private Entrance is a apartment in Dickinson County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Entire Top Floor Only: Okoboji Oasis/ Private Entrance

Entire Top Floor Only: Okoboji Oasis/ Private Entrance is a apartment in Dickinson County, with 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,401.

From$486/night

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Family-friendly vacation rentals in Dickinson County, IA

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

Spirit Lake Retreat - New 2-bedroom lakefront guest cottage in Orleans

Cottage, Dickinson County

Spirit Lake Retreat - New 2-bedroom lakefront guest cottage in Orleans is a cottage in Dickinson County, with parking, room for a group, and a quieter setting. This stay gives travelers a…

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About Spirit Lake Retreat - New 2-bedroom lakefront guest cottage in Orleans

Spirit Lake Retreat - New 2-bedroom lakefront guest cottage in Orleans is a cottage in Dickinson County, with parking, room for a group, 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,144.

From$306/night

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Family Fun Escape! 3BR, 2BA Bridges Bay condo sleeps 10 + 6 Waterpark Passes

Condo, Dickinson County

Family Fun Escape! 3BR, 2BA Bridges Bay condo sleeps 10 + 6 Waterpark Passes is a condo in Dickinson County, with pool access, easy beach access, and room for a group. This stay gives…

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About Family Fun Escape! 3BR, 2BA Bridges Bay condo sleeps 10 + 6 Waterpark Passes

Family Fun Escape! 3BR, 2BA Bridges Bay condo sleeps 10 + 6 Waterpark Passes is a condo in Dickinson County, with pool access, easy beach 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,705.

From$386/night

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Triboji Beach Club Cottage | Cozy West Okoboji Escape with Lake Access

Holiday Home, Dickinson County

Triboji Beach Club Cottage · Cozy West Okoboji Escape with Lake Access is a holiday home in Dickinson County, with easy beach access, parking, and kitchen access. This stay gives travelers…

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About Triboji Beach Club Cottage | Cozy West Okoboji Escape with Lake Access

Triboji Beach Club Cottage · Cozy West Okoboji Escape with Lake Access is a holiday home in Dickinson County, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,830.

From$404/night

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Okoboji BLUEtiful Cottage off Arnolds Park Amusement Park

Holiday Home, Dickinson County

Okoboji BLUEtiful Cottage off Arnolds Park Amusement Park is a holiday home in Dickinson County, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Okoboji BLUEtiful Cottage off Arnolds Park Amusement Park

Okoboji BLUEtiful Cottage off Arnolds Park Amusement Park is a holiday home in Dickinson County, 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 wifi, kitchen, with kitchen, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,920.

From$417/night

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