Vacation rentals in Dickinson County

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Top cities to explore in Dickinson County

Okoboji

Vacation Rentals
Okoboji

Top vacation rentals in Dickinson County

Beautiful 1500+ sq ft cabin with outdoor pool just steps off the patio

Beautiful 1500+ sq ft cabin with outdoor pool just steps off the patio

ARNOLDS PARK IA
3.47 mi from city center
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This cabin features an outdoor pool and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the gym and conveniences like a garden and laundry facilities.
Pool
Kitchen
Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes

Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes

Arnolds Park IA
3.39 mi from city center
$427 nightly
The price is $478 total per night
$478 total
Dec 23 - Dec 24
Total with taxes and fees
A water park and an outdoor pool are featured at this smoke-free condo. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the indoor pool and conveniences like a garden and barbecue grills.
Pool
Hot Tub
PRIME LOCATION AT BRIDGES BAY RESORT!!!

PRIME LOCATION AT BRIDGES BAY RESORT!!!

Arnolds Park IA
3.42 mi from city center
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A gym is featured at this vacation home, along with laundry facilities and barbecue grills.
Kitchen
Washer
Bring ALL of your family and friends to stay at the Central Stay Cation in Arnolds Park!

Bring ALL of your family and friends to stay at the Central Stay Cation in Arnolds Park!

Arnolds Park IA
3.71 mi from city center
$639 nightly
The price is $716 total per night
$716 total
Dec 14 - Dec 15
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Morehead Retreat on 75 ft of East Lake Okoboji

Morehead Retreat on 75 ft of East Lake Okoboji

2 out of 5
Spirit Lake IA
1.08 mi from city center
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This vacation home features a water park and barbecue grills.
Kitchen
Washer
Quiet 1 bedroom in Milford

Quiet 1 bedroom in Milford

Milford IA
7.49 mi from city center
$114 nightly
The price is $128 total per night
$128 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
This apartment features a water park, laundry facilities, and barbecue grills.
Kitchen
Washer
Amazing West Lake Okoboji Home! Location, Location, Location!!!

Amazing West Lake Okoboji Home! Location, Location, Location!!!

Arnolds Park IA
4.06 mi from city center
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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Okoboji Bridges Bay Cabin 111~ Waterpark Passes and Relaxing Retreat

Okoboji Bridges Bay Cabin 111~ Waterpark Passes and Relaxing Retreat

Arnolds Park IA
3.32 mi from city center
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A water park and an outdoor pool are featured at this smoke-free vacation home. There's an indoor pool on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
Penthouse Luxury with Lake Views & 6 FREE waterpark passes daily at Bridges Bay.

Penthouse Luxury with Lake Views & 6 FREE waterpark passes daily at Bridges Bay.

Arnolds Park IA
3.36 mi from city center
$421 nightly
The price is $472 total per night
$472 total
Dec 28 - Dec 29
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and conveniences like a garden and barbecue grills.
Pool
Hot Tub
Penthouse Perfection-Spacious 4 Bedroom-Panoramic Views & Waterpark Passes at BB

Penthouse Perfection-Spacious 4 Bedroom-Panoramic Views & Waterpark Passes at BB

Arnolds Park IA
3.56 mi from city center
$431 nightly
The price is $482 total per night
$482 total
Dec 21 - Dec 22
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A gym, a hot tub, and barbecue grills are also on offer.
Pool
Hot Tub
Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.

Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.

Arnolds Park IA
3.37 mi from city center
$393 nightly
The price is $440 total per night
$440 total
Dec 27 - Dec 28
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and conveniences like a garden and barbecue grills.
Pool
Hot Tub
The Good Life Cabin - Bridges Bay Resort in Okoboji, Iowa

The Good Life Cabin - Bridges Bay Resort in Okoboji, Iowa

Arnolds Park IA
3.4 mi from city center
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This cabin features an outdoor pool and an indoor pool. There's a gym on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
Cozy Lakeside Retreat with Beach Access, Scenic Views & Endless Amenities

Cozy Lakeside Retreat with Beach Access, Scenic Views & Endless Amenities

Spirit Lake IA
3.12 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Lakefront BB Corner Condo. Expanded deck & panoramic views & 6 waterpark passes.

Lakefront BB Corner Condo. Expanded deck & panoramic views & 6 waterpark passes.

Arnolds Park IA
3.35 mi from city center
Get rates
A water park and an outdoor pool are featured at this smoke-free condo. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the indoor pool and conveniences like a garden and laundry facilities.
Pool
Hot Tub
Sandy Beach Retreat | Lakefront on Big Spirit Lake

Sandy Beach Retreat | Lakefront on Big Spirit Lake

Orleans IA
2.55 mi from city center
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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Spacious 4 Bedroom Lakefront Luxury. Panoramic Views & 6 waterpark passes at BB.

Spacious 4 Bedroom Lakefront Luxury. Panoramic Views & 6 waterpark passes at BB.

Arnolds Park IA
3.56 mi from city center
Get rates
A water park and an outdoor pool are featured at this smoke-free condo. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the indoor pool and conveniences like a garden and laundry facilities.
Pool
Hot Tub
3 br. 2ba sleeps 14

3 br. 2ba sleeps 14

arnolds park IA
3.31 mi from city center
Get rates
A water park and an outdoor pool are featured at this smoke-free cabin. Enjoy the indoor pool and conveniences like a garden and laundry facilities.
Pool
Kitchen
Bridges Bay Boji Lake-View Condo For Rent!!

Bridges Bay Boji Lake-View Condo For Rent!!

Arnolds Park IA
3.45 mi from city center
$360 nightly
The price is $403 total per night
$403 total
Dec 15 - Dec 16
Total with taxes and fees
This condo features a water park, laundry facilities, and barbecue grills.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Dickinson County
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

The Best Way to Find Vacation Rentals in Dickinson County 

How cheap is a vacation rental in Dickinson County?


You can find Dickinson County vacation rentals from just $128 per night. 


How do you look for the best vacation rental deals in Dickinson County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Dickinson County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Dickinson County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Dickinson County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Dickinson County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Dickinson County?


Whether you’re a winter wanderer or planning a summer sojourn, Dickinson County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Dickinson County?


Take your pick from the excitement of the big Dickinson County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Dickinson County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Dickinson County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.