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Holiday houses in Dickinson County

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Top-rated holiday rentals in Dickinson County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A serene lakeside patio is presented, featuring two blue adirondack chairs positioned around a fire pit. A gas grill stands nearby, and the reflection of the sunset shimmering on the water enhances the peaceful ambiance. Boat docks line the shore in the background.
Home in Arnolds Park
4.92 out of 5 average rating, 25 reviews

Cozy Lake Front Cabin

Cozy 3 Bedroom Lake Front Cabin on East Lake - GREAT LOCATION Next to The Ritz - Private Dock The best of everything Okoboji has to offer in this lake front cabin nestled right next to the Ritz and within walking distance to all major attractions including Arnolds Park, The Farmers Market, Preservation Plaza, The Emporium, Mau Marina, The Okoboji Store, O'Farrell Sisters, Arnolds Park Public Beach, and more. Public Beach steps away, back yard with grill, fire pit, near boat ramps/ bike trails.

Top Guest favourite
A charming cottage is set against a backdrop of greenery, featuring a well-maintained front lawn and landscaped steps leading to a welcoming entrance. Two large windows on either side of the front door provide natural light to the interior, and a patio is visible to the side.
Cottage in Arnolds Park
4.89 out of 5 average rating, 139 reviews

A Place In the Park Cottage

A Place In the Park–Cozy Cottage near the Fun! Sleeps 5 | Superhost Welcome to A Place In the Park — your ideal escape in the heart of Boji! This home offers comfort, convenience, and adventure. Location: Steps from trails, restaurants, and shops — no car needed. Water Fun: Kayaking, paddleboarding, swimming, and more nearby! Walkability: Everything you need is a short stroll away. Perfect for families, couples, or small groups. As a Superhost, we're here to make your stay easy and memorable.

Top Guest favourite
A spacious living area features two brown leather sofas arranged around a decorative area rug. Exposed wooden beams adorn the ceiling, while natural light fills the room through large windows. Artwork is displayed on the walls, adding character to the inviting space.
Cabin in Okoboji
4.93 out of 5 average rating, 87 reviews

Okoboji Bunker House

Your family will be close to everything when you stay at this centrally-located place. This rustic cottage has a Western log cabin feel. The home is right across from East Lake Okoboji and is just walking distance to Barefoot Bar and Parks Marina! This spacious 4 bedrm/2 bath home offers laundry facilities, 4 queen beds, bicycles, outdoor wood-burning fireplace w/wood, natural gas grill, and most home furnishings including, but not limited to, pots, pans, silverware, toaster, coffee pot, etc!

Guest favourite
Home in Arnolds Park
4.98 out of 5 average rating, 80 reviews

Family Cabin Close To Waterpark, Fully Renovated!

Endless Summer is the ultimate kids cabin at Bridges Bay Resort and Waterpark. Our goal is to provide families with a comfortable and convenient place to gather and make new memories. Enjoy all of the amenities of Bridges Bay including 6 daily indoor/outdoor waterpark passes, arcade, zip line, fitness room and fishing ponds. On top of that our place has entertainment for all ages such as a giant connect 4, a putting green, bags game, kids fishing poles, board games, books, kids toys and more!

Guest favourite
An open-concept living area is presented, featuring a cozy seating arrangement with a gray sofa and circular coffee table. A well-equipped kitchen with modern appliances and an island bar is visible, alongside a dining table that accommodates several guests, all illuminated by natural light.
Home in Arnolds Park
4.95 out of 5 average rating, 138 reviews

Bright & Comfortable 3- Bedroom Bridges Bay Cabin

Newer single level, 3-bedroom, 2-bath house at the Bridges Bay Resort in Arnolds Park, Iowa. Bright, comfortable furnished space that is the perfect Okoboji vacation hub. Sleeps 10 comfortably. Screened-in game and entertainment garage space, plus back patio for grilling and relaxation. Neighborhood pool across the street and indoor/outdoor water park, arcade, gym (remodeled in 2020) and on location bars/restaurants are a 5-minute walk or short drive away. Six free waterpark passes each day.

Guest favourite
A two-story cabin is showcased, featuring a combination of light-colored siding and a grey shingle roof. A well-maintained lawn surrounds the home, and a concrete driveway leads to an attached garage. Clear blue skies serve as the backdrop.
Cabin in Arnolds Park
4.86 out of 5 average rating, 119 reviews

Okoboji Bridges Bay Cabin on Pond

Awesome cabin in Bridges Bay Resort located on the fishing pond. 2 enclosed bedrooms plus loft. Nicely finished garage provides additional hang-out space. 2 kayaks provided for pond use. Includes 6 passes daily to water park, walking distance to Bridges Bay restaurants and lake access. Over-sized patio with Weber gas grill. Extended driveway for up to 4 cars (street parking not allowed). Washer/dryer available in unit for guest use. Booking guest must be 25 or older, parties not allowed.

Top Guest favourite
A serene sunroom features large windows that provide views of the lake and surrounding trees. A cozy seating area with a plush sofa and a low coffee table is present, while wooden ceiling beams and ceiling fans add to the inviting ambiance.
Home in Spirit Lake
4.93 out of 5 average rating, 99 reviews

Breathtaking 3-14 Quiet Lakehome

Relax with the whole family at this peaceful place to stay. Enjoy a stay on a Quiet lake that is just minutes away from all the action. This Lake House boasts TWO 3-season rooms, an open concept with so many great views of the lake. Newly renovated, yet loads of charm and wonderfully decorated. Come relax and have a blast while you play games, read books, let the kids play with toys, or snuggle up and watch your favorite show. There is even a Sauna which might be just what you need.

Guest favourite
Condo in Arnolds Park
4.98 out of 5 average rating, 105 reviews

Rare POOL SIDE/LAKE VIEW condo -Bridges Bay Resort

Newly remodeled 3 bedroom. 2 bathroom condo at Bridges Bay Resort. Imagine grilling out on the patio while you play yard games, swim in the pool, and look out over East Lake Okoboji. Spend your days exploring the many outdoor activities that Okoboji has to offer, enjoying Boji Splash water park, or simply relaxing by the lake. This rare poolside and lake view condo comes with all the amenities! There is so much to do all year round. Let our vacation home be your next relaxing get away!

Guest favourite
Apartment in Arnolds Park
4.97 out of 5 average rating, 90 reviews

Cozy 1 bedroom suite with patio.

Looking for that cozy spot for a weekend away? Youve found it! Great little patio so you can relax and enjoy the outside before you head out to the local attractions. Queen Room with the opportunity to cook in the room or heat up something later. This is a great location for you to relax and enjoy your time away. Walk to the Ritz, Okoboji Store, Smiles with Miles, Okoboji Dough Factory are within seconds of parking your car. Take a selfie at the selfie walls inside the Stay Suites.

Top Guest favourite
A grassy area is seen from beneath a wooden deck, offering a view of the street and lush trees. The scene features a clear sky with scattered clouds, and paths lead toward Gilbert Park and East Lake Okoboji in the distance.
Apartment in Spirit Lake
4.96 out of 5 average rating, 24 reviews

Amazing Grace.LL

Clean, quiet, spacious flat with a view of East Lake Okoboji. Gilbert Park across the street, a short walk to downtown Spirit Lake, and only 4 blocks from the bike trail. This apartment has it's own unique flair with a beautifully updated walk-in tile shower, kitchenette, big screen tv, wi-fi, 1 bedroom queen bed, and a den with a full-sized futon. This apartment is perfect for the professional looking for a monthly home away from home. This is NOT a party house.

Top Guest favourite
A spacious lake cabin is situated alongside a large structure, possibly a garage. The property is surrounded by well-maintained greenery and trees, with autumn leaves scattered across the yard. A thoughtful landscaping design is evident around the cabin's entrance.
Cabin in Orleans
4.93 out of 5 average rating, 84 reviews

Barleans - Cozy Cabin Conveniently Located

1 bedroom 1 bathroom lake cabin with plenty of parking. Ice Fishing or Hunting Bungalow! Perfect for families or weekend getaways with 2 additional queen pull out sleepers. In the summer months enjoy the large patio by the barn, sand box for kids, and barleans bar for adults on the property (coming soon). Great for campfires and grill outs. Numerous amenities. RV hookup available upon request. Make some memories at this unique and family friendly place.

Top Guest favourite
A charming retreat is showcased, with a circular design and a clock tower prominent on the roof. Lush greenery surrounds the structure, complemented by vibrant orange and yellow flowers in the foreground. Two wooden chairs are positioned on a porch, inviting relaxation.
Home in Okoboji
4.93 out of 5 average rating, 60 reviews

On Julia Street

Step into a world of comfort and relaxation at our charming retreat on Julia Street. Nestled in the heart of Okoboji, this serene haven invites you to unwind and recharge amid picturesque surroundings. As you enter, you'll be greeted by a cozy interior adorned with modern amenities and thoughtful touches throughout. Close to the action and within walking distance of many of the Lake's Area favorite places.

Popular amenities for Dickinson County holiday rentals

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