Family-friendly holiday rentals in Dickinson County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Dickinson County

Guests agree: These family-friendly homes 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

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.

4.93 out of 5 average rating, 46 reviews

Guest favourite

Home in Okoboji

Nautical Okoboji House

Walk to Barefoot Bar! Spacious 3BR/3BA Park the cars and leave the keys! Located directly across from the iconic Barefoot Bar, our "Nautical Okoboji House" puts you at the heart of the action. Why guests love it: Privacy for Groups: With 3 full bathrooms for 3 bedrooms, everyone has their own space to get ready for the lake without the wait. Prime Spot: Located in a lovely neighborhood with a peaceful backyard, fire pit, and gas grill. Includes Wi-Fi, a 2-stall garage, and a large driveway!

4.94 out of 5 average rating, 144 reviews

Top Guest favourite

An inviting interior porch showcases a cozy seating area with four patterned chairs arranged around a small table. Natural light filters through multiple windows, illuminating a corner with cushions and a plant. A patterned rug adds warmth to the space.

Cabin in Spirit Lake

Lakefront Cabin | East Okoboji Lake | Private Dock

A historic lakefront cabin on East Okoboji Lake with a private dock, gas fire table, and sweeping lake views. Swim from the dock and wake up with a cup of coffee and the water right outside your door. Inside: a cozy bedroom, a sunlit porch overlooking the lake, a living room with a sleeper sofa, and a functional kitchen. The bike trail is right across the street. Whether you're celebrating an anniversary or simply overdue for a quiet lake weekend, this Okoboji cabin is your home away from home.

4.9 out of 5 average rating, 48 reviews

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

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!

4.92 out of 5 average rating, 104 reviews

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

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.

4.94 out of 5 average rating, 154 reviews

Guest favourite

Home in Arnolds Park

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!

4.98 out of 5 average rating, 96 reviews

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

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.

4.9 out of 5 average rating, 124 reviews

Guest favourite

Condo in Arnolds Park

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!

4.98 out of 5 average rating, 122 reviews

Top Guest favourite

The large deck features a round metal table surrounded by four chairs, each with floral cushions. A stunning sunset reflects on the lake's surface, casting warm hues across the tranquil water, with trees framing the scene.

Home in Spirit Lake

Quiet home on the lake

Enjoy this beautiful, quiet lakeside home in the Okoboji area: A special place for year-around fun and comfort for you and your loved ones. This 4 bedroom, 3 bath, 3000 sq. ft. home has 2 family rooms, fully equipped kitchen, and dining room with seating for 12. Large windows show off amazing sunsets and panoramic views of Center Lake; a special secret retreat in Great Lakes. Upper and lower patios are great for lake-side eating. This home is specifically curated for families.

5.0 out of 5 average rating, 33 reviews

Top Guest favourite

The exterior view of the lake house showcases three levels with a mix of outdoor seating and a hot tub area. White chairs are arranged around a fire pit, while a path leads up to the house, framed by lush greenery and the American flag positioned nearby.

Home in Spirit Lake

East Lake Okoboji House! Hot Tub!

Nestled on the shores of East Lake Okoboji, this charming lake house offers a perfect retreat. Boasting 6 bedrooms, including a loft for 6, and 4 bathrooms, it effortlessly accommodates family&friends. Recently renovated, the interior exudes modern elegance, while the exterior showcases spacious new decks, ideal for lakeside gatherings. Experience comfort and tranquility in this meticulously updated haven, where every detail reflects a blend of style and relaxation.

5.0 out of 5 average rating, 36 reviews

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

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.

4.94 out of 5 average rating, 77 reviews

Top Guest favourite

Cottage in Arnolds Park

Arnolds Park Cottage with Lake Views

Relax in this newly renovated Arnolds Park cottage with beautiful lake views from the porch. Walk to Arnolds Park Amusement Park, Oak Hill Marina, Broadway restaurants and nightlife, or enjoy nearby concerts from the back patio. With a comfortable, family-friendly layout and an unbeatable location in the heart of Okoboji, it’s the perfect home base for lake days, weekend getaways, and family vacations.

5.0 out of 5 average rating, 14 reviews