Family-friendly holiday rentals in Dickinson County

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.

Cabin #5

LOCATION, LOCATION, LOCATION! Row 1 Cabin #5 has 2 bedrooms with loft and sleeps 12. You will love this cabin with 2 bathrooms, open floor plan, vaulted ceilings, furnished kitchen, washer/dryer, and a finished garage space for hanging out. Head to the backyard for a BBQ on the patio, games in the greenspace and additional parking. Resort amenities include 6 daily passes, Lake Okoboji access, outdoor pools with slides and swim-up bar, an indoor waterpark, gym, arcade and on-site restaurants.

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.

In the heart of Arnolds Park - walk everywhere!

Park the car & walk to everything when you stay at this updated & spacious condo. You can’t beat this location. Stay directly across from Arnolds Park Amusement Park, steps from Preservation Plaza concerts, the boardwalk, bars, restaurants, and the beach. Park once — walk everywhere and soak up the best of Okoboji. You have the entire condo to yourselves with access to a pool right out the front door. Enjoy the large kitchen and living area with all amenities needed to prep meals! Sleeps 10!

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.

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.

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!

3 bedroom King Suite at Stay Suites-Browns Bay

Stay Suites are in the heart of Arnolds Park. We have added Multiple suites on the 2nd level of the former Table 316 Restaurant. These are in addition to our other Stay Properties across the street. Browns Bay Suite offers a comfy king bed with a full bathroom. There are 2 additional rooms, each with a queen bed. There is a full bathroom just off the kitchen. There is a stove, microwave, coffee pot (k cup and grounds) pots and pans. The living room area has couch, chairs and smart TV.

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.

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.

Lakefront Cove | 4BR 3BA Retreat

Welcome to The Lakefront Cove — a beautifully designed, spacious 4-bedroom, 3-bath lakefront home tucked away in a peaceful cove on East Lake Okoboji. Iowa Great Lakes attractions are just minutes away, including historic Arnolds Park Amusement Park, Central Emporium and seasonal Farmer’s Market. Shops, restaurants, live entertainment, walking trails, convenience stores, golf courses and more are close by too. Lake days are the best days!

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.