Family-friendly vacation 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 favorite

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

5 out of 5 average rating, 17 reviews

Quiet home on the lake

Enjoy this beautiful 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. Host requests 3-night minimum stay from May 20 until November 4, 2025.

Top guest favorite

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, 136 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.

Guest favorite

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

4.98 out of 5 average rating, 121 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 favorite

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, 115 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.

Guest favorite

Condo in Arnolds Park

4.98 out of 5 average rating, 103 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!

Top guest favorite

A row of three-story condos features multiple balconies with glass railings, providing an outdoor seating area. Large windows punctuate the white and light wood exterior, allowing natural light to enter. A lush green lawn extends in front of the buildings, complemented by a clear blue sky.

Home in Arnolds Park

5 out of 5 average rating, 27 reviews

Bougie Boji

Located centrally in the middle of Okoboji Iowa where you can enjoy all the activities within miles. This 3 story condo has it all! Arnolds Park is across the street, plus restaurants and bars located blocks away! Waking up to a sunset on the deck while you enjoy a nice cup of coffee just around the corner. Live music in the summer is extremely nice to hear from the comfort of the deck, or head on over to see it live. Take ease in this brand new condo with lots of entertaining space!

Top guest favorite

A cozy sleeping area features a black framed bed with light-colored linens. Two decorative pillows with text are placed atop the bed. Soft blue curtains frame the window, allowing natural light to brighten the room. A piece of wall art depicting sailboats is displayed above the bed.

Apartment in Arnolds Park

4.94 out of 5 average rating, 78 reviews

Suite with patio 1 bedroom queen bed

Intimate Suite at Stay Suites with a private patio. We have added several suites to the former 316 building. Stay Suites are in the heart of Arnolds Park, just off Hwy 71 south of the Ritz. We are steps from the public beach and dock. We are 4 blocks from the downtown strip area, you can walk to the night life. You can access our roof top patio on the west side of the 2nd level. This is open to all guests, but you do have your own small deck right off your suite.

Guest favorite

A green, two-story house sits elevated on a porch, framed by large trees. The exterior features large windows, allowing natural light inside. The surrounding yard is grassy, offering a spacious area for relaxation and outdoor activities.

Vacation home in Milford

4.92 out of 5 average rating, 26 reviews

Adorable Okoboji Guest House

The first floor is accessed by outside stairs into a massive porch. Perfect place to hang out and watch the deer. A set of stairs inside takes you to the second bedroom upstairs. The accommodations are perfect for two couples or a family of 4-5. Come to Okoboji to walk the nature trails (100 yards away), ride the bike trails (100 yards away), kayak (located on the canals), or boat (Emerson Bay boat ramp one mile away).

Top guest favorite

An open-concept living space is displayed, featuring a large kitchen with an island, dining area with a wooden table, and a comfortable black sofa. Natural light enters through multiple windows, highlighting the stone accent wall and the warm tones of the wood finishes.

Home in Arnolds Park

5 out of 5 average rating, 14 reviews

Premier Location with Lake View

Location!! Park the car for your stay, you won't need it. The Inn, Oak Hill Marina, and Lake Minnewashta are across the street. West Lake Okoboji, Central Emporium, the beach, Arnold's Park Amusement Park, The Roof Gardens, the Green Space, and Maxwell's beach cafe are a 5 minute walk. Broadway street with coffee, wine, nightlife, and restaurants is also conveniently within walking distance.

Guest favorite

A rustic barn door painted in navy blue features welcoming text that reads 'Welcome to our Lake Retreat.' The door is situated in a hallway, and the adjacent wall is finished in a neutral color, contributing to the inviting atmosphere.

Apartment in Spirit Lake

4.89 out of 5 average rating, 287 reviews

Center Lake Retreat Entire Lower Level Walk Out

As ofJuly 1, 2021 we moved into this beautiful Lakeside home. The AIRBNB is NOT our entire home but it is the entire lower level which is our home. Gorgeous, private lakeside views. It is spacious with a private entrance if suitable, large kitchenette, family room, dining room, 2 bedrooms, bath/shower full bathroom. Lakeside access. There is complete privacy with a Barn Door closure.

Guest favorite

The kitchen features dark wood cabinetry and white countertops, equipped with modern appliances including a refrigerator, microwave, and oven. A stainless steel sink is situated in the island, while coffee-making equipment is visible next to the countertop. Natural light illuminates the workspace.

Condo in Spirit Lake

5 out of 5 average rating, 6 reviews

Easy Iowa Great Lakes Area Getaway Unit E

A perfect place to unwind after a day of adventure! This brand-new 2 bed, 2 bath unit in Spirit Lake offers over 1,070 sq. ft. of modern comfort. Located minutes from the Iowa Great Lakes, enjoy easy access to boating, beaches, trails, and dining. Featuring a full kitchen, in-unit laundry, and stylish finishes—your relaxing retreat awaits in this newly built 8-plex community.

Superhost

A white door is framed by a light-colored wall, with a simple number 'B' displayed on the left side. The door features a modern handle and a keypad entry system, offering a convenient entrance to the space.

Apartment in Spirit Lake

4.72 out of 5 average rating, 95 reviews

Nice space, close to the lakes!

Two bedrooms with an additional pullout couch. Close to East Okoboji Lake, the splash pad at Memorial Park, and downtown shoppes and restaurants. Space for on street parking or off street parking in the back. No centralized air conditioning, but one window unit in the dining area and ceiling fans in the living room and both bedrooms. Great for families!