Holiday rentals in Dickinson County

5 out of 5 average rating, 10 reviews

Home in Spirit Lake

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 September 4, 2025.

Top guest favourite

4.94 out of 5 average rating, 18 reviews

Family Fun-walk to everything!

Newly remodeled home with backyard fun for adults and kids with bar shed, firepit, indoor and outdoor games in a quiet neighborhood. Walk to West Lake Okoboji beaches, East Lake Okoboji, Upper Gar, Arnolds Park Amusement Park rides and shops, waterfront restaurants, live entertainment, watersports rentals, sunset cruise, bike path, and convenience store. Boat ramp 2 blocks away. Sunday through Thursday rentals are cheaper and the lakes are less crowded, with most of the same activities to enjoy.

Top guest favourite

Cottage in Spirit Lake

5 out of 5 average rating, 12 reviews

Charming Lakes Cottage in the Woods!

Escape to a serene and tranquil abode with your loved ones. This cozy home is nestled amidst a wildlife refuge and is just a stone’s throw away from Pikes Point State Park, one of the most popular swim beaches in the Iowa Great Lakes region. Located on beautiful Lakeshore Drive, with shopping, and a plethora of restaurants and entertainment options that are available all year round. The property also offers ample outdoor space, parking, and a chance to spot some wildlife in your own backyard.”

4.76 out of 5 average rating, 38 reviews

Okoboji Perfection!

Your family will be close to everything when you stay at this centrally-located house in Arnolds Park that has had a complete renovation! There isn’t a better location to provide you with ALL things Okoboji within walking distance. One bedroom on main floor with twin over full bunk bed and large upstairs open bedroom with one queen, 2 full beds and a couch. Located one block south of Broadway and within walking distance to all the restaurants, bars and entertainment that Okoboji has to offer!

4.86 out of 5 average rating, 111 reviews

Cabin in Arnolds Park

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.

5 out of 5 average rating, 6 reviews

Home in Milford

Okoboji-Fun Vacation Home!

Beautiful house located just minutes away from the lake, amusement park, shopping, and more. With ample room to accommodate up to 12 guests, this home offers comfort and convenience. Whether you’re seeking a peaceful getaway or looking to partake in the fun of Okoboji, this charming house provides an ideal home base for your stay. Game room with ping pong, darts, and bags also ready for you! **HAVE AN EXTRA LARGE GROUP? "Sister" property within walking distance! Message for details.

5 out of 5 average rating, 3 reviews

Flat in Arnolds Park

Coronado 207. Lakefront condo

2 Bed 2 Bath 2nd floor condo LAKESIDE at Bridges Bay. Great location, Closest building to waterpark and restaurants. Everything you need to make you feel right at home: Fully stocked Kitchen, Stove, Oven, Microwave, Dishwasher, Coffee Maker(Keurig), Washer & Dryer, Bath Towels, Gas Grill, Flat Screen TV's in Living room, Master Bedroom & 2nd Bedroom and WiFi. ACTUAL BEDS HAVE ROOM FOR 7. CAN ALSO HAVE ACCESS TO A BLOW UP MATTRESS TO ACCOMMODATE MORE PEOPLE FOR SLEEPING.

4.87 out of 5 average rating, 61 reviews

Okoboji Bridges Bay Cabin Well Stocked!

Okoboji Bridges Bay Resort Vacation Cabin, Boat Hoist, and Golf Cart for Rent. Fully Stocked and Very Clean 3 Bedrooms with Loft acting as a 4th bedroom. 5 Large TV's W/streaming, and Wi Fi. Includes 6 free Water Park Passes. Also, Multiple Cabin Owner/Manager. We have another next door. Great for Large Groups who only want to deal with one host. All of our places are very well stocked like a home away from home. Boat Hoist or Golf Cart rentable for extra fee.

4.93 out of 5 average rating, 28 reviews

Flat in Spirit Lake

Steps to the Lake with a View!

Enjoy a Lakes area stay at this centrally-located rental in Spirit Lake. Bring your boat! A public access ramp is less than a mile away!! Just minutes to Arnolds Park, concerts, golfing, farmers market, restaurants & lively bar establishments! This Upper-level 3 bedroom/2 bathroom rental has its own washer, dryer, dishwasher, full kitchen, and parking space! Two Queen beds, One twin. great for a short stay while you're out enjoying your lakes vacation!

Apartment in Arnolds Park

4.94 out of 5 average rating, 50 reviews

Stunning condo overlooking Lake Okoboji!!

Three bedroom, two bath condo with great lake views at Bridges Bay Resort, the premier vacation resort on Lake Okoboji! Relax on the deck overlooking the lake, go for a swim in the pool right next to the condo or spend the day at the waterpark over at the hotel. Your stay in this condo includes six waterpark passes each day of your stay! If this condo is booked for your dates, send me an inquiry. I have two condos and two cabins!

4.96 out of 5 average rating, 56 reviews

House with lake view at Bridges Bay Resort!

OKOBOJI VACATION CABIN: Wonderful vacation cabin in the Bridges Bay Resort complex! This vacation home has 4 bedrooms, 2.5 bathrooms, and is in the heart of Okoboji's most popular vacation destination. Our cabin is directely down the road to all the resort amenities, meaning you can walk to all the pools and restaurants! Enjoy this cabin year round with your family or friends!