Holiday rentals in Estherville

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Top-rated holiday rentals in Estherville

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

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Top guest favourite

A welcoming entrance features a covered porch with white railings and steps leading to a grassy area. Decorative plants are arranged alongside a pathway of stones and red mulch, enhancing the cottage's charming exterior.

Home in Spencer

Country Cottage 15 Mins from Okoboji

This spacious cottage is centrally located between Spencer and the lakes area, right off of Hwy 71. The upstairs loft features a queen, full and a single bed, desk, and closet and lots of space. The main level has a full kitchen with dining space, large living room with two couches and a TV, and a full bathroom with washer and dryer. This is a great place for long term stays as it offers your own private accommodations and off-street parking. Note: Due to allergies, No smoking inside, No pets.

ValueFamilyIndoor spaces

4.92 out of 5 average rating, 113 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!

FamilyLocationBack garden

4.93 out of 5 average rating, 108 reviews

Guest favourite

The exterior of the home features a light-colored facade with a welcoming blue front door. Large windows on either side allow natural light to enter. A small staircase leads to the entrance, flanked by neatly landscaped flower beds. A concrete walkway provides access to the front door.

Home in Fairmont

Hummingbird Haven

Welcome to your home away from home in Fairmont! This cozy 3-bedroom house (if you only need 2 bedrooms ask about a discount) sleeps up to 6 and is just one block from the lake—perfect for peaceful walks, fishing, and stunning sunsets. Enjoy fresh coffee from the nearby café and take in the charm of this friendly small town. Clean, comfortable, and fully stocked for families, couples, or business travelers. Relax and unwind after a day of exploring. Located across from Little Red Cabin.

LocationFamilyCleanliness

4.95 out of 5 average rating, 38 reviews

Guest favourite

Home in Emmetsburg

Lula & Bill Legacy Inn-Cozy Vintage Charm in Iowa

Welcome to the Lula & Bill Legacy Inn - cozy historic home with vintage charm in the lakeside town of Emmetsburg. Just minutes from beautiful Five Island Lake, local shops, the family splash park, golf course, and Wild Rose Casino. Perfect for road trippers and families looking for a relaxing stop to rest and recharge. Traveling professionals working in the area are also welcome to contact us about extended stay options. ❤️We care about our guests and are always happy to help.❤️

ValueFamilyCleanliness

4.87 out of 5 average rating, 45 reviews

Guest favourite

A serene lakeside setting features a green lawn with two wooden chairs and a fire pit surrounded by grass. A swing hangs from a tree, and a private dock extends into the water, offering access for swimming and fishing.

Cottage in Spirit Lake

Lakeshore Cottage Waterfront listing!

Fun for the whole family! A fisherman’s haven with great fishing right off the dock. A bunkroom with sleeping for up to 5 kids. Relax around the fire pit at night or sunbathe on the dock during the day. Looking for some toys for the lake? No problem, we have kayaks, a water trampoline or Maui Mat for rent. Bike trails down the road. Longing for some nostalgia, less than 10 miles away is the Superior 71 Drive-In. Endless of fun for everyone!

LocationFamilyGetting around

4.84 out of 5 average rating, 32 reviews

Top guest favourite

Farm stay in Spencer

The Bunkhouse at Hobby Horse Acres

Beautiful rural acreage with private "bunkhouse" located minutes from the Okoboji Iowa Great Lakes, Historic Spencer, and the Clay County Fair, the world's greatest county fair. Enjoy the peaceful setting including outdoor fire pit area, gazebo area, playground, barn with animals to pet, fruit trees, and room to roam. Full kitchen is included. Two private bedrooms and plenty of hang-out space and extra sleeping spaces.

ValueLocationDecor

4.97 out of 5 average rating, 290 reviews

Top guest favourite

An outdoor seating area is arranged around a fire pit with multiple Adirondack chairs, offering a cozy spot for gatherings. A view of the water is visible in the background, enhancing the tranquil atmosphere of the space.

Home in Spirit Lake

Charming and cozy 4-Bedroom home with fire pit

Forget your worries in this spacious and serene newly remodeled 4-Bedroom home, which has a lot to offer for a family getaway or friends retreat. Great fishing is only a block away with entertainment at Arnolds Amusement Park and Barefoot Bar and Grill within a short drive to Okoboji. We want you to come and relax at our home and have lots of fun enjoying all the things Spirit Lake and Okoboji have to offer.

LocationFamilyAccuracy

4.96 out of 5 average rating, 81 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.

FamilyLocationView

4.94 out of 5 average rating, 78 reviews

Top guest favourite

A cozy studio apartment features a comfortable gray couch paired with a small wooden table. The sleeping area includes a spacious bed with white linens, while natural light filters in through nearby windows. A soft area rug adds warmth to the wood-like flooring.

Loft in Fairmont

City of Lakes Loft

Newly constructed studio apartment above our garage. Calm, cozy and sunny interior in a quiet neighborhood setting. We have only lived in Fairmont a short time and we love it! It has a "Hallmark" town feel. You may meet our Labradoodle in the backyard - she is very friendly and will want to say Hi. We look forward to hosting you in this city of 5 Lakes! Cleaning fee included in the nightly rate.

LocationValueSolo travel

4.98 out of 5 average rating, 250 reviews

Top guest favourite

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.

Flat in Spirit Lake

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.

FamilyLocationQuiet

4.9 out of 5 average rating, 367 reviews

Superhost

A newly remodeled cottage is shown, featuring a blue exterior with large windows on either side of a central front door. A small decorative planter is placed by the entrance, while a manicured lawn area extends in front of the home.

Home in Arnolds Park

Okoboji Getaway, a cozy cottage

Keep it simple at this peaceful and centrally-located cottage in the heart of Arnolds Park. Within walking distance of the Amusement Park, an array of local boutiques and shops, beaches, and many options for food and beverage. This newly remodeled cottage is a great place for a weekend getaway!

ValueFamilyNearby

4.78 out of 5 average rating, 88 reviews

Top guest favourite

The exterior of a renovated blue farmhouse is shown, featuring a covered porch with seating. Lush green grass surrounds the cottage, with landscaped areas highlighted by flowers. Mature trees provide shade, and a gravel pathway guides the view toward the welcoming entrance.

Cottage in Spirit Lake

Grant’s Cottage on the Coyote Ranch

Just minutes from the attractions of the Iowa Great Lakes, Grant’s Cottage is a perfect getaway for families or couples! Enjoy the character and charm of the fully renovated 1874 farm house, the peaceful park-like setting, and all the modern amenities you’ll need for an Okoboji vacation.

LocationFamilyKitchen

4.96 out of 5 average rating, 45 reviews