Holiday rentals in Iola

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Iola

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

1 of 1 pages1 / 1

Top guest favourite

A functional kitchen area features an island with seating for four. Light wood cabinetry contrasts with the dark countertop. A stone accent wall enhances the space, and modern appliances are visible, creating a welcoming environment for meal preparation.

Cottage in Wittenberg

4.94 out of 5 average rating, 126 reviews

River Road Peaceful Country Cottage WiFi, smart TV

Our Cottage is secluded in the country near a river, with no other houses nearby, just Wildlife and peace and quiet. A Front porch for relaxing and a newer deck on the back for cooking out or watching the wildlife. The inside has just been completely updated, with a few original antique touches. Upstairs there are 3 bedrooms and a half bath, downstairs a master bedroom with bathroom, open concept living room kitchen area. And Main level laundry area. Ready for a long vacation or a quick getaway.

LocationFamilySkiing

Top guest favourite

The exterior of the home showcases a single-story structure with a stone facade and a welcoming front door. A well-maintained lawn is bordered by a concrete walkway, with mature trees adding greenery to the setting. A chimney is visible on the roof.

Home in Waupaca

4.95 out of 5 average rating, 233 reviews

Entire House, hot tub, dogs, way cool bathrooms.

Wonderful open concept living featuring eat in kitchen/dining area, living space with a beautiful gas fireplace, fenced in yard, clamshell & sunken tub showers, and tasteful décor, relaxing. Waupaca is centrally located to many places you may wish to go. We have a beautiful park system, 22 connected lakes, wonderful culture, arts, library, main street, and best of all friendly people. Outdoors is fishing, silent sports, kayaking, tubing, hiking trails, and so much more. ATV/UTV friendly.

FamilyLocationCheckout

Top guest favourite

A spacious studio apartment is highlighted by a large, unique chandelier above the bed. Natural light floods the area through multiple windows, illuminating the polished wooden floors and cozy seating arrangement. The open layout includes a kitchenette visible in the background, enhancing the inviting atmosphere.

Loft in Amherst

4.96 out of 5 average rating, 226 reviews

Tiny Town Bakery Flatlet

Ever wanted to see what goes on in a commercial bakery? Imagine waking to the aroma of baking bread and cinnamon rolls? Get a bird's eye view into the kitchen of the Village Hive Bakery Kitchen while staying in the newly renovated "flatlet". Salvaged & repurposed building supplies used to create a unique studio apartment above the bakery retail. Guests can enjoy the retail farmhouse table and comfortable seating space by the Main Street picture window. Cooking/baking classes available.

ValueLocationKitchen

Superhost

A comfortable living area features a gray sofa with a red accent pillow, two light green chairs, and a round ottoman with decorative elements. Large windows allow natural light to fill the space, framed by soft, flowing curtains. A warm atmosphere is created by the natural hues of the furniture.

Home in Waupaca

4.94 out of 5 average rating, 116 reviews

Center Street Nest

Enjoy a cozy experience at this centrally-located classic home near downtown Waupaca. This quiet convenient retreat features a well-stocked retro kitchen, original woodwork, two peaceful bedrooms (upstairs), newly updated bathroom (main level), washer & dryer (basement), and a back porch for safe keeping of all your adventure necessities. Hosts live in adjacent unit, have decades of experience in customer service, and hope your time spent in this beautiful area is stress-free and memorable!

ValueLocationComfort

Guest favourite

A warm sleeping area features knotty pine walls and a spacious bed adorned with floral accents. Two bedside lamps provide soft lighting, while a sofa is positioned near a shelf of books. A large area rug adds comfort to the floor, enhancing the cozy atmosphere.

Home in Amherst

4.87 out of 5 average rating, 102 reviews

Indiglo-Unique Earth Home with fenced in courtyard

Experience Amherst like never before when you book this vacation rental. This 3-bedroom, 2-bath custom earth home (under ground) was Amish built in 1968. Uniquely designed w/ a western lodge feel and knotty pine throughout, this home still carries modern amenities like Smart TVs, free WiFi, and a fully equipped kitchen. The upper annex facing east overlooks the courtyard with a grill and sitting area, while the main living area captures natural light. Book today & enjoy this adventure!

FamilyLocationAccuracy

Guest favourite

A cozy bedroom features a metal framed bed with fresh linens and a decorative throw. Light-colored walls contrast with a wood accent wall. Two large windows provide natural light, with sheer white curtains framing the view. A bedside lamp and a small side table complete the space.

Guest suite in Waupaca

4.92 out of 5 average rating, 284 reviews

Adventure Outpost for 8 near Chain O Lakes

We’re located just outside of town with easy access to all that the beautiful Waupaca area has to offer. Only 10 minutes from the Chain! The property is surrounded by Maple and Oak mature forest yet has an open meadow perfect for picnics and star gazing. It is beautiful here; you can rest and recharge close to nature. Adventure Outpost is totally updated and designed for your comfort and convenience. The space is cozy, light and refreshing and big enough for the whole family!

ValueFamilyParking

Top guest favourite

A wooden dock extends into a serene lake, framed by tall grasses on either side. The sun shines brightly overhead, casting reflections on the water's surface. Lush trees line the opposite shore, contributing to the peaceful atmosphere.

Cabin in Iola

4.88 out of 5 average rating, 148 reviews

Charming cabin on a lake with 2 bedrooms, one bath

Escape to central Wisconsin in your own private cabin! One bedroom with a full bed and single bed. Second bedroom with a queen bed. Full kitchen. Full use of water toys and kayaks. Toddler toys to entertain the kids. You can also fit 3 to 4 campers on site with plenty of parking. Air conditioning. Central heat and electric fireplace. Refrigerator, microwave, electric stove, coffee pot. Private dock with public boat landing. There is not a beach. Wifi. Now open year round!

ValueFamilyCheckout

Top guest favourite

The exterior of a historic schoolhouse is displayed, featuring a white facade with a green metal roof. A charming open-air porch is visible, along with several windows framed in dark. The surrounding grounds include a grassy area, providing a peaceful rural setting.

Home in Scandinavia

4.95 out of 5 average rating, 182 reviews

Peterson Mill Schoolhouse

The Peterson Mill Schoolhouse is a rural and historic one classroom school converted into a guest house. Located next to a trout stream and operating dairy farm, you can sit on the open-air porch, relax by the creek, or take a walk on the country roads. The Schoolhouse is open year-around, welcoming all who enjoy fishing, biking, hunting, and other outdoor activities. Enjoy your time in the peaceful surroundings or drive 15 minutes to the beautiful Waupaca Chain-O-Lakes.

LocationFamilyTV

Top guest favourite

Home in Waupaca

4.99 out of 5 average rating, 173 reviews

The Raven | Modern Escape To The Woods

Welcome to The Raven, a modern escape to the woods tucked among towering pines near Hartman Creek State Park. Soak in the private hot tub beneath the stars, gather around the fire pit, hike nearby trails, or unwind with records, movies, and woodland views. Just minutes from the Chain O' Lakes, restaurants, and shops, The Raven combines contemporary comfort with the peace and privacy of the Wisconsin woods.

ValueLocationQuiet

Superhost

Home in Stevens Point

4.8 out of 5 average rating, 136 reviews

Lake Cottage-Hike, Mt Bike, frisby golf 1 mi. away

Leave city living for a countryside escape to this remodeled 3-bedroom, 1-bathroom Stevens Point duplex! Featuring a dock on Adams Lake, with beautiful serene surroundings and just 1-mile to Standing Rocks County Park for downhill & XC skiing, mountain biking, and hiking.The neighboring towns of Amherst, Stevens Point and Waupaca offer charming parks, great eats, and activities sure to please.

LocationValueAmenities

Top guest favourite

A spacious wooden lodge is showcased against a dusk sky. Large windows reflect the soft evening light, while a fire pit is placed in the foreground, surrounded by wooden benches. Lush greenery and landscaped stones frame the inviting outdoor space.

Cabin in Iola

4.92 out of 5 average rating, 48 reviews

Cozy log Cabin tucked away in natures serenity

Come and escape to a cozy space full of personality, space, privacy and beautiful scenery. A gem in the heart of Iola, Wisconsin. Absolutely great getaway location for families, couples, business men and women that want to unwind. The home is located on a dead end street so there is minimal traffic. It is truly peaceful and the beautiful surrounding woods will take your breath away.

LocationFamilyGrill

Top guest favourite

A modern kitchen space features a central island with barstools, accompanied by pendant lighting overhead. Nearby, a cozy living area is visible with a sectional sofa and artwork adorning the walls. Natural light fills the room through multiple windows, enhancing the inviting atmosphere.

Flat in Waupaca

4.98 out of 5 average rating, 209 reviews

Contemporary Retreat | Steps from Chain O' Lakes

Mid-century modern meets old-fashioned hospitality. A newly (and lovingly) remodeled duplex in the lakeside hamlet of King. Just steps from the pristine Chain O' Lakes, restaurants, boat-rentals, bars, shopping and more. Perfect for cottage overflow, an extended executive assignment, or road-trippers passing through Central Wisconsin to all points beyond.

ValueFamilyBreakfast