Iola Holiday Rentals

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Holiday Rentals in Iola

Relaxing Cottage Steps From the Lake

9.4 out of 10, Exceptional, (67)
"We enjoy staying here we look forward to being there again in the spring of 2025"
Relaxing Cottage Steps From the Lake

Lakeside Iola Hideaway: Stunning Nature Views

9.6 out of 10, Exceptional, (20)
"The home greeted us on a warm afternoon and we found the two-bedroom accommodations to a be a spacious, inviting,warmly decorated, comfortable home. Unlike cold motel rooms, this place had a lived-in feel that reflected the pride and love Jannifer, the host, provided. That evening the rising moon slowly smothered a sea of stars that captivated our attention and filled the night with a marvelous glow. The peace and silence of the place was only interrupted by the sounds of fish splashing the...
Lakeside Iola Hideaway: Stunning Nature Views

Wildlife Cabin! Spring-fed Ponds! Apple Orchard!

10.0 out of 10, Exceptional, (17)
"Needed a place where I could unplug and enjoy nature with my dog and the cabin totally had that!!! The cabin was clean and had everything one needed for relaxing. Lots of deer in the apple orchard. Welcome basket with wine and other goodies was a really nice touch and the wood burning stove was already started for me! I will be back"
Wildlife Cabin! Spring-fed Ponds! Apple Orchard!

Cozy log Cabin tucked away in natures serenity

9.8 out of 10, Exceptional, (32)
"We had a wonderful week here with our family. Excellent communication with the host. The house was very clean and plenty of space for our group with everything we needed to relax and enjoy our stay."
Cozy log Cabin tucked away in natures serenity

Green, unique, comfortable, open loft cabin

9.8 out of 10, Exceptional, (185)
"Really neat, fun, cozy place. We really appreciated how eco-friendly everything is. Peaceful place to hang out outside."
Green, unique, comfortable, open loft cabin

Shadow Lake Retreat House ~ Waterfront ~ Includes kayaks, paddle boards, bikes..

10.0 out of 10, Exceptional, (159)
"Beautiful property"
Shadow Lake Retreat House ~ Waterfront ~ Includes kayaks, paddle boards, bikes..

Beautiful modern rustic barn located near state parks and Chain o Lakes.

9.6 out of 10, Exceptional, (160)
"This is the second time we've stayed at the "Moose House" with our group of 9, 65+ year olds. The spacious, open kitchen, dining and living space is perfect for us. The Waupaca area provides a variety of activities for us as well."
Beautiful modern rustic barn located near state parks and Chain o Lakes.

Gorgeous view of Long Lake, Lakefrontcabin hottub fireplace kayaks paddleboards

10.0 out of 10, Exceptional, (35)
"This is our second year staying at this cabin, and we hope to come back for a third! Love that there’s enough space for our group to gather, but enough separate room when we want to spread out. The beds and pillows are comfy, and the deck views can’t be bear. Thanks for a great stay!"
Gorgeous view of Long Lake, Lakefrontcabin hottub fireplace kayaks paddleboards

Secluded Birnamwood Cottage w/ Deck & River Views!

10.0 out of 10, Exceptional, (97)
"The property was as beautiful as portrayed. The home and the communication were wonderful. We would love to visit again to enjoy the peace and quiet, in the nature that surrounded us."
Secluded Birnamwood Cottage w/ Deck & River Views!

Modern Style Lakefront Retreat with Hot Tub

10.0 out of 10, Exceptional, (19)
"This house was everything we could have imagined! It was the perfect setting for a family trip with my sisters, cousin and 81 year old mom. The only issue we had was the multi-level stairs for my mother. We stayed at the home the entire trip and cooked all meals there. Everything we needed was provided. My sister did some fishing, we played pickleball in the driveway with the portable net, and enjoyed the beautiful sunrises and the setting harvest moon over the lake. It was definitely a trip...
Modern Style Lakefront Retreat with Hot Tub

Relaxing Taylor Lake Retreat directly on the Chain of Lakes

9.0 out of 10, Wonderful, (15)
"Great place next to all the fun of King and a short drive to downtown waupaca. We had a great time, place had everything we needed!"
Relaxing Taylor Lake Retreat directly on the Chain of Lakes

Gorgeous lodge that offers beautiful view and access to the Little Wolf River

10.0 out of 10, Exceptional, (14)
"This property was beyond our expectation and everything was kept nice and clean!"
Gorgeous lodge that offers beautiful view and access to the Little Wolf River

5 bed/3 Bath Home in the Heart of Fremont! Steps from the beach and boat launch!

10.0 out of 10, Exceptional, (7)
"Our son’s wedding was in Fremont. This location and rental was perfect!!! It accommodated all of our family! Was a great place for all the guys to get ready. We really enjoyed the place!!! Would rent and recommend to others!! Very comfortable! "
5 bed/3 Bath Home in the Heart of Fremont! Steps from the beach and boat launch!

Lion on Otter Lake/Chain O' Lakes Waupaca/Waterfront/Pet Friendly/Private Pier

10.0 out of 10, Exceptional, (4)
"Loved our stay and couldn’t have asked for a better place to stay. The boat and place was awesome for our family stay. "
Lion on Otter Lake/Chain O' Lakes Waupaca/Waterfront/Pet Friendly/Private Pier

Spanish Charm 4bed/3bath Downtown Waupaca!

10.0 out of 10, Exceptional, (4)
"My husband and I stayed in this lovely home with extended family for a family gathering. The layout was perfect for our group. The renovations of the home have been well thought out and absolutely beautifully done. Communication with the owner was terrific, as was the ease of check-in and check-out. There were a few minor issues that I brought up directly with the owner when asked for suggestions or improvements that might make a stay even better. There wasn't much to suggest, and they were...
Spanish Charm 4bed/3bath Downtown Waupaca!

White Lake Home w/ Patio, Fire Pit, Boat Dock!

3.0 star property
White Lake Home w/ Patio, Fire Pit, Boat Dock!

Amazing enchanting historic property

9.4 out of 10, Exceptional, (16)
"Excellent experience. House was exactly as described/pictured. Everything was clean. House has a lot of charm. Host was helpful and communicative. Would absolutely recommend!"
Amazing enchanting historic property

Memories that will last a lifetime!

9.6 out of 10, Exceptional, (34)
"Overall,not bad,could use some work.”Llittle stuff”more for owners,no disrespect.Pictures in listing not accurate.Deck not like pictures at all.Deck, first sight after opening gate.Unfortunately,not good first impression. “Landscaping”in pictures,pretty much non-existent.Furniture & cushions scattered,cushions a little moldy.Looked drab,unwelcoming.Hot tub,not in listing but in notebook,no water,smelled horrible.Basement is really just a basement with beds,and some spiders.Felt a little...
Memories that will last a lifetime!

Lake cabin

9.6 out of 10, Exceptional, (8)
"We had a great weekend in this quirky cabin."
Lake cabin

Cabin Sweet Cabin! Shawano County Wisconsin Lake Cottages

8.6 out of 10, Excellent, (52)
"When compared with what you get to the price paid, this was a good value. The place could use a few up grades but for the most part it was all good. "
Cabin Sweet Cabin! Shawano County Wisconsin Lake Cottages
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Iola you may be interested in

Relaxing Cottage Steps From the Lake

9.4 out of 10, Exceptional, (67)
"We enjoy staying here we look forward to being there again in the spring of 2025"
Relaxing Cottage Steps From the Lake

Lakeside Iola Hideaway: Stunning Nature Views

9.6 out of 10, Exceptional, (20)
"The home greeted us on a warm afternoon and we found the two-bedroom accommodations to a be a spacious, inviting,warmly decorated, comfortable home. Unlike cold motel rooms, this place had a lived-in feel that reflected the pride and love Jannifer, the host, provided. That evening the rising moon slowly smothered a sea of stars that captivated our attention and filled the night with a marvelous glow. The peace and silence of the place was only interrupted by the sounds of fish splashing the...
Lakeside Iola Hideaway: Stunning Nature Views

Wildlife Cabin! Spring-fed Ponds! Apple Orchard!

10.0 out of 10, Exceptional, (17)
"Needed a place where I could unplug and enjoy nature with my dog and the cabin totally had that!!! The cabin was clean and had everything one needed for relaxing. Lots of deer in the apple orchard. Welcome basket with wine and other goodies was a really nice touch and the wood burning stove was already started for me! I will be back"
Wildlife Cabin! Spring-fed Ponds! Apple Orchard!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Iola?

Yes, there are holiday rentals close to the most popular sights in Iola, or you can select a more secluded option if you're looking for a relaxing stay. Iola is known for its restaurants.

What are some of the best holiday rentals that Iola has to offer?

Shadow Lake Retreat House ~ Waterfront ~ Includes kayaks, paddle boards, bikes..: This holiday home rental outside of Iola is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Iola?

While exploring the area, visit family-friendly sights like Wilderness Springs Trout Farm, or get outside and enjoy nature at Brainerd Bridge Park. Central Waters Brewing Company and Waupaca Woods Shopping Mall are a couple of places you'll find in the wider area.

What are holiday rentals like in Iola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Iola. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family trip.