Holiday rentals with a pool in Wisconsin

4.86 out of 5 average rating, 180 reviews

Tiny home in La Crosse

Come unwind with us at Kindred Tiny House.

Come unwind with us at Kindred Tiny House. Take in beautiful Wisconsin outdoors in a Scandinavian-inspired tiny home themed with simplicity & relaxation in mind. This home features a full bath, kitchenette, & room to sleep three. Step out to experience a wooded private outdoor space featuring a fire pit, access to trails, & seasonally available shared access to a large salt water pool. Located approximately 15 minutes from downtown La Crosse, you’ll be able to enjoy all the area has to offer!

4.97 out of 5 average rating, 124 reviews

Cabin in Nekoosa

Hot Tub | Fire Pit | Smart TV | Fireplace| BBQ

Explore everything beautiful Rome has to offer in this 4BR, 3BA log cabin with a firepit, BBQ and smart TV. Cozy up to the fireplace or relax in the hot tub to end your day! Custom designed with thoughtful touches, this vacation home in Central Wisconsin easily fits up to 10 guests in 6 comfortable beds. Guests have nearby access to 5 golf courses, hiking trails & the resort amenities of Lake Arrowhead including private beaches and an outdoor pool! This space has everything for a memorable stay.

4.97 out of 5 average rating, 140 reviews

Cozy LG Retreat! King Bed! Fireplace! WiFi!

Your cozy & relaxing getaway begins in a newly redesigned condo with balcony (courtyard view), and is conveniently located between Lake Como and Lake Geneva in peaceful Interlaken Resort community! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, and more! The resort community is located by Lodge Geneva National (formerly The Ridge Hotel), which adds additional restaurants and available amenities at an additional charge. Walk to the

4.78 out of 5 average rating, 169 reviews

Cabin in Warrens

Villa Jellystone/3Bears - ATV Trails, Water Park

We have added 2 air purifiers, H13 True HEPA air purifier. Our cabin is located next the Jellystone Yogi bear campground and Three Bears Lodge. *There is a 2nd villa right next door to us that sleeps 10 if you have a large group and need 2 villas* New furniture in living room. 50 inch TV w/Ruko 2 private bedrooms with queen beds, on main floor. TVs in both rooms/w Ruko 5 twin beds and bathroom upstairs in the loft. 40 inch TV w/Ruko , DVD player Fully stocked kitchen. Washer/dryer. Grill.

4.98 out of 5 average rating, 127 reviews

Home in Prairie du Chien

Ohio Street Retreat- hot tub, massage chair, pool

After a fun day in The Driftless Area, come relax and unwind in Prairie du Chien. Beautifully decorated 2 bedroom home with a spacious kitchen, large island, dishwasher, washer/dryer & 5' walk in shower. We supply all cooking/baking items/utensils so all you need are your food, drinks and ingredients. Full high-speed internet with smart TVs in both bedrooms and living room. Outdoor pool (seasonal), hot tub and massage chair. We love dogs too, so we provide a dog run (there is a pet fee).

4.95 out of 5 average rating, 103 reviews

Cabin in Lynxville

River Run Ridge 5 bed/4 bath w/ hot tub & pool!

Come enjoy the breathtaking views all around the living and dining area of this beautiful home located in Lynxville. This upgraded home with 5 bedrooms and 3 baths, can accommodate up to 14 people . Spacious dining/living area for family gatherings, bonus projector room in lower level and large deck to sit and enjoy the view of the Mississippi, be it day or night while grilling out in a summer night. Fully stocked for your getaway. Close proximity to many local attractions and boat ramp.

4.99 out of 5 average rating, 227 reviews

Penthouse, Lakefront, Pontoon Ride, No Resort Fees

NO RESORT FEES + FREE PONTOON RIDE + KAYAKS AND STAND UP PADDLE BOARD Penthouse with AMAZING VIEW Nestled in the heart of Wisconsin Dells, this condo offers breathtaking views of Lake Delton. Newly furnished with comfortable and stylish furniture, this condo ensures a cozy stay with smart TVs, jacuzzi tub, fireplace and functional furniture. This condo is just steps from the beach and centrally located in Wisconsin Dells, just blocks away from Noah’s Ark Waterpark and other businesses.

4.99 out of 5 average rating, 148 reviews

The Wanderlust at the Sunset Cove

Riverfront one bedroom condo in a tranquil area of Downtown Wisconsin Dells. Take a stroll near the beautiful River Walk and enjoy the magnificent scenery and unique attractions of Downtown Wisconsin Dells. Whether you need a few days to relax and decompress or if you are in town for business or games, our condo offers a fully equipped kitchen, a king size bed and a queen size pull out couch . There is an indoor community pool, hot tub and sauna. There is also a seasonal outdoor pool .

4.88 out of 5 average rating, 112 reviews

Home in Sussex

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Discover the allure of our 5BR Wisconsin retreat, where spacious elegance meets comfort. Enjoy a gourmet kitchen, a grand living room, and a game room with free arcade play. Dive into relaxation with our private, heated indoor pool. Outdoors, the terraced patio and fire pit invite memorable moments. Minutes from Milwaukee, our home is an idyllic base for both peaceful relaxation and lively exploration. Perfect for family or corporate escapes, it's a stay you'll cherish.

4.97 out of 5 average rating, 155 reviews

Magnificent waterfront views & cozy fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

Guest suite in Wisconsin Dells

4.84 out of 5 average rating, 380 reviews

★GLACIER CANYON RESORT WITH WATER-PARK AMENITIES★

Welcome to Wisconsin Dells and the city of Baraboo, a popular vacation playground best known for its beautiful river scenery, endless entertainment options and larger-than-life water parks. Inside the Wilderness Territory a theme park where family fun reign supreme is a top ranked indoor and outdoor water park. You can also find some excellent shopping, visit wineries for tastings, practice your swing on local golf courses, and win big at Ho-Chunk Casino.

4.96 out of 5 average rating, 188 reviews

Relaxing Villa with Amazing Amenities!

Resort day passes included with booking! Hot tub, indoor and outdoor pool, outdoor bar and fire pit, sauna, the list goes on! Only five minutes from downtown Lake Geneva, this second floor condo offers the best of both worlds. Enjoy the laid back Lake Como attractions, or have a blast in Lake Geneva! This hidden gem is perfect from golfers (only 5 minutes from Geneva National) to families. Give us a try, and enjoy a discount on your second stay!

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Popular amenities for Wisconsin rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 25 reviews

Home in Sturgeon Bay

Bay Cliff Cottage Retreat

MeganRating, 5 stars2 weeks ago

Great quiet, private location with unbeatable views of the bay! House was well equipped and matched the provided photos. Would definitely recommend!

5 out of 5 average rating, 13 reviews

Home in Lake Geneva

Elssys Ranch 80 Acre Lake Geneva Retreat

AlexRating, 5 stars3 weeks ago

We had an amazing time at Nick’s property, and Nick was a great host from booking through the end of our stay. The property is incredible and a perfect location between Lake Geneva and Lake Delevan. We used the pool and fire pit every night, and the space comfortably fit 12 guys for our golf trip. We will definitely be looking to rent this property again in the future! Thanks for everything Nick

4.92 out of 5 average rating, 140 reviews

Home in Milwaukee

The Gem of Brewers Hill w/hot tub & seasonal pool

GerryRating, 5 stars2 weeks ago

Excellent location and plenty of beds and bathrooms.

4.98 out of 5 average rating, 64 reviews

Home in Oshkosh

Hickory on the LakeWaterfront Luxury on Winnebago

RickyRating, 5 stars6 days ago

The stay was quite peaceful and a nice escape. The place was quite clean and well maintained. I would recommend the house for you next getaway

5 out of 5 average rating, 30 reviews

Home in Nekoosa

Luxury 4BR – Game Room, Theater, Near Golf & Lake

AnnaRating, 5 stars3 months ago

Angela was wonderful! The home was beautiful, and spotless! She supplied many cooking utensils and lots of kitchen supplies which made meals easy! Our group of 10 stayed here comfortably and we can’t wait to come back! Angela responded promptly with any questions we had and made sure we felt welcome! The price is incredible, this home can’t be beat!

4.93 out of 5 average rating, 30 reviews

Home in Danbury

Hangar House-Near the Clubhouse and Airstrip

JosephRating, 5 stars1 month ago

We had an excellent stay at the house! Very clean and comfortable. We enjoyed walking across the street to eat at the club. The area is beautiful and we can’t wait to stay here again.

4.88 out of 5 average rating, 215 reviews

Home in Wisconsin Dells

Spacious Pine Cabin at Island Pointe

KellyRating, 5 stars1 month ago

Cute little cabin near a lake in the WI Dells. It was too cold to use the lake or the pool but they were both very convenient.

4.88 out of 5 average rating, 24 reviews

Home in Two Rivers

Cool City, Warm Pool

KRating, 5 stars2 months ago

Our family had a lovely stay at this Airbnb. The pool was the highlight (especially during a cold and rainy spring break week) but the whole house was cozy and extremely well stocked for cooking and entertainment. Jill was a great communicator and offered us early check in and late check out. Lake Michigan is minutes away. Highly recommend this Airbnb!

Show all

Apartment rentals with a pool

4.91 out of 5 average rating, 96 reviews

Lakefront Condo - Private Beach | Boat Slip| Pool

DusanRating, 5 stars5 months ago

Amazing place .highly recommend!!

4.94 out of 5 average rating, 17 reviews

Condo in Wisc Dells for 10-14 ppl

JosueRating, 5 stars2 weeks ago

Me and my friends felt like we were at home and also being able to make such great memories

4.83 out of 5 average rating, 83 reviews

Entire Condo Sleeps 6 at Tamarack

AnnaRating, 5 stars2 days ago

We loved this location for a girls weekend. It was very peaceful with lots to do on the property. Close to Ishnala and Mirror Lake State park.

5 out of 5 average rating, 18 reviews

Chic Condo in Lake Geneva.

ZoeRating, 5 stars1 week ago

I absolutely loved staying here! Morgan was extremely responsive and super friendly whenever she reached out! The condo was very clean and had everything we needed for a nice weekend trip! And, compared to a lot of other places in Lake Geneva, I think the condo was very reasonably priced. I would absolutely love to come back here :)

4.93 out of 5 average rating, 183 reviews

Apartment in Egg Harbor

DoorCo Happy Place @Landmark Resort

RoseRating, 5 stars5 days ago

Quiet, restful location. The little porch was a nice touch. On the small side. Perfect for a couple, as I can't imagine sharing the space with kids. The location is perfect for exploring the Door. We did not use the pools, but would have if we remembered our suits! Well stocked kitchen if you feel like cooking, but no salt/pepper could be found. A pleasant stay overall!

4.83 out of 5 average rating, 232 reviews

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

KathrynRating, 5 stars2 months ago

Really nice apartment in a beautiful location right on the river. So peaceful in the morning. Very easy to find and get into. Exactly as described. Coffee pot with coffee bags, sugar and creamer including microwave popcorn and chocolate biscuits. Nice welcome pack. Lots of cutlery crockery and pans but didn’t see any oil or condiments. If you are going to cook you’d need to bring some. Had problems with the tv instructions but after contacting Ashley somebody came to the condo within 15 mins and sorted out for us. May need to update instructions or check settings haven’t been touched to save inconvenience. Just to note the smaller bedroom has the boiler in it which is very noisy. We had ear plugs so was ok for us but if you come in the cold weather and need heating you would need to bear in mind. Overall a lovely stay in a quiet area of town within a short walk to all amenities. Would recommend.

4.93 out of 5 average rating, 74 reviews

Dells Retreat - A Romantic Haven- Luxury Living

VivianaRating, 5 stars2 weeks ago

We loved our stay here! They had Splash Passes which gave you “buy 1, get 1” for multiple different places within the dells area! It was so helpful and made our trip so much more enjoyable!