Vacation rentals with a pool in Wisconsin

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Wisconsin

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Tiny home in La Crosse

4.94 out of 5 average rating, 123 reviews

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!

Guest favorite

Cabin in Nekoosa

4.97 out of 5 average rating, 105 reviews

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.

Guest favorite

Condo in Egg Harbor

4.93 out of 5 average rating, 171 reviews

DoorCo Happy Place @Landmark Resort

Welcome to this wonderful, full of positive energy and relaxing resort! The condo is a great place to relax, explore and rejuvenate! 1 bedroom with a queen size bed and queen sleeper sofa in the living room and fully equipped kitchen make enough room for 4 guests. The resort is a great place to enjoy- 1 indoor pool, exercise room and a game room located in the main building, hot tub, sauna in each building, 3 HEATED outdoor pools open seasonally (May- August), tennis court, playground, a trail.

Guest favorite

Home in Somerset

4.99 out of 5 average rating, 246 reviews

Resort LeMire Pool, hot tub and golf carts!

Secluded vacation style home on 50 acres of woods, tree farm and rolling hills-approx. 3 miles of trails. 3000 square foot home with 3 bedrooms plus a twin trundle (lower level), plus 2 auto-blow up queen mattresses and newly remodeled kitchen and living area. Pool, hot tub, in ground trampoline, basketball court, 70’ slip and slide, 2 golf carts! The hot is filled with fresh water for each reservation. Entire property! No pets. Text for video. Six,5, one. Three, 4, 3. Seven, 6, 4, three.

Guest favorite

Condo in Wisconsin Dells

4.97 out of 5 average rating, 213 reviews

1BR Riverfront w/in-room jacuzzi, pool & hot tub

Hello, welcome to our home! Our 1-BR riverfront condo offers a peaceful retreat, just a short walk from downtown. It's perfect for up to 4 guests with a queen bed, an in-room Jacuzzi, and a queen pullout sofa bed. Enjoy the convenience of a full kitchen and bathroom. Relax on the patio, grill your favorite meal or sip a cup of coffee and soak in the view of Crandalls Bay. Our indoor pool, hot tub, and sauna are open all year, and the outdoor pool is available from Memorial Day to Labor Day

Guest favorite

Condo in Lake Geneva

4.98 out of 5 average rating, 196 reviews

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

Guest favorite

Condo in Wisconsin Dells

4.88 out of 5 average rating, 264 reviews

The Docksider for Couples & Young Families

NO SMOKING The Docksider is the original Williamson Family Condo. Located right by the boat docks, this is perfect for a quick getaway as a couple or bring the kids. The property is situated right on beautiful Lake Delton in a quiet neighborhood in the heart of the Dells. The property has both indoor and outdoor (open seasonally only) pools and hot tubs for your year-round enjoyment. In the summer you are just steps away from the private beach and you can fish from the docks or the ice.

Guest favorite

Home in Prairie du Chien

4.99 out of 5 average rating, 105 reviews

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).

Guest favorite

Condo in Wisconsin Dells

4.98 out of 5 average rating, 124 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 .

Guest favorite

Condo in Lake Geneva

4.98 out of 5 average rating, 120 reviews

Magnificient views in a Lakefront condo, 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. Your stay promises a perfect balance of peaceful relaxation and recreational activities creating unforgettable memories in this beautiful Wisconsin setting.

Guest favorite

Condo in Lake Geneva

4.97 out of 5 average rating, 106 reviews

Lake Geneva Retreat! King Bed! Fireplace! WiFi!

Your cozy getaway begins in a newly remodeled, ground level condo with patio, conveniently located between Lake Como and Lake Geneva in Interlaken Resort! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, and more! The resort community is located by The Ridge Hotel, which adds additional restaurants and available amenities at an additional charge. Many local areas to explore & visit will await your arrival.

Superhost

Home in Sussex

4.87 out of 5 average rating, 101 reviews

Amazing Five Bedroom Milwaukee Vacation Home!!

Treat your friends and family to this five-bedroom vacation home just a half-hour from downtown Milwaukee on more than one acre of park-like, private surroundings. Guests of all ages will love the decked-out game room, the huge indoor pool and the comfy living space, with lots of room to spread out. Plus, you’re just 30 minutes from downtown. It’s all the peaceful feels of a country setting with the amenities of the city (think Uber, UberEats, and more).