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

Guest suite in Spring Green

4.9 out of 5 average rating, 112 reviews

Spring Green River Pines

Spend a few days in the beautiful countryside. A private entrance to the lower level of home (completely separate from our home) that includes a central room, 2 bedrooms with kitchenette, & 1 lg bath. WiFi >500 Mbps speed. Smart 60" TV, Bluetooth Airplay/stream compatible. Parking on sight. Great location 5 min from beautiful downtown Spring Green. Close to APT, Taliesin/Frank Lloyd Wrights Home/School, House on the Rock, WI River, Gov. Dodge State Park and 1/2 hr to Devils Lake State Park.

Oct 7 – 14

G$26,843 GYD per night

Guest favorite

Condo in Egg Harbor

4.93 out of 5 average rating, 151 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.

Dec 13 – 20

G$34,409 GYD per night

Guest favorite

Condo in Lake Geneva

4.98 out of 5 average rating, 174 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.

Nov 2 – 9

G$33,400 GYD per night

Superhost

Condo in Bayfield

4.79 out of 5 average rating, 314 reviews

One Minute Walk to Lake Superior. Brookside #11

Amazing location! This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. Strong Wifi, balcony, AC, CableTV , BBQ, fire pit, and bikes. 1 minute walk to the marina. Bayfield is 2.3 mi from Brookside. Hike or bike the Brownstone trail along the lake. Take the ferry to Madeline, cruise the apostles, Sail, fish, kayak, golf, orchards, ski and more!! The pool and restraunt opens July 1st. 5 minutes from Bayview beach, Mt Ashwabay, Big top and Adventure club Brewery.

Nov 15 – 22

G$23,622 GYD per night

Superhost

Home in Cudahy

4.81 out of 5 average rating, 103 reviews

Make Yourself At Home! Close to Lake & Airport!

I want you to be able to do things here that you can't do in a hotel. If you're grillilng out, having a bonfire or watching movies all night long, you can turn up that volumn as loud as you want all night long! I posted my listing under "entire home" as you do get so much more than just renting "a room". When I have guests I stay in my office or bedroom so my guests feel more comfortable utalizing entire home & yard. In fact, if you don't ask for breakfast, you may not even see me at all.

Feb 25 – Mar 4

G$15,645 GYD per night

Guest favorite

Condo in Wisconsin Dells

4.98 out of 5 average rating, 177 reviews

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

Welcome to our home! Our 1-BR riverfront condo is a peaceful and serene retreat within walking distance of downtown. It accommodates up to 4 guests with a queen bed, in-room Jacuzzi, and a queen pullout sofa bed. The full bathroom and kitchen add convenience to your stay. Step out to the patio and grill your favorite meal while admiring the tranquil view of Crandalls Bay. The indoor pool, hot tub and sauna are open year-round. The outdoor pool is available from Memorial Day to Labor Day.

Aug 6 – 13

G$49,183 GYD per night

Guest favorite

Boat in Racine

4.98 out of 5 average rating, 229 reviews

Charming Sailboat Stay

Welcome aboard our cozy 29' sailboat "Clementine." You will love falling asleep to the gentle rocking of a boat and waking up to the sounds of seagulls while you sip your coffee on the deck. She is setup as a full time Airbnb in a slip at Reefpoint Marina which has amenities like a heated pool with two hot tubs, a ships store, laundry facilities, the delicious Reefpoint Brewhouse restaurant, and top notch shower facilities. Its a quick walk into town for shopping and even more restaurants.

Sep 26 – Oct 3

G$35,136 GYD per night

Guest favorite

Condo in Fish Creek

4.91 out of 5 average rating, 207 reviews

Evergreen Hill A Whirlpool Condo by Pen State Park

It’s all about location and this is the perfect central location for your Door County adventure! 7 A rental condos are set on a lovely, peaceful street in Fish Creek. On warm days, enjoy hiking, swimming, biking, boating, camping, picnicking, fishing, and golf. When snow is on the ground, spend time cross-country skiing, snow shoeing, snowmobiling, and sledding. Daily housekeeping is not included. You can add it for $24 per day if you would like, just let us know when you pick up your key.

Dec 1 – 8

G$31,665 GYD per night

Guest favorite

Condo in Lake Geneva

4.97 out of 5 average rating, 100 reviews

Cozy Lake Geneva retreat! Fireplace! King bed!

Your peaceful 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.

Dec 20 – 27

G$40,223 GYD per night

Superhost

Home in Allouez

4.86 out of 5 average rating, 188 reviews

Amazing Six Bedroom Green Bay Vacation Home!!

Amazing one-of-a-kind home is built for entertaining and full of amenities. You'll love the huge indoor pool that is heated year-round! Very spacious layout. Home has hosted celebrities & Packers Hall of Fame Players. Amenities include a full arcade, outdoor sauna, theatre room, large open kitchen and living room, high-end massage chair, poker table, and more! Six-minute drive to Lambeau, five-minute drive to the airport, very close to everything. 5,200 Sq Feet

Feb 3 – 10

G$151,568 GYD per night

Guest favorite

Home in Somerset

4.99 out of 5 average rating, 224 reviews

Resort LeMire

Secluded vacation style home on 50 acres of woods, tree farm and rolling hills with approx. 3 miles of trails. 3000 square foot home with 3 bedrooms and newly remodeled kitchen and living area. Pool, hot tub, in ground trampoline, basketball court, 50’ slip and slide, 2 golf carts! The hot is filled with fresh water for each reservation. The price listed is for the entire house and property! No pets. Text me for video. Six,5, one. Three, 4, 3. Seven, 6, 4, three.

Dec 3 – 10

G$180,004 GYD per night

Guest favorite

Condo in Lake Geneva

4.93 out of 5 average rating, 428 reviews

Charming, Cozy & Quaint Condo in Lake Geneva!

Quaint 1 BD 1 BA Condo by Lake Como. The association outdoor pool is newly remodeled. There is a boat launch and parking, paddle board rentals, and tennis court. The hotel next door has pools to use for a fee. Dine at the popular nearby Mars restaurant or check out the Ridge Hotel’s coffee shop, restaurant & huge outdoor fire pit! Condo offers towels, toiletries, games, WiFi, basic cable, Roku, electric grill, gas fireplace, drip & K-cup coffee, tea, & water!

Oct 7 – 14

G$25,249 GYD per night