Vacation rentals with a pool in Wisconsin

4.86 out of 5 average rating, 186 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, 126 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, 145 reviews

Condo in Lake Geneva

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, 171 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, 130 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, 149 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 .

4.97 out of 5 average rating, 479 reviews

COZY, Lakefront, Fireplace, Kayaks, Pontoon Ride

NO RESORT FEES + PONTOON RIDE Relax on the porch and watch the boats glide by, soaking in the serene lake views. Whether you're looking for relaxation or recreation, our condo offers the best of both worlds. Book your stay today and experience the ultimate lakeside escape! Resort-Style Amenities • Free Kayaks and Stand Up Paddle Board • Indoor and outdoor pools • Hot tub • Walking distance to Noah's Ark • First Responder Discounts • Smart TVs • Jetted Tub • Fireplace • Washer/Dryer

4.9 out of 5 average rating, 269 reviews

Home in Madison

Luxurious BBQ and Pool House

Hosting a summer barbecue, a pool party, or just looking for a relaxing getaway with your friends? The unique combination of indoor and outdoor space provides something for everyone. This is a modern, spacious, and luxurious 3 bedroom, 2.5 bath home, conveniently located 15 minutes from downtown. Situated on a 3/4 acre lot, this house is fully equipped w/ premium amenities for your friends and family:Swimming pool, hot tub, big yard, deck with a gas grill and dining area

4.79 out of 5 average rating, 159 reviews

Condo in Bayfield

One Minute Walk to Lake Superior. Brookside #10

Amazing location! This Comfy Studio Condo sleeps 4, King bed & Queen sofa sleeper. kitchen, balcony, AC, CableTV, Strong WiFi, BBQ, fire pit, jet-tub/shower. Walk to the restaurant, bar, marina and pool. The pool opens in July. Brookside is 2.3 miles from Bayfield. Hike or bike the Brownstone trail along the lake. Ride the ferry to Madeline or cruise the Apostles. Sail, fish, kayak, golf, orchards, ski. Mt Ashwabay, Big top , Bayview beach plus many trails within minutes.

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, 159 reviews

Condo in Lake Geneva

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Apartments

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

5 out of 5 average rating, 19 reviews

Home in Hager City

MINNeSTAY* Riverfront Inn | Hot tub

KellyRating, 5 stars1 month ago

This property is utterly blissful! The home is luxurious, comfortable, and fully stocked with thoughtful amenities. Every surface, inside and out, was sparkling clean and well cared for. The property is serenely beautiful, and the views will take your breath away. The pool was the finest of any Airbnb pool we have ever had the pleasure of enjoying: pristine, well heated, and meticulously cared for by a kind gentleman who went above and beyond to ensure perfection. The sunsets over the fire pit are priceless. Correspondence with the host was immediate, helpful, and friendly. We are verklempt! Thank you sincerely for sharing this treasure with us!

4.96 out of 5 average rating, 26 reviews

Home in Sturgeon Bay

Bay Cliff Cottage Retreat

JodiRating, 5 stars1 week ago

This is the cleanest Airbnb we have ever rented! Everything we needed was included. Beautiful location! The pool was and extra perk that we enjoyed. I would definitely rent this place again.

4.92 out of 5 average rating, 140 reviews

Home in Milwaukee

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

GerryRating, 5 stars1 month ago

Excellent location and plenty of beds and bathrooms.

5 out of 5 average rating, 33 reviews

Home in Lake Geneva

Cozy cabin getaway near Lake Como and Lake Geneva

DanielRating, 5 stars2 weeks ago

Sasha’s place was even better than expected. We all felt at home and it was very relaxing. We had plenty of room to accommodate all of the guests.

4.98 out of 5 average rating, 65 reviews

Home in Oshkosh

Hickory on the LakeWaterfront Luxury on Winnebago

LaurenRating, 5 stars2 weeks ago

This place was perfect. It was very peaceful. We felt like we were on a mini-vacation even though we were attending our son's soccer tournament. Highly recommend.

4.94 out of 5 average rating, 34 reviews

Home in Chippewa Falls

Dockside at Wissota

SamanthaRating, 5 stars1 month ago

Linda's place was fantastic - as was Linda. She was incredibly responsive and worked really hard to get the pool up and running as quickly as possible during our stay (a gift considering the unusually hot weather we had in early May during our stay). The house was immaculate and had everything we needed in terms of kitchen supplies, toys for the kids, linens, and plenty of spaces for people to relax and unwind. We loved it so much we are hoping to either return to Linda's place one day or get a place of our own in Chippewa Falls.

4.98 out of 5 average rating, 61 reviews

Home in New Richmond

The Pool House - beautiful country farmhouse

BrianRating, 5 stars3 weeks ago

We used the Pool House for a leadership retreat. The accommodations were outstanding. The pool saw some use as one of the days was rainy and cool. The outdoor space was great for yard games and we made use of the tennis court. The house was spacious, clean, and items were easy to find. I would definitely recommend it for family vacations or a retreat.

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!

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Condo rentals with a pool

5 out of 5 average rating, 21 reviews

Condo in Lake Geneva

Chic Condo in Lake Geneva

MichaelRating, 5 stars3 days ago

Morgan's Chic Condo in Lake Geneva was perfect for our trip to attend a wedding in Lake Geneva. It was close enough to all of the venues and restaurants, but far enough away to be quiet and peaceful! We took a walk along the Lake Shore Path, which is a great feature of the area. We also appreciated the kitchen equipment, as well as complimentary coffee and basket of treats! I would definitely stay there again, if our travels take us to the area.

4.94 out of 5 average rating, 185 reviews

Condo in Egg Harbor

DoorCo Happy Place @Landmark Resort

RoseRating, 5 stars2 weeks 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, 233 reviews

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

MirenasRating, 5 stars3 weeks ago

Very cute corner unit. My dad would just sit out on the patio, watching people put their boats in the water and take their boat out of the water. Beds were very comfortable place was nice and clean. I would stay here again.

4.91 out of 5 average rating, 151 reviews

2BR Serene Riverfront • Spacious • Pool & Hot Tub

BobRating, 5 stars4 days ago

Best place to stay in the Dells if you’re bringing a boat. Hosts are amazing, and responsive. We will keep coming back here as long as they own it.

4.83 out of 5 average rating, 161 reviews

Condo in Egg Harbor

[L a n d m a r k] condo! Spectacular Views!

DanRating, 5 stars1 week ago

I was very happy with my stay. Place was exactly as advertised, and loved the added amenity of a 24 hour (adults only) pool located just a short walk away. Location was prime for Door County, located right between Sturgeon Bay and Sister Bay, making it easily accessible and drivable for all the wineries and sight-seeing you want to do in the peninsula. Thank you Carrie!

4.75 out of 5 average rating, 170 reviews

Condo in Bayfield

Superior Hideaway

MarcRating, 5 stars5 days ago

Sarah communicated well and followed up. we had one small problem with water pressure and she responded immediately and had the problem fixed right away.

Condo in Fontana-on-Geneva Lake

5 out of 5 average rating, 14 reviews

Luxurious Condo Experience at Lakeside Villa |Pool

BrittanyRating, 5 stars3 weeks ago

Had a wonderful time here for my sister’s bachelorette party. The town home was beautiful and newly renovated. We had an amazing time at the nearby pool and other attractions close by. Overall great stay!