Holiday rentals with a pool in Milwaukee

Farmhouse with Heated Pool on almost 160 Acres!

Set on almost 160 acres of rolling farmland, this unique retreat in Elkhorn, Wisconsin offers an immersive experience on a working regenerative farm in progress, where you can wake up to the sounds of farm animals and take in the peaceful countryside. Just a short drive away, you’ll find Lake Geneva’s stunning waterfront, quaint downtown shops, and outdoor adventures like hiking, boating, and local wineries, making Big Foot Valley Farmhouse an ideal destination for relaxation and exploration.

Cozy cabin getaway near Lake Como and Lake Geneva

Beautiful and spacious 5 bedroom home with plenty of space for a big family or multiple families to be together and still have their own space. The cabin has a full updated kitchen with a dining table that can fit your whole group and a big TV to gather around to watch movies, sports games, or play music on as you're hanging out. Enjoy the beautiful views of nature on the backyard patio while you grill, splash around in the pool seasonally, and make smores on the fire pit year round!

3/3 | 2 Fenced Acres |Pool |Hike & Beach| in Town

Meadow Hill Acres is a 3 BR/3 BA home provides a beautiful retreat within a central location, stocked with the comforts of home. Seated on 2 acres of land, the property is fully fenced and dog friendly. Naga-Waukee Park borders the property, offering walking trails (and usually deer friends) right outside your door. Nagawicka Lake and Beach are also just next door. The Delafield shops, restaurants and Hwy 94 are minutes away. Enjoy a nature retreat while central to everything!

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.

Grand Geneva in Lake Geneva

This 4-star resort and spa is in Lake Geneva, Wisconsin, 10 minutes from downtown. It has 2 championship golf courses, a luxury spa and wellness center and a pay per use waterpark. These are timeshare units that are part of the Holiday Inn Vacation Club and are not part of the Grand Geneva hotel although they are around a 100 yards away and walking distance or short tram ride from the hotel. Prices do not include resort fee of $36 for 1br or $72 for 2 br.

Villa Near Lake Geneva, close to Lake

Our comfortalble one bedroom villa has got you covered on your next getaway! Nearby, you will find a local ski hill, plus canoeing and ziplining outfits. At the resort, you will have access to two championship golf courses, pools, seven on-site restaurants, a spa, and more - all serviced by a local shuttle service. With the additional in-suite washer/dryer and full kitchen, you will be sure to call this property your home away from home!

Vessel: Irish Mist V - 32' @ Reefpoint W1-3

Enjoy Marina life at Reefpoint Marina. Close to the beach and on the water. The “Irish Mist” can sleep up to 4. There are two Staterooms- Sleeps 2 each. Enjoy beautiful sunsets and sunrises, a cool lake breeze, and star gazing at night. Amenities include hot showers, a heated pool with two hot tubs (Seasonal) , gas grills and a patio, a ships store, and laundry facilities.

Kettle 2BR Cabin on 15 lush acres w pool and lake

2BR 2 Bath Cabin in the heart of Kettle Moraine on 15 luscious acres with gorgeous pool and private lake. Queen beds in ea BR, 2 sleeper sofas in LR/DR + upstairs loft-attic for kids. Fully stocked kitchen. Stunning fall colors, gazebo, great fishing, disc golf course on property, hiking and mountain bike/ xc ski trails all around. Surrounded by Nature Conservancy land.

Cute and cozy 2 bedroom house perfectly located!

You’ll have everything you need within miles of you. Located conveniently right in between Milwaukee and Madison, you won’t have to travel far for anything. Delafield also offers a ton of great restaurants, coffee shops and cute boutiques within walking distance! Unfortunately during the winter months the pool is not able to be used and outside furniture is tucked away.