Holiday rentals with a pool in Waukesha

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.

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!

Nestled in the Southern Kettle Moraine Forest

Large two bedroom located in the forest on 6 1/2 acres. Walk right onto the hiking/cross country skiing trails and a quick ride to the John Muir and Emma Carlin bike trails. Hang out with Alpacas, eat fresh eggs from the coup, be entertained by our goats and meet Angel, Charlie and Poopsie! A private entrance gives you all the benefits of a whole house rental with the high touch customer service of a B&B. A perfect get away for couples or families ready to get away and unwind!

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.

Great Place - 1BD/Kitchen/Pool

Between Chicago and Milwaukee, there’s a perfect place for families to get away. With activities skiing, snowboarding and sleigh rides in the winter and championship golf, boat tours to Black Point Estate and horseback riding in warmer months. • Pools, Gym and spa  • Accommodate up to 4 people  • One guest in the party, must be at least 21 y/o or older.    *** Tickets for the Aquatic Park has extra cost and starts at U$25.00. NO RESORT FEE

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!

The Peacock Place w/ Shared Seasonal Outdoor Pool

This 3 bedroom, 1 bath, open concept lower unit of a duplex is located in Brewer's Hill. This unit has tons of natural light, original hard wood floors, pocket doors and claw foot soaking tub. This pet friendly unit has off street parking for 2 vehicles or motorcycles, and a private yard with patio and BBQ grill for your use. Walking distance to Brady Street, downtown and Fiserv Forum.

Kettle 2BR Cabin on 15 lush acres w private 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.