Holiday rentals with a pool in Waukesha

Unplug - Boat, pool, hot tub on Lake Michigan!

Have you stayed in a boat allowing the sun to wake you up? Have you experienced the joy of doing nothing? In the lazy waves of Lake Michigan lies UNPLUG where we encourage you to practice the joy of doing nothing. Unplug has one large bed on board that can sleep 2 (Q size), a smaller Full bed, a small sofa, and a kitchen on board with basic amenities. The bathroom on board is not usuable but guests can use the clean well kept marina bathrooms and showers just a short walk away. Come unplug!

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.

Close to Lake with Great Ammenities & Breakfast!

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.

7 1/2 Acre Private Estate w/inground pool, hot tub

Any event needs to be approved. First 4 guests 10 y/o and up are included in the nightly rate. Then I charge per person per night over 4 guests. PETS ALLOWED FOR $200.00 3 Bedroom, 3 Bathroom, 3000 Sq/ft Heated Pool!!, Hot Tub!!, Fishing Pond!!, Game Room all on 7 1/2 Acres!!!!!! It is a ONE OF A KIND!! NEW REC ROOM!! 1/2 Acre Fishing pond Stocked with MANY FISH!!! Sand Beach and Pier with boat, Paddle Boards. heated in ground pool, (open May1 - October 1st), hot tub.

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!

2-acre retreat steps from Nagawicka Lake

Private Lake Country Retreat on 2 Acres | Pool, Park & Prime Location Relax at this private Lake Country retreat on 2 secluded acres surrounded by mature trees. Enjoy a private outdoor pool, spacious yard, and peaceful setting just steps from a county park with trails and a public beach. A nearby boat launch makes lake days easy, while shopping, restaurants, and coffee spots are only minutes away. Perfect for families, couples, or extended stays seeking privacy with convenience.

Private Pool and Hot Tub! Private Backyard Oasis!

Escape to a Summer Splash Pad, a private backyard oasis featuring a deep pool, relaxing hot tub, and space for families and groups. Enjoy a fully stocked coffee bar with espresso, perfect for starting your morning. Located minutes from Lake Michigan, North Beach, downtown Racine, and a short drive to Milwaukee. Whether you're planning a family vacation, weekend getaway, or summer retreat, Nautical Splash Pad offers the perfect blend of comfort, fun, and relaxation.

Home away from Home

Welcome to Home Away From Home! Our warm and inviting retreat is the perfect place to relax, reconnect, and make lasting memories. Enjoy the in-ground heated pool, unwind in the sunroom, cozy up by the fireplace in fall and winter, or have fun in the game room with family and friends. Just a short walk to downtown Lake Geneva, you’ll be close to shops, restaurants, and attractions while enjoying the peace of a quiet neighborhood. We can’t wait to host you! V&T

Spacious Home Near Lake Geneva - Heated Pool

Secluded open concept home located on the scenic hillside by the Grand Geneva Resort and just minutes from downtown Lake Geneva. This hideaway with 4000sf of living space with sweeping views of nature and tranquility is meant to be enjoyed inside and out with a private pool (Memorial to Labor Day), multiple decks, chef's kitchen and a dedicated entertainment room with a wet bar, pool and foosball table. Grandview Point presented by Stay at Lake Geneva.

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.

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.

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.