Holiday rentals with a pool in Brookfield

Location! Inground pool! Multi-month only.

This multi-month private 2 room/1 bath apartment, in a historic home overlooking Lake Michigan, is located in a highly sought after location! For travel professionals, interns, or relocation, there is easy freeway access and the apt is a 2-15 min drive to hospitals, UWM, and Greater Milwaukee Area corporations. It is perfect for someone who loves to walk to cafes, restaurants, parks, cinemas, grocery stores, beaches, and cultural venues. Walking, running, and bike paths are across the street. :)

Vacation home: heated inground pool on 4+ acres

TIMELESS CHARM MEETS MODERN ELEGANCE **MAY SPECIAL GUARANTEED 80 degrees pool temp no extra cost thru 5/22 Where the charm of classic aesthetics seamlessly intertwines with the conveniences of contemporary living. 4 acre + estate with plenty of room for outdoor activities such as swimming, water basketball & volleyball, outdoor basketball, sunbathing, barbecues or picnics. This vacation retreat is only minutes away from Lake Michigan, movie theaters, restaurants, golf courses, coffee shops.

Lace & Woods Farm "Hammer Hideaway"

HEATED POOL MAY-SEPT FOR ADDITIONAL CHRG. Cozy designer custom built guest house nestled amongst a 10 acre hobby farm. come for a relaxing getaway. This home is an artistic gem! Boasting an open concept, with a queen bed on main level and twin mattress underneath , a full kitchen, cozy living area, wood burning fireplace. The loft has extra sleeping with a double bed and twin bed.Custom designed. Great location winter and summer, enjoy snowmobiling trails and skiing near by or beaches & hiking

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.

Home in Oconomowoc!

Your family will be close to everything when you stay at this centrally-located home. This beautifully maintained home was built within the last four years. The neighborhood is ideally situated near shopping, restaurants, and convenient highway access. The home is perfectly positioned in the desirable Oconomowoc–Delafield area. You'll benefit from excellent neighborhood amenities, including a community pool, walking trails, and a pickleball court—offering something for everyone to enjoy.

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.

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.

Luxury 5BR | Indoor Pool + Theater | Sleeps 12+

Perfect for groups, this luxury 5BR home sleeps 12+ and is built for entertaining. Enjoy a heated indoor pool, private theater room, massive chef’s kitchen, and a stunning 4-seasons sunroom surrounded by nature. Unwind by the fireplace, relax in spa-style bathrooms, or spread out across multiple living areas—there’s space for everyone. Whether you’re here for a getaway, family gathering, or weekend with friends, this home delivers comfort, space, and unforgettable experiences.

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.

Pool and Hot Tub Retreat! Private Yard, Spacious

😎 Relax at this private pool & hot tub retreat near Lake Michigan, perfect for families, weekend getaways, and group stays. Designed for comfort and fun, this spacious home offers everything you need for a stress-free stay in a quiet & safe neighborhood 😊 The pool and hot tub are seasonal and currently closed. Opening date is June 1st. ☆STOCKED KITCHEN & COFFEE BAR ☕️ ☆PLENTY OF TOWELS 👍 ☆ 📣 PLENTY OF SEATING ☆ ☆ PLENTY OF SPACE ☆☆

Brewers Hill Gem w/hot tub & seasonal shared pool

Your family will be close to everything when you stay at this centrally-located place. Walking distance to Brady Street, the Milwaukee River Walk, shops, restaurants and coffee houses. Less than a mile from Fiserv Forum, downtown Milwaukee and just minutes from Bradford Beach. This pet friendly unit has a private fenced in yard, BBQ grill, off street parking for your vehicles and motorcycles, and a hot tub for your use.

Olympia VOA Oconomowoc WI Great getaway for fun

1, 2, and 3 bedroom condos availability at Olympia Vacation Owners Association with some dogs under 40 lb friendly units. Close to Madison and Milwaukee with Golfing and beaches in the area. The Olympia Hotel has been torn down and replaced with housing and store fronts so no pool access is available. Area has theatre, dining, shopping, water parks. Only an hour from Wisconsin Dells.