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. :)

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

Location · Family · Pool

Southern WI scenic view Luxury Home+pool+hot tub

Modern home on 5 wooded acres with all the amenities nestled on secluded hilltop with priceless views, large heated saltwater pool,and hot tub (mid May to mid September) Plenty of amenities, modern kitchen, 2 dishwasher, 3 bathrooms, 4 bedrooms with 9 beds, gameroom, 2 TVs, 2 floors, gas & wood fire pits, wooded trail on property and walking access 2 public trails, 10 Minutes to Alpine Valley, 7 minute drive to down town East Troy. If you want nature and relaxation this is the house for you

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.

Location · Family · Cleanliness

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.

Location · Family · 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.

Location · Hospitality · Condition

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.

Location · Family · Accuracy

Bridgerton Themed House/Very Spacious/4bd 3bath

The Bridgerton-themed home features over 2500 square feet, 4 bedrooms, 3 full baths, 2 spacious living rooms, large dining room, large kitchen and a three-season room. Enjoy the 8-foot-deep private pool with a 3-foot shallow end, all within a fully fenced yard for maximum privacy and relaxation. Every room is equipped with a smart TV for your entertainment needs. Conveniently located just minutes from local beaches, the Racine Zoo, downtown, and other popular attractions

Value · Family · Outdoor spaces

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.

Value · Family · Amenities

Beautiful 6 bedroom with Heated Pool & Jacuzzi

Relax with the whole family at this peaceful place to stay right in the middle of beautiful Whitnall Park. You won't find a more peaceful view of the woods and park. Our beautiful home has a large heated pool with brand new 6 person jacuzzi. Brand new Kitchen and updated bathrooms. Master suite is very romantic with steam shower, jacuzzi tub, and luxury bed and fireplace. Family Friendly OR Romantic Getaway!

Family · Value · Outdoor spaces

North End 519

This special place is close to everything, making it easy to plan your visit. North End is a lively property where we offer fully furnished studios, stocked with everything you need to feel at home. North End is in a community that includes a Fitness Center, Lounge, and Covered Parking - Fee may apply. North End is a Walker's Paradise with a Walk Score of 92, a Transit Score of 67, and a Bike Score of 83.

Location · Comfort · Cleanliness

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.

Location · Family · Check-in