Holiday rentals with a pool in Brookfield

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Top-rated rentals with a pool in Brookfield

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Farm stay in Germantown

4.97 out of 5 average rating, 99 reviews

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

Superhost

Home in Elkhorn

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.

Guest favourite

Home in Cudahy

4.78 out of 5 average rating, 152 reviews

Make Yourself At Home! Close to Lake & Airport!

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.

Guest favourite

Home in Hartland

5 out of 5 average rating, 8 reviews

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!

Guest favourite

Home in Riverwest

4.92 out of 5 average rating, 26 reviews

Central Location w/ Skyline View

Central location for walking the city with a skyline view. Explore all of Milwaukee's most popular neighborhoods from here. Fenced in yard for your pup to run around and play. Gated area for motorcycle parking and a large patio area with basketball hoop. 1 bedroom with full kitchen and large living room with 2 dedicated workspaces with desks. Basement with free laundry facilities and an old foosball table. Queen size bed in the bedroom plus a pull out full size bed and a futon.

Guest favourite

Home in Mequon

5 out of 5 average rating, 10 reviews

Vacation home: heated inground pool on 4+ acres

TIMELESS CHARM MEETS MODERN ELEGANCE Where the charm of classic aesthetics seamlessly intertwines with the conveniences of contemporary living. Nestled amidst the serene landscapes of Wisconsin. 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.

Superhost

Home in Sussex

4.88 out of 5 average rating, 112 reviews

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.

Guest favourite

Home in Racine

4.89 out of 5 average rating, 27 reviews

Nautical Escape •Spacious Home•Pool /Cedar Hot Tub

Experience tranquility in this spacious home just steps away from Lake Michigan and local parks. Tucked away in a peaceful neighborhood yet close to dining and shopping, it boasts a beautiful fenced backyard with a 10 foot deep pool and cedar soaking hot tub. Inside, enjoy many smart TVs with free access to Disney+ and Hulu, and indulge in the fully stocked coffee and espresso bar for the ultimate relaxation. The pool will be open on June 1st.

Guest favourite

Villa in Hales Corners

4.92 out of 5 average rating, 37 reviews

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!

Top guest favourite

Home in Brewer's Hill

4.97 out of 5 average rating, 176 reviews

The Peacock Place w/ Seasonal Outdoor Heated 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.

Superhost

Boat in Racine

4.85 out of 5 average rating, 122 reviews

Vessel: Irish Mist V - 32' @ Reefpoint E1-3

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.

Top guest favourite

Cabin in East Troy

5 out of 5 average rating, 37 reviews

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.

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House rentals with a pool

Guest favourite

Home in Brewer's Hill

4.92 out of 5 average rating, 140 reviews

The Gem of Brewers Hill w/hot tub & seasonal pool

GerryRating, 5 stars4 weeks ago

Excellent location and plenty of beds and bathrooms.

Home in Caledonia

4.85 out of 5 average rating, 75 reviews

7 1/2 Acres! Pool! Hot Tub! Fishing Pond!

SherriRating, 5 stars3 months ago

I think this was my favorite place I’ve rented. I’m glad I found it just an hour outside the suburbs of Chicago. It’s a country feel with a ton of activities as described, plus a few extra. My boys really enjoyed the game room. There’s a TV so we played music videos while playing darts, billiards, and I enjoyed throw back video games like Donkey Kong, Centipede and Dig dug. It was cooler outside so I definitely want to return in the summer to enjoy the pool, bonfire, fishing pond, but we had one nice day so still got to enjoy the large property, paddle boat, swings, bocce ball and hot tub. The house has very comfortable furniture, like the beds and couches. We watched movies at night and slept well. Robert was a great host and I appreciated all the helpful notes around the house. I almost felt guilty it was just me and my boys, but it was a perfect getaway. Plenty to do, or do nothing and enjoy the views.

Home in Racine

Bridgerton Pool House/ Near Beach, Zoo & Downtown

CindyRating, 5 stars1 month ago

We stayed at the Bridgerton Pool House and WOW, what an amazing house in a perfect location to be able to enjoy the lake, zoo and downtown restaurants. The house was spacious, clean and the beds were very comfortable. The furnishings were so beautiful. We also enjoyed having two living rooms spaces which gave us a perfect family balance. The house was a short walking distance to the beach and the house provided a wagon for convenience. Matt was the perfect host! He answered all of my questions promptly and we look forward to coming back in the summer to enjoy the pool! The backyard would be perfect for a barbecue and day spent outside in the pool. Lastly, the house was stocked with amenities. I would highly recommend this property for your stay in the Racibe area...10/10