
Vacation rentals with a pool in Waukesha County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Waukesha County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

Lake Geneva Cloud 9
A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

Lake Geneva Retreat! Fireplace! WiFi!
Your cozy getaway begins in a newly redesigned condo with patio (there are stairs to get to villa), conveniently located between Lake Como and Lake Geneva in Interlaken Resort! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, & more! The resort community is located by Lodge Geneva National, which adds additional restaurants and available amenities at an additional charge. Many local areas to explore & visit will await your arrival.

Lake Geneva relaxation!
4 mi to Downtown Lake Geneva, WI. Rent kayaks on Lake Como. New pool and tennis courts, amazing wildlife. Snowboard, cross country ski, sled on hills during our amazing Wisconsin winters. Dine at The Ridge restaurant CRAFTED or just buy a bottle of wine from the guest store and watch the sunset. Quiet corner of the condominium complex. Completely furnished. Beautiful comfortable King size bed, kitchen, cook and eat in! Balcony overlooking peaceful grounds. Private entry, laundry in building.

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.

Lakeview at CasaComo
Mi Casa Como es su Casa Como Escape the daily grind and plan your getaway to our newly remodeled condo on Lake Como in Lake Geneva. We’re located just 5 minutes outside downtown Lake Geneva, so very convenient for shopping & dining, but peacefully located on quiet Lake Como. We have an outdoor community pool and tennis courts and just a few steps for The Ridge Hotel. We have all that you could want or need within walking distance, so keep your car parked. Come to Casa Como, stay & enjoy!

LakeView-SummerPool-FamilyFriendly-CloseToTown
Enjoy your stay at our family's Serene Lake condo with outdoor pool. NEWLY UPDATED Stylish and comfortable with amenities for any family to feel at home. Part of Interlaken community and set on Lake Como, we are surrounded by peaceful woods and often seen wild life, yet a quick drive into down town Lake Geneva, William's Bay and Fontana. Enjoy golfing, dining, water sports and all the region has to offer, then cozy up and relax with a view. NO RV, BOAT or TRAILER parking is allowed.

Big BLUE Skyline VIEW
This bright and roomy 2 bedroom unit is the lower level of a 1900 Victorian duplex in the heart of Milwaukee was renovated 3 years ago. Situated on the edge of downtown, overlooking the river and downtown skyline you’ll have easy walking access to all the best neighborhoods. With 9 foot ceilings and a big fenced in yard with basketball hoop and patio furniture you'll be very comfortable staying with us. We are not a corporation, just a nice couple sharing our place. FREE PARKING too

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.

Serene Lakefront condo with magnificent view, pool
Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

Relaxing Villa with Amazing Amenities!
Resort day passes included with booking! Hot tub, indoor and outdoor pool, outdoor bar and fire pit, sauna, the list goes on! Only five minutes from downtown Lake Geneva, this second floor condo offers the best of both worlds. Enjoy the laid back Lake Como attractions, or have a blast in Lake Geneva! This hidden gem is perfect from golfers (only 5 minutes from Geneva National) to families. Give us a try, and enjoy a discount on your second stay!

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.
Popular amenities for Waukesha County rentals with a pool
House rentals with a pool

Lighthouse | 9BR Resort · Pool · Arcade · Hot Tub

Large In-Ground Heated Pool |Two-Tiered Deck |New

Cozy cabin getaway near Lake Como and Lake Geneva

Vacation home: heated inground pool on 4+ acres

Cedar Hot Tub•Spacious Home•Quite Neighborhood

Newly Updated Modern Lake Condo

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

Nestled in the Southern Kettle Moraine Forest
Condo rentals with a pool

Charming 1BR Condo with Patio, Near The Lake Genev

Stylish Lake View Condo in Lake Geneva

Sailor’s Delight: lakefront condo w/fireplace

Quaint, quiet condo minutes from Lake Geneva

Elegant 4-Season Lake Geneva Condo w/ Fireplace!

Flexible rental In Lake Geneva Area

Gorgeous 2 Bed 2 Bath Condo w/Patio in Interlaken!

Best Location in Lake Geneva!
Other vacation rentals with a pool

Home in Lake Geneva Town With In Ground Pool

Fall Specials Family friendly & dogs welcome

Artful Lake Geneva Escape

Villa Near Lake Geneva | Close to the Airport

Lake Geneva Resort 1 Bedroom

Great Place - 1BD/Kitchen/Pool

Keefe Avenue-Upscale Queen Bedroom/Full Office

Discover Wauwatosa! Indoor Pool, Free Parking!
Destinations to explore
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- Six Flags Great America
- Alpine Valley Resort
- Erin Hills Golf Course
- Illinois Beach State Park
- Wilmot Mountain Ski Resort
- Lake Kegonsa State Park
- Harrington Beach State Park
- Milwaukee County Zoo
- Racine North Beach
- Richard Bong State Recreation Area
- West Bend Country Club
- Bradford Beach
- Milwaukee Country Club
- Moraine Hills State Park
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Discovery World
- Milwaukee Public Museum
- Springs Water Park
- Heiliger Huegel Ski Club
- Sunburst
- America's Action Territory
- Blue Mound Golf and Country Club
- The Rock Snowpark
- Little Switzerland Ski Area




