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

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 with 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.

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.

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.

Lakefront condo with magnificent view & fireplace
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.

Home away from Home
Our cozy and inviting home is designed for relaxation and fun, offering a wide range of amenities to make your stay unforgettable. Enjoy a refreshing dip in the in-ground pool, cozy up by the fireplace, or challenge your friends and family in the game room. just a short walk from the downtown area with shops, restaurants, and attraction all while enjoying the peace and comfort of a relaxing retreat. We look forward to hosting you!

Beautiful Villa with Amenities Galore
Escape to the lake! Resort passes included with your stay. This beautiful villa happily welcomes families and adults 25 and older. Just five minutes from downtown Lake Geneva, and Williams Bay, this clean and comfortable second floor condo offers the best of both worlds. After your day or night's adventures, return home to the privacy of your own lake condo! Being a peaceful location, you'll appreciate our "no parties" rule.

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.

Kettle 2BR Cabin on15 stunning acres by Ski trails
2BR 2 Bath Cabin in the heart of Kettle Moraine on 15 stunning 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. Gorgeous in all seasons, gazebo, great fishing, disc golf course on property, hiking, xc ski and mtb trails all around. 15 min from Alpine Valley for downhill. Surrounded by Nature Conservancy land.

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

Home in Lake Geneva Town With In Ground Pool

Fall Specials Family friendly & dogs welcome

Artful Lake Geneva Escape

Cozy cabin getaway near Lake Como and Lake Geneva

Newly Updated Modern Lake Condo

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

Nestled in the Southern Kettle Moraine Forest

Dream Country Retreat on 15 acres
Condo rentals with a pool

Cozy Condo at Interlaken! Stay & Play on Lake Como

Sailor’s Delight: lakefront condo w/fireplace

Quaint, quiet condo minutes from Lake Geneva

Elegant 4-Season Lake Geneva Condo w/ Fireplace!

Enjoy onsite Waterpark in this family friendly 1BD

Sunset + Lake View Stylish Condo in Lake Geneva

Luxury Lake Geneva Condo with Patio

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

North End 519

Lake Geneva Resort 1 Bedroom

Condo onsite Grand Geneva Golf Resort Ski Spa

Lake Geneva Resort 1 Bedroom

Peaceful Geneva Matterhorn Villa

Cute n Cozy Lake Geneva Interlaken Condo!

Flexible rental In Lake Geneva Area

Townhome Villa private oasis
Quick stats about vacation rentals with a pool in Waukesha

Nightly prices starting at
Waukesha vacation rentals start at ﺩ.ﺇ1,102 per night before taxes and fees

Verified guest reviews
Over 10 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Waukesha rentals

4.6 Average rating
Waukesha stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Chicago Vacation rentals
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- Six Flags Great America
- Alpine Valley Resort
- Wilmot Mountain Ski Resort
- Erin Hills Golf Course
- Illinois Beach State Park
- Milwaukee County Zoo
- Bradford Beach
- Sunburst
- Milwaukee Public Museum
- Baird Center
- Discovery World
- American Family Field
- Riverside Theater
- Little Switzerland Ski Area
- Marquette University
- Gurnee Mills
- Betty Brinn Children's Museum
- Lake Geneva Cruise Line
- Fiserv Forum
- Lake Park
- Holy Hill National Shrine of Mary
- Lake Geneva Public Library
- Atwater Park
- Lake Geneva Ziplines & Adventures




