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.

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Guest favorite

Home in Saukville

4.98 out of 5 average rating, 45 reviews

The Lighthouse Pool/Hot Tub/Tennis/Movie Room/Gym

Secluded country retreat redefines the term, "having it all", setting an unparalleled standard within the Milwaukee Metro. area 3 Master suites, pool, hot tub, tennis/pickleball and basketball court, movie theater & gym 9 bedrooms include; a nursery & bunk room with pull-out sofa. 7 BRs LivRm. oversized furniture and 75-inch tv. Dreamy back Pool patio and expansive parking. YouTube TV and WIFI Great for family gatherings. Inquire about special requests. No smoking allowed. No fires

Guest favorite

Condo in Lake Geneva

4.98 out of 5 average rating, 196 reviews

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.

Guest favorite

Home in Milwaukee

5 out of 5 average rating, 8 reviews

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

Guest favorite

Home in Whitewater

5 out of 5 average rating, 77 reviews

Nestled in the Southern Kettle Moraine Forest

Large two bedroom located in the forest on 6 1/2 acres. Walk right onto the hiking/cross country skiing trails and a quick ride to the John Muir and Emma Carlin bike trails. Hang out with Alpacas, eat fresh eggs from the coup, be entertained by our goats and meet Angel, Charlie and Poopsie! A private entrance gives you all the benefits of a whole house rental with the high touch customer service of a B&B. A perfect get away for couples or families ready to get away and unwind!

Guest favorite

Condo in Lake Geneva

4.95 out of 5 average rating, 128 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

Enjoy your stay at our family's Serene Lake condo with outdoor pool. 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.

Guest favorite

Condo in Lake Geneva

4.98 out of 5 average rating, 120 reviews

Magnificient views in a Lakefront condo, 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. Your stay promises a perfect balance of peaceful relaxation and recreational activities creating unforgettable memories in this beautiful Wisconsin setting.

Guest favorite

Condo in Lake Geneva

4.97 out of 5 average rating, 106 reviews

Lake Geneva Retreat! King Bed! Fireplace! WiFi!

Your cozy getaway begins in a newly remodeled, ground level condo with patio, 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, and more! The resort community is located by The Ridge Hotel, which adds additional restaurants and available amenities at an additional charge. Many local areas to explore & visit will await your arrival.

Superhost

Home in Sussex

4.87 out of 5 average rating, 101 reviews

Amazing Five Bedroom Milwaukee Vacation Home!!

Treat your friends and family to this five-bedroom vacation home just a half-hour from downtown Milwaukee on more than one acre of park-like, private surroundings. Guests of all ages will love the decked-out game room, the huge indoor pool and the comfy living space, with lots of room to spread out. Plus, you’re just 30 minutes from downtown. It’s all the peaceful feels of a country setting with the amenities of the city (think Uber, UberEats, and more).

Guest favorite

Condo in Lake Geneva

4.96 out of 5 average rating, 165 reviews

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!

Guest favorite

Home in Lake Geneva

4.92 out of 5 average rating, 145 reviews

Home away from Home

Looking for a fun, cozy and relaxing get away? This home is perfect for that! We have lots of amenities to enjoy. Heated in ground Pool, Beach towels, Sunroom, Game room and so much more! We are walking distance to Downtown lake Geneva attractions, Beach, Restaurants and Shopping! but far enough away in this quiet part of town. This house is well stocked for a great getaway and awesome memories!

Guest favorite

Home in Milwaukee

4.97 out of 5 average rating, 142 reviews

The Peacock Place

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, 121 reviews

Vessel: Irish Mist V - 32' @ Reefpoint E5-3

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.