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Vacation rentals with a pool in Waukesha

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Waukesha

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

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Top guest favorite

A cozy living area is highlighted by a gas fireplace and a large Smart TV mounted on the wall. A sliding glass door leads to a balcony with views of the green courtyard. Comfortable seating is arranged around a rustic coffee table that complements the relaxed atmosphere.

Condo in Lake Geneva

4.97 out of 5 average rating, 153 reviews

Lake Geneva Retreat! King Bed! Fireplace!

Your cozy & relaxing getaway begins in a newly redesigned condo with balcony (courtyard view), and is conveniently located between Lake Como and Lake Geneva in peaceful Interlaken Resort community! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, and more! The resort community is located by Lodge Geneva National (formerly The Ridge Hotel), which adds additional restaurants and available amenities at an additional charge. Walk to the

Farm stay in Germantown

4.97 out of 5 average rating, 111 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

Top guest favorite

A patio area features multiple seating options and a glass door leading into the condo. Lush greenery and colorful flowers border the concrete walkway, providing a serene outdoor setting. A second-level balcony is visible above, adding depth to the outdoor space.

Condo in Lake Geneva

4.98 out of 5 average rating, 229 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.

A view from the outdoor deck shows a circular pool surrounded by well-maintained green grass and trees. Colorful flowers are planted in decorative boxes along the railing. Umbrellas and lounge chairs are positioned around the pool area, providing shaded seating options.

Condo in Fontana-on-Geneva Lake

4.84 out of 5 average rating, 103 reviews

Best Pool View 2 BR 2 BA Abbey Villa D

Pool view sunlight Villa. It's great for a girls weekend, golfing trip or a family reunion. The condo next door is also available. Located adjacent to the Abbey Resort, Avani Spa & Big Foot Golf. Our 2-bedroom, 2-bath Villa features an open floor plan and has the comforts of resort living, including a pool. The second floor, walk-up unit has an outdoor dining area with seating for six and and a deck overlooking the pool and grounds. Essentials included. No parties. New pool coming summer 2026!

The image showcases a clear swimming pool surrounded by a concrete deck. A shallow area is indicated, with safety signage specifying '3 ft 0 in No Diving.' Poolside loungers and umbrellas provide shade, while pool steps offer easy access for swimmers.

Condo in Lake Geneva

4.88 out of 5 average rating, 114 reviews

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.

An outdoor pool area is surrounded by well-maintained landscaping, featuring several lounge chairs and tables. A patio with umbrellas provides shaded seating options. The pool is enclosed by a fence, with a clear view of greenery in the background. An adjacent gazebo offers additional space for relaxation.

Condo in Lake Geneva

4.96 out of 5 average rating, 158 reviews

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.

An open living area features hardwood floors and a white brick fireplace. Comfortable red leather sofas are arranged around a white coffee table. A dining area is visible, adjacent to the kitchen, with a wooden table and chairs. Natural light filters through large windows.

Condo in Fontana-on-Geneva Lake

4.79 out of 5 average rating, 191 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

Enjoy a fun romantic get away or time away to connect with family and friends in Fontana-on-Geneva. Condo is an open concept kitchen, dining, and family room with fireplace. Enjoy the outdoors while relaxing on the screened in porch attached to the great room. First floor Master Bedroom has a semi-private full bath. Downstairs has a large second bedroom and full bath. There is also an office area which has a large double bed and a common area with TV and 2 extra twin beds.

A spacious indoor pool area is showcased, featuring a large, well-maintained pool surrounded by smooth flooring and exposed stone walls. Wooden beams and decorative lighting add character to the space, while comfortable seating areas and bar stools offer ample places to relax.

4.88 out of 5 average rating, 120 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.

Top guest favorite

A breathtaking view of the sunset over Lake Como is framed by large glass doors. The patio features comfortable seating, adorned with potted plants, while the tranquil lake and lush greenery create a serene backdrop.

Condo in Lake Geneva

4.98 out of 5 average rating, 173 reviews

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.

Top guest favorite

A view from the balcony captures a well-maintained lawn with a cloudy sky backdrop. A tennis court is visible in the foreground, while trees and a body of water create a serene atmosphere in the background.

Condo in Lake Geneva

4.97 out of 5 average rating, 204 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!

Top guest favorite

A heated in-ground pool is surrounded by a spacious patio. Bright orange umbrellas provide shade over lounge chairs, while a gas grill is positioned nearby. Lush greenery adds to the tranquility of the outdoor space, inviting relaxation and enjoyment.

Home in Lake Geneva

4.93 out of 5 average rating, 162 reviews

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!

An outdoor pool area is presented with sunbathers lounging on chairs surrounding the clear water. A variety of colorful towels and pool floats are scattered on the pool deck. Lush greenery outlines the backdrop, contributing to a relaxing ambiance.

Cottage in Fontana-on-Geneva Lake

4.98 out of 5 average rating, 110 reviews

Fontana, Wis, Lake Geneva 4bd 2.5ba Abbey Springs

4 Bedroom 2 1/2 bath vacation cottage in Abbey Springs Resort Community on Lake Geneva. Resort Pass is required for all guests (included) and gives entry to the resort plus indoor and outdoor pool (Memorial to Labor Day), hot tub, games room , gym, tennis courts , pickle ball. 2 restaurants beach and fire pit on site. Newly Renovated Golf Course not included but available by paying at club house . We welcome all .

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Popular amenities for Waukesha rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A single-story house is presented with a light exterior and a welcoming porch. A shaded area is provided by the overhanging roof, and a bench is positioned on the porch. A well-maintained lawn stretches in front, framed by lush green trees.

Home in Delafield

4.95 out of 5 average rating, 43 reviews

Cute and cozy 2 bedroom house perfectly located!

A refreshing pool surrounded by a wooden deck is visible, complemented by several loungers for relaxation. Lush greenery frames the area, providing a serene backdrop. Colorful flowers in the foreground add a touch of vibrancy to the peaceful outdoor setting.

Home in Lake Geneva

4.97 out of 5 average rating, 37 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

An outdoor pool area is shown, surrounded by a spacious deck. Umbrellas provide shade over lounge chairs, and various seating options are arranged around the pool. Lush greenery is visible in the background under a partly cloudy sky.

5 out of 5 average rating, 13 reviews

Vacation home: heated inground pool on 4+ acres

Top guest favorite

Two black Adirondack chairs and a small side table are positioned on a patio, overlooking a lush green landscape under a cloudy sky. The view encompasses rolling hills and tree foliage, providing a serene outdoor setting.

Home in Lake Geneva

5 out of 5 average rating, 48 reviews

Newly Updated Modern Lake Condo

A spacious outdoor pool area is presented, surrounded by a clean concrete deck. Several round tables with chairs are arranged around the pool, providing seating. Lush greenery and trees are visible in the background, contributing to a serene environment.

Home in Lake Geneva

4.95 out of 5 average rating, 92 reviews

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

Top guest favorite

Home in Whitewater

5 out of 5 average rating, 84 reviews

Nestled in the Southern Kettle Moraine Forest

The backyard features a large in-ground pool surrounded by a wooden deck, adorned with comfortable seating areas and a pergola. Lush greenery frames the space, contributing to a peaceful atmosphere. Sunlight reflects off the water, offering a refreshing contrast to the well-maintained surroundings.

Home in Lake Geneva

5 out of 5 average rating, 8 reviews

Oasis on Oak | Private In-Ground Pool | Hot Tub

5 out of 5 average rating, 13 reviews

Bridgerton Pool House/ Near Beach, Zoo & Downtown

Condo rentals with a pool

Top guest favorite

The spacious living area is illuminated by natural light from large windows. A leather sofa is paired with an accent chair, while a round rug centers the space. A modern coffee table sits atop the rug, and a dining counter with two bar stools is positioned nearby.

Condo in Lake Geneva

5 out of 5 average rating, 34 reviews

Chic Condo in Lake Geneva

A circular swimming pool is surrounded by a spacious patio with numerous lounge chairs. Lush greenery and trees frame the area, while nearby, a gazebo offers shaded seating. The multi-story condominium buildings in the background complete the inviting outdoor environment.

Condo in Fontana-on-Geneva Lake

4.99 out of 5 average rating, 69 reviews

2 BD 2 BA Abbey Villa with Pool

A cozy living area features a grey sectional sofa with patterned cushions and a comfortable armchair. A flat-screen television is mounted on a brick wall above a fireplace, complemented by nautical décor. Light enters through adjacent windows, enhancing the relaxed ambiance.

Condo in Lake Geneva

5 out of 5 average rating, 10 reviews

Sailor’s Delight: lakefront condo w/fireplace

An outdoor pool area is enclosed by a black fence, surrounded by lounge chairs and umbrellas. Lush green grass leads to the area, with trees and a nearby building visible in the background. Clear blue skies create a bright and open atmosphere.

Condo in Geneva

4.92 out of 5 average rating, 48 reviews

Quaint, quiet condo minutes from Lake Geneva

An indoor pool area is visible, featuring clear blue water and a gently sloping entry. Large windows allow natural light to illuminate the space, revealing striped awnings overhead. Surrounding seating areas are designed with modern lounge chairs, adding to the relaxing environment.

Condo in Lake Geneva

4.85 out of 5 average rating, 74 reviews

Lock-off Villa at Lake Geneva's GRAND Resort

A stylish open-plan living area features a cozy seating arrangement with plush chairs and a modern coffee table. The fireplace serves as a focal point, complemented by a large wall-mounted TV. A kitchen bar with blue stools adds a vibrant touch, promoting an inviting atmosphere.

Condo in Lake Geneva

4.88 out of 5 average rating, 32 reviews

Lake Geneva Gem: Luxury, Comfort & Prime Location

A cozy living area is presented, featuring a light blue sofa adorned with various throw pillows. A matching armchair sits nearby, and a coffee table with decorative items occupies the center. Natural light enters through a glass door, highlighting the warmth of the space.

Condo in Geneva

4.95 out of 5 average rating, 20 reviews

Cozy 2 Bedroom Condo - Lake Geneva

The exterior of a resort building is illuminated at dusk, showcasing multiple balconies. A pool area with lounge chairs is positioned in the foreground, featuring water jets adding a dynamic element to the scene. The inviting lighting highlights the architectural details of the building.

Condo in Lake Geneva

4.87 out of 5 average rating, 46 reviews

Best Location in Lake Geneva!

Other vacation rentals with a pool

A cozy living area is depicted, featuring a comfortable couch and a wooden coffee table amidst light green walls. A television is positioned next to a bookshelf filled with books. A dining area with black chairs and a large table is visible in the background, enhancing the inviting atmosphere.

Home in Milwaukee

4.75 out of 5 average rating, 12 reviews

Lilac Cottage

Top guest favorite

A modern living area features large windows that allow natural light to fill the space. Two white sofas are positioned around a round coffee table, with a cozy fireplace visible against a brick wall. Soft decorative pillows add comfort to the seating arrangement.

Home in Fontana-on-Geneva Lake

5 out of 5 average rating, 11 reviews

Lake Geneva Cozy Getaway

A spacious dining area features a wooden table surrounded by colorful chairs. A pendant light hangs above, illuminating a vibrant centerpiece. In the background, a cozy living space is visible with a fireplace and large windows providing natural light.

Home in Fontana-on-Geneva Lake

4.88 out of 5 average rating, 8 reviews

Abbey Dreams - on Geneva Lake

A spacious outdoor area features a large pool surrounded by a wooden deck. A two-story house is visible in the background, featuring a combination of brown wood siding and multiple levels. Outdoor seating is provided under colorful umbrellas, enhancing the scenic, wooded surroundings.

Apartment in Waterford

4.93 out of 5 average rating, 61 reviews

Cozy lower level 2 bedroom apartment.

A community pool is surrounded by a paved deck and lounge chairs. Sun umbrellas offer shade, while trees provide a natural backdrop. The water is a vibrant blue, reflecting the sky, with a small hot tub visible nearby.

Condo in Fontana-on-Geneva Lake

5 out of 5 average rating, 20 reviews

Abbey Harborfront Villa on Lake Geneva

The exterior of the condo is displayed, featuring a well-maintained facade with a combination of dark wood and beige accents. A manicured lawn stretches in front, leading to a concrete pathway. Symmetrical windows and entryways characterize the building's design, adding to its inviting appearance.

Apartment in Lake Geneva

4.67 out of 5 average rating, 9 reviews

Charming, Cozy Condo in Lake Geneva

A well-maintained pathway leads toward a serene outdoor pool area surrounded by lush landscaping. Several lounge chairs are arranged around the pool, which is partially shaded by trees. A sun umbrella stands by the edge, enhancing the tranquil atmosphere.

Condo in Lake Geneva

4.91 out of 5 average rating, 96 reviews

LG Quaint Condo on Lakeshore Dr.

Top guest favorite

A rustic stone building features a white door framed by weathered wood, set against a backdrop of leafy trees. Two large wheels are positioned on either side, adding a touch of character. A neatly arranged stone wall borders the scene.

Home in Hartford

5 out of 5 average rating, 8 reviews

Dream Country Retreat on 15 acres

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