Vacation rentals with a pool in Waukesha

4.97 out of 5 average rating, 116 reviews

An inviting outdoor space showcases a wooden deck with two striped chairs positioned beside a large double door. A barbecue grill rests nearby, and a sign reading 'Hammer Hideaway' is mounted on the wall. Lush greenery and a clear sky provide a relaxed atmosphere.

Farm stay in Germantown

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

A manicured lawn gently slopes towards a serene body of water in the distance, framed by tall trees on either side. The landscape features lush greenery under a partly cloudy sky, creating an open and inviting outdoor space.

4.98 out of 5 average rating, 237 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 welcoming living area features a comfortable sectional sofa facing a gas fireplace and a 65" Smart TV mounted on the wall. Sliding glass doors provide access to the outdoor patio, allowing natural light to fill the space. A decorative wreath adorns the door.

4.94 out of 5 average rating, 108 reviews

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.

A spacious living area features a large sectional couch and a soft ottoman. A wooden table stands nearby, with a laptop resting on it. The kitchen area is visible, showcasing a bar with seating for four. Soft lighting enhances the neutral color palette.

4.87 out of 5 average rating, 119 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.

5 out of 5 average rating, 11 reviews

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.

An open living and dining area features a dark wooden dining table surrounded by black chairs. A light blue wall complements a cozy seating arrangement with armchairs and a sofa. Natural light enters through a large sliding door, with decorative elements and a chandelier enhancing the space.

4.9 out of 5 average rating, 208 reviews

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!

The living area features a dark leather sofa adorned with blue throw pillows, accompanied by a light gray couch. A round woven pouf and an antique-style trunk serve as accent furniture. Large glass doors provide access to a balcony, with lake-themed decor on the wall.

4.96 out of 5 average rating, 165 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.

4.89 out of 5 average rating, 18 reviews

A cozy living room features a light-colored sectional sofa complemented by colorful throw pillows. A plush, vibrant area rug adds warmth to the space. Two windows with light-filtering shades allow natural light, while a recliner and wooden table provide additional seating and surface space.

Home in Riverwest

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

4.89 out of 5 average rating, 125 reviews

An indoor pool area is showcased, featuring a large, clear pool with a projector screen positioned above. Natural stone walls and wood beams enhance the space, complemented by soft lighting. Large windows allow natural light to brighten the inviting environment.

Home in Sussex

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.

A cozy living area features a dark sofa set against a textured wall, with a small decorative pillow. An open kitchen bar with four modern black stools invites gatherings, while greenery enhances the room's decor. Natural light is filtered through large windows.

4.97 out of 5 average rating, 216 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!

A cozy bedroom features a plush king-sized bed with a light-colored duvet and decorative cushions. Natural light enters through large windows adorned with soft curtains. A comfortable bench sits at the foot of the bed, alongside a dark wood dresser and a small television.

4.97 out of 5 average rating, 116 reviews

The Landis, elegant with fireplace!

Kick back and relax in this calm, elegant One bedroom Villa with a KING size bed. This vacation rental is in a quiet area of Lake Geneva, but just minutes from all the vibrancy of downtown Lake Geneva or Williams Bay. It is within walking distance to Mars Resort, The Getaway or The Ridge. This is a perfect spot for couples looking for a relaxing getaway. Local laws require all guests names and address be provided prior to check in.

4.97 out of 5 average rating, 200 reviews

A charming duplex stands with a triangular roof, featuring a colorful facade and multiple balconies. Stairs lead up to the front porch, where seating areas are present. Lush greenery and colorful flowers are visible in front of the stone boundary wall, complementing the vibrant exterior.

Home in Brewer's Hill

The Peacock Place w/ Shared Seasonal Outdoor 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.

Popular amenities for Waukesha rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 27 reviews

A charming porch is furnished with two rocking chairs, inviting relaxation. A well-maintained garden bed with green plants and flowers surrounds the entrance, while a spacious lawn connects to the driveway. The home's exterior features neutral siding and shutters, framed by mature trees in the background.

Home in Delavan

Fall Specials Family friendly & dogs welcome

Superhost

A three-story lodge-style home is surrounded by well-maintained landscaping. Large windows dominate the upper level, allowing ample natural light. A spacious deck is visible, furnished with a table and umbrellas. Comfortable outdoor seating is arranged on stone pathways beneath the structure.

4.79 out of 5 average rating, 28 reviews

Lodge Home - 2.8 Miles to Town - 3 Acres

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.

4.98 out of 5 average rating, 41 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

5 out of 5 average rating, 13 reviews

A spacious outdoor patio surrounds the inviting swimming pool, featuring lounge chairs, umbrellas, and shaded seating areas. Lush greenery and trees frame the scene, enhancing the tranquil atmosphere. The bright blue sky is dotted with clouds, offering a relaxing space for sunbathing or gathering.

Home in Mequon

Vacation home: heated inground pool on 4+ acres

4.93 out of 5 average rating, 41 reviews

A spacious living area is highlighted by natural light streaming through large windows. Light-colored furniture is arranged around a central coffee table on a decorative rug. An inviting dining space is visible, along with a modern kitchen area in the background.

Home in Racine

Cedar Hot Tub•Spacious Home•Quite Neighborhood

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.

5 out of 5 average rating, 54 reviews

Newly Updated Modern Lake Condo

A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.

4.95 out of 5 average rating, 96 reviews

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

5 out of 5 average rating, 84 reviews

A spacious living area features a combination of leather seating and a wooden coffee table. Natural light streams in from large windows. A dining table with four chairs is positioned nearby, accentuated by decorative wall art and soft lighting fixtures.

Home in Whitewater

Nestled in the Southern Kettle Moraine Forest

Condo rentals with a pool

A spacious living area is characterized by light-colored leather sofas and a fireplace, providing a cozy atmosphere. A large television is mounted on the wall, and sliding glass doors lead to an outdoor space with seating visible beyond. The room features wooden flooring and brick walls.

4.86 out of 5 average rating, 22 reviews

Charming 1BR Condo with Patio, Near The Lake Genev

A dining area features a round marble table surrounded by four black chairs, illuminated by a unique chandelier. A stylish desk with two lamps and chairs is positioned next to a comfortable living space, which is brightened by large windows offering natural light.

4.94 out of 5 average rating, 17 reviews

Comotose by the Lake

Superhost

A cozy living area is presented with a comfortable sofa and a rustic fireplace surrounded by brick. A large TV is mounted on the wall, and a round mirror adds a decorative touch. Natural light enters through patio doors, enhancing the inviting atmosphere.

4.78 out of 5 average rating, 9 reviews

Stylish Lake View Condo in Lake Geneva

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.

5 out of 5 average rating, 11 reviews

Sailor’s Delight: lakefront condo w/fireplace

4.92 out of 5 average rating, 50 reviews

A cozy living area is depicted, featuring a brick fireplace beneath a mounted television. Soft furnishings include a gray couch adorned with decorative pillows, positioned around a dark coffee table. Sheer curtains filter light from the nearby window, adding a touch of warmth to the space.

Condo in Geneva

Quaint, quiet condo minutes from Lake Geneva

A balcony features a small table surrounded by two chairs, offering a view of the lush greenery and trees beyond. The scene reflects a peaceful outdoor setting, with a road visible in the distance under a clear sky.

4.97 out of 5 average rating, 33 reviews

Elegant 4-Season Lake Geneva Condo w/ Fireplace!

Superhost

A serene view of Lake Como at dusk, with calm water reflecting soft pastel hues of pink and purple in the sky. The distant shoreline is framed by trees, and small lights from boats can be seen twinkling along the lake.

4.64 out of 5 average rating, 285 reviews

Flexible rental In Lake Geneva Area

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.

4.87 out of 5 average rating, 47 reviews

Best Location in Lake Geneva!

Other vacation rentals with a pool

A spacious living area features smooth tiled flooring and a high wooden ceiling. A large sectional sofa invites relaxation, while an area rug adds color. A flat-screen TV is mounted on the wall, and large glass doors lead to an outdoor space, enhancing the open atmosphere.

Artful Lake Geneva Escape

A welcoming living area is presented with a sofa and two accent chairs. A wooden coffee table is adorned with a floral arrangement. Artwork hangs on the wall above the sofa, and soft lighting is provided by two lamps beside the couch.

4.26 out of 5 average rating, 34 reviews

Condo onsite Grand Geneva Golf Resort Ski Spa

A spacious sleeping area is highlighted by a large bed with white linens, complemented by decorative pillows. A wooden bench rests at the foot of the bed, and a bedside table is positioned on one side. Natural light filters through the window, enhancing the soft wall colors.

Apartment in Lake Geneva

Lake Geneva Resort 1 Bedroom

A spacious outdoor pool is surrounded by lounge chairs and shaded under large umbrellas. The clear blue water reflects the bright sky, with a partial view of the resort's exterior providing a sense of place. Lush landscaping adds greenery to the setting.

Apartment in Lake Geneva

Great Place - 1BD/Kitchen/Pool

Apartment in Milwaukee

New place to stay

Keefe Avenue-Upscale Queen Bedroom/Full Office

Apartment in Wauwatosa

Discover Wauwatosa! Indoor Pool, Free Parking!

New place to stay

Sunset + Lake View Stylish Condo in Lake Geneva