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 light wood flooring and neutral-colored walls. A large window provides natural light and views of the outdoor space. Comfortable seating includes two armchairs and a sofa, with a coffee table centered on a patterned rug. A brick fireplace adds an element of warmth.

4.85 out of 5 average rating, 104 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!

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.

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, 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 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.

4.98 out of 5 average rating, 183 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.

Superhost

An open kitchen area is showcased with a wooden dining table and two white chairs. Modern appliances, including a microwave and a decorative wall with floral wallpaper, add a touch of charm. An oversized clock hangs above, contributing to the inviting ambiance.

4.9 out of 5 average rating, 102 reviews

LG Quaint Condo on Lakeshore Dr.

Charming 1+1 condo off Lakeshore Blvd, just minutes from downtown Lake Geneva. A perfect blend of quaint and modern, with a full coffee and tea station and a fully equipped kitchen. Stroll to the lake, take a boat ride, or enjoy a scenic drive to downtown. Experience the peaceful charm of Lake Geneva with the convenience of being close to all its attractions. Book this condo alone or with another in the same building for extra space.

A spacious living room features comfortable seating arrangements, including a sleeper sofa and armchair. Natural light filters through large sliding doors, leading to a balcony. A cozy gas fireplace adds warmth to the space, complemented by a round coffee table and a flat-screen TV mounted on the wall.

4.94 out of 5 average rating, 200 reviews

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.

4.94 out of 5 average rating, 170 reviews

A historic Victorian-style home is showcased with a blue exterior and ornate architectural details. Bright green foliage frames the entrance, leading to the front steps. The sky is clear, enhancing the home's inviting appearance.

Home in Brewer's Hill

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 rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 7 reviews

Home in Saukville

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

4.95 out of 5 average rating, 43 reviews

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

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.

4.98 out of 5 average rating, 41 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

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

Home in Fontana-on-Geneva Lake

The exterior of a two-story home is shown, featuring a wooden deck with steps leading to the entrance. Lush green grass and landscaped gardens surround the house, with smooth stones arranged along a small water feature, providing a natural setting.

5 out of 5 average rating, 13 reviews

Treetop Lakehouse at Abbey Springs

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

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 private balcony offers stunning views of the tranquil lake at sunset, framed by lush greenery and a well-manicured lawn. The sky is painted with soft hues of orange and blue, reflecting on the calm water's surface.

5 out of 5 average rating, 14 reviews

Glass Vista: Modern 2BR Condo, Stunning Views

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.

5 out of 5 average rating, 44 reviews

Chic Condo in Lake Geneva

A bright and open living space is visible, showcasing a seamless transition from the kitchen to the dining area. Light wood floors run through the area, while large glass doors provide views of the outside greenery. Soft furnishings add a touch of comfort to the inviting atmosphere.

4.99 out of 5 average rating, 69 reviews

2 BD 2 BA Abbey Villa with Pool

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 corner of the living room features a brick fireplace with a warm fire. A decorative candle holder stands beside a beautifully lit Christmas tree. A plush sofa, adorned with a patterned pillow, invites relaxation, while a simple table holds a remote and holiday decor.

4.78 out of 5 average rating, 195 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

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

Superhost

A serene lakeside scene features a wooden dock extending into the water, with several boats anchored nearby. Lush greenery and gentle waves can be seen in the background, creating a peaceful atmosphere. The clear sky hints at a warm day, inviting outdoor leisure activities.

4.75 out of 5 average rating, 53 reviews

Abbey Springs - Lake Geneva - 2 BR - Sleeps 6

Other vacation rentals with a pool

A tranquil outdoor area is highlighted by a well-lit inground pool reflecting the evening sky. Cozy seating, including an outdoor sectional and a shaded table with an umbrella, are positioned nearby, creating a welcoming space for gathering and relaxation.

4.57 out of 5 average rating, 14 reviews

Home in Lake Geneva Town With In Ground 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

A spacious backyard features a private in-ground pool surrounded by a well-maintained lawn. A wooden deck with red umbrellas offers seating areas for relaxation. The home, highlighted by large windows, is framed by lush trees and greenery, enhancing the outdoor gathering space.

5 out of 5 average rating, 21 reviews

Lake Geneva Home w/ Pool near the Lake!

Home in Fontana-on-Geneva Lake

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.

5 out of 5 average rating, 11 reviews

Lake Geneva Cozy Getaway

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

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

4.62 out of 5 average rating, 13 reviews

Charming, Cozy Condo in 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!