Vacation rentals with a pool in Waukesha

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.

4.97 out of 5 average rating, 145 reviews

Cozy LG Retreat! King Bed! Fireplace! WiFi!

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

4.97 out of 5 average rating, 99 reviews

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 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.

4.98 out of 5 average rating, 212 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.

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.

4.87 out of 5 average rating, 103 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.

4.96 out of 5 average rating, 142 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.

5 out of 5 average rating, 8 reviews

Home in Hartland

3/3 | 2 Fenced Acres |Pool |Hike & Beach| in Town

Meadow Hill Acres is a 3 BR/3 BA home provides a beautiful retreat within a central location, stocked with the comforts of home. Seated on 2 acres of land, the property is fully fenced and dog friendly. Naga-Waukee Park borders the property, offering walking trails (and usually deer friends) right outside your door. Nagawicka Lake and Beach are also just next door. The Delafield shops, restaurants and Hwy 94 are minutes away. Enjoy a nature retreat while central to everything!

4.88 out of 5 average rating, 112 reviews

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.

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 spacious balcony features two lounge chairs and flower pots, overlooking manicured green lawns towards the waterfront. Trees line the horizon under a colorful sunset sky, enhancing the serene lakeside ambiance.

4.97 out of 5 average rating, 158 reviews

Magnificent waterfront views & cozy 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.

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, 178 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.

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.

4.92 out of 5 average rating, 150 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!

4.97 out of 5 average rating, 177 reviews

Home in Brewer's Hill

The Peacock Place w/ Seasonal Outdoor Heated 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.

4.85 out of 5 average rating, 122 reviews

A white motor yacht, named 'Irish Mist,' is docked at Reefpoint Marina. The boat features a spacious top deck with a black canopy and is surrounded by other yachts in the water, with a soft sunset glow illuminating the scene.

Boat in Racine

Vessel: Irish Mist V - 32' @ Reefpoint E1-3

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.

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Popular amenities for Waukesha rentals with a pool

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House rentals with a pool

An inviting swimming pool glistens under a bright sky, surrounded by lush greenery. The spacious patio features a covered area and lounge chairs, while the elegant home showcases large windows and a welcoming design, inviting relaxation in a serene outdoor setting.

4.94 out of 5 average rating, 18 reviews

Woodhaven, a Luxury Lake Geneva HotTub-Pool Estate

KarinRating, 5 stars1 month ago

Woodhaven was the perfect house for our women’s weekend away! The large living room and beautiful kitchen were perfect for our group of 10 but we were fortunate to have nice weather to be able to check out the downtown and spend most of our time outside on the patio. Even when the pool was still closed, we thoroughly enjoyed the backyard and patio space. Thanks for opening your home!

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.

4.64 out of 5 average rating, 11 reviews

Home in Lake Geneva Town With In Ground Pool

JackRating, 5 stars10 months ago

The property was outstanding, especially the backyard, with an oversized yard with an exceptional in-ground pool. Phenomenal sitting area w/fire pit and a very nice B-BQ. Plenty of room for 6-8 adults with everything you need, towels, kitchen utensils and two areas to watch tv. This is a can't miss rental opportunity.

5 out of 5 average rating, 24 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

Family friendly & dogs welcome

LindseyRating, 5 stars4 months ago

We felt right at home at Jane's place. everything was as listed, the place was super homey, and Jane was a great host.

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.

5 out of 5 average rating, 33 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

DanielRating, 5 stars2 weeks ago

Sasha’s place was even better than expected. We all felt at home and it was very relaxing. We had plenty of room to accommodate all of the guests.

5 out of 5 average rating, 10 reviews

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.

Home in Mequon

Vacation home: heated inground pool on 4+ acres

AvremiRating, 5 stars1 month ago

Was a wonderful stay at the home, will definitely go back again in the summer for a nice swim in the beautiful pool! If you are looking for a little getaway in a quiet area with a home that's both comfortable and modern I highly recommend this stay!

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, 40 reviews

Newly Updated Modern Lake Condo

LaurenRating, 5 stars1 month ago

Loved this house! It was in a great location, a few mins away from town, walking distance to Lake Como and super easy to find and navigate. Everyone had a great time. Only drawback was a tiny kitchen for multiple people but the rest of the living areas were great!

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.

4.96 out of 5 average rating, 77 reviews

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

CindyRating, 5 stars3 days ago

We only stayed for one night so weren't able to take advantage of all the community amenities, but the house was very comfortable and we had a good night's sleep. Seemed like a peaceful retreat just outside of the main shopping/dining area of Lake Geneva. We would return!

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.

5 out of 5 average rating, 6 reviews

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

ADAMRating, 5 stars3 weeks ago

House was great and matches the description and photos. House is spacious, good for a group of 6-7 people and private from other neighbors. It’s also less than 10 minutes from downtown Lake Geneva. It is an ideal house if you are looking for a quiet weekend retreat, close to the areas activities. In addition, the host is responsive and helpful. Looking forward to our next stay with you all!

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Condo rentals with a pool

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, 21 reviews

Chic Condo in Lake Geneva.

MichaelRating, 5 stars1 day ago

Morgan's Chic Condo in Lake Geneva was perfect for our trip to attend a wedding in Lake Geneva. It was close enough to all of the venues and restaurants, but far enough away to be quiet and peaceful! We took a walk along the Lake Shore Path, which is a great feature of the area. We also appreciated the kitchen equipment, as well as complimentary coffee and basket of treats! I would definitely stay there again, if our travels take us to the area.

Condo in Fontana-on-Geneva Lake

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.

5 out of 5 average rating, 58 reviews

2 BD 2 BA Abbey Villa with Pool

GavinRating, 5 stars10 months ago

Great spot! The condo was clean, comfortable, and quiet. It was a short walk to the beach and restaurants. Mandy’s detailed directions and instructions made checking in a breeze. Our group of four had a fantastic time.

4.91 out of 5 average rating, 44 reviews

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

Quaint, quiet condo minutes from Lake Geneva

AlenaRating, 5 stars1 month ago

Lively apartment, beautiful area, attentive host. Place was clean and spacious. We enjoyed our stay. Could hear the neighbors from upstairs. Didn’t bother me, but if you are not used to having neighbors it can be distracting.

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.

4.84 out of 5 average rating, 70 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

TracyRating, 5 stars3 months ago

Clean, roomy place. Short drive to stores or walk/shuttle to resort pool/restaurants. We enjoyed our stay and would definitely stay again. The only disappointment was the golf course was closed.

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.

4.94 out of 5 average rating, 86 reviews

LG Quaint Condo on Lakeshore Dr.

ValerieRating, 5 stars3 weeks ago

Great place to stay. Unique building. Very peaceful

A private balcony is showcased with two green chairs, offering a view of the shared outdoor pool below. Lush trees provide shade in the distance, and clear skies suggest a bright day. The railing provides safety while enjoying the surrounding scenery.

4.7 out of 5 average rating, 44 reviews

Poolside Lookout at the Cove Hotel |Downtown LG

LindaRating, 5 stars4 weeks ago

Samantha was an excellent host! We really enjoyed staying there and the location was perfect. It was great to just park the car and be able to walk around town.

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.

4.82 out of 5 average rating, 22 reviews

Lake Geneva Gem: Luxury, Comfort & Prime Location

DarrenRating, 5 stars2 months ago

Great location perfectly located between Delavan and Lake Geneva. Views from balcony are amazing for sunset's. So close to Mars resort, Niche wine bar. Great location for week or weekend stay. only downside, which we know before booking is we rented for a month and no laundry facilities on site, so you have to drag laundry to laundromat on weekly basis for long term rental. overall 5 stars across board on this rental.