Vacation rentals with a pool in Milwaukee

4.97 out of 5 average rating, 109 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, 228 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.

Superhost

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, 102 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.

4.88 out of 5 average rating, 112 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, 156 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.

The spacious living room features a large sectional sofa in neutral tones, focused around a gas fireplace. A flat-screen smart TV is mounted above the brick hearth. Sliding glass doors open to the outdoor patio, allowing natural light to fill the space.

4.98 out of 5 average rating, 158 reviews

Cozy Lake Geneva Retreat | Amenities | WiFi

Discover Blue Lakes Escape, a newly-redecorated condo, steps away from Lake Como. Relax in the spacious great room with a smart TV, fireplace, desk area & access to quaint patio. Sit outside with a coffee, a good book, or a delicious BBQ. Enjoy free access to the shared amenities, including an outdoor pool, sports courts, & walking trails. Lake Como – 6 min walk Lodge Geneva National – 6 min walk Downtown – 8 min drive Book For Lasting Memories In Lake Geneva—See Details Below!

Superhost

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, 188 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 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, 169 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.

4.93 out of 5 average rating, 160 reviews

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

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!

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, 190 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.

Cottage in Fontana-on-Geneva Lake

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.

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 .