Vacation rentals with a pool in Madison

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Madison

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

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Guest favorite

Guest suite in Spring Green

4.9 out of 5 average rating, 134 reviews

Spring Green River Pines

Spend a few days in the beautiful countryside. A private entrance to the lower level of home (completely separate from our home) that includes a central room, 2 bedrooms with kitchenette, & 1 lg bath. WiFi >500 Mbps speed. Smart 60" TV, Bluetooth Airplay/stream compatible. Parking on sight. Great location 5 min from beautiful downtown Spring Green. Close to APT, Taliesin/Frank Lloyd Wrights Home/School, House on the Rock, WI River, Gov. Dodge State Park and 1/2 hr to Devils Lake State Park.

Guest favorite

Condo in Lake Geneva

4.98 out of 5 average rating, 193 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

Home in Milton

4.84 out of 5 average rating, 207 reviews

Tree Top House with mini indoor pool and sauna

Welcome to the tree top house. A great place to stay any time of year Situated in a wooded setting on 10.5 acres this beautifully hand crafted home offers a great outdoor environment and many amenities including a mini indoor heated pool, sauna, two fireplaces, cathedral wood ceiling great room and dining area, spacious deck and private fire pit. Four private bedrooms, two of which have fireplaces in them and all with beautiful wood views. Three nature paths are available for taking walks.

Guest favorite

Condo in Wisconsin Dells

4.88 out of 5 average rating, 256 reviews

The Docksider for Couples & Young Families

NO SMOKING The Docksider is the original Williamson Family Condo. Located right by the boat docks, this is perfect for a quick getaway as a couple or bring the kids. The property is situated right on beautiful Lake Delton in a quiet neighborhood in the heart of the Dells. The property has both indoor and outdoor (open seasonally only) pools and hot tubs for your year-round enjoyment. In the summer you are just steps away from the private beach and you can fish from the docks or the ice.

Superhost

Condo in Lake Geneva

4.9 out of 5 average rating, 192 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!

Guest favorite

Home in Spring Green

4.92 out of 5 average rating, 50 reviews

Golf Course/$0 Cleaning Fee/Hot Tub/The Hemlock

Our 4 bedroom, 2.5 bath home in downtown Spring Green, Home to Frank Lloyd Wright’s Taliesin, American Players Theater, the House on the Rock, and Tower Hill State Park, the vibrant village of Spring Green is a place where nature and art meet. Just 45 minutes from Madison, And the Dells Waterpark. Do You enjoy Golfing Or snow mobile Riding? Relax with the whole family at this peaceful place to stay. walk to downtown or the Rec Park with soft ball diamond and skate board Park.

Guest favorite

Home in Madison

4.92 out of 5 average rating, 245 reviews

Luxurious BBQ and Pool House

Hosting a summer barbecue, a pool party, or just looking for a relaxing getaway with your friends? The unique combination of indoor and outdoor space provides something for everyone. This is a modern, spacious, and luxurious 3 bedroom, 2.5 bath home, conveniently located 15 minutes from downtown. Situated on a 3/4 acre lot, this house is fully equipped w/ premium amenities for your friends and family:Swimming pool, hot tub, big yard, deck with a gas grill and dining area

Guest favorite

Condo in Lake Geneva

4.96 out of 5 average rating, 121 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

Enjoy your stay at our family's Serene Lake condo with outdoor pool. 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.

Guest favorite

Condo in Lake Geneva

4.98 out of 5 average rating, 122 reviews

Retreat close to DT Lake Geneva! Pool! King Bed!

Your peaceful getaway begins in a newly remodeled, ground level condo with patio, 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, and more! The resort community is located by The Ridge Hotel, which adds additional restaurants and available amenities at an additional charge. Many local areas to explore & visit will await your arrival.

Guest favorite

Condo in Lake Geneva

4.97 out of 5 average rating, 107 reviews

Magnificient views in a Lakefront condo, 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. Your stay promises a perfect balance of peaceful relaxation and recreational activities creating unforgettable memories in this beautiful Wisconsin setting.

Guest favorite

Condo in Lake Geneva

4.97 out of 5 average rating, 68 reviews

LG Quaint Condo on Lakeshore Dr.

1+1 condo off Lakeshore Blvd, just minutes from downtown LG. Home is the perfect balance of quaint meets modern touch. Wake to a full coffee and tea station, cook in your own full kitchen. Walk to the lake, take a boat out just a few blocks away, or enjoy a scenic drive downtown. Experience the quiet and original charm of Lake Geneva without sacrificing the convenience of being close to DT LG. Book alone or with another condo in the same building.

Guest favorite

Condo in Lake Geneva

4.96 out of 5 average rating, 160 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!