
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.

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.

*Family Retreat* *Indoor Pool* *Arcade*
The Pool House is the perfect family retreat for any group that wants quality time with quality amenities. Come enjoy everything our home has to offer and make all those wonderful memories with the ones you love. The indoor heated pool is perfect for that private party experience that can be followed up with the fully loaded arcade room. Enjoy the pinball machines and great classic arcade games then go off to the full size Golden Tee and Buck Hunter and see if you can get the new high score.

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 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.

The Wanderlust at the Sunset Cove
Riverfront one bedroom condo in a tranquil area of Downtown Wisconsin Dells. Take a stroll near the beautiful River Walk and enjoy the magnificent scenery and unique attractions of Downtown Wisconsin Dells. Whether you need a few days to relax and decompress or if you are in town for business or games, our condo offers a fully equipped kitchen, a king size bed and a queen size pull out couch . There is an indoor community pool, hot tub and sauna. There is also a seasonal outdoor pool .

HD Jameson House at River’s Edge
Nestled on the Rock River, the HD Jameson House, a National Historic Register gem, blends historic charm with modern amenities. Enjoy river views and with quaint shops and restaurants exploring the Village of Rockton is a perfect family-friendly retreat. This haven is surrounded by nature but close to numerous attritions, ideal for a romantic getaway or peaceful escape. The HD Jameson House offers a heavenly retreat, blending past beauty with present allure for everyone in the family.

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.

Lake Geneva - Fireplace - Pool - Fast 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!

Cozy Home/Large Backyard/Privacy FenceThe 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.

Luxurious Chula Vista Retreat
No resort fees! Experience all the Wisconsin Dells has to offer while staying in this luxurious condo, located inside the action-packed Chula Vista Resort! Enjoy the resort's restaurants, 18-hole golf course, zip line and so much more! Minutes from all of the area's attractions including Mt. Olympus, Noah's Ark and hiking trails! Then relax in our Jacuzzi tub, cozy up to our two fireplaces, hang out in our spacious living room or cook a family meal in our full-size kitchen!

Family-Friendly Dells Stay | Sleeps 8 + Jacuzzi
Perfect for groups! This condo sleeps 8 and features a king master suite with private bath, plus 2nd bedroom with 2 queens. Enjoy new LVP floors, ROKU Smart TVs, a full kitchen stocked with cookware & basics, and an in-suite jacuzzi tub. Capture insta-worthy shots at the neon green wall before exploring Wisconsin Dells attractions just minutes away. 🌊 Water park passes not included. Complimentary WiFi (sometimes can be spotty) Please read "other details section below."

Dells Retreat At Tamarack Resort
Welcome to Dells Retreat (A Dellsvacations Club property), your ultimate vacation destination in the heart of Wisconsin Dells. Nestled in the picturesque Tamarack Resort, our property offers a serene and scenic setting for your vacation. With endless amenities and attractions just minutes away, Dells Retreat is the perfect escape for travelers of all ages. Each stay at Dells Retreat also includes two free splash passes, providing access to even more attractions.
Popular amenities for Madison rentals with a pool
House rentals with a pool

Lakefront cabin in the woods.

The Ho Hum East on Apple Canyon Lake

Lodge Home - 2.8 Miles to Town - Minutes to Ski

Cozy cabin getaway near Lake Como and Lake Geneva

Treetop Lakehouse at Abbey Springs

Spacious Pine Cabin at Island Pointe

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

Nestled in the Southern Kettle Moraine Forest
Condo rentals with a pool

Lakefront Condo - Private Beach | Boat Slip| Pool

Spacious Condo Retreat for 10-14 ppl

Room w/Balcony at Chula Vista Resort-Pet Friendly!

FUN-tana All Year Round Abbey Springs Fontana WI

Charming Lake Geneva Condo for 6

Hotel-Style Room with a View

Luxury Family Getaway | 4BR Condo - Glacier Canyon

Wyndham Glacier Canyon |2BR/2BA King Suite w/ Balc
Other vacation rentals with a pool

Kettle 2BR Cabin on15 stunning acres by Ski trails

Beautiful Abbey Springs!

Newly Remodeled Mid-Century Modern Lake Condo

Ground level Poolside Villa on Lake Delton

Hot Tub! King Beds! Game Room! 4bd/3ba Log Cabin!

Quaint, quiet condo minutes from Lake Geneva

Epic 6BR w/ Movie Theater + Pool + Dock Access

Adeline's House of Cool, The most fun Airbnb in WI
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ316 | ﺩ.ﺇ323 | ﺩ.ﺇ342 | ﺩ.ﺇ441 | ﺩ.ﺇ430 | ﺩ.ﺇ437 | ﺩ.ﺇ459 | ﺩ.ﺇ437 | ﺩ.ﺇ437 | ﺩ.ﺇ400 | ﺩ.ﺇ367 | ﺩ.ﺇ364 |
| Avg. temp | -7°C | -5°C | 1°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 3°C | -4°C |
Quick stats about vacation rentals with a pool in Madison

Total vacation rentals
Explore 60 vacation rentals in Madison

Nightly prices starting at
Madison vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

Verified guest reviews
Over 1,050 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Madison vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Madison rentals

4.8 Average rating
Madison stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Madison's top spots, include Henry Vilas Zoo, Wisconsin State Capitol, and Olbrich Botanical Gardens
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- Devil's Lake State Park
- Glacier Canyon Lodge
- Noah's Ark Waterpark
- Wisconsin State Capitol
- Lake Kegonsa State Park
- Mirror Lake State Park
- Cascade Mountain
- Henry Vilas Zoo
- Wollersheim Winery & Distillery
- House on the Rock
- Kohl Center
- Madison Childrens Museum
- Chazen Museum of Art
- Camp Randall Stadium
- Governor Dodge State Park
- Monona Terrace Community And Convention Center
- American Players Theatre
- Overture Center For The Arts
- Dane County Farmers' Market




