
Holiday 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.

The Williamson's Waterfront Condo - Pickleball
NO SMOKING The 4th Williamson Family Condo is unit #410 at Lighthouse Cove. It is a waterfront unit situated on beautiful Lake Delton with a large 2nd floor patio allowing guests to relax and watch as life on the lake flows by. Ideally located near all of the attractions that the Dells has to offer, this 2 bed & 2 bath condo is perfect for a couple's weekend, golf trips, girls' weekend or a family getaway. The condo is beautifully appointed with comfortable beds & Roku TV's for rainy days.

Lake Geneva Condo with King Bed & Fireplace
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

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.

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown
INDOOR & OUTDOOR POOL ACCESS| DISCOUNTED ATTRACTION TIX | WATERFRONT The Riverwalk Retreat is the perfect spot to enjoy your next WI Dells trip with friends or family. This cozy vacation rental is located at the Sunset Cove Condo complex just 2 blocks off of Broadway & overlooks Crandalls Bay. Enjoy your morning coffee with a spectacular view of the WI River & the adjoining bay. This central location provides easy access to the area’s many athletics venues, nightlife, dining, & shopping.

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 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 .

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.

Hot Tub/$0 Cleaning Fee/Golf Course/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.

Spacious Pine Cabin at Island Pointe
Relax on Lake Delton and escape to fresh air, calm waters, and beautiful sunsets. Lake Delton is minutes away from Wisconsin Dells so you can enjoy all the activities at the waterparks. Nestled on fifteen acres of towering pines with two private sandy beaches, you’ll feel far from the commotion of the Dells, yet just minutes away. Once you’re here you can enjoy the many amenities we have on-site, such as a heated outdoor pool, playground, picnic area, and two sandy beaches.

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 waterparks, restaurants, 18-hole golf course, zip line and so much more! Minutes from all of the area's attractions including 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!

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!
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

The Lodge |Golf Cart |Abbey Springs |Beach

Cozy cabin getaway near Lake Como and Lake Geneva

Red Oak Lodge @ Spring Brook Resort

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

Sunset retreat oasis Pool hot tub river fishngame

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

Wyndham 3BR ChulaVista Condo w/FREE Water ParkPass

Condo in Wisc Dells for 10-14 ppl

Wyn Glacier Canyon, 2 BR, 8 FREE WaterPark Passes!

2 BD 2 BA Abbey Villa with Pool

FUN-tana All Year Round Abbey Springs Fontana WI

Spacious 3BR Condo Retreat

Flexible rental In Lake Geneva Area

Lake Geneva relaxation!
Other holiday rentals with a pool

Abbey Springs Home! Hot Tub + Golf Cart

Country Living/Downtown Access

Newly Remodeled Mid-Century Modern Lake Condo

Boat Dock & Backyard: 'Rock River Retreat'

Your Home Away From Home!

Family Home w/ Deck, Yard, Dock on Rock River

Bluegreen Odyssey Waterpark

Luxurious BBQ and Pool House
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $111 SGD | $113 SGD | $120 SGD | $155 SGD | $151 SGD | $153 SGD | $161 SGD | $153 SGD | $153 SGD | $126 SGD | $115 SGD | $111 SGD |
| 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 holiday rentals with a pool in Madison

Total holiday rentals
Explore 60 holiday rentals in Madison

Nightly prices starting at
Madison holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 980 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Madison holiday rentals include wifi 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
- Mt. Olympus Water & Theme Parks
- Noah's Ark Waterpark
- Wisconsin State Capitol
- Mt. Olympus Parks, Outdoor Theme Park
- Lake Kegonsa State Park
- Mirror Lake State Park
- Yellowstone Lake State Park
- Tyrol Basin
- Cabin 857-1- Christmas Mountain Village
- Kalahari Indoor Water Park
- Mt. Olympus Parks, Parthenon Indoor Theme Park
- Henry Vilas Zoo
- Cascade Mountain
- Wild Rock Golf Club
- Alligator Alley
- Lost World Water Park
- Wollersheim Winery & Distillery
- Wild West water park
- Tom Foolerys Adventure Park
- Klondike Kavern Water Park
- University Ridge Golf Course
- Pirate's Cove Adventure Golf
- Extreme World




