
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.

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.

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.

*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.

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.

Lakefront Condo - Private Beach | Boat Slip| Pool
Experience lake life at our luxury, lakefront condo. Wake up to morning coffee on the balcony with breathtaking views of Lake Delton. Our spacious 2 bedroom, 2 bathroom condo features a beautiful master suite with a king bed, en suite bathroom complete with a jetted massage tub and walk in shower with 3 directional shower heads. It is the perfect escape for those who want to feel like they are a world away, but are also minutes from all the fun and excitement of the Dells.

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.

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!

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."

Kate's Place - Newly Remodeled - Romantic
NO SMOKING Max Occupancy: 4 People (2 Adults) Upgrade to our Noah's Ark package after booking! Kate's Place is recently updated and located in Lighthouse Cove on Lake Delton in the heart of the Dells. Enjoy beach access, indoor & outdoor pools and hot tubs, and convenient parking. This condo is great for a couples or small families. The kitchen has all the tools you need to stay in, but the location is super close to great supper clubs for an evening out as well.

Dells Retreat - A Romantic Haven- Luxury Living
GIFTS FOR THE GUESTS: 1. TWO MT. OLYMPUS WATER PARK PASSES INCLUDED WITH A MINIMUM OF 4 NIGHT STAY. 2. TWO SPLASH PASSES INCLUDED WITH EACH STAY, BUY 1 GET 1 DEAL FOR NATURA WATER PARK PASSES & MORE. EXCLUSIVE DISCOUNTS FOR GOLF, ADVENTURES, WATER PARKS, RESTAURANTS & THEATER Dells Retreat is located in Tamarack Resort. A perfect escape in the heart of Wisconsin Dells. An ideal place for travelers of all ages. Endless amenities and so close to all 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

Cozy cabin getaway near Lake Como and Lake Geneva

3bed lake house, private pool near WI Dells

Spacious Pine Cabin at Island Pointe

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

Nestled in the Southern Kettle Moraine Forest

Cozy Winter Retreat: Hot Tub & Family Fun
Condo rentals with a pool

Wyndham Glacier Canyon |1BR/1BA King Suite w/ Balc

Riverview Paradise Suite (3 Bedrms/3 Bath/2040 SF)

FUN-tana All Year Round Abbey Springs Fontana WI

Hotel-Style Room with a View

Abbey Villas Condo Steps to Pool Near Beach

Beautiful Condo at Chula Vista!

Luxury Family Getaway | 4BR Condo - Glacier Canyon

Luxury Lake Geneva Condo with Patio
Other vacation rentals with a pool

Condo in Wisc Dells for 10-14 ppl

Kettle 2BR Cabin on15 stunning acres by Ski trails

Newly Remodeled Mid-Century Modern Lake Condo

Ground level Poolside Villa on Lake Delton

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

★GLACIER CANYON RESORT WITH WATER-PARK AMENITIES★

Luxurious BBQ and Pool House

Epic 6BR w/ Movie Theater + Pool + Dock Access
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 74 | € 76 | € 80 | € 103 | € 101 | € 102 | € 107 | € 102 | € 102 | € 84 | € 76 | € 74 |
| 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 € 17 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
- Camp Randall Stadium
- Kohl Center
- Monona Terrace Community And Convention Center
- Chazen Museum of Art
- Overture Center For The Arts
- Madison Childrens Museum
- Dane County Farmers' Market
- American Players Theatre
- Governor Dodge State Park




