
Vacation rentals with a pool in Madison
Find and book unique homes with a pool on Airbnb
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 $28 CAD per night before taxes and fees

Verified guest reviews
Over 720 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Madison vacation rentals include wifi access

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

4.7 Average rating
Madison stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Madison’s top spots, include Henry Vilas Zoo, Wisconsin State Capitol, and Olbrich Botanical Gardens
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.

Private Pool - Hot Tub - Sauna - Game Room - Pets
🔹Private fenced-in backyard w/ heated pool, hot tub, sauna, deck & fire pit 🔸Outdoor living w/ lounge seating, pool toys, & outdoor dining 🔹Large families & groups - 2 King, 6 Queen 🔸Game room w/ pool table, ping pong & arcade games 🔹3 min to Sun Prairie restaurants & shopping 🔸Basement gym w/ free weights & equipment 🔹Pickleball court in the garage 🔸You'll find "The Kohl Center, UW-Madison, Camp Randall Stadium, State Street, The Capitol, & The Alliant Energy Center" within 20min

The Ho Hum East on Apple Canyon Lake
The Ho Hum East is a beautiful lake house with private dock on pristine Apple Canyon Lake! The house is named in honor of my grandparents who ran the Ho Hum Motel in Denison, Iowa :) A place to unwind, de-stress, and have some family fun! The house features all brand new mattresses in 3 bedrooms plus flex space; master bedroom with queen bed, guest bedroom with 1 queen and 1 twin, loft bedroom with 2 queens, pull out couch in living room, and 2 couches in the loft that pull out into twin beds.

*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 Lodge 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.

Beachfront Condo Retreat at Delton Grand
Upgrade to our Noah's Ark package after booking! NO SMOKING This waterfront studio condo at Delton Grand is a perfect getaway spot for any couple. Our guests enjoy waterfront views and all of the amenities at Delton Grand, including indoor and outdoor (seasonal) pools, indoor hot tub, 2 beaches, fishing docks, gas grills, and fire pits. Being within walking distance to Del-Bar, Embers, and Summer House makes this property ideal for couples coming to enjoy the areas finest restaurants.

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.

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!

Dells Retreat - Sleeps 8 + Jacuzzi | Waterpark
LAND OF NATURA VOUCHERS INCLUDED $25 OFF/Per Person. Memorial Day - Labor Day Perfect for families & groups! This spacious condo sleeps 8 with a king master suite + private bath and a second bedroom with two queens. Enjoy new LVP floors, Roku Smart TVs, a fully stocked kitchen, and a relaxing in-suite jacuzzi tub. Snap fun photos at the neon green accent wall before exploring Wisconsin Dells attractions just minutes away. 🌊 Water park passes not included.

The Landis, spacious condo w/ pool & king bed
Kick back and relax in this calm, elegant one bedroom Villa with a KING size bed. This vacation rental is in a quiet area of Lake Geneva, but just minutes from all the vibrancy of downtown Lake Geneva or Williams Bay. It is within walking distance to Mars Resort, The Getaway or The Lodge Geneva National. This is a perfect spot for couples looking for a relaxing getaway. Local laws require all guests names and address be provided prior to check in.

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.

Cozy cabin getaway near Lake Como and Lake Geneva

4 Bed, 3 Bath with Pool, Hot Tub, Gym, Fire Pit

Spacious Pine Cabin on Lake Delton

Sunset retreat oasis Pool hot tub river fishngame

Serenity Now @ Spring Brook Resort

Farmhouse with Heated Pool on almost 160 Acres!

Private Pool - Hot Tub - Game Room - 20 min DT
Condo rentals with a pool

Lakefront Condo - Private Beach | Indoor Pool

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

FUN-tana All Year Round Abbey Springs Fontana WI

Upper Dells River Walk [1BR]

Spacious 3BR Condo Retreat

Abbey Villas Condo Steps to Pool Near Beach

LakeView-SummerPool-FamilyFriendly-CloseToTown

Sunset + Lake View Stylish Condo in Lake Geneva
Other vacation rentals with a pool

Farm in the Driftless | Private + Family-Friendly

Private yet close to everything! NEW

Newly Updated Modern Lake Condo

Apple Cub Cabin: Hot Tub, Game Room & King Beds &

Modern Cabin with pool, hot tub and outdoor sauna

Spacious Delightful 2 Bedroom Home

Homestead Hideaway Seven Sisters Suite

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 | $132 CAD | $138 CAD | $139 CAD | $156 CAD | $163 CAD | $166 CAD | $174 CAD | $166 CAD | $166 CAD | $152 CAD | $139 CAD | $138 CAD |
| 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 |
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- Devil's Lake State Park
- House on the Rock
- Noah's Ark Waterpark
- Wisconsin State Capitol
- Lake Kegonsa State Park
- Mirror Lake State Park
- Glacier Canyon Lodge
- Wollersheim Winery & Distillery
- Cascade Mountain
- Governor Dodge State Park
- Henry Vilas Zoo
- Camp Randall Stadium
- American Players Theatre
- Chazen Museum of Art
- Tyrol Basin
- Overture Center For The Arts
- Dane County Farmers' Market
- Monona Terrace Community And Convention Center
- Madison Childrens Museum
- Ho-Chunk Gaming Wisconsin Dells
- Cave Of The Mounds Lowest Point
- Parfrey's Glen State Natural Area
- Blue Mound State Park
- Tommy Bartlett Exploratory





