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Vacation rentals with a pool in Madison

Find and book unique homes with a pool on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Madison rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Top guest favorite
A charming gray house is set against a backdrop of colorful autumn foliage. The front porch features a red door, framed by shrubs and well-maintained landscaping. A clear blue sky provides a bright contrast to the warm tones of the trees.
Home in The Galena Territory
4.97 out of 5 average rating, 299 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

Guest favorite
A gravel fire pit area is positioned in the foreground, surrounded by a circular stone border. The spacious yard is framed by trees, providing a natural setting. In the background, a cozy wooden house with a deck is partially visible, blending harmoniously into the landscape.
Home in The Galena Territory
4.94 out of 5 average rating, 253 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Guest favorite
A round dining table is set outdoors with four yellow plates, each topped with a drink garnished with olives and celery. A bottle of cocktail mix rests beside the glasses, surrounded by textured placemats. Lush greenery provides a natural backdrop.
Home in The Galena Territory
4.92 out of 5 average rating, 108 reviews

Perfect Location! Owner Club Access, Steps to Pool

Guest favorite
A tranquil vacation home is set in a lush green landscape. The house features a screened-in porch and multiple balconies, surrounded by a wooden fence. Mature trees provide shade, and the inviting lawn enhances the serene outdoor environment.
Home in The Galena Territory
4.93 out of 5 average rating, 211 reviews

Galena Getaway

Top guest favorite
A spacious home is situated on a gently sloping landscape, framed by mature trees. The exterior features a combination of stone and wood elements, with a welcoming front porch and large windows that enhance natural light. A paved driveway leads up to the property.
Home in The Galena Territory
5 out of 5 average rating, 76 reviews

Stunning 5 bdm home on The General in Galena Terr!

Superhost
A warm and inviting living area features wood paneling and exposed beams. A spacious sofa, adorned with patterned throws, faces a large flat-screen TV. Natural light filters through sliding glass doors that lead to an outdoor space. A rustic stone fireplace adds a cozy touch.
Home in Wisconsin Dells
4.89 out of 5 average rating, 225 reviews

Spacious Pine Cabin at Island Pointe

Top guest favorite
The exterior of a spacious home is displayed, featuring a wraparound deck and large windows that allow ample natural light. Outdoor seating options, including blue chairs and a stone fire pit, are positioned on a grassy area surrounded by mature trees.
Home in The Galena Territory
4.94 out of 5 average rating, 165 reviews

Awesome Lodge in Galena Territory

Top guest favorite
A charming exterior view of the house is showcased, featuring a welcoming front porch with white railings and two rocking chairs. Lush greenery surrounds the home, and a stone pathway leads to the entrance. Sunlight filters through the trees, casting gentle shadows on the lawn.
Home in The Galena Territory
4.95 out of 5 average rating, 149 reviews

Family-Friendly Wooded Retreat- 3 Ensuite Bedrooms

Condo rentals with a pool

Top guest favorite
The spacious living area is illuminated by natural light from large windows. A leather sofa is paired with an accent chair, while a round rug centers the space. A modern coffee table sits atop the rug, and a dining counter with two bar stools is positioned nearby.
Condo in Lake Geneva
5 out of 5 average rating, 38 reviews

Chic Condo in Lake Geneva

Guest favorite
An indoor pool area is featured with large windows allowing for ample natural light. Two separate outdoor seating areas overlook the water, with patio chairs positioned along the poolside and balcony. A comfortable living room setup includes a sofa, coffee table, and window view of the surroundings.
Condo in Wisconsin Dells
4.83 out of 5 average rating, 248 reviews

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

Guest favorite
An aerial view showcases a welcoming living room with a sectional sofa positioned near a stone fireplace. A patterned area rug contrasts with the wood flooring. Large windows allow natural light to fill the space, complemented by decorative elements like throw pillows and a coffee table.
Condo in The Galena Territory
5 out of 5 average rating, 19 reviews

Fall Golf Bliss at Lucky Bunker - Swing Into Galen

Guest favorite
A spacious outdoor wave pool is surrounded by shaded lounge areas and seating. Guests are seen enjoying the water on inflatable floats, while a nearby snack bar is partially visible in the background, framed by lush greenery.
Condo in Wisconsin Dells
5 out of 5 average rating, 21 reviews

Hotel-Style Room with a View

Superhost
An open living area features large windows that provide a view of the lush garden outside. A sectional sofa, accompanied by a coffee table, is arranged near a brick fireplace. A rustic dining table with benches completes the inviting space, illuminated by a stylish chandelier.
Condo in Lake Geneva
4.9 out of 5 average rating, 41 reviews

Charming Lake Geneva Condo for 6

Guest favorite
A spacious family room is equipped with a comfortable sectional sofa and recliner chairs. A modern electric fireplace is positioned against a feature wall, while a large TV displays various channels. Natural light enters through sliding doors, leading to a patio with scenic views.
Condo in Wisconsin Dells
4.95 out of 5 average rating, 62 reviews

Dells Lake Villa - A Waterfront property

Guest favorite
A spacious living area features a comfortable sectional sofa adorned with patterned cushions and a coffee table. The kitchen and dining area in the background showcase modern appliances and cabinetry, with warm wood flooring creating a cohesive flow throughout the space.
Condo in Fontana
5 out of 5 average rating, 21 reviews

Abbey Villa Getaway |Patio | Pool | Walk to Water

The spacious living room features two comfortable sofas and a central coffee table. Soft lighting is provided by a side table lamp. Large windows offer natural light and views, complemented by warm, earthy wall colors and a patterned area rug beneath the furniture.
Condo in Wisconsin Dells
4.79 out of 5 average rating, 146 reviews

Beautiful Condo at Chula Vista!

Other vacation rentals with a pool

Guest favorite
The lake house is situated on a sloping hillside, surrounded by trees. A stone pathway leads down to the water's edge, where a private dock can be seen. The calm lake reflects the blue sky and scattered clouds, creating a serene setting.
Home in Apple Canyon Lake
4.93 out of 5 average rating, 88 reviews

The Ho Hum East on Apple Canyon Lake

Guest favorite
A charming cabin is surrounded by lush greenery, with well-maintained flower beds featuring red blooms. A large window provides natural light, and a stone border separates the garden from the grassy area. A tall tree offers additional shade, enhancing the serene outdoor environment.
Cabin in East Troy
4.98 out of 5 average rating, 44 reviews

Kettle 2BR Cabin on 15 lush acres w private lake

Guest favorite
A refreshing pool surrounded by a wooden deck is visible, complemented by several loungers for relaxation. Lush greenery frames the area, providing a serene backdrop. Colorful flowers in the foreground add a touch of vibrancy to the peaceful outdoor setting.
Home in Lake Geneva
4.98 out of 5 average rating, 40 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

An inviting outdoor pool surrounded by a spacious patio is featured, with lounge chairs arranged nearby. A rustic wooden chalet stands in the background, adorned with flower-filled balconies. Lush greenery adds to the serene atmosphere, under a clear blue sky.
Chalet in New Glarus
4.83 out of 5 average rating, 81 reviews

Authentic Swiss Chalet

Top guest favorite
A charming two-story cottage features blue siding and a decorative front door, framed by small windows on either side. A front pathway, bordered by greenery, leads to the entrance, while a lamp post stands nearby, illuminating the welcoming exterior.
Cottage in The Galena Territory
4.98 out of 5 average rating, 54 reviews

Storybook Countryside Cottage

Top guest favorite
A well-maintained cabin is set amid lush greenery, featuring a stone accent facade. The exterior includes a two-car garage with a vibrant teal door, and a welcoming porch with blue chairs inviting relaxation. Spacious lawns surround the cabin, enhancing the natural setting.
Cabin in The Galena Territory
4.99 out of 5 average rating, 82 reviews

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Superhost
A spacious living area features large, panoramic windows allowing natural light to fill the room. A comfortable sectional sofa is positioned centrally, with a vibrant orange toy resting on it. A cozy fireplace adorns the far wall, surrounded by decorative wooden accents.
Home in The Galena Territory
4.88 out of 5 average rating, 82 reviews

Fox Wood Path l HOT TUB l A&D Rise Getaways

Guest favorite
A modern, two-story house is set against a lush green landscape, featuring dark exterior siding and a pitched roof. A welcoming entrance is framed by two white chairs on a front porch, with trees and a bright blue sky in the background.
Home in The Galena Territory
5 out of 5 average rating, 8 reviews

Modern Home in Galena Territory

Quick stats about vacation rentals with a pool in Madison

  • Total rentals

    60 properties

  • Nightly prices starting at

    € 17 before taxes and fees

  • Total number of reviews

    980 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Dane County
  5. Madison
  6. Rentals with pools