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.

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Guest favorite

A private swimming pool is covered and surrounded by a spacious patio area. Lush greenery and tall trees outline the backyard, creating a serene environment. A wooden pergola with climbing vines is visible, along with a small seating area featuring green picnic table seating.

Guest suite in Spring Green

4.91 out of 5 average rating, 163 reviews

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.

Superhost

An indoor swimming pool area is presented, featuring a large swimming pool with a shallow children's section. Lounge chairs are positioned along the poolside, and bright overhead lighting offers visibility. The walls are painted in a calming blue hue, enhancing the spacious atmosphere.

Condo in Wisconsin Dells

4.87 out of 5 average rating, 113 reviews

Grace-Jo @ Tamarack Highland 5

Upgrade to our Noah's Ark package after booking! This home is a beautiful one-bedroom at the Tamarack and Mirror Lake Resort. We offer plenty of amenities to keep guests of all ages busy. Conveniently located near all of the attractions the Dells are known for. The condo is attractive, clean and includes a well-equipped kitchen, comfortable beds, and smart TV's for the rainy days. This property is great for a couple or a family and is near the included pools and activities at the resort.

Guest favorite

A cozy living area is highlighted by a gas fireplace and a large Smart TV mounted on the wall. A sliding glass door leads to a balcony with views of the green courtyard. Comfortable seating is arranged around a rustic coffee table that complements the relaxed atmosphere.

Condo in Lake Geneva

4.97 out of 5 average rating, 152 reviews

Cozy LG Retreat! King Bed! Fireplace! WiFi!

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

Top guest favorite

A custom log cabin is framed by lush greenery and manicured landscaping. The warm wooden exterior features multiple gabled roofs and large windows. A stone pathway leads through the vibrant garden, creating an inviting approach to the entrance.

Cabin in Galena

4.95 out of 5 average rating, 106 reviews

Private, Galena Log Cabin

This custom log cabin is the perfect getaway for friends & family seeking the solitude of the Galena Territory and fine dining and shops just 10 minutes away on Galena's Main Street. Each of the 3-levels offers an owner's suite with bath. Cozy up to 2 fireplaces, grill on the deck, or make 'smores at the firepit. The cabin has high speed, fiber internet and the lower-level walkout features a 55” flat screen TV. Guests can access swimming pools & pool tables at the Owner's Club 7 minutes away.

Top guest favorite

A cozy living area is featured with a warm fireplace and a mounted television above it. Two side tables are positioned beside the fireplace, enhancing comfort. Natural light enters through the windows adorned with wooden blinds, creating an inviting space for relaxation.

Villa in Galena

4.98 out of 5 average rating, 143 reviews

King bed, Wood Fireplace, Near Spa, Golf, Trails

✓Peaceful, nature views ✓Serene, wooded backdrop ✓Semi-private outdoor pool, steps away ✓Well equipped kitchen w/modern appliances ✓Gas grill on deck ✓Smart TV on each level ✓Computer desk ✓Fireplace w/supply of firewood ✓King sized bed ✓2 Full baths ✓Near hiking trails & paved walking trails ✓Stonedrift Spa, 3 min drive ✓North Course & Driving Range, 2 min drive ✓Downtown Galena, 15 min drive ✓Owner's Club access ✓Indoor pool ✓Lake access ✓Chestnut Mountain (Ski & Zipline), 25 min drive

Top guest favorite

The living area showcases a spacious layout with a leather pullout couch and armchair, complemented by a modern coffee table. A smart TV is mounted on one wall, while an electric fireplace adds warmth. The kitchen features a bar with three stools, enhancing the inviting atmosphere.

Condo in Wisconsin Dells

4.98 out of 5 average rating, 167 reviews

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 .

Guest favorite

Home in Galena

4.96 out of 5 average rating, 104 reviews

Secluded Treehouse, w/great views, close to Hwy 20

Enjoy the many charms of this one of a kind Tuscan style treehouse with different levels showcasing spectacular views. This home has every amenity and personal touch of home to make your stay relaxing and memorable. Conveniently located approximately 1 mile off Highway 20 in the Galena Territory, backing up to hole 13 on The General Golf Course. Set back off the main road you will enjoy privacy without sacrificing convenience and access to the many amenities offered during your stay.

Top guest favorite

An outdoor pool is surrounded by lounge chairs and shaded by trees, creating a relaxing environment. A few red umbrellas are positioned near the poolside, offering spots for shade. The pool's clear water reflects the sky, inviting guests for a refreshing swim.

Condo in Wisconsin Dells

4.97 out of 5 average rating, 490 reviews

COZY, Pickleball, Fireplace, Kayaks, Pontoon Ride

NO RESORT FEES + PONTOON RIDE Relax on the porch and watch the boats glide by, soaking in the serene lake views. Whether you're looking for relaxation or recreation, our condo offers the best of both worlds. Book your stay today and experience the ultimate lakeside escape! Resort-Style Amenities • Free Kayaks and Stand Up Paddle Board • Indoor and outdoor pools • Hot tub • Walking distance to Noah's Ark • First Responder Discounts • Smart TVs • Jetted Tub • Fireplace • Washer/Dryer

Guest favorite

An outdoor pool area is surrounded by well-maintained landscaping, featuring several lounge chairs and tables. A patio with umbrellas provides shaded seating options. The pool is enclosed by a fence, with a clear view of greenery in the background. An adjacent gazebo offers additional space for relaxation.

Condo in Lake Geneva

4.96 out of 5 average rating, 156 reviews

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.

Top guest favorite

The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.

Treehouse in Galena

4.98 out of 5 average rating, 170 reviews

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Top guest favorite

A two-story house is set on a spacious lawn, framed by trees exhibiting autumn colors. The exterior features a welcoming porch with white railings. A paved driveway leads to a garage, and a privacy fence encloses the backyard, contributing to a tranquil environment.

Home in Spring Green

4.96 out of 5 average rating, 119 reviews

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.

Guest favorite

A round swimming pool is situated within a spacious yard, surrounded by lush greenery and trees. The pool features a white safety cover and a set of steps leading down into the water. A wooden deck runs alongside the pool, enhancing the outdoor space.

Home in Madison

4.9 out of 5 average rating, 279 reviews

Luxurious BBQ and Pool House

Hosting a summer barbecue, a pool party, or just looking for a relaxing getaway with your friends? The unique combination of indoor and outdoor space provides something for everyone. This is a modern, spacious, and luxurious 3 bedroom, 2.5 bath home, conveniently located 15 minutes from downtown. Situated on a 3/4 acre lot, this house is fully equipped w/ premium amenities for your friends and family:Swimming pool, hot tub, big yard, deck with a gas grill and dining area