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.

0 of 0 items showing

1 of 3 pages

Top guest favorite

An indoor heated pool reflects vibrant blue water, surrounded by colorful lounge chairs. Nearby, an arcade room features classic pinball machines and video game consoles, set against polished wooden flooring. Large windows allow natural light to fill the space, creating a bright and energetic atmosphere.

Home in Janesville

5 out of 5 average rating, 72 reviews

*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.

Top guest favorite

A patio area features multiple seating options and a glass door leading into the condo. Lush greenery and colorful flowers border the concrete walkway, providing a serene outdoor setting. A second-level balcony is visible above, adding depth to the outdoor space.

Condo in Lake Geneva

4.98 out of 5 average rating, 206 reviews

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.

Guest favorite

A spacious log home is showcased, featuring large floor-to-ceiling windows that illuminate the interior. The fenced-in pool area is surrounded by landscaped gardens, with lounge chairs positioned near the water. Lush greenery and trees create a serene backdrop for the property.

Cabin in Lodi

4.96 out of 5 average rating, 28 reviews

Modern cabin with pool and Hot Tub!

Forget your worries in this spacious and serene space. Secluded yet close to a big city (Maddison and Wisconsin Dells) and lots of entertainment! 20 min away from 2 ski resorts, an amazing winery and distillery, spas, restaurants, casino! 3 mile away from lake Wisconsin. Hiking trailers, 24 hour ferry service across the lake and more. This luxurious villa combines comfort and style, you won't want to leave it, but the area is full of enviting places to go to, so plan for a few extra days!

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, 138 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.

Guest favorite

A dining area features a round wooden table surrounded by four wicker chairs. A brick accent wall and green paneling provide texture, while natural light enhances the space. A doorway in the background leads to additional areas of the villa.

Condo in Fontana-on-Geneva Lake

5 out of 5 average rating, 12 reviews

Luxurious Condo Experience at Lakeside Villa |Pool

Vacation memories await at this 2 bedroom, 2 full bathroom Abbey Villa at the West end of Geneva Lake. A true standout within the association, Lakeside Villa has been finished with thought and detail to deliver a luxurious condo experience. Walk-able to everything Fontana has to offer, including restaurants, boat rentals, and the beach- not to mention, the fantastic Abbey Villa pool that is just steps away! Book today to discover why guests return to the Abbey Villas year-after-year!

Guest favorite

Condo in Wisconsin Dells

4.91 out of 5 average rating, 96 reviews

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.

Top guest favorite

A hot tub sits on a patio, surrounded by a well-maintained yard. Colorful fall foliage is visible in the background, with vibrant red and yellow leaves contrasting against a white privacy fence. Steam rises gently from the water, suggesting a warm and inviting experience.

Home in Spring Green

4.94 out of 5 average rating, 88 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

4.91 out of 5 average rating, 264 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

Superhost

An indoor pool area features a tranquil atmosphere with a wooden ceiling and walls. The pool is bordered by a tiled deck, and multiple lounge chairs are arranged along the sides. Natural light enters through windows, illuminating the water's surface.

Condo in Wisconsin Dells

4.84 out of 5 average rating, 282 reviews

Williamson Family Condo at Lighthouse Cove

NO SMOKING Upgrade to our Noah's Ark package after booking! Williamson Family Condo II is recently updated and located in Lighthouse Cove on Lake Delton in the heart of the Dells. Enjoy beach access, in & outdoor pools w/ hot tubs, and convenient parking. This condo is great for a couples or families. Let the older kids wander to and from Noah's Ark or go fishing at the lake while you take a much-deserved time out. Inquire about using our boat slip.

Guest favorite

A view from the balcony captures a well-maintained lawn with a cloudy sky backdrop. A tennis court is visible in the foreground, while trees and a body of water create a serene atmosphere in the background.

Condo in Lake Geneva

4.97 out of 5 average rating, 182 reviews

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!

Guest favorite

A clear swimming pool is surrounded by a concrete deck, featuring multiple white lounge chairs. Lush green trees frame the area, enhancing the serene environment. Two wooden cabins are visible in the background, providing a rustic charm to the outdoor space.

Cabin in Wisconsin Dells

4.88 out of 5 average rating, 215 reviews

Lake-view 3-bedroom Cabin Home on Lake Delton

Our place is close to ALL Lake Delton, WI Dells Downtown attractions. You’ll love our place because of the views of lake & pine trees, quiet setting, brand-new remolded interior with upscale furnishings, high ceilings, and the cabin coziness. Our Large, cabin accommodates up to 8 people very comfortable at over 1600 sq. ft. Best Resort in Town!!! Family fun atmosphere with two sandy beaches & large swimming pool. Kids love to fish off the piers.

Top guest favorite

A swimming pool is surrounded by a patio with several lounge chairs and umbrellas, providing a relaxing atmosphere. The pool features a crystal-clear blue surface, and a small building with a roof is visible in the background, likely used for amenities.

Condo in Wisconsin Dells

4.97 out of 5 average rating, 175 reviews

Stunning Condo, Beachfront, Fireplace, Jacuzzi

This condo is not just a place to stay; it’s a retreat where luxury meets convenience, offering an unforgettable beachside experience. HIGHLIGHTS - Jacuzzi Tub - Modern Fireplace - Large Smart Tvs - Open Concept, new furniture - Short walk to Noah's Ark - A few steps to the beach and picnic area - New beds with memory foam mattresses - Free use of Kayaks - Free Pontoon ride - Great outdoor space with comfy furniture - First Responder Discounts