Holiday 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 favourite

Guest suite in Spring Green

4.9 out of 5 average rating, 141 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.

Guest favourite

Cabin in Galena

4.96 out of 5 average rating, 116 reviews

Fam Winter Vaca! <-Hot tub- Fire place-Game room->

Escape to our cozy luxe cabin in Galena Territory, the perfect retreat for winter! Start your mornings sipping coffee by the gas fireplace, then warm up each evening in the hot tub! Enjoy friendly competition with arcade games, board games, air hockey, and darts. With 10 amenity cards, you can access the owner’s club for swimming and exercise including indoor pickle ball-rackets and balls at the house! Experience relaxation and adventure in this tranquil haven—your unforgettable getaway awaits!

Guest favourite

Home in Galena

4.97 out of 5 average rating, 127 reviews

Newly Remodeled! Hot tub, views, 6BR/6BA

Welcome to The Double Eagle! Experience Galena and the Territory while you relax in this 6 bedroom/6 bath home overlooking the fairway. This well-stocked and spacious three story home easily accommodates multiple families or large groups and has many outdoor spaces to enjoy! Sip your morning coffee in the 3-season room with cozy sectional, make the most of your afternoon playing pool or foosball in the game room, and finish the day by grilling out on the back deck and relaxing in the hot tub.

Guest favourite

Home in Galena

4.97 out of 5 average rating, 116 reviews

Holiday Hot Tub Escape-Open for Christmas!

Step into Rolling Hills Retreat, a sanctuary from the everyday bustle! Our dog-friendly rental offers breathtaking views and numerous amenities for your pleasure and relaxation. Enjoy a swim in the indoor or outdoor pool, and discover a variety of amenities that promise an unforgettable stay. *Pickle Ball *Basketball *Pool Tables *Hiking Trails *Workout Room *Tennis Courts *Brand new (June 2024) Marina with boat rental (additional charge) *Ping Pong tables *Arcade *Scenic Waterfall *Kayaking

Guest favourite

Villa in Galena

4.98 out of 5 average rating, 110 reviews

King Bed, Woodburning Fireplace, Pool, Near Spa

◆ Quiet, wooded retreat ◆ King bed ◆ Indoor pool, year round access ◆ Well equipped kitchen ◆ Smart TV on each level w/Roku & YouTube TV ◆ Woodburning fireplace w/supply of firewood ◆ Computer desk ◆ 2 Full baths ◆ Queen sofa bed ◆ Gas grill ◆ Fitness center ◆ Paved walking trails nearby ◆ North Course & driving range conveniently up the road ◆ Stonedrift Spa, 3 min. drive ◆ Downtown Galena, approx. 15 min drive ◆ Winter sports at Nordic Center ◆ Chestnut Mountain Ski , approx. 25 min drive

Guest favourite

Apartment in Wisconsin Dells

4.97 out of 5 average rating, 216 reviews

1BR Riverfront w/in-room jacuzzi, pool & hot tub

Hello, welcome to our home! Our 1-BR riverfront condo offers a peaceful retreat, just a short walk from downtown. It's perfect for up to 4 guests with a queen bed, an in-room Jacuzzi, and a queen pullout sofa bed. Enjoy the convenience of a full kitchen and bathroom. Relax on the patio, grill your favorite meal or sip a cup of coffee and soak in the view of Crandalls Bay. Our indoor pool, hot tub, and sauna are open all year, and the outdoor pool is available from Memorial Day to Labor Day

Guest favourite

Apartment in Lake Geneva

4.98 out of 5 average rating, 196 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 favourite

Apartment in Wisconsin Dells

4.88 out of 5 average rating, 266 reviews

The Docksider for Couples & Young Families

NO SMOKING The Docksider is the original Williamson Family Condo. Located right by the boat docks, this is perfect for a quick getaway as a couple or bring the kids. The property is situated right on beautiful Lake Delton in a quiet neighborhood in the heart of the Dells. The property has both indoor and outdoor (open seasonally only) pools and hot tubs for your year-round enjoyment. In the summer you are just steps away from the private beach and you can fish from the docks or the ice.

Guest favourite

4.95 out of 5 average rating, 230 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.