Vacation rentals with a pool in Madison

Guest suite in Spring Green

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.

4.91 out of 5 average rating, 148 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.

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.

4.85 out of 5 average rating, 103 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.

An indoor pool area is presented with a spacious swimming pool, surrounded by large windows allowing natural light to fill the space. Comfortable lounge chairs are arranged along the poolside, with towels neatly placed on the side. The ceiling showcases exposed wooden beams, adding a warm touch to the atmosphere.

4.97 out of 5 average rating, 147 reviews

Pools, Hot Tub, Fire tables, dog friendly

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

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.

4.97 out of 5 average rating, 145 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

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.

4.98 out of 5 average rating, 212 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.

4.94 out of 5 average rating, 150 reviews

Awesome Lodge in Galena Territory

Bring the whole family to our Galena home for fun, games, and making memories! Located 1.3 miles from the Owner's Club in The Galena Territory, enjoy many amenities and everything Galena has to offer! 15 mins to downtown! 3 bedrooms and 3 full bathrooms, the house is equipped with great Wi-Fi and 8 key cards to access Territory amenities! There is tons of space to spread out across 3 floors . Enjoy the game room, hot tub, three seasons room, deck, and outdoor space in this awesome home!

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.

4.99 out of 5 average rating, 149 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 .

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.

4.97 out of 5 average rating, 478 reviews

COZY, Lakefront, 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

4.98 out of 5 average rating, 161 reviews

The living room showcases a bright orange sofa paired with a modern coffee table, amidst natural wood accents and greenery outside. A large television is mounted against a backdrop of floor-to-ceiling windows, providing ample light. Colorful wall art adds a playful touch to the space.

Treehouse in Galena

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

4.9 out of 5 average rating, 269 reviews

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

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

A spacious balcony features two lounge chairs and flower pots, overlooking manicured green lawns towards the waterfront. Trees line the horizon under a colorful sunset sky, enhancing the serene lakeside ambiance.

4.97 out of 5 average rating, 158 reviews

Magnificent waterfront views & cozy fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

Guest suite in Wisconsin Dells

An aerial view of the Glacier Canyon Resort showcases a sprawling layout featuring the water parks, landscaped grounds, and accessible parking areas. Multiple buildings accommodate guests, while green spaces surround the resort, enhancing the inviting atmosphere of this family-friendly destination.

4.84 out of 5 average rating, 380 reviews

★GLACIER CANYON RESORT WITH WATER-PARK AMENITIES★

Welcome to Wisconsin Dells and the city of Baraboo, a popular vacation playground best known for its beautiful river scenery, endless entertainment options and larger-than-life water parks. Inside the Wilderness Territory a theme park where family fun reign supreme is a top ranked indoor and outdoor water park. You can also find some excellent shopping, visit wineries for tastings, practice your swing on local golf courses, and win big at Ho-Chunk Casino.

Vacation rentals for every style

Get the amount of space that is right for you

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A space thats all yours, with room for everyone

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Quaint homes, peaceful surroundings

Popular amenities for Madison rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious outdoor area is showcased with a hot tub situated beneath a wooden deck. The hot tub is surrounded by a stone patio and features steps leading up to it. Natural stone walls provide a rustic backdrop, enhancing the tranquil environment.

4.96 out of 5 average rating, 283 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

AnitaRating, 5 stars2 days ago

This is our 2nd time staying at James's beautiful Galena home. James thought of everything. All the kitchen appliances that you need to make your meals. Plenty of room for everyone. James was quick to respond and very helpful. We plan to stay here again.

A spacious living area features a navy blue sectional sofa and a modern brown armchair. Large windows provide views of the surrounding greenery. A round, marble coffee table is centered in the room, with a fireplace beneath a mounted television, creating a cozy environment.

4.98 out of 5 average rating, 85 reviews

Cozy Galena Townhome

KathleenRating, 5 stars5 days ago

The condo was immaculate and comfortable. Check in was easy and the host provided helpful information about finding the local store as well as a route suggestion to avoid exiting the neighborhood on a blind curve. Would definitely stay here again.

Home in Fontana-on-Geneva Lake

5 out of 5 average rating, 16 reviews

Abbey Springs Home! Hot Tub + Golf Cart

KathyRating, 5 stars2 months ago

A wonderful home that was well appointed, clean & a great location! We hosted Easter here with my adult Kids and grandson. We all enjoyed the beautiful surroundings and all the wildlife-many deer and even a coyote! So much room and a great layout for us to enjoy the home together!

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.

4.92 out of 5 average rating, 101 reviews

Perfect Location! Owner Club Access, Dog Friendly!

TaewonRating, 5 stars3 weeks ago

Our family—including me, my wife, our daughter, and our puppy—had a wonderful time. Ginger was very kind and provided detailed information, including how to use the amenities like the swimming pools. The property was clean, cozy, and conveniently located near downtown, where we had a great time exploring. We’d definitely recommend this place to any family and would love to return on our next trip to Galena.

A spacious living area is highlighted by a large sectional sofa in warm tones. Natural light pours in through skylights, illuminating wooden floors. A dining table with multiple chairs is visible, alongside a well-equipped kitchen in the background, creating an inviting and open atmosphere.

4.89 out of 5 average rating, 127 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

LindaRating, 5 stars3 weeks ago

Brian and Jonny were very responsive and communicative from beginning to end. It was a last minute trip and we were lucky to find a pet friendly place during the start of the summer season. The house was clean, cozy and close to walking trails. Although we did not take advantage of the outdoor grill or hot tub (they have a wood burning fireplace for the winter), we enjoyed the screened in porch and open concept layout of the house, as pictured in the profile. The house is situated between two other houses blocked somewhat by the trees. I would describe as semi-private where we could see their back patio/hot tub/fire pit and vice versa. But whatever your personal comfort level, you can’t beat the proximity to trails, Owners Club, and easy access to Hwy 20 to Galena! We enjoyed our stay and exploring!

4.93 out of 5 average rating, 200 reviews

Galena Getaway

ChrisRating, 5 stars1 week ago

Great location. So close to everything. Would definitely stay again!

4.88 out of 5 average rating, 217 reviews

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

Spacious Pine Cabin at Island Pointe

MarjorieRating, 5 stars1 week ago

Lovely updated cabin among other cabins in resort on Lake Delton. Spent 3 days with my 2 sisters and enjoyed the peaceful surroundings as great getaway from, yet easy to reach Dells attractions. As summer fully starts next week I expect the place will be much busier as it seems a very good family resort with pool and playground for kids. Nice, sandy beach on lake a short walk away. There are stairs to access the cabin from the deck. Use key pad hidden behind upper deck screen/storm door. Lower level has nice extra family room to spread out guests. Bring Duraflame type logs if you’d like to use fireplace. We enjoyed that on a cooler night.

4.94 out of 5 average rating, 135 reviews

Family-Friendly Wooded Retreat- 3 Ensuite Bedrooms

NicoleRating, 5 stars1 month ago

Joel’s place was absolutely beautiful! It was secluded and peaceful but also very close to down town. I loved drinking my coffee outside in the mornings it was so peaceful! I’d recommend Joel’s air bnb to anyone wanting to travel to galena. I’d go back in a heartbeat! Joel was a great host. He gave us all the information and checked In on us throughout our stay. We had a great time!

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Condo rentals with a pool

4.91 out of 5 average rating, 96 reviews

Lakefront Condo - Private Beach | Boat Slip| Pool

DusanRating, 5 stars5 months ago

Amazing place .highly recommend!!

A private balcony offers stunning views of the tranquil lake at sunset, framed by lush greenery and a well-manicured lawn. The sky is painted with soft hues of orange and blue, reflecting on the calm water's surface.

5 out of 5 average rating, 9 reviews

Glass Vista: Modern 2BR Condo, Stunning Views

AnubhavRating, 5 stars1 month ago

Great peaceful location, very clean and great host! Highly recommend this property!

A comfortable living area features a beige sofa and a patterned chair, arranged around a glass coffee table. Natural light pours in through sliding glass doors, which open to a patio area. A warm glow is provided by table lamps beside the seating and a framed artwork decorates the wall.

4.83 out of 5 average rating, 87 reviews

Entire Condo Sleeps 6 at Tamarack

AlexanderRating, 5 stars3 days ago

very nice place for an affordable rate. nice and quiet community

A covered patio area features a set of four cushioned chairs and a small decorative table. The view overlooks a calm stretch of water, with boat docks visible in the distance and gently sloping green grass leading down to the water's edge.

4.83 out of 5 average rating, 233 reviews

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

MirenasRating, 5 stars3 weeks ago

Very cute corner unit. My dad would just sit out on the patio, watching people put their boats in the water and take their boat out of the water. Beds were very comfortable place was nice and clean. I would stay here again.

An outdoor swimming pool is enclosed by a black fence, set against a backdrop of green grass and trees with autumn foliage. Walking paths meander through the area, providing access to the pool and nearby structures.

4.93 out of 5 average rating, 75 reviews

Dells Retreat - A Romantic Haven- Luxury Living

CharityRating, 5 stars2 weeks ago

Our host was very responsive and guided us well. we used the amenities at Tamarack activity center and had so much fun. The location was also like 10mins from everything we wanted to do. I would definitely stay there again if in the area.

An outdoor pool area is featured with a clear blue swimming pool, surrounded by several lounge chairs. Large windows of the building provide a view into the pool area. A fence encloses the space, ensuring privacy and safety.

4.94 out of 5 average rating, 47 reviews

Upper Dells River Walk [1BR]

BonnieRating, 5 stars2 weeks ago

This was a great condo. It had everything we needed and was close enough to the main drag that we could walk there in just a few minutes. The beautiful, peaceful location was perfect for our family wedding weekend!

Condo in Fontana-on-Geneva Lake

The kitchen features dark cabinetry against a brick wall, complemented by a large island with seating for six. Pendant lights hang above, illuminating the cooking area which includes modern appliances and tasteful decor. A dining table is positioned in the background, promoting an open-concept feel.

5 out of 5 average rating, 14 reviews

Luxurious Condo Experience at Lakeside Villa |Pool

BrittanyRating, 5 stars3 weeks ago

Had a wonderful time here for my sister’s bachelorette party. The town home was beautiful and newly renovated. We had an amazing time at the nearby pool and other attractions close by. Overall great stay!