Holiday rentals with a pool in Madison

Guest suite in Spring Green

A well-maintained home exterior is surrounded by a lush garden, featuring a variety of plants and shrubs. The entrance is framed by a decorative archway, and a large tree provides shade. An inviting walkway leads up to the front door, enhancing the overall charm of the property.

4.91 out of 5 average rating, 172 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.

A manicured lawn gently slopes towards a serene body of water in the distance, framed by tall trees on either side. The landscape features lush greenery under a partly cloudy sky, creating an open and inviting outdoor space.

4.98 out of 5 average rating, 239 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.

An open living and dining area features a dark wooden dining table surrounded by black chairs. A light blue wall complements a cozy seating arrangement with armchairs and a sofa. Natural light enters through a large sliding door, with decorative elements and a chandelier enhancing the space.

4.9 out of 5 average rating, 208 reviews

Lakeview at CasaComo

Mi Casa Como es su Casa Como Escape the daily grind and plan your getaway to our newly remodeled condo on Lake Como in Lake Geneva. We’re located just 5 minutes outside downtown Lake Geneva, so very convenient for shopping & dining, but peacefully located on quiet Lake Como. We have an outdoor community pool and tennis courts and just a few steps for The Ridge Hotel. We have all that you could want or need within walking distance, so keep your car parked. Come to Casa Como, stay & enjoy!

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.

4.97 out of 5 average rating, 190 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 .

4.97 out of 5 average rating, 101 reviews

Home in Rockton

HD Jameson House at River’s Edge

Nestled on the Rock River, the HD Jameson House, a National Historic Register gem, blends historic charm with modern amenities. Enjoy river views and with quaint shops and restaurants exploring the Village of Rockton is a perfect family-friendly retreat. This haven is surrounded by nature but close to numerous attritions, ideal for a romantic getaway or peaceful escape. The HD Jameson House offers a heavenly retreat, blending past beauty with present allure for everyone in the family.

The living area features a dark leather sofa adorned with blue throw pillows, accompanied by a light gray couch. A round woven pouf and an antique-style trunk serve as accent furniture. Large glass doors provide access to a balcony, with lake-themed decor on the wall.

4.96 out of 5 average rating, 167 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.

The spacious living room features a large sectional sofa in neutral tones, focused around a gas fireplace. A flat-screen smart TV is mounted above the brick hearth. Sliding glass doors open to the outdoor patio, allowing natural light to fill the space.

4.98 out of 5 average rating, 175 reviews

Lake Geneva Retreat | King Bed + Fireplace + Pool

Discover Blue Lakes Escape, a newly-redecorated condo, steps away from Lake Como. Relax in the spacious great room with a smart TV, fireplace, desk area & access to quaint patio. Sit outside with a coffee, a good book, or a delicious BBQ. Enjoy free access to the shared amenities, including an outdoor pool, sports courts, & walking trails. Lake Como – 6 min walk Lodge Geneva National – 6 min walk Downtown – 8 min drive Book For Lasting Memories In Lake Geneva—See Details Below!

4.97 out of 5 average rating, 150 reviews

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

Cozy Home/Large Backyard/Privacy FenceThe 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.

A unique A-frame exterior features a mix of black wooden siding and natural brown shingles. A small patio area is visible with a round table and four black chairs, surrounded by well-kept shrubs and landscaped gravel.

4.9 out of 5 average rating, 111 reviews

Dells Retreat-A Romantic Haven-Jacuzzi,Pool&HotTub

Welcome to Dells Retreat, your ultimate vacation destination in the heart of Wisconsin Dells. Owned & managed by Dellsvacations Club. Nestled in the picturesque Tamarack Resort, our property offers a serene and scenic setting for your vacation. With endless amenities and attractions just minutes away, Dells Retreat is the perfect escape for travelers of all ages. Each stay at Dells Retreat also includes two free splash passes, providing access to even more attractions.

4.91 out of 5 average rating, 112 reviews

A cozy seating area features a blue sectional sofa complemented by two bedside tables with lamps. A vibrant green wall adorned with faux plants adds a natural element. A neon sign stating 'Wisconsin Dells' is prominently displayed above the sofa.

Home in Wisconsin Dells

Family-Friendly Dells Stay | Sleeps 8 + Jacuzzi

Perfect for groups! This condo sleeps 8 and features a king master suite with private bath, plus 2nd bedroom with 2 queens. Enjoy new LVP floors, ROKU Smart TVs, a full kitchen stocked with cookware & basics, and an in-suite jacuzzi tub. Capture insta-worthy shots at the neon green wall before exploring Wisconsin Dells attractions just minutes away. 🌊 Water park passes not included. Complimentary WiFi (sometimes can be spotty) Please read "other details section below."

A welcoming living area with a spacious sofa and a wooden coffee table is presented. A modern ceiling fan is installed, and a large Roku TV is positioned on a console. The area also includes a dining table with chairs and access to a patio through glass doors.

4.87 out of 5 average rating, 178 reviews

Kate's Place - Newly Remodeled - Romantic

NO SMOKING Max Occupancy: 4 People (2 Adults) Upgrade to our Noah's Ark package after booking! Kate's Place is recently updated and located in Lighthouse Cove on Lake Delton in the heart of the Dells. Enjoy beach access, indoor & outdoor pools and hot tubs, and convenient parking. This condo is great for a couples or small families. The kitchen has all the tools you need to stay in, but the location is super close to great supper clubs for an evening out as well.

A breathtaking view of the sunset over Lake Como is framed by large glass doors. The patio features comfortable seating, adorned with potted plants, while the tranquil lake and lush greenery create a serene backdrop.

4.97 out of 5 average rating, 194 reviews

Lakefront condo with magnificent view & 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.

Popular amenities for Madison rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Apple Canyon Lake

A stone fire pit is depicted in the foreground, with flames brightly rising as the sun sets in the background. The calm water reflects the evening light, and several leafless trees are visible, adding a serene ambiance to the scene.

5 out of 5 average rating, 6 reviews

Lakefront cabin in the woods.

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.

4.98 out of 5 average rating, 42 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

4.79 out of 5 average rating, 28 reviews

Lodge Home - 2.8 Miles to Town - Minutes to Ski

Two black Adirondack chairs and a small side table are positioned on a patio, overlooking a lush green landscape under a cloudy sky. The view encompasses rolling hills and tree foliage, providing a serene outdoor setting.

5 out of 5 average rating, 56 reviews

Newly Updated Modern Lake Condo

Home in Fontana-on-Geneva Lake

The exterior of a two-story home is shown, featuring a wooden deck with steps leading to the entrance. Lush green grass and landscaped gardens surround the house, with smooth stones arranged along a small water feature, providing a natural setting.

5 out of 5 average rating, 13 reviews

Treetop Lakehouse at Abbey Springs

4.89 out of 5 average rating, 228 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

A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.

4.95 out of 5 average rating, 97 reviews

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

5 out of 5 average rating, 85 reviews

Home in Whitewater

Nestled in the Southern Kettle Moraine Forest

Condo rentals with a pool

4.9 out of 5 average rating, 42 reviews

Spacious Condo Retreat for 10-14 ppl

4.86 out of 5 average rating, 14 reviews

The outdoor water park features multiple waterslides and a spacious pool area. Sun loungers and umbrellas are arranged around the pool, alongside playful water attractions. The lodge-style buildings are visible in the background, enhancing the resort atmosphere under a blue sky with scattered clouds.

Condo in Baraboo

Wyndham Glacier Canyon |1BR/1BA King Suite w/ Balc

4.84 out of 5 average rating, 61 reviews

Your Boho Retreat

Condo in Fontana-on-Geneva Lake

A cozy corner of the living room features a brick fireplace with a warm fire. A decorative candle holder stands beside a beautifully lit Christmas tree. A plush sofa, adorned with a patterned pillow, invites relaxation, while a simple table holds a remote and holiday decor.

4.78 out of 5 average rating, 197 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

A serene night view of the Wisconsin River is captured from a patio. The calm water reflects lights from nearby buildings and trees along the shore. A boat is moored nearby, enhancing the tranquil riverside ambiance.

4.94 out of 5 average rating, 62 reviews

Upper Dells River Walk [1BR]

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.

5 out of 5 average rating, 24 reviews

Hotel-Style Room with a View

4.9 out of 5 average rating, 42 reviews

Lake Geneva Condo with Pool, Fireplace & Parking

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.

4.79 out of 5 average rating, 159 reviews

Beautiful Condo at Chula Vista!

Other holiday rentals with a pool

Cottage in Wisconsin Dells

An indoor pool area is visible, featuring a variety of colorful water play structures, including a frog-shaped slide and small boats. Natural light is allowed in through large windows, illuminating the smooth surface of the water and creating an inviting space for families.

4.89 out of 5 average rating, 9 reviews

Ski @ Christmas Mountain Village - 2BR Cottage I

4.98 out of 5 average rating, 45 reviews

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

Kettle 2BR Cabin on15 stunning acres by Ski trails

The exterior of the resort is showcased, featuring a blend of rustic and modern architecture. Lush grass and well-maintained landscaping surround the entrance. A clear blue sky and subtle clouds highlight the inviting atmosphere of the complex.

5 out of 5 average rating, 17 reviews

3 bedroom deluxe Wyndham Glacier Canyon WI Dells

4.84 out of 5 average rating, 38 reviews

A cozy living room features two sofas, a lounge chair, and a stone-surrounded gas fireplace. Natural light filters in through a nearby window, creating a warm ambiance. Open shelving displays decorative items, and the kitchen area is visible in the background with modern appliances.

Villa in Wisconsin Dells

Ground level Poolside Villa on Lake Delton

Townhouse in Fontana-on-Geneva Lake

A modern dining area features a round table with four upholstered chairs set on a textured area rug. Large glass doors provide access to a deck surrounded by greenery, while a stone accent wall adds visual interest. A glimpse of the kitchen area is visible in the background.

4.81 out of 5 average rating, 94 reviews

Abbey Springs 5 Star Resort on Lake Geneva

Guest suite in Wisconsin Dells

The exterior view showcases a modern multi-story building, featuring balconies with railings and stone accents. Lush greenery and decorative rocks landscape the property, creating a welcoming atmosphere. A paved road leads to the entrance, providing access to the well-maintained surroundings.

4.84 out of 5 average rating, 480 reviews

★GLACIER CANYON RESORT WITH WATER-PARK AMENITIES★

4.89 out of 5 average rating, 300 reviews

An expansive outdoor deck is revealed, featuring a canopy-covered dining area alongside several lounge chairs. Umbrellas provide shade over seating arrangements, surrounded by lush trees. A glimpse of a pool is visible in the background, enhancing the inviting outdoor space.

Home in Madison

Luxurious BBQ and Pool House