Holiday rentals with a pool in Wisconsin Dells

4.9 out of 5 average rating, 124 reviews

A log cabin-style home features a wide front deck with sturdy railings, complemented by large windows that allow natural light to flood the interior. A stone chimney and well-maintained landscaping add to the inviting exterior.

Cabin in Nekoosa

Lake Arrowhead Brown Bear Lodge Sand Valley GOLF

Lake Arrowhead Brown Bear Lodge in Rome WI. 2 HOA golf courses + Sand Valley Golf resort 1.5 miles away. Enjoy all lake Arrowhead offers including Heated private pools (seasonal), 4 private beaches, 2 club houses. Ski Chalet & winter activities. ATV friendly area with miles and miles of trails. This home is also on the Snowmobile trail! Wood burning fire place, lower level wet bar with slate pool table, hardwood floors, new appliances and furnishings. 4 Tvs, wifi and beautiful north woods view!

4.97 out of 5 average rating, 152 reviews

A wood-paneled living area features a stone fireplace as a focal point. Comfortable seating surrounds a dark coffee table, with soft textures provided by throw pillows and blankets. Natural light filters through double windows, offering views of the outdoors.

Cabin in Nekoosa

Hot Tub | Fire Pit | Smart TV | Fireplace| BBQ

Explore everything beautiful Rome has to offer in this 4BR, 3BA log cabin with a firepit, BBQ and smart TV. Cozy up to the fireplace or relax in the hot tub to end your day! Custom designed with thoughtful touches, this vacation home in Central Wisconsin easily fits up to 10 guests in 6 comfortable beds. Guests have nearby access to 5 golf courses, hiking trails & the resort amenities of Lake Arrowhead including private beaches and an outdoor pool! This space has everything for a memorable stay.

A cozy family room features a stone fireplace and a mounted TV. Comfortable seating includes a small dining table with chairs and a lounge chair. Soft carpeting covers the floor, and natural light enters through nearby windows, illuminating the inviting space.

4.88 out of 5 average rating, 135 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.

5 out of 5 average rating, 3 reviews

Condo in Baraboo

Luxury Family Getaway | 4BR Condo - Glacier Canyon

Wyndham Glacier Canyon – Spacious Resort Getaway in Wisconsin Dells Escape to the Wyndham Glacier Canyon Resort, perfectly located in the heart of Wisconsin Dells, the “Waterpark Capital of the World.” This spacious suite combines the comfort of home with resort-style luxury, giving your family or group everything needed for an unforgettable vacation. Whether you’re here for thrilling waterparks, natural beauty, or a relaxing retreat, Wyndham Glacier Canyon puts you at the center of it all.

Apartment in Wisconsin Dells

A spacious living area features a plush gray sofa, accompanied by a glass coffee table and a side table. Soft lighting is provided by wall sconces. A dining table for four is visible near a large window, with a jacuzzi located nearby, creating an inviting setting.

4.81 out of 5 average rating, 70 reviews

Spacious Condo at Chula Vista Resort-Pet Friendly!

Forget your worries in this spacious space! This beautiful two bedroom condo sleeps 8 with a king suite w/ full bath, two queen sized beds and a second full bath, and two pull out beds. Also included is a fully equipped kitchen, spacious living room, fireplaces, and jacuzzi. Condo rental includes use of outdoor condo pools (open seasonally) and sand volleyball court & bocce ball courts (bring your own ball). While condo is located at Chula Vista Resort, it is privately owned and operated.

An indoor pool area is featured with large windows allowing for ample natural light. Two separate outdoor seating areas overlook the water, with patio chairs positioned along the poolside and balcony. A comfortable living room setup includes a sofa, coffee table, and window view of the surroundings.

4.84 out of 5 average rating, 253 reviews

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

INDOOR & OUTDOOR POOL ACCESS| DISCOUNTED ATTRACTION TIX | WATERFRONT The Riverwalk Retreat is the perfect spot to enjoy your next WI Dells trip with friends or family. This cozy vacation rental is located at the Sunset Cove Condo complex just 2 blocks off of Broadway & overlooks Crandalls Bay. Enjoy your morning coffee with a spectacular view of the WI River & the adjoining bay. This central location provides easy access to the area’s many athletics venues, nightlife, dining, & shopping.

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, 187 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 .

A sandy beach area stretches along the tranquil shore of Lake Delton. White lounge chairs are arranged in neat rows, facing the calm water. Gentle waves lap at the edge of the shore, bordered by lush greenery and a stone embankment.

4.9 out of 5 average rating, 116 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.

An indoor arcade area features a variety of brightly colored game machines. Flashing lights illuminate air hockey tables and claw machines, while a large ticket redemption game stands prominently in the back, creating a lively entertainment space.

4.79 out of 5 average rating, 111 reviews

Luxurious Chula Vista Retreat

No resort fees! Experience all the Wisconsin Dells has to offer while staying in this luxurious condo, located inside the action-packed Chula Vista Resort! Enjoy the resort's waterparks, restaurants, 18-hole golf course, zip line and so much more! Minutes from all of the area's attractions including Noah's Ark and hiking trails! Then relax in our Jacuzzi tub, cozy up to our two fireplaces, hang out in our spacious living room or cook a family meal in our full-size kitchen!

4.91 out of 5 average rating, 109 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 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.

4.89 out of 5 average rating, 104 reviews

Dells Retreat - A Romantic Haven- Luxury Living

GIFTS FOR THE GUESTS: 1. TWO MT. OLYMPUS WATER PARK PASSES INCLUDED WITH A MINIMUM OF 4 NIGHT STAY. 2. TWO SPLASH PASSES INCLUDED WITH EACH STAY, BUY 1 GET 1 DEAL FOR NATURA WATER PARK PASSES & MORE. EXCLUSIVE DISCOUNTS FOR GOLF, ADVENTURES, WATER PARKS, RESTAURANTS & THEATER Dells Retreat is located in Tamarack Resort. A perfect escape in the heart of Wisconsin Dells. An ideal place for travelers of all ages. Endless amenities and so close to all attractions.

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

**Please note: the resort will charge you a $145 housekeeping fee when you check in. Christmas Mountain Village is a four season resort. The resort offers a wide variety of amenities, including snow skiing, snow boarding, snow tubing, 27-hole golf courses, one indoor and four seasonal outdoor swimming pools, FREE miniature golf, tennis courts, workout facilities, sauna, fishing (no fishing license required), and FREE paddleboat use.

Popular amenities for Wisconsin Dells rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious game room features a hockey table with blue pucks and a television mounted on the wall. A bar-style table with stools is positioned nearby, while a mini putting green and a net for a ball game are visible in the background.

4.96 out of 5 average rating, 24 reviews

Lake Arrowhead Retreat. Game Room, VIP Pool Access

The front of the house is framed by a well-kept lawn, featuring a wide concrete walkway that leads to the entrance. A circular seating area with chairs surrounds a fire pit, enhancing the outdoor space. Tall trees border the property, providing a natural backdrop.

4.94 out of 5 average rating, 16 reviews

Entire Lakehouse with Game Room on Lake Arrowhead

5 out of 5 average rating, 24 reviews

An aerial view of a spacious Amish-built cabin surrounded by lush greenery, featuring a prominent green metal roof. Two outbuildings are visible, along with a large driveway leading to the main entrance, creating a tranquil and inviting setting amidst expansive natural landscapes.

Home in Mauston

Revilo Moose Ridge Mauston

4.81 out of 5 average rating, 48 reviews

A circular, above-ground swimming pool with clear, inviting water is visible, surrounded by lush greenery. The pool deck features wooden planks, and a set of steps leads into the water, creating easy access. The tranquil lake can be seen in the background.

Home in Montello

3bed lake house, private pool near WI Dells

A single-story home is set against a backdrop of autumn foliage. The structure features a covered front porch with two columns. A two-car garage is visible on the left side, and a well-maintained lawn leads to the driveway.

5 out of 5 average rating, 44 reviews

Be Blessed at Kinship Casa in Rome, WI

A covered deck overlooks a lush golf course, furnished with a table and chairs under a shaded umbrella, providing a perfect outdoor relaxation space. The kitchen features modern appliances and ample counter space, seamlessly integrating functionality and style.

5 out of 5 average rating, 35 reviews

Tranquil Retreat on Lake Arrowhead Golf Course

An outdoor dining area features a stone fireplace with light strings overhead, creating a cozy ambiance. A table surrounded by metal chairs is positioned on a concrete patio, with steps leading to a pool area in the background. Lush trees provide a natural backdrop.

4.93 out of 5 average rating, 27 reviews

Brown Bear Cottage - Pet Friendly Home

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

Condo rentals with a pool

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.

4.76 out of 5 average rating, 127 reviews

Entire Condo Sleeps 6 at Tamarack

The exterior of a resort building features a blend of stone and wood materials. A large porch with railings is visible, complemented by an inviting entrance. Surrounding greenery adds to the setting, which is located in a spacious parking area.

4.53 out of 5 average rating, 76 reviews

Wyndham Chula Vista Resort Villa w/Free Water Park

5 out of 5 average rating, 17 reviews

The spacious living area features a comfortable seating arrangement, including a sofa and striped armchairs. A wooden coffee table sits in the center, with a ceiling fan overhead. The dining area, visible in the background, is furnished with a large table surrounded by matching chairs.

Condo in Arkdale

3BR/2BA Northern Bay Condo - Golf Lake Pool Fun

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.

4.8 out of 5 average rating, 157 reviews

Beautiful Condo at Chula Vista!

A vibrant waterpark area is featured, showcasing colorful water slides and a large pool space filled with lounge chairs. The backdrop consists of a spacious timber lodge structure under a bright blue sky with scattered clouds, indicating a lively family leisure environment.

Condo in Baraboo

4.83 out of 5 average rating, 6 reviews

Rustic Lodge Resort-Wyn. Glacier Canyon-2 Bd Dlx

A spacious living area features a cozy seating arrangement with a patterned sofa and armchair, complemented by a wooden coffee table. A round dining table with a slate top is also visible. A large Jacuzzi is set in a nook nearby, and soft lighting creates an inviting ambiance.

4.51 out of 5 average rating, 98 reviews

3BR Wyndham ChulaVista Condo w/FREE Water ParkPass

A cozy living area features a brown upholstered sofa with decorative pillows, positioned beside a wooden coffee table. Natural light enters through sliding glass doors that lead to a private balcony. The warm-toned walls and soft carpet create a welcoming environment.

4.67 out of 5 average rating, 9 reviews

Studio with scenic balcony, AC, & on-site golf

The exterior of a one-story timber cabin is showcased, featuring a sloped roof and large windows. The cabin is surrounded by a grassy area with scattered leaves and trees, offering a natural setting. The warm wood tones of the cabin are highlighted against the earthy landscape.

5 out of 5 average rating, 5 reviews

Christmas Mountain Village Timbers

Other holiday rentals with a pool

A modern living area is highlighted by a sleek fireplace, filled with warm flames against a dark accent wall. A large television is mounted above the fireplace. A cozy gray sectional sofa is positioned nearby, with a plush area rug featuring a subtle patterned design.

5 out of 5 average rating, 10 reviews

Sand Valley Golfers Favorite-The Pines Sanctuary

A studio room features two queen beds adorned with themed bedding. A large mural depicting a space scene is displayed on one wall. A wooden dresser and a compact television are positioned opposite the beds, with a private balcony visible in the background.

Loft in Wisconsin Dells

4.82 out of 5 average rating, 39 reviews

Wisconsin Dells Resort Condo: Golf Course On-Site

The spacious living area features a stone fireplace, cozy seating, and pendant lighting above a granite kitchen island. A round dining table with metal chairs is positioned near the window, while rich wooden accents and warm colors create a welcoming environment.

Apartment in Wisconsin Dells

4.73 out of 5 average rating, 15 reviews

Updated Condo w/ views and waterparks

A spacious living area features a leather sectional sofa positioned near a stone fireplace. A wooden dining table with eight chairs is visible in the background, along with a modern kitchen equipped with wood cabinetry. Natural light floods the space through a skylight.

Home in Wisconsin Dells

4.8 out of 5 average rating, 256 reviews

Tree House Home

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, 464 reviews

★GLACIER CANYON RESORT WITH WATER-PARK AMENITIES★

4.8 out of 5 average rating, 10 reviews

A charming wooden cabin sits surrounded by lush greenery. A small porch features two adirondack chairs, inviting relaxation. Nearby, a picnic table is positioned on a gravel surface, ideal for outdoor dining. The natural setting provides a serene backdrop for the cabin.

Cabin in Baraboo

Forest Nook Cabin 79

4.92 out of 5 average rating, 12 reviews

A row of rustic wooden cabins is visible, surrounded by a snowy landscape. Warm yellow light glows from the windows, contrasting with the winter scene. A wooden fence runs in the foreground, creating a welcoming boundary that enhances the serene atmosphere.

Villa in Wisconsin Dells

Christmas Mountain Villa