Airbnb your place

Holiday rentals with a pool in Columbia County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Columbia County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Guest favourite
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.
Apartment in Wisconsin Dells
5 out of 5 average rating, 17 reviews

3 bedroom deluxe Wyndham Glacier Canyon WI Dells

I am a Wyndham owner & rent some rooms. Includes wristbands & use of waterparks at Wilderness Resort. There are 3 Indoor Waterparks and 4 outdoor. Confirmation RCO0027280018BR Let me know how many rooms & nights you would like. You will receive up to 10 wristbands. The 3 bedroom sleeps 10. Please send an inquiry before booking as inventory is constantly changing to check availability. Presidential units may be available Contact for a discount at six zero ate for eight seven six to six three

Guest favourite
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.
Apartment in Wisconsin Dells
4.84 out of 5 average rating, 251 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.

Top guest favourite
Cabin in Lodi
4.98 out of 5 average rating, 52 reviews

Modern Cabin with pool, hot tub and outdoor sauna

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!

Top guest favourite
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.
Apartment in Wisconsin Dells
4.97 out of 5 average rating, 179 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 .

Top guest favourite
Apartment in Wisconsin Dells
5 out of 5 average rating, 12 reviews

Dells Lakefront Luxe - A Waterfront Property

A Luxe Retreat in the heart of Wisconsin Dells and situated right on beautiful lake Delton. Newly Remodeled 2-bedroom 2 -bathroom retreat offers stunning water views and a spacious patio where guests can relax, unwind, and soak in the scenery. A perfect place for a couples weekend, business travelers, girls trip, golfers or family gatherings. State of the art hot tub. This lakefront condominium provides the ideal blend of comfort, luxury and convenience for your Wisconsin Dells Stay.

Guest favourite
The spacious living area combines a fully equipped kitchen with a dining space and comfortable seating. A stone fireplace adds warmth, while large windows allow natural light to fill the room. Pendant lights hang above the bar-height countertop, enhancing the modern design.
Apartment in Sauk County
4.9 out of 5 average rating, 10 reviews

Wyn Glacier Canyon, 2 BR, 8 FREE WaterPark Passes!

At Club Wyndham Glacier Canyon you’ll get *FREE ACCESS* to four indoor & four outdoor waterparks. There are an astounding 500,000 square feet of indoor and outdoor water parks throughout The Wilderness Territory! You’ll also be able to choose from optional-fee amenities like indoor/outdoor go-kart courses, video arcades, zip lines, laser tag, laser mazes, and walking trails. Guests may arrive at the resort as early as 12 PM on their check-in day to start using the onsite water parks.

Guest favourite
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
4.89 out of 5 average rating, 226 reviews

Spacious Pine Cabin at Island Pointe

Relax on Lake Delton and escape to fresh air, calm waters, and beautiful sunsets. Lake Delton is minutes away from Wisconsin Dells so you can enjoy all the activities at the waterparks. Nestled on fifteen acres of towering pines with two private sandy beaches, you’ll feel far from the commotion of the Dells, yet just minutes away. Once you’re here you can enjoy the many amenities we have on-site, such as a heated outdoor pool, playground, picnic area, and two sandy beaches.

Guest favourite
A modern multi-level home is shown from the exterior, with a large deck extending from the second floor. A swimming pool is visible in the foreground, surrounded by a grassy area. The backdrop features a wooded landscape under a clear blue sky.
Home in Portage
5 out of 5 average rating, 12 reviews

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

The perfect place to relax, play and explore. Three levels of luxury and drenched with natural light. Wolf/Sub Zero/Miele kitchen. Kohler fixtures and spacious tiled showers for self pampering. Restoration Hardware furniture & two 77” TV's 5 Deck Areas: sip coffee, sun bathe, read, yoga sessions * Pickleball * Clearlight Infrared 4 person Sauna * 9 Person Hot Tub * In-ground Pool 48' x 24' with Sun Deck * 13 acres * Nearby ski, golf, Wis. Dells, Madison

Guest favourite
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.
Guest suite in Wisconsin Dells
4.84 out of 5 average rating, 443 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.

Guest favourite
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
4.84 out of 5 average rating, 38 reviews

Ground level Poolside Villa on Lake Delton

Step out from your private screened in porch to soak up some sun on the pool deck or enjoy some time on one of the 2 private beaches! The property sits on 15 acres of tall pines for beautiful seclusion while boasting a large heated swimming pool, 2 private beaches, a kid’s playground, volleyball court, horseshoe pits, & private dock. This peaceful space is private when needed, yet only minutes from all the Wis Dells attractions!

Guest favourite
The image displays a scenic view of a riverfront condo complex with balconies overlooking the water. A red boat is docked nearby, reflecting blue skies and clouds. Below, a cozy interior is showcased with a queen bed, a television, and a seating area featuring a fireplace and large windows for natural light.
Apartment in Wisconsin Dells
4.93 out of 5 average rating, 276 reviews

1BR UpperDells Riverfront: Jacuzzi, Pool & Hot Tub

Hello, Welcome to our home! Relax in our cozy 1BR condo (688 sq ft), steps from downtown. Sleeps 4—queen bed with in-room Jacuzzi and a pull-out queen sofa bed. 📍 Ideal Location: Near downtown fun! 🌅 Peaceful Retreat: Serene river views! 🍽️ Convenience: Full kitchen & outdoor grill! 🏊 Clubhouse: Pools, hot tub & sauna! 🚤 Private boat slip included (please contact host) Book your getaway today!

Guest favourite
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.
Apartment in Wisconsin Dells
4.93 out of 5 average rating, 59 reviews

Upper Dells River Walk [1BR]

Wisconsin Dells offers plenty of year-round activities for you and your family. Sunset Cove is located only a few blocks from downtown. The River Walk is a safe, scenic walk to get you to all the Dells has to offer in shopping, dining, sporting events and attractions. Book this recently updated one bedroom condo for your next riverside vacation and soak up the beautiful views of the Wisconsin River.

Popular amenities for Columbia County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

A spacious living area is presented with plush seating, including a light-colored sofa and an armchair, complemented by a coffee table. Natural light enters through large windows, illuminating the soft carpet. Additional furniture and decor items add a cozy touch to the inviting space.
Home in Wisconsin Dells
4.67 out of 5 average rating, 12 reviews

2BR Waterfront Condo | Pool | Hot Tub | Sauna

Guest favourite
A comfortable living area features wooden ceilings and stone accents. Two sofas and an armchair are arranged around a coffee table. A television is mounted on the wall, while a dining area with wooden chairs and a table is visible in the background.
Home in Wisconsin Dells
4.91 out of 5 average rating, 67 reviews

Cozy Cabin at Island Pointe

Guest favourite
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, 251 reviews

Tree House Home

A two-story home is depicted, surrounded by a well-manicured lawn and various shrubs. The inviting entrance features a porch with white railings. A spacious driveway leads to a garage, and trees dot the landscape, offering a sense of openness in the rural setting.
Home in Poynette
4.81 out of 5 average rating, 47 reviews

Your Home Away From Home!

A unique foam home is showcased with a curved roof and large windows, blending into the wooded surroundings. A small patio area is visible, with two chairs and a barbecue grill. Lush green grass and trees frame the outdoor space, enhancing the serene atmosphere.
Home in Wisconsin Dells

Xanadu Retreat @ Sherwood Forest

Apartment rentals with a pool

Guest favourite
A spacious living area is accentuated by large sliding doors leading to a private balcony, offering views of the lake. Comfortable seating includes a dark sofa and two accent chairs. A modern ceiling fan and artwork complete the inviting space, with natural light enhancing the ambiance.
Apartment in Wisconsin Dells
4.95 out of 5 average rating, 40 reviews

Beachview Twin #1 at Delton Grand (428)

Guest favourite
A cozy family room features a large sectional sofa with decorative pillows, a wooden coffee table, and a stylish electric fireplace. A mounted television is displayed above the fireplace, while large windows provide natural light, illuminating the wood flooring.
Apartment in Wisconsin Dells
4.92 out of 5 average rating, 106 reviews

Lakefront Luxury for Families or Couples

The exterior of Club Wyndham Glacier Canyon showcases a rustic lodge design with timber accents and stone features. Lush green lawns frame the entrance, where a wide pathway leads to the inviting lobby area under a gabled roof. Surrounding trees provide a natural backdrop.
Apartment in Baraboo

Wyndham Glacier Canyon 1 Bedroom Suite

Guest favourite
Apartment in Wisconsin Dells
4.84 out of 5 average rating, 305 reviews

Williamson Family Condo at Lighthouse Cove

Guest favourite
The family room features a comfortable sofa with decorative pillows facing a large 58" Roku TV mounted on a wooden accent wall. An electric fireplace adds warmth, while a coffee table occupies the center space. Large windows allow natural light and open to a door leading outside.
Apartment in Wisconsin Dells
4.87 out of 5 average rating, 320 reviews

The Docksider for Couples & Young Families

Guest favourite
Apartment in Wisconsin Dells
4.97 out of 5 average rating, 129 reviews

The Dockview on Lake Delton - Pickleball & Pools

Guest favourite
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.
Apartment in Wisconsin Dells
4.86 out of 5 average rating, 169 reviews

Kate's Place - Newly Remodeled - Romantic

The resort exterior is reflected in the calm waters of a nearby pond, surrounded by lush greenery and trees. The multi-story building features wooden accents and large windows, harmonizing with the serene landscape under a clear blue sky.
Apartment in Baraboo

Family Fun! Waterparks with Passes Included!

Other holiday rentals with a pool

Guest favourite
A spacious living area features a large sectional sofa and two cozy armchairs. Natural light filters through the sliding glass doors, revealing a view of the lake. Decorative wall art and a ceiling fan enhance the inviting atmosphere.
Apartment in Wisconsin Dells
5 out of 5 average rating, 21 reviews

Julie's Lakefront Retreat at Delton Grand

Superhost
The image showcases a vibrant waterpark area at the resort, featuring colorful water slides and a large outdoor pool filled with sun loungers. The backdrop includes a multi-story building with an inviting design, set against a partly cloudy sky.
Apartment in Sauk County
5 out of 5 average rating, 3 reviews

Wyn Glacier Canyon, 2 BR, 8 FREE WaterPark Passes!

Superhost
The resort's entrance showcases a large, welcoming facade with a steeply pitched roof and wooden beams. The exterior blends warm colors with stone accents, surrounded by well-maintained greenery and trees. Evening light casts a serene glow, enhancing the inviting atmosphere.
Guest suite in Wisconsin Dells
4.77 out of 5 average rating, 44 reviews

2 BEDROOM PRESIDENTIAL SUITE ✦6 Water-Park Passes!

Guest favourite
The family room features leather seating that accommodates multiple guests and a warm electric fireplace. A large smart TV is mounted on the wall, with a wooden dresser and decorative art displayed nearby. Double doors lead to the patio, with natural light illuminating the space.
Apartment in Wisconsin Dells
4.89 out of 5 average rating, 19 reviews

Dells Family Stacation-Lake Access-Hiking-Golf

Guest favourite
A comfortable family room is showcased with a soft recliner and a cozy couch. The space features a decorative electric fireplace set within a stone mantel. A large TV is mounted on the wall, and dining seating for four is visible at the nearby kitchen island.
Apartment in Wisconsin Dells
4.93 out of 5 average rating, 82 reviews

Ethel's Beachfront Retreat

Superhost
A spacious resort entrance features a large wooden awning, welcoming guests. Surrounding landscaping includes neatly trimmed trees and shrubs, with a pathway leading to the entrance. The building showcases a combination of stone and earth-toned exterior, with multiple levels visible under a clear blue sky.
Guest suite in Wisconsin Dells
4.81 out of 5 average rating, 236 reviews

✦ Glacier Canyon Resort ✦ 3 Bedroom Deluxe Suite✦

Superhost
A spacious family room features a cozy seating area with a gray sofa and patterned armchair. A wooden dining table with four chairs is positioned nearby. The room is brightened by large windows and includes an electric fireplace beneath a mounted television.
Apartment in Wisconsin Dells
4.82 out of 5 average rating, 49 reviews

Dells Lake Lookout - Jacuzzi, Pool & Hot Tub

Guest favourite
The image captures a serene view of a resort building reflected in a calm pond, surrounded by lush greenery. Tall grasses and reeds frame the foreground, while soft pastel hues of sunset illuminate the sky, adding a tranquil ambiance to the scene.
Guest suite in Wisconsin Dells
4.85 out of 5 average rating, 595 reviews

Spacious 2 Bedroom - 8 Complimentary Park Passes!

Destinations to explore