Holiday rentals with a pool in Wisconsin Dells

4.9 out of 5 average rating, 118 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!

A scenic view of the outdoor pool area is displayed, with clear blue water surrounded by lush green trees. Guests are seen enjoying the pool, while the resort's lounging area is visible in the background, featuring wooden structures and sunlit spaces.

5 out of 5 average rating, 28 reviews

Spacious 3BR Condo Retreat

Escape to Riverfront Serenity Indulge in the beauty of Wisconsin Dells at our spacious 3BR, 3BA condo. Perfect for groups of up to 14, this cozy retreat offers stunning views and all the comforts of home. Relax and Unwind: * Spacious Living: Enjoy ample room to spread out and relax * Modern Kitchen: Cook up delicious meals in our fully-equipped kitchen * Indoor Jacuzzi: Soak away your stress in our private indoor jacuzzi Book your stay today and experience the ultimate riverfront getaway!

4.97 out of 5 average rating, 143 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.

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.

4.87 out of 5 average rating, 316 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.

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.

4.83 out of 5 average rating, 248 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, 173 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 .

5 out of 5 average rating, 4 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.

4.89 out of 5 average rating, 226 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

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.

This vibrant indoor water park features several water slides of varying heights and twists, surrounded by playful structures. Shallow pools for children and lounging areas are visible, while guests engage in water activities. Lush tropical landscaping enhances the fun environment.

4.79 out of 5 average rating, 97 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!

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.

4.85 out of 5 average rating, 402 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.

A welcoming living area is highlighted by a comfortable seating arrangement, featuring a leather sofa and accent chairs. Natural light pours in through the windows, illuminating the wood flooring and a stone fireplace. A large SMART TV is mounted on the wall, adding modern convenience.

4.97 out of 5 average rating, 499 reviews

COZY, Pickleball, Fireplace, Devils Lake

NO RESORT FEES, WATERFRONT 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 • Indoor and outdoor pools • Hot tub • Walking distance to Noah's Ark • First Responder Discounts • Smart TVs • Jetted Tub • Fireplace • Washer/Dryer

4.84 out of 5 average rating, 37 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

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!

Popular amenities for Wisconsin Dells rentals with a pool

Kitchen

Wifi

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, 23 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

A spacious game room garage features a pool table, foosball table, and a round table for games. Lounge seating is available, along with modern lighting and blue walls adorned with the word 'BIRDIES.' The layout encourages social interaction and fun after a day outdoors.

4.89 out of 5 average rating, 9 reviews

The Arrowhead House – Golfer’s Paradise Retreat

5 out of 5 average rating, 19 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, 43 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, 33 reviews

Tranquil Retreat on Lake Arrowhead Golf Course

The living room features a comfortable leather sofa adorned with plush throw pillows, complemented by a wooden coffee table. Natural light floods in through large windows, blending with the rustic stone fireplace and wooden ceiling, creating a cozy and inviting ambiance.

4.89 out of 5 average rating, 18 reviews

Stylish Cabin-Hot Tub Game Room Near Sand Valley

Apartment rentals with a pool

An open living space is featured with a cozy sofa and armchair arranged around a wooden coffee table. A round dining table occupies one corner, and a large Jacuzzi tub is visible in the background, paired with stone wall accents. Soft lighting enhances the tranquil environment.

4.63 out of 5 average rating, 51 reviews

Wyndham 3BR ChulaVista Condo w/FREE Water ParkPass

The living area features comfortable plaid sofas and a wooden coffee table, complemented by a plush area rug. A ceiling fan provides ventilation. The open space extends into the dining area, where wooden chairs surround a large table, and the kitchen is visible in the background.

4.94 out of 5 average rating, 31 reviews

Gorgeous Lakeview Balcony 4 Bedrooms next to pool

4.8 out of 5 average rating, 30 reviews

Riverview Big Family Condo 3 bedroom/3 bath for 16

The living area features comfortable striped sofas positioned near a stone fireplace. A wooden coffee table rests in the center, complemented by a lamp. Beyond, large windows provide views of the outdoor space, while a dining table is visible to the side.

5 out of 5 average rating, 15 reviews

Northern Bay 3 bedroom Condo on Castle Rock Lake

A luxurious 4-person jacuzzi is shown, with water flowing from the sleek chrome faucet. A warm, holographic fireplace is visible in the background, nestled among stone details, contributing to a cozy ambiance in the space.

4.82 out of 5 average rating, 11 reviews

Exclusive Studio Condo+H20 Passes at Chula Vista!

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.

5 out of 5 average rating, 17 reviews

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.

4.79 out of 5 average rating, 147 reviews

Beautiful Condo at Chula Vista!

The main room features a spacious sectional couch and a separate sofa bed, arranged around a wooden coffee table. A stone gas fireplace adds warmth, while large windows provide natural light. Two additional chairs complement the seating area, creating an inviting space for relaxation.

4.93 out of 5 average rating, 29 reviews

Updated 1st Floor Northern Bay Retreat!

Other holiday rentals with a pool

4.9 out of 5 average rating, 20 reviews

A multi-story resort building is set against a vibrant blue sky, with green lawns surrounding it. Outdoor seating arrangements, including picnic tables, are visible. The property features a pool area with lounge chairs and tropical decor, creating an inviting space for relaxation and recreation.

Flat in Wisconsin Dells

Aloha Beach-2 Bedroom Apartment

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.

Apartment in Baraboo

4.91 out of 5 average rating, 11 reviews

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

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.

4.51 out of 5 average rating, 73 reviews

Wyndham Chula Vista Resort Villa w/Free Water Park

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, 126 reviews

Entire Condo Sleeps 6 at Tamarack

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

Cottage in Wisconsin Dells

The resort entrance is framed by lush greenery and decorative flower beds. A rock waterfall feature adds a natural touch, while the spacious driveway leads to a charming building with a sloped roof and wooden accents.

4.85 out of 5 average rating, 54 reviews

Enjoy Fun & Relaxation This Fall in Wis. Dells!

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.

5 out of 5 average rating, 10 reviews

Brown Bear Cottage - Pet Friendly Home

A cozy living area features a comfortable sofa and armchair, complemented by a wooden dining table with chairs. A stone fireplace serves as a focal point, and a flat-screen television is mounted above. Natural light streams through the door leading to the outside.