Vacation rentals with a pool in Dell Prairie

4.88 out of 5 average rating, 43 reviews

An outdoor view of a two-story home features a large heated saltwater pool surrounded by a concrete patio. Several lounge chairs are positioned next to the pool. Mature trees and greenery create a natural backdrop, lending a sense of privacy to the space.

Home in Wisconsin Dells

Papas Pool House: Private Pool Family Retreat

Welcome to Papas Pool House, your private winter retreat in Wisconsin Dells. Surrounded by serene nature, this 3-bedroom, 3-bath home offers the perfect combination of cozy comfort, family-friendly space, and memorable experiences. Whether you’re planning a romantic getaway, a festive holiday, or a family escape, our home invites you to relax and reconnect with lasting memories. Just minutes from downtown, ski hills, and Just A Game, you’ll have access to winter-friendly activities for all ages.

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.

4.89 out of 5 average rating, 145 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.

4.79 out of 5 average rating, 163 reviews

Beautiful Condo in Wisconsin Dells!

Bring your family or friends to this lovely condo where you can enjoy a classic Wisconsin Dells experience. Everything is available at your fingertips, including restaurants & bars, golfing, spa, and of course Wisconsin Dells waterparks, and more! (Chula Vista waterpark passes not included with your booking) This top floor condo is spacious, private, and has everything for your group to relax. Enjoy sunset views over the Wisconsin River, or head down to one of the complimentary outdoor pools!

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, 257 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, 195 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 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, 115 reviews

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

Noah's Ark Package Upgrade available after the booking!. Welcome to Dells Retreat, your ultimate vacation destination in the heart of Wisconsin Dells 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.

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, 117 reviews

Lakefront Condo - Private Beach | 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.

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

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.

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.

4.81 out of 5 average rating, 119 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 restaurants, 18-hole golf course, zip line and so much more! Minutes from all of the area's attractions including Mt. Olympus, 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!

4.97 out of 5 average rating, 37 reviews

The exterior of a rustic log cabin is visible, featuring a sloped roof and large wooden deck with railings. The cabin is surrounded by a grassy area, with trees and blue sky in the background, creating a serene countryside setting.

Cabin in Lyndon Station

Cozy Boho Cabin w/ POOL!!

Nestled on 26 acres in the beautiful countryside, this is the perfect retreat for your Wisconsin Adventure! Fantastic location minutes from all this area has to offer and located directly off 90/94. From the house you will find: Downtown Wisconsin Dells - 10 miles Wisconsin Dells Racetrack - 4 miles Christmas Mountain Ski & Golf - 8 miles Trappers Turn Golf Course - 9 miles Rocky Arbor State Park - 8 miles Castle Rock Lake - 15 miles

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 (Private Pool-20 mins to Dells)

🌸 Spring & Summer Getaway in the Heart of Wisconsin 🌞 Enjoy Smoky Mountain vibes at our 3,000 sq ft Amish-crafted lodge on 15 private acres. Sleeps 10 (12 on request) with rustic charm and modern comfort. Hike, bike, explore peaceful trails, or relax on the porch. Just 20 min to Wisconsin Dells, 10 min to Castle Rock Lake, 40 min to Cascade or Devils Head. Gather by the fire pit under the stars for a memorable stay!

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.

4.92 out of 5 average rating, 291 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!

Popular amenities for Dell Prairie 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, 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

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.

4.93 out of 5 average rating, 14 reviews

The Arrowhead House – Golfer’s Paradise Retreat

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, 263 reviews

Tree House Home

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, 37 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.

4.95 out of 5 average rating, 38 reviews

Brown Bear Cottage - Pet Friendly Home

5 out of 5 average rating, 17 reviews

Home in Portage

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

Condo rentals with a pool

Superhost

The exterior of the resort is showcased, featuring a rustic design with timber accents and a large, inviting entrance. A manicured lawn with trees surrounds the building, and a clear blue sky provides a bright backdrop.

Condo in Baraboo

4.82 out of 5 average rating, 11 reviews

Wyndham Glacier Canyon |2BR/2BA King Suite w/ Balc

4.99 out of 5 average rating, 249 reviews

Penthouse, Fireplace, Lake View, Pickleball

The living area features a stone fireplace and a flat-screen TV mounted above it. A round dining table with metal accents is surrounded by four chairs. Soft lighting from side lamps illuminates a comfortable sofa and a cozy armchair, creating a welcoming environment.

4.83 out of 5 average rating, 18 reviews

Wisconsin Dells Resort Condo w/ 2 Fireplaces

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, 19 reviews

3 bedroom deluxe Wyndham Glacier Canyon WI Dells

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

Superhost

A spacious living area features a stone fireplace as a focal point. Comfortable seating is arranged with couches and armchairs. A wooden dining table with multiple chairs provides ample seating, while large windows offer views of the surrounding greenery.

Condo in Arkdale

4.83 out of 5 average rating, 18 reviews

Two Unit at Northern Bay - 7 Bedroom Sleeps 24!

5 out of 5 average rating, 6 reviews

The lodge-style building is positioned beside a serene pond, with its exterior reflecting in the calm water. Lush grass and trees surround the area, showcasing a natural landscape under a clear blue sky.

Condo in Baraboo

Wyndham Glacier Canyon |2BR/2BA King Suite w/ Balc

4.86 out of 5 average rating, 7 reviews

2BR 5th-Floor | Hot Tub | Elevator

Other vacation 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.

4.77 out of 5 average rating, 133 reviews

Entire Condo Sleeps 6 at Tamarack

An outdoor area features a small fenced pool surrounded by neatly trimmed grass and shrubbery. Wooden structures with stone accents provide a rustic touch, while a tree-lined backdrop enhances the natural setting.

4.53 out of 5 average rating, 76 reviews

Wyndham Chula Vista Resort Villa w/Free Water Park

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, 485 reviews

★GLACIER CANYON RESORT WITH WATER-PARK AMENITIES★

A rustic cabin exterior is framed by tall pine trees, featuring a covered porch with two picnic tables. The brown wooden structure has a green roof and twin chimneys, while a concrete pathway leads to the entrance, providing a welcoming approach.

Cabin in Wisconsin Dells

4.66 out of 5 average rating, 79 reviews

Duplex Cabin Vacation BC

5 out of 5 average rating, 24 reviews

Cottage in Nekoosa

Prime 18 Pines Golf Home – 5 Min to Sand Valley!

4.99 out of 5 average rating, 83 reviews

An indoor hot tub is positioned under a ceiling lined with wooden beams, featuring steps leading into the water. Natural light filters through large windows, illuminating the stone fireplace and warm wooden accents throughout the space.

Cabin in Markesan

Adeline's House of Cool, The most fun Airbnb in WI