Holiday rentals with a pool in Wisconsin Dells

Apartment in Wisconsin Dells

A spacious dining area features a large wooden table surrounded by eight chairs. Natural light fills the room from nearby windows, highlighting a stone fireplace and a flat-screen television mounted above the mantel. Comfortable seating is visible in the adjoining living area.

4.77 out of 5 average rating, 44 reviews

First Floor Condo - Pet Friendly!

Relax with the whole family at this peaceful place! This beautiful two bedroom condo includes a king suite w/ full bath, two queen sized beds and a second full bath, and sofa beds. Also included is a fully equipped kitchen, spacious living room, fireplaces, and jacuzzi. Condo rental includes use of outdoor condo pools (open seasonally) as well as 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, 188 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 .

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!

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, Chula Vista's indoor/outdoor waterpark, (waterpark passes not included with your booking) and more! This top floor condo is spacious, private, and has everything for your group to relax. Enjoy amazing sunset views over the Wisconsin River, or head down to one of the complimentary outdoor pools!

4.8 out of 5 average rating, 41 reviews

Waterfront Boho Retreat

Perfect for families or for a couples retreat, this rental offers all the comforts of home in a tranquil and upscale setting. Take a dip in the outdoor pool or hot tub, play a game of tennis/Pickle-ball, or explore the surrounding area for endless entertainment options. With its modern amenities and prime location, this is the perfect accommodation for your next getaway. Don't miss out on the opportunity to stay in this beautiful place. Book now and make your dream vacation a reality!

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.

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.

4.8 out of 5 average rating, 113 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!

4.91 out of 5 average rating, 111 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, 174 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 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, 106 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.

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

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 kitchen features wooden cabinetry and granite countertops. Seating for four is provided at a central island. Stainless steel appliances, including a microwave and oven, are surrounded by stone accents and warm wood paneling, contributing to an inviting cooking space.

Home in Arkdale

4.73 out of 5 average rating, 11 reviews

Lakefront Golf Resort Condo, Pool and Hot tub

5 out of 5 average rating, 24 reviews

Home in Mauston

Revilo Moose Ridge Mauston

A wide driveway leads to a modern house surrounded by lush trees. A spacious patio can be seen in front, equipped with seating areas. The natural landscape provides a serene setting, enhancing the privacy of the home.

Home in Necedah

4.67 out of 5 average rating, 3 reviews

4 Bedroom 2 Bath Home Necedah,WI

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 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!

5 out of 5 average rating, 14 reviews

Home in Portage

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

Home in Adams

5 out of 5 average rating, 3 reviews

Pinecone Getaway - breathe deep, relax, and stay.

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

Condo rentals with a pool

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

4.67 out of 5 average rating, 3 reviews

The resort is seen across a calm body of water, reflecting its five-story structure. The facade features a combination of warm wood and stone, surrounded by landscaped greenery and trees. A clear blue sky completes the serene outdoor setting.

Condo in Baraboo

Wyndham Glacier Canyon |3BR/2BA King Suite w/ Balc

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

4.88 out of 5 average rating, 26 reviews

A spacious living area features comfortable seating arrangements, including a sofa and armchairs. A wooden dining table accommodates several chairs, and a kitchenette is visible with modern appliances. Natural light enters through a window, creating a welcoming environment.

Condo in Arkdale

Spectacular Golf/Lake Condo + Golf Cart & Pool

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

4.88 out of 5 average rating, 8 reviews

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

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

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.

Condo in Arkdale

4.84 out of 5 average rating, 31 reviews

Updated 1st Floor Northern Bay Retreat!

Other holiday rentals with a pool

4.99 out of 5 average rating, 249 reviews

Penthouse, Pickleball, Pontoon Ride No Resort Fees

A wooden cabin is nestled in a green, natural setting, with a small porch supported by timber beams. A picnic table made of weathered wood stands nearby, surrounded by lush vegetation and trees, creating a peaceful outdoor space.

Cabin in Baraboo

4.8 out of 5 average rating, 5 reviews

Evergreen Cabin 98

Apartment in Wisconsin Dells

A welcoming living space is highlighted by a cozy sofa, an armchair, and a wooden coffee table. Soft lighting from two bedside lamps enhances the atmosphere. A large window offers views of the surrounding area, while a jacuzzi is positioned nearby for relaxation.

4.9 out of 5 average rating, 21 reviews

Chula Vista Resort Condo

A charming rustic cabin is shown with a vibrant red exterior complemented by green shutters. Large windows invite natural light, and the surrounding trees display autumn foliage, enhancing the serene atmosphere. The stonework at the base adds a touch of craftsmanship.

Cabin in Wisconsin Dells

4.65 out of 5 average rating, 48 reviews

Disconnect to Reconnect With Your Family - Cabin

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.

4.8 out of 5 average rating, 56 reviews

Dells Lake Lookout-Jacuzzi, Pool & Hot Tub

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.

4.86 out of 5 average rating, 56 reviews

Enjoy Fun & Relaxation This Fall in Wis. Dells!

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, 470 reviews

★GLACIER CANYON RESORT WITH WATER-PARK AMENITIES★

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.