Holiday rentals with a pool in Dell Prairie

4.91 out of 5 average rating, 55 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

Private Pool 5 min. from Downtown at Papas Legacy

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.

4.98 out of 5 average rating, 105 reviews

A spacious wooden cabin is surrounded by lush pine trees. A stone pathway leads to the entrance, while a gazebo with seating is visible in the foreground. The well-maintained lawn complements the natural setting.

Home in Adams

Calming Pines Htd Pool/hot tub/ fireplace/firepit

Escape to 9 private acres of serene pine forest, just 25 minutes from the excitement of Wisconsin Dells and 10 minutes from the shores of Castle Rock Lake. Our peaceful haven offers the perfect blend of privacy, comfort, and fun — ideal for families and friends looking to create unforgettable memories. Enjoy: -Refreshing dips in the outdoor pool -Relaxing soaks in the hot tub under the stars -Friendly games of pool in the cozy basement -Volleyball matches in the fresh air -Evenings by the fire

Guest favourite

A spacious living area is furnished with a large sectional sofa and a wooden coffee table. A kitchenette is visible in the background, equipped with wooden cabinetry and modern appliances. Soft lighting from table lamps emphasizes the warm palette of the room.

Flat in Wisconsin Dells

4.83 out of 5 average rating, 72 reviews

Condo in Wisconsin Dells, WI

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 a blow up mattress. Also included is a fully equipped kitchen, spacious living room, two fireplaces, and jacuzzi. Condo rental includes use of outdoor condo pools (open seasonally) as well as sand volleyball court and bocce ball courts (bring your own ball). Located at Chula Vista Resort, condo 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, 265 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.

4.98 out of 5 average rating, 203 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 .

An outdoor pool area is surrounded by a forest of trees, featuring a curved shape with a spacious deck. Numerous lounge chairs are arranged nearby, and a shaded pavilion is visible in the background under a bright blue sky with scattered clouds.

4.92 out of 5 average rating, 66 reviews

Spacious Riverside Condo 10-14 ppl

Pools open Memorial Day weekend! Enjoy the natural beauty, water parks, and diverse attractions of WI Dells at our cozy yet spacious 3BR 3BA condo (sleeps 10-14). Perfect for multi-family or friend reunions, our welcoming retreat provides a stunning getaway with the amenities of home. You will love the: Contemporary kitchen equipped for preparing delicious meals Cozy, open living space for games, socializing, and relaxing Private fire-side jacuzzi Amenities to make your stay simple

Guest favourite

A spacious living area features a large sectional sofa and a round coffee table. A modern indoor jacuzzi is positioned nearby, with a charming wooden accent wall illuminated by 'River Roost' signage. Natural light filters in through sliding glass doors that lead to an outdoor space.

Flat in Wisconsin Dells

4.97 out of 5 average rating, 32 reviews

Riverfront Getaway | Mins to Waterparks/Downtown

Please Note: This property is a condo conveniently located at the Chula Vista Resort. Indoor water park passes are not included, but you will enjoy guaranteed first floor accommodation, 2 porches, a personalized experience, game room, new fireplace & jacuzzi, 2 porches, and nature-inspired decor. - Discounted summer deals and 3+ night stays - First floor condo = convenience with 2 porches - No resort fees - Comforts of home, excitement of a resort, and the serenity of the river

4.88 out of 5 average rating, 230 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 on Lake Delton

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.

4.78 out of 5 average rating, 133 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!

4.89 out of 5 average rating, 124 reviews

Home in Wisconsin Dells

Dells Retreat - Sleeps 8 + Jacuzzi | Waterpark

LAND OF NATURA VOUCHERS INCLUDED $25 OFF/Per Person. Memorial Day - Labor Day Perfect for families & groups! This spacious condo sleeps 8 with a king master suite + private bath and a second bedroom with two queens. Enjoy new LVP floors, Roku Smart TVs, a fully stocked kitchen, and a relaxing in-suite jacuzzi tub. Snap fun photos at the neon green accent wall before exploring Wisconsin Dells attractions just minutes away. 🌊 Water park passes not included.

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, 127 reviews

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

Upgrade to the Noah's Ark & Land Of NATURA Waterpark Packages after booking! See below for details. 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 from the downtown and Lake Delton. A perfect escape for travelers of all ages.