Holiday rentals with a pool in Sheboygan County

Road America Retreat-4 BDRM-2BA-Hot Tub+Pool

NEW BOOKINGS: Stay 3 nights & enjoy a 4 PM checkout (Sep–Dec2026)! Private 4-BR Craftsman Home in Plymouth, just 4 miles from Road America. Relax in the year-round hot tub or seasonal heated pool (June–Sept). Sleeps 8 with 2 baths, garage + street parking, and easy access to dining, shopping & area attractions. Perfect Getaway for couples, families, golfers, crafters, & crisp fall bonfire nights. Quiet neighborhood; no pets. Holidays & Road America race weekends require a 3-night stay.

VicVill | WaterViews | Vintage Charm Meets Comfort

☀︎Welcome to VicVill! Historic charm meets lakeside comfort in this 2BD/2BA Condo. Located in Elkhart Lake Beach Resort Enjoy stunning lake and pool views throughout Relax at the private resort beach+seasonal indoor/outdoor pool Plush King master+matching twin-over-full bunks Steps to TikiBar Walk to village shops, restaurants, and water sports rentals Perfect for track fans (5 mins to Road America), golfers (20 mins to Whistling Straits) Settle In+Check Out+Enjoy your time away!

Lakefront Condo, Private Beach/Pool, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, private outdoor pool, hot tub, water sports rentals, Tiki Bar and nearby Osthoff Lake Deck, hiking, golfing, and town. Fall brings vibrant foliage, trail hiking, and golf on scenic courses. Winter offers cross-country skiing, snowshoeing, ice skating, sledding and trail hiking, while spring delights with blooming wildflowers, birdwatching, and farmers markets. Experience nature’s magic any season!

Resort Condo on Elkhart Lake

Enjoy Lake life on Elkhart Lake in our resort condo steps to beach, in and outdoor pool. 2 miles to Road America, 2 minutes walk to the clear waters of Elkhart Lake, multiple options for dining, cocktails, and coffee: The Tiki bar with live music, and the famous "Off The Rails" for a perfect coffee beverage. Our home features: 2 bedrm ensuite with extra 1/2 bath, Living rm with fireplace, huge windows and lake views. Deck with lake views and Kitchen with everything you might need.

Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!

Endless family fun awaits at this pet-friendly, 5-bedroom, 4-bath vacation rental in Elkhart Lake, WI! This spacious home features countless comforts, like Smart TVs, a fireplace, and a fully equipped kitchen. Spend a sunny day on Elkhart Lake, hit the links at a championship golf course, or go for a day hike along the Ice Age National Scenic Trail —just steps from your door. Later, return home to unwind in the indoor pool, fire up the grill for dinner, and stargaze by the fire pit!

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Elkhart Lake Beach Resort (Formerly The Shore Club of Wisconsin) & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach and Tiki bar. A unique blend of updates, convenience, comfort & relaxation. Just steps away from local favorites including village restaurants, bars, farmers market, shops & neighboring resorts like Osthoff and Siebkens Resorts.

Resort Life 2 Queen Suite

WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is located along a picturesque freshwater lake and within walking distance to exciting events and adventures! Our rooms offer easy access to seasonal pool, fresh water lake, and so much more! Victorian Inn is situated in the heart of downtown Elkhart Lake near several specialty shops and restaurants. We're also just 2 miles from Road America, 8 miles from Kettle Moraine State Forest, and a short drive to PGA golf courses!

Hart & Sol in Elkhart Lake

Welcome to your perfect lakeside escape in Elkhart Lake! Our condo offers a beautifully updated, family-friendly retreat blending the comfort of home with a world-class resort footprint. Whether you are visiting for a race weekend at Road America or looking to spend long days on the water, our condo puts you right at the center of everything Elkhart Lake has to offer. Designed with family fun in mind, our sunlit, multi-level layout features a modern, welcoming aesthetic.

Secluded Elkhart Retreat | Pool, Hot Tub & Sunset

Nestled just minutes from Downtown Elkhart Lake, this custom-built cordwood home offers a secluded sanctuary experience. Perched atop a hill, the unique 16-sided house provides breathtaking views of the state forest and surrounding farmland. Despite its remote feel, you’re only a 5-minute drive from the charming Elkhart Lake business district. Day hikes on the ice age trail are just steps away from the home. Tap the ❤️ to save this listing!

Sheboygan Ranch w/your own private pool

Completely remodeled 3BR 2 bath home with its own PRIVATE POOL and fenced in yard. Relax and enjoy everything Sheboygan has to offer. Ideal for families, groups, or golf getaways. Only 10 mins to Kohler and World class Golf and 5 minute drive to Lake Michigan! Includes driveway parking, Wi-Fi and self check-in. This home has everything to make your time here perfect. From the large deck in the backyard to the wonderful inground pool.

Lake Views | Walk Everywhere | 3BR Beach Resort

Stay Together at Elkhart Lake Beach Resort | 3BR Lakeview Condo for Couples & Friends Skip the split hotel rooms—this rare 3-bedroom, 3-bath condo at the Elkhart Lake Beach Resort is designed for groups who want to actually spend time together. Perfect for 2–3 couples or a small group of friends, you’ll have a true shared living space plus full access to one of Elkhart Lake’s most social, walkable resort experiences.

Road America lake house.

Road America adjacent lake house. Great location, two minutes to the track. Towns of Elkhart Lake, Plymouth and Kohler are minutes away. Whistling Straits golf course is twenty minutes down the road. Four bedroom house with full kitchen and laundry room. House features an indoor pool, gazebo on the deck overlooking the lake. Three kayaks and a row boat down lakeside. Ping pong table inside on the pool level.