Vacation rentals with a pool in Elkhart Lake

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

Stay 3 nights & enjoy a 4 PM checkout (Sep–Dec)+ no cleaning fee! Private 4-BR Craftsman 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, women's grouos, golfers, crafters, families, & crisp fall bonfire nights. Quiet neighborhood; no pets. Holidays & Road America race weekends require a 3-night stay.

Family · Location · Getting around

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!

Location · Family · View

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 · Location · Comfort

Barndominium on Flower Farm | Pool + Vanity Space

Welcome to your dream stay in Oshkosh! Nestled on a working flower farm, this beautifully designed Magnolia Farms style barndominium offers the perfect blend of charm, comfort, and convenience—tailor-made for wedding parties, small family gatherings, and group getaways. With 3 spacious bedrooms, 7 beds, 3 full bathrooms, and an open-concept layout, there’s room for everyone to relax. Whether you're prepping for a big day or enjoying a weekend retreat, this home has everything you need.

Family · Location · Layout

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!

Family · Location · Bathroom

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!

Family · Location · Layout

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.

Family · Location · Sleep quality

Private Beach, Pools & Full-Kitchen

🌊 Million-Dollar Views of Elkhart Lake from Covered Patio 🏊‍♂️ Outdoor Pools 🌿 Expansive Green Spaces 🚤 Private Beach & Lake Access 🍳 Full Kitchen w/High-End Gas Stove 🛁 Spacious Bathroom w/ Walk-In Tiled Shower 🛌 Charming Bedroom w/ Classic Touches & Historic Character 🏖️ Access to Private Shore Club Beach on Elkhart Lake 🕰️ Historic Touch: Part of the Old Schwartz Hotel + Prohibition-Era FBI Lookout Tower 📍 Unique, Standalone Condo

Location · Family · Hot tub

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!

Family · Location · Outdoor spaces

Wooded Retreat w/ Hot Tub & Private Beach

Hidden 2-acre retreat on Lake Michigan, panoramic lake views, and peaceful wooded surroundings. Perfect for vacations, reunions, weddings, romantic weekends, parties and getaways. Hot tub Fire pit & BBQ 2 equipped kitchens Spacious gathering areas High speed internet Birds & wildlife Families, groups & extended stays Nearby restaurants, wineries, breweries, golf, hiking, boating, shopping, outdoor recreation Smaller unit available inquire

Location · Family · Kitchen

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.

Family · Location · Accuracy

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.

Location · Family · Cleanliness