Vacation rentals with a pool in Oshkosh

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!

Family · Location · Bathroom

Top guest favourite

Guest favourite

A Sweet Suite in Freedom! Country Comfort!

Visiting friends or family in Freedom? Why bother them for an air mattress when you can stay right in town!? Going to a Packer Game and looking for a comfy place to stay with a super short drive? Found it! Set up with a king bed but can add a queen to the space when needed. Ask about using the game room, golf simulator, or pool while you're here too! There's not a FULL kitchen!! Just one burner, and a flat griddle, microwave and mini fridge. Overall, it's a suite. We think you'll LOVE it!

Family · Location · Condition

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 · Comfort

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 · Indoor spaces

Rustic Retreat!

Bring the whole family to this great place with lots of room for fun. We have a beautiful 3 bedroom 2 bath house. For those that want to camp without the camping! This amazing house is settled in the heart of Rustic Woods Campground. We have Volleyball, Horseshoes, a swimming pool, a game room, pickleball and basketball. Full Bar & Grill Open 4pm-9pm Thursday and Friday and 11am-8pm Saturday and Sunday. Activities for kids and adults. Come join us. You won't be disappointed.

Location · Checkout · Comfort

Top guest favourite

Guest favourite

Indoor Pool, Hot Tub & 2 Bed Suite w/ Onsite Staff

Ahoy, Mates! Please note that this is a private guest suite inside our home, not a detached guesthouse or an entire home rental. You’ll have your own private entrance and dedicated guest space complete with hosted concierge service. There is a fun & functional little kitchenette but not a fully stocked kitchen. Experience the comfort of a luxury hotel with the warmth of a welcoming home. The privacy you want and the assurance that we’re nearby if you need anything.

Family · Location · Kitchen

Top guest favourite

Guest favourite

Lambeau View | Pool | Rooftop | Entertainment Room

You’ve found it — the perfect stay steps from Lambeau Field and the Resch Center. Whether you're here for a game, a show or just the energy of Green Bay, Shambeau has you covered. All your questions? Answered. Ultimate experience? Yes.😊 ⭐ 2,300ft² vacation property located 500 feet from Lambeau, Resch Center, Restaurants & Entertainment District. ✨Shambeau got an upgrade with a fresh layout & one of the coolest heated pools with a spillover Spa on the market ✨

Family · Location · Accuracy

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 · Accuracy

Top guest favourite

Guest favourite

5 Br Wooded Lake Retreat 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

Family · Location · Walkability

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

Whether families, friends, or couples are spending time together, Adeline's House of Cool was designed to provide a memorable experience for everyone. Get ready for the most fun Airbnb in Wisconsin! If you like relaxing and playing in the water, you'll love the 20-foot hot tub. With a private pier and channel access to Lake Puckaway, fishing, boating, kayaking, and other water activities, even in the winter, are as close as the backyard.

Location · Family · Nearby

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.

Location · Family · Amenities

Sail Away in Elkhart Lake!

Welcome to Sail Away in Elkhart Lake, a stylish privately owned studio retreat located in The Victorian Inn within The Elkhart Lake Beach Resort (formerly known as Shore Club Wisconsin). Guests enjoy access to resort amenities including the seasonal outdoor pool, hot tub, sandy beach area, and lively tiki bar — all while being just a short stroll from the heart of downtown Elkhart Lake.

Location · Family · Accuracy