Holiday rentals with a pool in Oshkosh

4 BR home w/pool (lg groups) kid friendly

Welcome to our beautifully remodeled 4 bed 3.5 bath home. Lg brand new fully stocked kitchen{Heated} pool (10ftmaxdpth) & lg backyard w/ creek. Tons of outdoor space to enjoy & you'll even see some wildlife around property. This home offers plenty of space & privacy. The lower level has a pool table & other games. We are 2.3 miles from Austin Straubel Airport/Oneida Casino 3.3 miles to Lambeau Field, Resch Center, Titletown. There is tons of entertainment & dining a short drive in any direction.

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!

Relax! Pool/HotTub/TheaterRoom/Sleeps 15!

Welcome! There's no place like home! Walk to Lambeau! Something for everyone, from swimming in the pool (open from mid May-October) relax in the hot tub year round. Enjoy quite nights on the swing under the gazebo. Garage is fully heated with 85" TV, bar, pub tables, billiards, corn hole, Tennis table, dart board and video games. Game room offers pool table, shuffle board and foosball. Enjoy movie night in the theater room with it's very own popcorn machine. Full kitchen and coffee bar!

Indoor Pool&HotTub, Sauna, Game Room, Movie Room

Step into luxury at our expansive home designed for entertainment and relaxation. Located just 2 miles from all the excitement Titletown has to offer, Oneida Casino, and numerous restaurants, this stunning property is packed with amenities that make it perfect for groups and families looking to unwind and have fun. -Private heated indoor pool and hot tub -Friendly competition in the game room -Catch every game in the bar room -Enjoy the ultimate movie experience in the theater room

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.

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 ✨

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

Private Craftsman home in Plymouth, WI—just 4 miles from Road America. Ideal for race teams and families, this two-story home offers 4 BDRMS, 2 BA, a private outdoor hot tub, and a seasonal heated inground pool (June-Sep). Free on-street parking plus a garage and shared driveway provide convenient vehicle access. Located in a quiet neighborhood near grocery stores, dining, and local attractions. No pets. Summers, Holidays, & RA race weekends require 3 night min.

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! 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. There's also a microwave and small refrigerator/freezer, but overall, it's a suite. We think you'll LOVE it!

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

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!

7BR Luxury Penthouse with Heated Pool

Experience luxury in Green Bay! This brand-new 7-bed, 6-bath home sleeps 18, located directly across from Lambeau Field & Titletown. Enjoy a private heated pool, hot tub, and a unique entertainment garage bar. Perfect for large groups, this home blends high-end design with ultimate comfort and convenience, offering a one-of-a-kind 'Nashville meets Green Bay' getaway. Walk to the stadium and local hotspots from this prime location.

Cozy Urban Escape | Pool & Hot Tub

Modern 4-bedroom retreat in Princeton, WI perfect for spring and summer stays. Sleeps up to 10 with a hot tub, seasonal outdoor pool, wood-burning fireplace, large deck, and partially fenced yard. Walk to downtown shops, dining, and the seasonal flea market. Stylish, comfortable spaces designed for families, friends, and relaxing getaways. Dog-friendly (pet fee applies).