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.

Cool City, Warm Pool

Your Northeast Wisconsin oasis awaits right here in Two Rivers, WI. Located less than 45 minutes from Green Bay, a large, indoor, heated pool makes this home perfect for a relaxing vacation. Three bedrooms and two baths means room for the whole family. If swimming pools aren't your thing, the basement rec room features a pool table, fusball, and video game consoles to hustle your housemates. Quiet neighborhood in a beautiful city boasting some of the best beaches Lake Michigan has to offer!

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!

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!

Blakeford 1113 Shadow Ln w/Heated POOL

This brand new home (completed August 2024) boasts 6 bedrooms and 3 bathrooms with ample gathering space, an enormous backyard patio that wraps around the side of the house (partially covered) and enters into the party garage. Six spacious bedrooms all with luxurious king or queen beds & two queen premium pull out couches can accommodate your group for any event/weekend stay. Fast internet provided by Spectrum. Hot tub and heated pool (seasonal).

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!

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.