Vacation rentals with a pool in Oshkosh

4 BR home w/pool - 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.

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!

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.

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.

Amazing Six Bedroom Green Bay Vacation Home!!

Amazing one-of-a-kind home is built for entertaining and full of amenities. You'll love the huge indoor pool that is heated year-round! Very spacious layout. Home has hosted celebrities & Packers Hall of Fame Players. Amenities include a full arcade, outdoor sauna, theatre room, large open kitchen and living room, high-end massage chair, poker table, and more! Six-minute drive to Lambeau, five-minute drive to the airport, very close to everything. 5,200 Sq Feet

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 ✨

Lake Michigan and Door County Fun

The timeshare activity center with its indoor and outdoor pools is closed and there is no targeted reopening date. Guests do have access to the hotel indoor pool and hot tub which is right next to the resort. Resort is in a small village 10 minutes from the beautiful Two Rivers Beaches; 45 minutes to Door County and 30 minutes to Lambeau field. Condos have 2 bedroom 3 bths with 2 being whirlpool tubs. King Master and 2 doubles in 2nd. Full kitchen

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).

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!

Luxury Lambeau Home w/ Pool & Spa

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.