Holiday rentals with a pool in Oshkosh

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

NEW BOOKINGS: 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, families, golfers, crafters, & crisp fall bonfire nights. Quiet neighborhood; no pets. Holidays & Road America race weekends require a 3-night stay.

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!

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!

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!

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 ✨

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

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

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.

Luxury 5BR Lambeau Pool House & Hot Tub

Steps from Lambeau Field on Green Bay's 'Hollywood Boulevard,' this modern luxury home is the ultimate game day retreat for up to 17 guests. Enjoy a heated pool, hot tub, and the one-of-a-kind Lombardi Pool House. Features a fully fenced yard, stylish interiors, and a dedicated workspace. Perfect for large groups seeking comfort and entertainment in the heart of the stadium district.

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).