Holiday rentals with a pool in Oshkosh

4.97 out of 5 average rating, 58 reviews

An outdoor area features a heated swimming pool filled with clear blue water, surrounded by a spacious deck. A wooden pavilion with seating is positioned nearby, offering shade and a place to relax. Poolside lounge chairs are arranged for sunbathing.

Home in Plymouth

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

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, women's grouos, golfers, crafters, families, & crisp fall bonfire nights. Quiet neighborhood; no pets. Holidays & Road America race weekends require a 3-night stay.

LocationFamilyIndoor spaces

Guest favourite

4.96 out of 5 average rating, 71 reviews

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.

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Superhost

New place to stay

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!

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Guest favourite

An aerial view captures the expansive waters of Elkhart Lake, with shimmering reflections of sunlight. The shoreline is lined with lush greenery and a sandy beach, complemented by a few boats gently floating on the surface. Nearby, various residential structures can be seen nestled among the trees.

4.96 out of 5 average rating, 25 reviews

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!

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Guest favourite

A spacious studio condo is showcased with two queen beds, a cozy sitting area, and a fully equipped kitchenette. A flat-screen TV is mounted on the wall, while a high-top table for two is featured in the background, providing a functional living space.

4.97 out of 5 average rating, 33 reviews

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.

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5 out of 5 average rating, 21 reviews

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 ✨

FamilyLocationOutdoor spaces

Superhost

A spacious bedroom features a king-sized bed with a rich burgundy and cream bedspread. Two bedside tables with lamps sit beside the bed, and a comfortable armchair is placed in the corner. Soft carpet covers the floor, enhancing the cozy atmosphere.

Condo in Mishicot

4.65 out of 5 average rating, 23 reviews

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

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4.97 out of 5 average rating, 91 reviews

An aerial view captures a spacious property featuring a rectangular pool surrounded by lounge chairs. Manicured grass and trees provide greenery, while nearby homes and a winding road are visible in the background.

Guesthouse in Freedom

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!

ValueFamilyDecor

5 out of 5 average rating, 15 reviews

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).

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Superhost

5 out of 5 average rating, 11 reviews

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

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Earthen home in Elkhart Lake

4.97 out of 5 average rating, 154 reviews

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!

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