Holiday rentals with a pool in Lake Winnebago

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Top-rated rentals with a pool in Lake Winnebago

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A view from atop a waterslide into a pool, showcasing a spacious backyard. In the distance, shaded by trees, are several structures including a camper, a playground, and a storage shed. A clear blue sky enhances the serene landscape.
Home in Rosendale
4.81 out of 5 average rating, 16 reviews

Retreat! Delightful stay with a pool.

Rosendale is just 15 minutes from Fond du Lac, Oshkosh, Ripon and Green Lake. Enjoy our peaceful backyard in our camper that sleeps 5 comfortably. Many activities to choose right on site including a pool, basketball, volleyball, firepit and a walking/biking trail that goes all the way to Fond du lac. We are responsive hosts that are regularly available to make sure your stay is stellar. We have an activity book of all the area attractions if you are looking for ways to enhance your stay further!

Top guest favourite
Two yellow Adirondack chairs are positioned on a wooden dock overlooking a calm river, reflecting the warm hues of the sunset. The water stretches out smoothly, with trees lining the opposite shore and a soft glow from the sun creating a serene atmosphere.
Home in Menasha
5 out of 5 average rating, 12 reviews

Riverfront Oasis w/ hot tub and seasonal pool

Riverfront home on Doty Island in peaceful residential area. Built in 1936, our home has character + charm. Seasonal heated pool, hot-tub & waterfront patio. Relax, kayak or fish off of the riverfront dock. 100 feet of Fox River frontage - minutes from Lake Winnebago by boat or kayak and 8 min to the highway. Come for some R&R or for an event (EAA) our family home is in the heart of it all! 5 bedrooms, 3 bathrooms. Hens providing fresh eggs daily! Licensed by the Menasha Health Department.

Guest favourite
A spacious dining area features a large marble table surrounded by upholstered chairs. A modern chandelier hangs above, providing ambient lighting. Floor-to-ceiling windows offer views of the outdoor greenery, enhancing the dining experience with natural beauty.
Home in Appleton
4.95 out of 5 average rating, 40 reviews

Riverfront Appleton Home with Pool & Boat Dock!

Situated along the banks of the Fox River lies this 3-bed, 2.5-bath Appleton vacation rental! Boasting a fully equipped kitchen, a pool, and a private boat dock, this home has it all. Spend your days splashing around in the pool, grilling out on the patio, or fishing from the dock. End the night cozied up by the fire pit, watching the sunset and roasting marshmallows. Whether it’s an exciting adventure or a peaceful escape you seek, this retreat is the perfect place for your next getaway!

Guest favourite
The outdoor area features a spacious pool surrounded by multiple lounge chairs and umbrellas. Lush greenery and landscaped gardens enhance the inviting atmosphere. The house in the background complements the serene setting, providing a relaxed environment for gatherings and leisure activities.
Home in Appleton
4.95 out of 5 average rating, 40 reviews

Sunny Days Await | Seasonal Pool & Hot Tub Retreat

Looking for a relaxing summer escape? Whether you're here to explore or soak in the hot tub, you've found the perfect place to call home! ➤ Best for large groups and families ➤ Jacuzzi Spa w TV ➤ Outdoor smoker/grill combo ➤ Private Seasonal Pool (closed until May 1st) ➤ Dedicated Workspace | Fast wifi ➤ Outdoor Lounging & Bar with mini fridge ➤ Fully finished basement w/ 75" TV & bar! ➤ 2 Cozy indoor gas fireplaces (+ 3 outdoor) ➤ Fully Equipped Kitchen ➤ Local cafe & food mins away

Guest favourite
A spacious single-story home is set within a wooded area, featuring a gravel driveway leading to a two-car garage. Flower beds with colorful plants line the front of the house, and a lush green lawn surrounds the property, creating an inviting outdoor setting.
Home in Oshkosh
5 out of 5 average rating, 18 reviews

5 BR Oshkosh Home: 7 ml to EAA/1 ml to Hwy 41

Our home is big enough to host a large number of guests and also less than a mile to interstate 41, putting you at a quick 10 minute trip across town to the EAA, or less than a mile from Sunnyview Expo Center. We offer parking for several vehicles with an extra wide parking lot, as well as reservation dates prior to events if needed. We live in the northern township of Oshkosh, and are comfortably set just a bit in the country for privacy, yet close to town and all it has to offer.

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.
Apartment in Elkhart Lake
5 out of 5 average rating, 22 reviews

Lakefront Condo, Private Beach/Pools, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, pools (indoor & outdoor), hot tub, water sports rentals, Tiki Bar, and easy access to 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!

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.
Apartment in Elkhart Lake
5 out of 5 average rating, 19 reviews

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Shore Club of Wisconsin & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach, Tiki bar, on site restaurant, indoor pool & game room. 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.

An aerial view presents a spacious outdoor area featuring a large swimming pool surrounded by a sun deck with lounge chairs. The multi-tiered landscape includes lush greenery and decorative shrubs, while the house is visible in the background with expansive windows and a covered patio.
Home in Wrightstown
4.64 out of 5 average rating, 70 reviews

**NEW** Waterfront Vacation DREAM HOUSE

**NEW** Incredible one-of-a-kind waterfront dream home was built for entertaining and full of amenities. Boat access, dock equip with boat lift and two jet ski lifts, boat house and breathtaking views. House features huge pool, full basketball court, theater room with six reclining massage chairs, arcade, gym, in ground fire pit, spacious interior layout and two fireplaces. Centrally located right between Green Bay and Appleton. 15 minute Uber to Lambeau Field.

Top guest favourite
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.
Guest house in Freedom
4.97 out of 5 average rating, 78 reviews

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!

Superhost
An open layout features a cozy sleeping area with a spacious bed framed by light walls and large windows. A modern kitchen with dark cabinetry and stainless steel appliances is complemented by a round coffee table on a textured area rug. A comfortable seating area is visible.
Apartment in Elkhart Lake
5 out of 5 average rating, 8 reviews

Private Beach, Pools & Full-Kitchen

🌊 Million-Dollar Views of Elkhart Lake from Covered Patio 🏊‍♂️ Indoor & 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

Top guest favourite
Home in Plymouth
4.95 out of 5 average rating, 44 reviews

Winter Getaway-Private Home for 6ppl w/ Hot Tub

Family friendly, private home in Plymouth, WI. Approx. 4 miles to Road America. A beautiful Two-Story, 3 bedroom, 2 bath home with an outdoor hot tub. Close to grocery stores, various local events, bars, restaurants, and child-friendly places within walking distance. NO PETS allowed on property. *For Longer Stays over 7 days, please contact us. Book today if you're looking for a WINTER GETAWAY!

Guest favourite
An indoor swimming pool is surrounded by large windows, allowing natural light to illuminate the clear water. There are colorful lounge chairs positioned nearby, and artwork of fish adorns the walls, enhancing the pool's relaxed atmosphere.
Guest suite in Combined Locks
4.76 out of 5 average rating, 17 reviews

Luxurious Retreat with Pool & Hot Tub

Indulge in a serene escape at the TnTBnB Guest Suite, a remarkable haven that seamlessly blends luxury with comfort. TnTBnB is based inside a welcoming home in the vibrant Fox Valley. Shared with friendly hosts and their two adorable Pomskies, this unique stay offers a blend of companionship and privacy, perfect for those seeking a memorable escape.

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