Vacation rentals with a pool in Lake Winnebago

Find and book unique homes with a pool on Airbnb

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 favorite
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.
Condo 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, and easy access to 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!

Top guest favorite
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 favorite
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 favorite
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 favorite
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 favorite
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.
Condo 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
4.65 out of 5 average rating, 71 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 favorite
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
4.97 out of 5 average rating, 79 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!

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

Craftsman Retreat Near Road America-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 bedrooms, 2 baths, a private outdoor hot tub, and a seasonal inground pool (summer–mid-September). 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. Longer stays (7+ nights) by request.

Top guest favorite
An indoor hot tub is positioned under a ceiling lined with wooden beams, featuring steps leading into the water. Natural light filters through large windows, illuminating the stone fireplace and warm wooden accents throughout the space.
Cabin in Markesan
4.99 out of 5 average rating, 81 reviews

Adeline's House of Cool, The most fun Airbnb in WI

Whether families, friends, or couples are spending time together, Adeline's House of Cool was designed to provide a memorable experience for everyone. Get ready for the most fun Airbnb in Wisconsin! If you like relaxing and playing in the water, you'll love the 20-foot hot tub. With a private pier and channel access to Lake Puckaway, fishing, boating, kayaking, and other water activities, even in the winter, are as close as the backyard.

Guest favorite
An inviting inground pool is framed by a neatly landscaped backyard, featuring comfortable lounge chairs and shaded seating areas. A stone outdoor fireplace adds a cozy element, while large umbrellas provide relief from the sun. Vibrant greenery surrounds the space, enhancing the peaceful ambiance.
Home in Menasha
5 out of 5 average rating, 19 reviews

Resort in the city

1920's character home on Doty Island perfect for relaxation or home base to explore the Fox Cities. Private backyard, inground heated pool along with 23 acre Smith Park out your front door make this an easy choice to find something that suits everyone's wants. Enjoy a walk or bike-ride around the quiet neighborhoods or link to the many bike trails accessible out the front door. Enjoy dinner on the front porch while watching the sunset.

Superhost
Condo in Elkhart Lake
5 out of 5 average rating, 8 reviews

Waterfront condo w/ lake access & pool

Welcome to your peaceful lakeside retreat - a cozy condo with historic character & calming water views. Unwind, recharge, and enjoy easy access to Elkhart Lake year-round. - Sleeps 2 | 1 bedroom | 1 bed | 1 bath - Waterfront w/ lake & beach views - Seasonal pool & hot tub (Memorial Day-Labor Day) - Lake access via path or dock - Covered patio & outdoor dining area - Kitchen, wifi & private entrance

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