Vacation rentals with a pool in Oshkosh

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Oshkosh

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

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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.
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!

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

Superhost
An indoor heated pool is framed by wooden paneling and large windows, allowing natural light to enhance the space. Comfortable seating is arranged nearby, and a fireplace adds warmth. The pool's surface reflects the serene environment for a relaxing atmosphere.
Home in Green Bay
4.79 out of 5 average rating, 19 reviews

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

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.
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.

Superhost
A rustic log cabin is surrounded by greenery, featuring wooden walls and a peaked roof. A picnic table and flower planter are positioned in front of the cabin. A neighboring RV is visible in the background, integrating outdoor living with nature.
Cabin in Montello
4.95 out of 5 average rating, 20 reviews

The Rabbit Retreat #1

Relax at Kilby Lake Campground in our beautiful log cabin, the Rabbit Retreat. This camping cabin is a perfect transition to camping; rustic enough to immerse yourself in the outdoors without the hassle of sleeping on the ground in a balmy tent! Share in our nature-centric campground and wander through the tranquil woods. If you desire more action, head to the playground, play a game of cornhole, paddle around the lake, or lounge in our heated pool that is open seasonally.

Superhost
An indoor pool with clear blue water is featured, surrounded by smooth concrete flooring. Bright overhead lights illuminate the space, while large glass doors offer views of the outdoor landscape. Greenery decorates the walls, adding a touch of nature to the area.
Home in Allouez
4.85 out of 5 average rating, 251 reviews

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

Guest favourite
Home in Green Bay
4.94 out of 5 average rating, 32 reviews

Touchdown Retreat | Indoor Pool, Hot Tub & Games!

Touchdown Retreat – Indoor Pool, Hot Tub & Games! Unmatched entertainment awaits at this 6,500 sq. ft. retreat just 5 miles from Lambeau Field! Enjoy a heated indoor pool 🏊‍♂️, hot tub ♨️, movie theater 🎬, and epic game rooms 🎯🎮 with air hockey, arcade games, and more. Six spacious bedrooms, brand-new furnishings, and a private fenced yard with a fire pit. Perfect for families & game-day getaways! Book now for the ultimate Green Bay experience! 🚀

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.
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 favourite
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 favourite
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.

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

Historic condo w/ lake access & pool

Welcome to your peaceful Elkhart Lake escape - a private waterfront retreat where historic character meets cozy comfort and serene lake views. - Sleeps 2 | 1 bedroom | 1 bed | 1 bath - Waterfront w/ lake view & beach view + lake access - Seasonal pool & hot tub (Memorial Day-Labor Day) - Covered patio & outdoor dining area - Full kitchen, Wifi & arcade games - Private entrance, free parking & long term stays allowed

Top guest favourite
A spacious kitchen and dining area is visible, featuring modern white cabinetry and a large island with a stone surface. A wooden dining table is surrounded by four chairs, and sunlight is let in through multiple windows that offer a bright atmosphere.
Home in Ashwaubenon
4.98 out of 5 average rating, 132 reviews

Indoor Pool, 5 Bedrooms, 10 Min Walk to Lambeau

In order to gain the access code to the pool you will have to acknowledge and consent to the Pool Agreement and Rules. Forget about your worries in this spacious and serene space. This unique home features an indoor swimming pool! The house is large enough to accommodate large groups, with 5 bedrooms and 4.5 bathrooms. It is located just minutes away from Lambeau Field and the Titletown District.

Popular amenities for Oshkosh rentals with a pool

Quick stats about vacation rentals with a pool in Oshkosh

  • Total vacation rentals

    Explore 40 vacation rentals in Oshkosh

  • Nightly prices starting at

    Oshkosh vacation rentals start at $232 CAD per night before taxes and fees

  • Verified guest reviews

    Over 300 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Oshkosh vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oshkosh rentals

  • 4.9 Average rating

    Oshkosh stays are highly rated by guests—averaging 4.9 out of 5!

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