Holiday 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

Home in Green Bay

5 out of 5 average rating, 48 reviews

4 BR home w/pool (lg groups) 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.

Superhost

Home in Newton

4.88 out of 5 average rating, 8 reviews

Country Cottage Indoor pool-HOT TUB NFL Draft avai

Relax with the whole family at this peaceful place. Take a dip in the indoor pool and hot tub. Living room features a grand fireplace that will keep you relaxed during your stay. Enjoy Nature while sitting on the patio grilling out. Open concept kitchen and dining area seats up to 22. Great Location. Close to 5 golf courses. Road America in 25 minutes away. Whistling Straits is 18 mins. NFL DRAFT Green Bay packer stadium is only 48 mins. EAA is 1 hour 10 min. Door county is less than 2 hours.

Superhost

Home in Montello

4.84 out of 5 average rating, 32 reviews

3bed lake house with a private pool near WI Dells

Relax with the whole family at this peaceful pool lakeside home. If you enjoy kayaking, paddle boating, fishing/ice fishing or taking a dip in a pool then this place is for you! This home offers so many activities for the whole family to enjoy. Relax on the wrap around house deck with it’s own fireplace, grill, outdoor dinning or lounge area. Relax on the porch swing. Looking for a little more activity, head over to the pool deck, basketball court, or challenge your family to a yard game.

Top guest favourite

Home in Two Rivers

4.95 out of 5 average rating, 21 reviews

Cool City, Warm Pool

Your Northeast Wisconsin oasis awaits right here in Two Rivers, WI. Located less than 45 minutes from Green Bay, a large, indoor, heated pool makes this home perfect for a relaxing vacation. Three bedrooms and two baths means room for the whole family. If swimming pools aren't your thing, the basement rec room features a pool table, fusball, and video game consoles to hustle your housemates. Quiet neighborhood in a beautiful city boasting some of the best beaches Lake Michigan has to offer!

Guest favourite

Home in Suamico

5 out of 5 average rating, 15 reviews

The Grand on Longtail - Top Lux -Pool/Lake/Theater

Introducing The Grand on Longtail – the ultimate luxury escape! This massive 10,400 sq. ft. estate boasts your own Lazy River, Sauna, and stunning views of the Bay of Green Bay. With 6 bedrooms, 7 baths, a private theater, sports bar, and rec room, it's perfect for entertaining. Cook like a chef in the gourmet kitchen with a Butler’s Pantry, or relax in the grand family room with 32 ft ceilings. Enjoy lakefront serenity, your own elevator, and more! The perfect retreat for unforgettable stays!

Guest favourite

Home in Wisconsin

4.95 out of 5 average rating, 21 reviews

Draft Day Stay | 25 Mins to Green Bay | Hot Tub

Looking for your 2025 NFL Draft Day stay? Nestled in North Appleton just 25 mins to Lambeau and the EAA airshow, this is the place to be! ➤ Best for large groups and families ➤ Jacuzzi Spa w TV ➤ Outdoor smoker/grill combo ➤ 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 ➤ Pool is closed for the season (Reopens May 1, 2025)

Guest favourite

Hotel room in Elkhart Lake

5 out of 5 average rating, 5 reviews

Resort Life 2 Queen Suite

WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is located along a picturesque freshwater lake and within walking distance to exciting events and adventures!Our rooms offer easy access to an indoor pool, outdoor pool, fresh water lake, and so much more! Victorian Inn is situated in the heart of downtown Elkhart Lake near several specialty shops and restaurants. We're also just 2 miles from Road America, 8 miles from Kettle Moraine State Forest, and a short drive to PGA golf courses!

Guest favourite

Home in Brillion

5 out of 5 average rating, 18 reviews

Sleeps 20 * 4,400 Sq Ft * Indoor Heated Pool

Bring the whole family to this great home with lots of room for fun. We would be happy to host your next large family get together, bachelorette party, shower, or any other fun event! We have it ALL. Indoor, in- ground pool , arcade games, 5 bedrooms, large kitchen island for hosting and many other amazing amenities to enjoy! We are located in the fox valley of Wisconsin near the new Airen's nordic center. This offers many winter activities as well as peaceful hiking trails in the summer!

Superhost

Home in Green Bay

5 out of 5 average rating, 3 reviews

JAmbers 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. Please message for special rates on Packer Home Games & other Special Events

Top guest favourite

Home in Ripon

5 out of 5 average rating, 8 reviews

Indoor Pool, hot tub, near lake

Make some memories at this unique and family-friendly place. 8000 square foot home, with indoor pool, hot tub and minutes from downtown, local breweries, boutique shops and restaurants. The home is nestled on a large lot, with trees surrounding the property to give it a private park like feel. Minutes from beautiful Green Lake, golf courses, & a local vineyard. Oshkosh & the EAA grounds are a short 20-minute drive. The home is furnished w games, bikes, trampoline, 2 full kitchens.

Superhost

Cottage in Wild Rose

5 out of 5 average rating, 3 reviews

Water's Edge Cottage @ Evergreen Campsites&Resort

Welcome to Waters Edge where you will feel right at home in this bright contemporary home! Our spacious home and the best deck in the resort will be sure to delight your family and friends. This pet free cottage features 2 bedrooms and 1 spacious bathroom perfect for your family getaway in any season. During the summer months you will be able to use all the resort's amenities and during the winter cozy up next to the fireplace after spending the day at the local ski and tubing hill.

Top guest favourite

Apartment in Elkhart Lake

5 out of 5 average rating, 11 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!