Holiday rentals with a pool in Oshkosh

4.95 out of 5 average rating, 65 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.

4.91 out of 5 average rating, 34 reviews

An indoor heated pool is framed by light-colored walls adorned with subtle marine-themed decor. Smooth tiles line the edge of the pool, while several white chairs are arranged nearby. Natural light filters through windows, reflecting on the calm water.

Home in Two Rivers

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!

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.

4.81 out of 5 average rating, 21 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

5 out of 5 average rating, 18 reviews

Home in Ashwaubenon

Green Bay 3 miles Lambeau Field 4bd room/2.5 bath

Only about 3.4 miles to Lambeau Field! Welcome to The Packers Pool House! This 4 bedroom 2 & 1/2 bath ranch home is the perfect place to gather with friends or family! Located off of Onieda with access to tons of restaurants and shopping and a straight shot to Lambeau field! The private yard with inground pool is the perfect spot to hang out, relax around the Gas Bonfire Pit! We offer 5 cable ready TVs as well as high speed internet. 4 Queen beds and 1 King 2 Kitchens 2 Family rooms

5 out of 5 average rating, 3 reviews

A compact RV is parked among tall trees, featuring an extendable awning and colorful outdoor lights. A picnic table is positioned nearby, accompanied by a cooler and a neatly arranged mat, all set against a backdrop of natural greenery.

Campervan/RV in Montello

The Happy Hamlet

Relax at Kilby Lake Campground cozy 16' RV, the Happy Hamlet. This thoughtfully equipped RV 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! Equipped with a full size bed, and dry bath. Share in our nature-centric campground and wander through the tranquil woods. For more action, head to the playground, play a game of cornhole, paddle around the lake, or lounge in our heated pool.

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

4.96 out of 5 average rating, 25 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.

5 out of 5 average rating, 18 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 ✨

4.96 out of 5 average rating, 48 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

Private Craftsman home in Plymouth, WI—just 4 miles from Road America. Ideal for race teams and families, this two-story home offers 4 BDRMS, 2 BA, a private outdoor hot tub, and a seasonal heated inground pool (June-Sep). 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. Summers, Holidays, & RA race weekends require 3 night min.

4.96 out of 5 average rating, 83 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!

4.81 out of 5 average rating, 53 reviews

A circular, above-ground swimming pool with clear, inviting water is visible, surrounded by lush greenery. The pool deck features wooden planks, and a set of steps leads into the water, creating easy access. The tranquil lake can be seen in the background.

Cottage in Montello

Lakefront Escape, Exclusive Pool, near WI Dells

Ideally located 30 minutes from the Wisconsin Dells and about 20 minutes from Cascade Mountain. Experience refined relaxation with family and friends at this peaceful lakeside residence, complete with a private pool. From your sunrise coffee to glowing sunsets and fireside s’mores, every moment is designed for relaxation. We created this home for memorable getaways, it delivers a variety of experiences and activities for guests of every generation.

Guest favourite

5 out of 5 average rating, 10 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).