Vacation rentals with a pool in Oshkosh

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!

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, Tiki bar & indoor pool. 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.

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

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

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

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

The perfect place to relax, play and explore. Three levels of luxury and drenched with natural light. Wolf/Sub Zero/Miele kitchen. Kohler fixtures and spacious tiled showers for self pampering. Restoration Hardware furniture & two 77” TV's 5 Deck Areas: sip coffee, sun bathe, read, yoga sessions * Pickleball * Clearlight Infrared 4 person Sauna * 9 Person Hot Tub * In-ground Pool 48' x 24' with Sun Deck * 13 acres * Nearby ski, golf, Wis. Dells, Madison

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!

Premier Lakefront Escape Exclusive Pool near 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 tranquil lakeside residence, complete with a private pool. From sunrise coffee to glowing sunsets and fireside s’mores, every moment is designed for relaxation. Created for memorable getaways, this home delivers a rich variety of experiences for guests of every generation.

Lakefront condo w/ pool access & patio

Welcome to your peaceful Elkhart Lake escape - a cozy waterfront condo with historic character and serene views, perfect for a relaxing stay by the water. - Sleeps 2 | 1 bedroom | 1 bed | 1 bath - Waterfront w/ lake view, beach view & lake access - Seasonal pool (Memorial Day-Labor Day) - Covered patio & private entrance - Full kitchen, Wifi, TV, heating & air conditioning - Free parking on premises & long term stays allowed

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.

Lombardi 5BR Pool House & Hot Tub

Steps from Lambeau Field on Green Bay's 'Hollywood Boulevard,' this modern luxury home is the ultimate game day retreat for up to 17 guests. Enjoy a heated pool, hot tub, and the one-of-a-kind Lombardi Pool House. Features a fully fenced yard, stylish interiors, and a dedicated workspace. Perfect for large groups seeking comfort and entertainment in the heart of the stadium district.

Cozy Urban Escape | Fireplace & Hot Tub

Modern 4-bedroom retreat in Princeton, WI perfect for spring and summer stays. Sleeps up to 10 with a hot tub, seasonal outdoor pool, wood-burning fireplace, large deck, and partially fenced yard. Walk to downtown shops, dining, and the seasonal flea market. Stylish, comfortable spaces designed for families, friends, and relaxing getaways. Dog-friendly (pet fee applies).