Holiday rentals with a pool in Elkhart Lake

Great EAA Location by the Airport

Three bedroom (5 beds), 2 full bathroom home available for for rent the week of EAA. Located only a couple minutes from the EAA grounds, vendor entrance, HWY 41, & Seaplane Base. Enjoy amenities like a swimming pool, large deck, gas grill, in a country setting where you can still see some of the airshow after a long day! Also a fire table on the deck, trampoline in the backyard, and a bar area on the lower level... free to use it all at your own risk of course 😜 The home is yours for your stay

Family · Value · Hospitality

VicVill | WaterViews | Vintage Charm Meets Comfort

☀︎Welcome to VicVill! Historic charm meets lakeside comfort in this 2BD/2BA Condo. Located in Elkhart Lake Beach Resort Enjoy stunning lake and pool views throughout Relax at the private resort beach+seasonal indoor/outdoor pool Plush King master+matching twin-over-full bunks Steps to TikiBar Walk to village shops, restaurants, and water sports rentals Perfect for track fans (5 mins to Road America), golfers (20 mins to Whistling Straits) Settle In+Check Out+Enjoy your time away!

Location · Family · Bathroom

Barndominium on Flower Farm | Pool + Vanity Space

Welcome to your dream stay in Oshkosh! Nestled on a working flower farm, this beautifully designed Magnolia Farms style barndominium offers the perfect blend of charm, comfort, and convenience—tailor-made for wedding parties, small family gatherings, and group getaways. With 3 spacious bedrooms, 7 beds, 3 full bathrooms, and an open-concept layout, there’s room for everyone to relax. Whether you're prepping for a big day or enjoying a weekend retreat, this home has everything you need.

Family · Location · Air conditioning

Resort Condo on Elkhart Lake

Enjoy Lake life on Elkhart Lake in our resort condo steps to beach, in and outdoor pool. 2 miles to Road America, 2 minutes walk to the clear waters of Elkhart Lake, multiple options for dining, cocktails, and coffee: The Tiki bar with live music, and the famous "Off The Rails" for a perfect coffee beverage. Our home features: 2 bedrm ensuite with extra 1/2 bath, Living rm with fireplace, huge windows and lake views. Deck with lake views and Kitchen with everything you might need.

Location · Family · Beach

Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!

Endless family fun awaits at this pet-friendly, 5-bedroom, 4-bath vacation rental in Elkhart Lake, WI! This spacious home features countless comforts, like Smart TVs, a fireplace, and a fully equipped kitchen. Spend a sunny day on Elkhart Lake, hit the links at a championship golf course, or go for a day hike along the Ice Age National Scenic Trail —just steps from your door. Later, return home to unwind in the indoor pool, fire up the grill for dinner, and stargaze by the fire pit!

Location · Family · Access

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.

Family · Location · Beach

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.

Family · Location · Condition

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 seasonal 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!

Location · Value · Hot tub

Road America Retreat-4 BDRM-2BA-Hot Tub+Pool

Fall Special-book 3 nights & get a 4pm Check-Out (Sep-Nov). 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. Located in a quiet neighborhood near grocery stores, dining, and local attractions. No pets. Summers, Holidays, & RA race weekends require 3 night min.

Family · Location · Cleanliness

Road America lake house.

Road America adjacent lake house. Great location, two minutes to the track. Towns of Elkhart Lake, Plymouth and Kohler are minutes away. Whistling Straits golf course is twenty minutes down the road. Four bedroom house with full kitchen and laundry room. House features an indoor pool, gazebo on the deck overlooking the lake. Three kayaks and a row boat down lakeside. Ping pong table inside on the pool level.

Location · Family · Pool

Sail Away in Elkhart Lake!

Welcome to Sail Away in Elkhart Lake, a stylish privately owned studio retreat located in The Victorian Inn within The Elkhart Lake Beach Resort (formerly known as Shore Club Wisconsin). Guests enjoy access to resort amenities including the seasonal outdoor pool, hot tub, sandy beach area, and lively tiki bar — all while being just a short stroll from the heart of downtown Elkhart Lake.

Family · Location · Sleep quality

Luxury Pool Retreat-2 Acres-Near Whistling Straits

Escape to your private Sheboygan retreat on two acres! This spacious home is perfect for golf trips and family getaways, comfortably hosting large groups. Enjoy a seasonal heated pool, game room with ping pong, and a cozy fire pit. Located just 8 minutes from Whistling Straits and a short drive to Lake Michigan and Road America. Your ideal basecamp for Wisconsin adventure awaits!

Location · Family · View