Vacation rentals with a pool in Elkhart Lake

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Quick stats about vacation rentals with a pool in Elkhart Lake

  • Total vacation rentals

    Explore 50 vacation rentals in Elkhart Lake

  • Nightly prices starting at

    Elkhart Lake vacation rentals start at ๏บฉ.๏บ‡ย 294 per night before taxes and fees

  • Verified guest reviews

    Over 150 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Elkhart Lake vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Elkhart Lake rentals

  • 4.9 Average rating

    Elkhart Lake stays are highly rated by guestsโ€”averaging 4.9 out of 5!

Top-rated rentals with a pool in Elkhart Lake

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

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A spacious wooden deck features comfortable seating arrangements, including cushioned chairs. A swimming pool is visible in the background, surrounded by a lush green lawn and trees. Various potted plants add a touch of nature to the deck area.
Home in Oshkosh
4.75 out of 5 average rating, 4 reviews

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 ๐Ÿ˜œ The home is yours for your stay

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Superhost
Condo in Elkhart Lake
New place to stay

VicVill | WaterViews | Vintage Charm Meets Comfort

โ˜€๏ธŽWelcome 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!

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Guest favorite
A living room featuring large windows that provide views of the surrounding landscape. A patterned armchair invites relaxation alongside a small side table. A white fireplace serves as a focal point, with a stylish arrangement of decorative items above it. A soft area rug covers the hardwood floor.
Apartment in Elkhart Lake
5 out of 5 average rating, 12 reviews

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.

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Guest favorite
Barn in Oshkosh
5 out of 5 average rating, 9 reviews

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 convenienceโ€”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, thereโ€™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.

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Guest favorite
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
4.96 out of 5 average rating, 25 reviews

Lakefront Condo, Private Beach/Pool, Walk to Town

Elkhart Lakeโ€™s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, private outdoor pool, hot tub, water sports rentals, Tiki Bar and 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 natureโ€™s magic any season!

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Guest favorite
A spacious single-story home is set within a wooded area, featuring a gravel driveway leading to a two-car garage. Flower beds with colorful plants line the front of the house, and a lush green lawn surrounds the property, creating an inviting outdoor setting.
Home in Oshkosh
5 out of 5 average rating, 20 reviews

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.

LocationFamilyIndoor spaces

Guest favorite
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
4.97 out of 5 average rating, 32 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.

LocationFamilyBeach

A well-lit room features two spacious beds dressed in crisp white linens. A flat-screen television is mounted on the wall, while a dresser provides storage. A small desk is set against one wall, accompanied by a decorative indoor plant in a pot.
Hotel room in Elkhart Lake
4.8 out of 5 average rating, 10 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 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!

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Top guest favorite
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
4.96 out of 5 average rating, 57 reviews

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, WIโ€”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.

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Superhost
Condo in Elkhart Lake
5 out of 5 average rating, 11 reviews

Private Beach, Pools & Full-Kitchen

๐ŸŒŠ Million-Dollar Views of Elkhart Lake from Covered Patio ๐ŸŠโ€โ™‚๏ธ Outdoor Pools ๐ŸŒฟ Expansive Green Spaces ๐Ÿšค Private Beach & Lake Access ๐Ÿณ Full Kitchen w/High-End Gas Stove ๐Ÿ› Spacious Bathroom w/ Walk-In Tiled Shower ๐Ÿ›Œ Charming Bedroom w/ Classic Touches & Historic Character ๐Ÿ–๏ธ Access to Private Shore Club Beach on Elkhart Lake ๐Ÿ•ฐ๏ธ Historic Touch: Part of the Old Schwartz Hotel + Prohibition-Era FBI Lookout Tower ๐Ÿ“ Unique, Standalone Condo

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Top guest favorite
Home in Port Washington
5 out of 5 average rating, 12 reviews

Wooded Retreat w/ Hot Tub & Private Beach

Hidden 2-acre retreat on Lake Michigan, panoramic lake views, and peaceful wooded surroundings. Perfect for vacations, reunions, weddings, romantic weekends, parties and getaways. Hot tub 1.5 Acres Fire pit & BBQ Two equipped kitchens Split level High speed internet Birds & wildlife Families, groups & extended stays Nearby restaurants, wineries, breweries, golf, hiking, boating, shopping, outdoor recreation Smaller unit available inquire

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Guest favorite
An indoor pool is framed by natural stone and wood paneling, with large windows allowing natural light. Lounge chairs are arranged at one end of the pool, offering a relaxed setting. The pool area is spacious, creating a calming atmosphere for leisure activities.
Home in Plymouth
5 out of 5 average rating, 6 reviews

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.

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Popular amenities for Elkhart Lake rentals with a pool