Holiday rentals with a pool in Elkhart Lake

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Elkhart Lake

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

%{current} / %{total}1 / 1
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
4.67 out of 5 average rating, 3 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 😜 The home is yours for your stay

A spacious country home is set back amidst tall trees and a green yard. A circular driveway leads to the entrance, featuring a large garage and a basketball hoop. Sunlight filters through the leaves, creating a serene outdoor atmosphere.
Home in Fond du Lac
4.9 out of 5 average rating, 10 reviews

4 br 4.5 acre secluded country property

Secluded country property 4 minutes from FDL, 20 minutes to EAA, 40 minutes to Road America, 60 minutes to Milwaukee or Green Bay. Very private set back 505 ft from road. Lots to do outside w/ pond, pool, large deck, woods w/ walking trails, large yard, amazing bunk house w/ loft & 2 bunk beds. Inside the 2300 sq ft home all of the rooms are well sized. Plenty of room to spread out for a large family or group. Enjoy 2 living rooms and a movie theater room in the basement w/ 110 inch screen.

The exterior of a two-story home is displayed, featuring a neatly manicured lawn and a spacious driveway. A dark pickup truck is parked in front of the attached garage. Surrounding trees provide a natural backdrop, contributing to the home's secluded setting.
Home in Oshkosh
5 out of 5 average rating, 4 reviews

3 bedrooms, 5 miles to EAA & 45 miles to Green Bay

Home features 3 bedrooms, finished basement with pull out couch, 4 full baths, up to date kitchen , pool & raised brick patio with fire pit & gas grill. House is located less than 5 minutes from EAA grounds. Easy access to Hwy 41 for shopping & restaurants. This home is ideal for EAA vendors who after a long day are looking to come back to a peaceful place to relax but also gives the amenities of home for a family on vacation. This secluded place has everything you need for a peaceful stay.

Guest favourite
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
5 out of 5 average rating, 8 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
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.
Flat in Elkhart Lake
5 out of 5 average rating, 11 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.

Guest favourite
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.
Apartment in Elkhart Lake
5 out of 5 average rating, 21 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!

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.
Apartment in Elkhart Lake
5 out of 5 average rating, 19 reviews

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Shore Club of Wisconsin & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach, Tiki bar, on site restaurant, indoor pool & game room. 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.

An open layout features a cozy sleeping area with a spacious bed framed by light walls and large windows. A modern kitchen with dark cabinetry and stainless steel appliances is complemented by a round coffee table on a textured area rug. A comfortable seating area is visible.
Apartment in Elkhart Lake
5 out of 5 average rating, 8 reviews

Private Beach, Pools & Full-Kitchen

🌊 Million-Dollar Views of Elkhart Lake from Covered Patio 🏊‍♂️ Indoor & Outdoor Pools 🌿 Expansive Green Spaces 🚤 Private Beach & Lake Access 🍳 Full Kitchen w/High-End Gas Stove 🛁 Spacious Bathroom w/ Walk-In Tiled Shower 🛌 Charming Bedroom w/ Classic Touches & Historic Character 🏖️ Access to Private Shore Club Beach on Elkhart Lake 🕰️ Historic Touch: Part of the Old Schwartz Hotel + Prohibition-Era FBI Lookout Tower 📍 Unique, Standalone Condo

Top guest favourite
The exterior of a two-story home is portrayed, featuring a welcoming front porch with potted plants. Lush green grass lines the pathway leading to the stairs. The facade combines traditional elements with modern updates, reflecting a craftsman style. A clear sky with scattered clouds adds to the scene.
Home in Plymouth
4.98 out of 5 average rating, 43 reviews

Holiday Home for 8ppl w/ Hot Tub for the Holidays

Family friendly, private home in Plymouth, WI. Approx. 4 miles to Road America. A beautiful Two-Story, 4 bedroom, 2 bath home with an outdoor hot tub. Close to grocery stores, various local events, bars, restaurants, and child-friendly places within walking distance. NO PETS allowed on property. *For Long Stays over 7 days, please contact us. HOLIDAY DECORATIONS for NOV-DEC 2025 BOOKINGS! Ready to host families in town for the holidays! Book today!

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, 3 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.

Guest favourite
An outdoor patio area features a stone fireplace with a chimney, surrounded by several metal chairs positioned around a circular fire pit. A charcoal grill stands nearby. Lush green trees border the space, providing a natural backdrop under a partly cloudy sky.
Campervan/Motorhome in Campbellsport
4.79 out of 5 average rating, 14 reviews

Breezy Acre...Relaxing small family get a way.

Close to home get away. Awesome 21 foot camper that sleeps 2 adults, 1 child OR 3 adults. Kitchen, shower, refrigerator with freezer, stove with oven, electric, water, in backyard of country home in Campbellsport, WI. Use of hot tub, pool(weather permitting...usually up and running by June 15th) and outside grill available. Come enjoy your stay at Breezy Acre....

Top guest favourite
A round above-ground pool is surrounded by a wooden deck. A shaded seating area with dark wicker furniture is located nearby, providing a spot for relaxation. Lush green artificial turf and decorative stones complement the outdoor space, while a wooden pergola offers shelter.
Home in Oshkosh
4.84 out of 5 average rating, 93 reviews

Home Away From Home

Family friendly neighborhood near downtown. 2 large bedrooms 1 w/ California king bed, futon, tv. 1 bedroom w/queen, tv. A large living room w/ plenty of room for all guests, dining room, & kitchen.There is a fenced in back yard w/ a pool, deck, fire pit, and grills. We live here, and are not professional cleaners, but try and make your stay as best as we can!

Popular amenities for Elkhart Lake rentals with a pool

Quick stats about holiday rentals with a pool in Elkhart Lake

  • Total holiday rentals

    Explore 30 holiday rentals in Elkhart Lake

  • Nightly prices starting at

    Elkhart Lake holiday rentals start at $170 SGD per night before taxes and fees

  • Verified guest reviews

    Over 130 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Elkhart Lake holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Elkhart Lake rentals

  • 4.7 Average rating

    Elkhart Lake stays receive an average rating of 4.7 out of 5 from guests