Holiday rentals with a pool in Lake Winnebago

Riverfront Oasis w/ hot tub and seasonal pool

Riverfront home on Doty Island in peaceful residential area. Built in 1936, our home has character + charm. Seasonal heated pool, hot-tub & waterfront patio. Relax, kayak or fish off of the riverfront dock. 100 feet of Fox River frontage - minutes from Lake Winnebago by boat or kayak and 8 min to the highway. Come for some R&R or for an event (EAA) our family home is in the heart of it all! 5 bedrooms, 3 bathrooms. Hens providing fresh eggs daily! Licensed by the Menasha Health Department.

Riverfront Appleton Home with Pool & Boat Dock!

Situated along the banks of the Fox River lies this 3-bed, 2.5-bath Appleton vacation rental! Boasting a fully equipped kitchen, a pool, and a private boat dock, this home has it all. Spend your days splashing around in the pool, grilling out on the patio, or fishing from the dock. End the night cozied up by the fire pit, watching the sunset and roasting marshmallows. Whether it’s an exciting adventure or a peaceful escape you seek, this retreat is the perfect place for your next getaway!

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!

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.

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.

7 Mi to Eldorado Marsh: Family Home w/ Pool

Pool Toys Provided | Multiple Living Areas | Private Outdoor Space Bring the family and settle into a place that feels like home. With Francis J. Simon Field across the street and a kid-approved backyard, this 2-bedroom, 1-bath vacation rental near Fond du Lac is set up for all-ages fun! Spot wildlife at Eldorado Marsh, cast a line in Lake Winnebago, then come home to swim, grill, and share s’mores by the fire. From marsh walks to marshmallows — your Eldorado stay starts here!

Stunning 4BD w Pool in Beautiful Neighborhood

Incredible 7 year old 4 bedroom 3 full bath home in a beautiful, quiet, family friendly neighborhood! Fireplace and finished basement as well. Take a dip in the inground pool and relax in the sun on the lounge chairs! Enjoy the sunset while you sit by the outdoor propane fire area! The house is only 3 min. from Hwy 41, about 10 min. from Appleton, and about 15 min. from Lambeau Field. This is our family's home, so you will definitely see touches of "us" throughout the house!

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.

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!

Private Beach, Pools & Full-Kitchen

🌊 Million-Dollar Views of Elkhart Lake from Covered Patio 🏊‍♂️ 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

Lake Views | Walk Everywhere | 3BR Beach Resort

Stay Together at Elkhart Lake Beach Resort | 3BR Lakeview Condo for Couples & Friends Skip the split hotel rooms—this rare 3-bedroom, 3-bath condo at the Elkhart Lake Beach Resort is designed for groups who want to actually spend time together. Perfect for 2–3 couples or a small group of friends, you’ll have a true shared living space plus full access to one of Elkhart Lake’s most social, walkable resort experiences.

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.