Holiday rentals with a kayak in Waukesha County

Luxury Lake Home-Miles of Lake Views-Private Pier

This newly built Pewaukee Lake home has 3 levels of living space & sleeps 11 with 4 BRMS 3.5. baths & 40' of private lake frontage walking distance to 2 restaurants/bars. Only 2 miles from Downtown Pewaukee Beach, Shops & Restaurants. This modern lake home commands magnificent lake views for miles with private pier, kayak, paddle board, pedal boat, private outdoor fire pit & grilling/lounge area at the shoreline. Enjoy stunning lake views including views of Downtown Pewaukee City lights @ night!

Lake House Retreat on Phantom Lake

A cozy secluded retreat like being "up North" without having to go up North. Quiet private road, and quiet lake. Great swimming and fishing off the dock in this sandy bottom lake with clean spring fed water, and large grassy area for lawn games and relaxing. Great for families, ladies retreats, golf groups, or concert goers. Only 5 mins to grocery stores. Lots of space in the house, and lots of space for spending time outside on the deck or the dock or lawn by the lake. Feel free to inquire!

Pewaukee Lake Home steps from water & restaurants!

Take it easy at this tranquil lake getaway. Our cozy cottage is steps from Pewaukee Lake. Spend your time relaxing and taking advantage of the lake access! It’s the perfect spot to enjoy beautiful Wisconsin summers, but also ice fishing/winter activities too! We are very close to the adorable downtown Pewaukee Village area, where you will find the beach, shopping, and great restaurants. There are also a few bars and restaurants within walking distance from the house. The location can’t be beat!

Simply Maple Farm Tipi

Off the beaten path, with no other campers nearby. Comes with 2 kayaks for the Fox River which is nearby. You may go up or down river easily and can fish from shore or from the kayaks. There are two adult life jackets also. There is a tipi at this site that you may choose to use. There is a fire ring, weber grill, charcoal, picnic table, benches, porta potty and garbage/recycle bins. Enjoy peace and quiet served daily at Simply Maple, with no other tents in sight!

Pewaukee Serenity Cottage: Whimisical by the Lake

Unplug, unwind, and savor the tranquility of the lake, just a stone's throw away from our inviting cottage. Offering an open-concept layout, this is your ticket to carefree living at its finest. Your dream escape to Pewaukee awaits. Secure your spot now and immerse yourself in the harmonious blend of relaxation, adventure, and comfort that our charming cottage promises. It's time to create memories, recharge your spirits, and rediscover the joys of small town living.

Forest Bay Cottage

Lakefront Getaway on Okauchee Lake – Cozy Cottage with Stunning Views! Escape to the serene beauty of Okauchee Lake with this charming 2-bedroom, 1-bath cottage, in Wisconsin’s Lake Country. Whether you're seeking a quiet retreat or outdoor adventure, this vacation rental offers it all. Located just 30 minutes west of Milwaukee and 50 minutes from Madison, you’ll have easy access to some of the best lakeside activities in the area!

Blue Chair Retreat -New Lakefront Home

Gorgeous newly built home tucked in centrally located bay on Pewaukee Lake. Blue Chair Retreat features everything you need and is only 25 minutes from Milwaukee and 50 minutes from Madison. Great area for biking, hiking, paddle boarding, boating and more. A turnkey home offering all the amenities of home plus more. The open backyard and lake is available to use anytime. Hot tub, fire pit, lake frontage and pier all included.

Okauchee Lakefront Cabin Escape

The perfect lake house for a family or a group of friends: kayaks, fire pit, gas grill, bags, jukebox, darts, bumper pool and sunsets on the deck. Near Erin Hills for golfers (15 minutes). Down the road from the Kettle Moraine hiking trails (10 minutes) and the Nashotah dog park (5 minutes). Several bars and restaurants within 5 minutes. The very best in lake life, outdoor life and night life.

Cozy Cottage Lake Country

Welcome to our newly renovated 2-bedroom cottage in the heart of Lake Country! This cozy retreat features a living area with fireplace, fully equipped kitchen, dining nook, dedicated workspace, and modern amenities. Midway between Milwaukee and Madison, you’ll be near multiple lakes, hiking and biking trails, shopping, dining, festivals, and numerous other activities.