Vacation rentals with a kayak in Waukesha County

A serene view of Pewaukee Lake is captured, featuring a large tree on the lawn and multiple docks lined along the water's edge. The sky is adorned with soft clouds reflecting colorful hues, complementing the peaceful lake setting.

5.0 out of 5 average rating, 66 reviews

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!

LocationOutdoor spacesSleep quality

4.97 out of 5 average rating, 29 reviews

A wooden dock extends toward a calm lake, featuring a covered boat and a sunbathing area with a chair. A yellow floating mat lies nearby, and the water reflects the surrounding greenery. Swimmers can be seen enjoying the gentle waves in the distance.

Home in Mukwonago

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!

Outdoor spacesLocationGrill

The front view of the cottage displays a charming exterior, featuring a combination of light-colored wooden siding and stone accents. A wooden porch with a railing leads to the entrance, and a circular wreath adorns the front door. Large windows allow natural light into the living space.

4.91 out of 5 average rating, 34 reviews

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!

LocationValueCheckout

4.89 out of 5 average rating, 28 reviews

Lakefront Views, Walk to Dining | Kayaks + Firepit

Wake up to sparkling water views, spend your days enjoying the amenities, and end the evening with dinner, drinks, and music—all just steps from your door. Welcome to Water’s Edge Cottage! Our lakefront home offers unbeatable views, lake amenities, and one of the best locations in Lake Country—perfect for guests who want to relax and enjoy everything the area has to offer. Whether you're here for summer lake days, fall sunsets, or a cozy winter reset, this is memorable lake living at its best.

Outdoor spacesLocationSleep quality

Superhost

4.86 out of 5 average rating, 14 reviews

Lake Country Wellness Escape- Sauna, Hot Tub- Pier

Brought to you by NCL Properties, this serene getaway is designed for relaxation, restoration, and a laid back lake vibe. Wake up to lake views, sip your morning brew from our coffee bar, and let the calm energy of the water set the tone for your stay. Unwind in the hot tub, or infrared sauna for a soothing reset. We also have a dedicated fitness corner features a Peloton. Spend your days lounging on the deck, kayaking, or soaking in the peaceful setting that makes Pewaukee lake so special.

Outdoor spacesLocationIndoor spaces

4.92 out of 5 average rating, 116 reviews

A charming home is set among lush greenery, showcasing large windows that allow plenty of natural light. A stone wall supports a decorative patio area with several outdoor chairs and potted plants, creating a serene outdoor space. Tall trees frame the scene.

Home in Nashotah

Beautiful home on Okauchee Lake, WI

I have a beautiful home on a fun lake. It is just 25 mins from Milwaukee and 50 mins from Madison. There are several bars and restaurants on&off the water; you can either walk, drive or boat to. I have a boat slip available if you want to bring your own 18' or smaller boat. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. Nearby is the Nashotah Park, with a dog park and hiking trails. Lions park has an area for parties.

Outdoor spacesLocationKitchen

4.86 out of 5 average rating, 127 reviews

A two-story house features a blue exterior with large windows illuminated by natural light. Lush green shrubs flank the entrance, while a small seating area consisting of metal chairs is set on a well-maintained lawn. A concrete path leads to the front door.

Home in Oconomowoc

Oconomowoc Downtown River View

Stunning view of the Oconomowoc river, locate in the heart of downtown Oconomowoc. Whether you are traveling for fun or work there is something for everyone. Walk to sandy beaches, six nearby parks, tennis court, or just walk around beautiful Lac La Belle Lake and Fowler Lake. Bring your kayaks or boat. Local boat rentals are available in town. Enjoy live bands and events at restaurants and bars or have a peaceful dinner at one of many fine dining restaurants also in walking distance.

LocationOutdoor spacesGetting around

4.97 out of 5 average rating, 66 reviews

The exterior of the cottage is showcased, with dark wood siding and a well-maintained garage door. Lush green trees surround the property, providing shade and a natural feel. A walkway leads to the entrance, enhancing the inviting atmosphere of the home.

Cottage in Mukwonago

Charming Phantom Lake Cottage

Come relax at our cottage located on Phantom Lake. This 2 bedroom, 2 bath, plus sleeping loft area home is comfortably furnished and a perfect space to enjoy all lake life offers year round. Free public boat launch located nearby with our private pier/dock and anchored swim raft available for use on a seasonal basis along with multiple kayaks, paddleboard, and paddle boat on site. Attached composite deck and crushed stone fire pit area are perfect spots to enjoy the outdoors.

Outdoor spacesLocationCheckout

Superhost

A tipi is illuminated from within as dusk settles, casting a warm glow against the evening sky. The structure features an open entrance, framed by tall grass, with the silhouette of distant trees in the background. Utility lines are visible along the horizon.

Tent in Mukwonago

4.91 out of 5 average rating, 32 reviews

Simply Maple Farm Tipi

Off the beaten path, with no other campers nearby. Comes with 2 kayaks and you may rent more from local business. 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!

Outdoor spacesLocationPets

4.98 out of 5 average rating, 93 reviews

An open-concept living area showcases contemporary design elements. A cozy seating area is complemented by a large sectional sofa. Bright yellow chairs surround a dining table, while modern lighting fixtures and unique wall art add character to the space. Large windows provide ample natural light.

Cabin in Pewaukee

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.

LocationOutdoor spacesCleanliness

5.0 out of 5 average rating, 41 reviews

Home in Oconomowoc

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!

ValueOutdoor spacesAccuracy

The exterior of the home is illuminated at night, featuring a spacious patio furnished with sectional seating and lounge chairs. String lights hang overhead, creating a relaxed ambiance. A lawn area is visible, leading towards the house with multiple balconies overlooking the outdoor space.