Pet-friendly holiday rentals in Pewaukee

4.95 out of 5 average rating, 280 reviews

A charming red farmhouse is set against a snowy landscape, surrounded by a white fence. Leafless trees create a serene backdrop, enhancing the rural setting. The house features a mix of traditional and modern architecture with snow covering the yard.

Guest house in Richfield

Peaceful weekend or extended stay, full amenities

The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.

4.94 out of 5 average rating, 195 reviews

A historic home features a multi-gabled roof and intricate architectural details. The exterior showcases a blend of light and dark hues, complemented by well-maintained landscaping and a spacious lawn. A charming porch wraps around the front, providing an inviting entrance with rocking chairs nestled on one side.

Home in Wales

Beautifully Restored Historic Victorian

Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

4.78 out of 5 average rating, 175 reviews

A cozy living room is highlighted by a light gray sofa adorned with decorative cushions. A small blue coffee table sits in front, complemented by a candle and a framed picture. Natural light enters through a window, brightening the neutral-colored walls.

Home in West Allis

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

Welcome to this cozy beach themed home located in the heart of West Allis. Close to public transportation and a few minutes driving to State Fair Park, Milwaukee County Zoo, Potawatomi Hotel & Casino, bars, restaurants, and more! Peaceful and quiet residential spot with plenty of parking on premises (up to 3 cars.) Amenities include: Spacious Parking, Smart TV, WiFi, Self Check in, Fresh Sheets and Towels, Shampoo & Conditioner, Soap & Hand Sanitizer, Fully Stocked Kitchen, and much more!

4.93 out of 5 average rating, 107 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.

A spacious living area features a cozy seating arrangement with a dark blue sofa and two patterned armchairs around a glass coffee table. A decorative rug lies on the hardwood floor, while a modern light fixture hangs from the ceiling. A fireplace and TV are positioned on the wall.

4.88 out of 5 average rating, 114 reviews

Entire Wauwatosa Home!

Private, Renovated Home in Wauwatosa w/ Master Bedroom Suite, Workspace, Free Parking, Full Kitchen & Fitness Area 6 guests, 4 beds, 3 bedrooms, 2 full baths In walking distance of local restaurants & bars Near Hospitals 3.6 mi to State Fair Park 4.6 mi to Fiserv Forum 6.3 mi to Miller High Life Theater 6.9 mi to Summerfest Grounds -Washer & Dryer -WIFI -Smart TV -Fitness bike & equipment -Coffee bar -Towels -Toiletries -Dishes, Dishwasher -Games -Security System -Fenced Yard

4.86 out of 5 average rating, 104 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.

A newly remodeled kitchen features wooden cabinetry and a dark countertop, paired with modern appliances. A large sink and a stovetop are highlighted, along with a window that provides a view of the outside. The flooring is made of warm wood, enhancing the overall design.

4.98 out of 5 average rating, 205 reviews

Spacious Wauwatosa Home In Prime Location

We just finished remodeling the kitchen and all 3 bathrooms in our unique tri-level mid-century modern home. There are 4 bedrooms offering an array of accommodations as well as a couch with a pull-out queen bed. If you like to cook, our new kitchen is amazing! There is a fireplace room with a lovely view outside, a laundry room and a TV with cable, a DVR, and streaming apps like Netflix. WIFI is available. This is a quiet family neighborhood. No parties and please be respectful.

A single-story ranch-style home is presented, featuring a well-maintained exterior with a light-colored stone façade. Green grass surrounds the property, complemented by neatly trimmed bushes and a paved walkway leading to the front door. The roof is covered with gray shingles under a partly cloudy sky.

4.92 out of 5 average rating, 103 reviews

Relax close to everything in Milwaukee

Ranch Style home in a quiet Neighborhood. You will feel at home and comfortable! The home is well maintained and very clean. In the winters you could cozy up to a nice fire upstairs and relax with a glass of wine. Downstairs is a second fireplace you have going and play a game of pool. In The summer you can enjoy the three seasons room, with looking a cup of coffee and look at the planted flower garden. Close to the Wauwatosa village down town. Even closer to Elm Grove Village.

4.94 out of 5 average rating, 131 reviews

A brightly colored living area features an orange couch with patterned cushions, complemented by a unique coffee table. A round ottoman sits nearby, while large windows allow ample natural light. Open shelving holds decorative items, enhancing the vibrant atmosphere of the open-concept space.

Home in Bay View

Bright 1.5BR in the Heart of Bay View - w/ Parking

Perfectly located in Milwaukee’s eclectic Bay View 4 blocks from the lake. Minutes from downtown, Summerfest, art museum, etc. You’ll have the entire second floor of this sunny duplex. The space is open concept - 1 bed with a King Casper mattresses, a bright kitchen with tons of space, a stylish living room with art throughout, and an office (with an air mattress). Fenced-in back yard that's great for pets and chill around the outdoor table for optimal hangs and BBQs.

4.81 out of 5 average rating, 289 reviews

A modern living area features exposed brick walls and a comfortable gray sofa, complemented by decorative pillows. A geometric blue and white area rug is placed beneath a set of small, stacked tables. Natural light is provided by a nearby window, framed by greenery.

Flat in Milwaukee

Heart of Walkers Point | 3BR | Spa Shower | AC

Enjoy a newly remodeled apartment nestled between Bayview and downtown Milwaukee. This 1,200 square foot space is ideal for group stays. Perfect for hosting a trip with friends to see your favorite band at Summerfest or to cheer on your favorite team at Fiserv Forum. Located in a very active neighborhood, above a festive bar, local tattoo shop, and nightlife within a very short walk of the bustling restaurants and local bars which can at times be heard.

4.93 out of 5 average rating, 186 reviews

Townhouse in Waukesha

Cozy 2BR charm | Big Yard, Fire pit, Replenishing!

Wake up to the sunrise over a peaceful backyard and enjoy your favorite blend on your private balcony. Evenings are perfect by the fire pit under a starry sky. This renovated home has gas stove/oven, microwave, coffee maker, full-size fridge/freezer, in-unit washer & dryer, smart TV, and Wi-Fi - ideal for couples, small families, or traveling professionals. Only 1 mile from I-94 and 20 minutes from Milwaukee, blending quiet comfort with city convenience.

4.97 out of 5 average rating, 186 reviews

A quiet country home is nestled among trees and well-maintained shrubs, showcasing a wide, inviting front lawn. The façade features a mix of symmetry with multiple windows and a central entrance, complemented by a light-colored exterior that reflects a serene environment.

Home in Muskego

3 Bedroom Muskego Home

Be our guest in a Country like 1,800 sq ft home nestled in a wetlands setting with a 1 car garage. Sleeps 6 in a master suite and 2 smaller bedrooms. Home has 2 full bathrooms with 2 showers. Full kitchen with a refrigerator and a dishwasher. Has a Laundry room with washer and dryer. A gas stone fireplace graces the family room. A Large deck is out back with an outdoor gas grill. Also, a 220 Volt EV charger is available for your use

Popular amenities for Pewaukee pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.82 out of 5 average rating, 211 reviews

An inviting living area features a wooden dining table with four chairs, complemented by a cozy chair and a side table. A decorative sign is mounted on the wall, while an air conditioning unit is visible near the window. A faux stove adds aesthetic charm to the room.

Home in Lake Geneva

Cozy Cottage 1.5 Blocks From The Lake

4.93 out of 5 average rating, 15 reviews

A serene waterfront view showcases a calm lake under a clear blue sky. A fire pit is placed on a stone patio, surrounded by several white adirondack chairs. A private pier extends into the water, providing a clear line of sight across the lake.

Home in Pewaukee

Cozy Cottage on Pewaukee Lake| Dog Friendly

4.89 out of 5 average rating, 105 reviews

Home in Riverside Park

East Side MKE |3BR | Walkable | Sauna | Parking

4.92 out of 5 average rating, 183 reviews

A welcoming living area is presented, featuring a spacious black sectional sofa and a cozy round chair. Natural light floods in through sliding glass doors, leading to an outside view. A subtle decor with plants and a table lamp adds to the inviting ambiance.

Home in Lake Geneva

Lake Geneva cottage with private beach access

4.98 out of 5 average rating, 66 reviews

The living area features high, exposed wooden beams and large windows that allow ample natural light. A central island offers workspace in the kitchen, while a cozy seating area consists of a white chair and a unique side table, contributing to the open layout.

Home in Okauchee Lake

Cheerful, open space, and relaxing 1 bedroom home.

4.94 out of 5 average rating, 129 reviews

A comfortable living area features a black leather sofa and an accent chair, complemented by a long ottoman. A decorative lamp stands on a glass side table, and large windows allow natural light to fill the room. A television is mounted on the wall.

Home in Bay View

Charming Bayview House, steps from MKE Merriment!

4.95 out of 5 average rating, 66 reviews

The exterior of a spacious home is displayed, showcasing a well-maintained lawn with seasonal foliage. A covered entrance is flanked by windows, and decorative plants are positioned at the base of the house. The facade features sleek horizontal siding and contrasting blue shutters.

Home in Waukesha

Beautiful Home in Waukesha

4.88 out of 5 average rating, 128 reviews

An open-concept kitchen and dining area features a wooden dining table surrounded by stylish black chairs. Exposed wooden beams enhance the high ceiling, while modern appliances, including a gas range and dishwasher, are neatly integrated into the sleek cabinetry. Natural light floods the space through large windows.

Home in Milwaukee

The Foundry Loft | 3BR Walker's Point Home

Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 45 reviews

A charming cabin is surrounded by lush greenery, with well-maintained flower beds featuring red blooms. A large window provides natural light, and a stone border separates the garden from the grassy area. A tall tree offers additional shade, enhancing the serene outdoor environment.

Cabin in East Troy

Kettle 2BR Cabin on15 stunning acres by Ski trails

4.96 out of 5 average rating, 46 reviews

A single-story house is presented with a light exterior and a welcoming porch. A shaded area is provided by the overhanging roof, and a bench is positioned on the porch. A well-maintained lawn stretches in front, framed by lush green trees.

Home in Delafield

Cute and cozy 2 bedroom house perfectly located!

4.93 out of 5 average rating, 42 reviews

A spacious living area is highlighted by natural light streaming through large windows. Light-colored furniture is arranged around a central coffee table on a decorative rug. An inviting dining space is visible, along with a modern kitchen area in the background.

Home in Racine

Wisconsin Retreat• Family Favorite• Spacious Home

Apartment in Fontana-on-Geneva Lake

A cozy corner of the living room features a brick fireplace with a warm fire. A decorative candle holder stands beside a beautifully lit Christmas tree. A plush sofa, adorned with a patterned pillow, invites relaxation, while a simple table holds a remote and holiday decor.

4.78 out of 5 average rating, 197 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

Townhouse in Fontana-on-Geneva Lake

A modern dining area features a round table with four upholstered chairs set on a textured area rug. Large glass doors provide access to a deck surrounded by greenery, while a stone accent wall adds visual interest. A glimpse of the kitchen area is visible in the background.

4.81 out of 5 average rating, 94 reviews

Abbey Springs 5 Star Resort on Lake Geneva

4.86 out of 5 average rating, 78 reviews

An aerial view captures the spacious outdoor area featuring a heated pool surrounded by lounge chairs. A fully stocked fishing pond is visible alongside a grassy yard, with a trampoline and fire pit area situated near the residence. Lush trees add to the greenery.

Home in Caledonia

7 1/2 Acre Private Estate MSG Owner for Discounts

4.97 out of 5 average rating, 208 reviews

A charming duplex stands with a triangular roof, featuring a colorful facade and multiple balconies. Stairs lead up to the front porch, where seating areas are present. Lush greenery and colorful flowers are visible in front of the stone boundary wall, complementing the vibrant exterior.

Home in Brewer's Hill

The Peacock Place w/ Shared Seasonal Outdoor Pool

4.78 out of 5 average rating, 154 reviews

An outdoor patio space is presented, featuring a paved area surrounded by various seating options, including green chairs and a red umbrella. A grilling station is visible, and the background includes a garage with an open door. Lush greenery provides a natural border.

Home in Cudahy

Make Yourself At Home! Close to Lake & Airport!

Private, pet-friendly home rentals

4.93 out of 5 average rating, 68 reviews

The interior of the log cabin features warm wood finishes and an open layout. Soft lighting is provided by string lights, enhancing the cozy atmosphere. A large screen TV is visible in the living area, while the fully equipped kitchen is designed for convenience and social gatherings.

Home in Pewaukee

Luxe Spa Cabin: Hot Tub + Sauna + Fire

4.98 out of 5 average rating, 48 reviews

A comfortable living area features two recliner sofas positioned around a soft, neutral-colored area rug. A small tabletop lamp provides gentle lighting beside a window, which is dressed with purple curtains. Glass-paneled doors lead to adjacent spaces, enhancing natural light.

Home in West Allis

Your home away from home

4.91 out of 5 average rating, 22 reviews

Cottage in Pewaukee

Lakeside Pewaukee Cottage

4.97 out of 5 average rating, 146 reviews

The living area features a stone fireplace and a flat-screen TV mounted above it. Two dark armchairs and a comfortable sofa create a cozy seating arrangement. Natural light enters through multiple windows, highlighting the original woodwork and a vibrant area rug on the hardwood floor.

Flat in Bay View

Spacious & Private 2 bdrm in the heart of Bayview

4.85 out of 5 average rating, 234 reviews

A studio apartment is displayed with a spacious sleeping area featuring a cozy bed and a vibrant red couch. The kitchen area includes modern appliances and a dining space with wooden chairs. Natural light illuminates the warm wood flooring.

Flat in Bay View

The LuLu Nest: Bay View Studio, 5 min to downtown!

A comfortable living room is depicted, featuring a tan leather sofa and a matching accent chair. A coffee table sits on a light area rug, and natural light filters through large windows. A wooden piano and wall art add character to the space.

5 out of 5 average rating, 46 reviews

Beautiful safe quiet home in great location

4.97 out of 5 average rating, 79 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