Pet-friendly holiday rentals in Milwaukee

4.95 out of 5 average rating, 130 reviews

*Fenced in yard/parking/parks and plants*

Perfect for families! We have a cozy light filled home in a quiet walkable neighborhood of Bayview. Enjoy the back porch with a coffee or local brew. We are a 5 minute drive from the airport, 10 min to downtown Mke and 5 minute walk to public transit. Parks are in walking distance as well as cafes & restaurants. Our home is a great place for couples, solo adventurers, business travelers, families, groups, and furry friends (Fee of $150 up to two well behaved dogs) Relax, unwind & enjoy our home!

4.99 out of 5 average rating, 103 reviews

A modern kitchen features sleek cabinetry and open shelving. The space is illuminated by natural light through multiple windows. A wooden countertop extends into a dining area with bar stools, while brick accents add a touch of character.

Home in Lower East Side

Cream City Lounge | Parking| AC | Patio | Pets

Welcome to Milwaukee! This remodeled home offers a spacious and stylish retreat for up to 11 guests. With four bedrooms, two full bathrooms, and charming cream city brick accents, this home seamlessly blends modern comfort with historic charm. Enjoy the coffee bar with an outdoor patio, fireplace, and dining area. Private parking for up to 4. Lounge-style living. Close to Brady St. Restaurants, bars, salons, shops and convenient stores just outside the front door. Bring the family dog as well!

4.97 out of 5 average rating, 150 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

Beautiful 2 bedroom first floor buglalow in trendy Bayview with original details, updated kitchen & updated bathroom. Spacious open floor plans. Perfect to host families, groups of friends or a couple. Access to a private fenced backyard with fire pit, Infrared Sauna and grill. Add'l front seating on the cozy front porch. Perfect for relaxing with morning coffee or quiet dinners staying in. Easy street parking. Laundry in unit. Steps away from public transportation. Walkable restaurants/bars.

4.97 out of 5 average rating, 114 reviews

Home in Murray Hill

Belleview House: Hot Tub, Backyard, Fire Table

Welcome to Belleview House, a delightful pet-friendly 3-bedroom home nestled in the heart of the vibrant Murray Hill/East Side neighborhood. We have renovated and redecorated the entire home and backyard (November 2025)! ✔ Hot Tub - closed during quiet hours ✔ Fast Wi-Fi ✔ Workspace ✔ Smart TVs ✔ Comfy king, queen, and twin beds ✔ Fenced Backyard with outdoor fire table ✔ Lawn bowling, horseshoe & cornhole ✔ Outdoor dining table ✔ 0.9 mi to Bradford Beach on Lake Michigan ✔ Stocked kitchen

The living room features a stylish tan sofa accompanied by a textured throw and decorative pillows. A round mirror hangs on the wall, reflecting the room's layout. A light fixture hangs overhead, and colorful artwork is displayed. A modern coffee table is positioned on a striped rug.

4.91 out of 5 average rating, 129 reviews

Funky 2BR in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in MKE's eclectic Bay View directly next to restaurants and bars. Minutes from downtown, Summerfest, art museum. You’ll have the entire first floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, record player, a work space in the master, and a comfy living room with a smart TV. The space has a small backyard area, an in-unit washer & dryer as well as 1 off-street parking space.

5 out of 5 average rating, 151 reviews

A stylish living room features a combination of modern and vintage decor. A leather sofa and two vibrant red chairs are arranged around a wooden coffee table. Decorative plants and unique light fixtures add character, while floral wallpaper and a colorful dining area can be seen in the background.

Home in Walker's Point

Fabulous Walkers Point Mansion w/ Bar andFireplace

This stunning Walker's Point historic mansion is completely re-imagined with interior spaces that will delight you and your guests. Host a memorable get together with friends or family and relax by the bioethanol fireplace, enjoy everything the vibrant neighborhood has to offer. We have some beautiful spaces for your enjoyment, including a finished-attic hangout space, and a secret vintage-inspired lounge in the basement. Enjoy plenty of Milwaukee history in a spectacular new form!

Superhost

The living space features a bright seating area with two dark sofas facing a clear coffee table, surrounded by framed artwork on the walls. A circular light fixture hangs above, while a dining table for two is visible in the corner, accentuated by a well-equipped kitchen in the background.

Townhouse in Halyard Park

4.81 out of 5 average rating, 277 reviews

Remodeled Victorian | Downtown | AC | Full Kitchen

Urban comfort in 2BD/2BA duplex near Fiserv Forum, Water St district, and Lakefront Brewery. Unique Milwaukee neighborhood with parking and restaurants nearby. Spacious bedrooms, private bath. Fully equipped kitchen includes a Keurig. Spa-inspired master bathroom. Netflix available. Convenient freeway access. Ideal for shows at the Miller High Life, Riverside, or Pabst Theater. Enjoy a Bucks game at the Fiserv Forum. Uber to attractions like the Milwaukee Art Museum or Summerfest!

4.9 out of 5 average rating, 303 reviews

A cozy living area is presented with two dark leather sofas, accompanied by bright red cushions. A glass coffee table occupies the center, while light enters through two large windows adorned with navy blue curtains. A stylish lamp and a decorative piece complete the room.

Home in Riverside Park

Historic East Side Duplex, 3BD. No Cleaning Fee!

Minutes from downtown Milwaukee by car or bus, the whole group will enjoy easy access to the city from this central location less than a mile from the UWM campus. A block from the Urban Ecology Center and Oak Leaf Trail access and easy walking distance to North Avenue's restaurants, bars, and the Oriental Theater, there's no shortage of activities, entertainment, and dining options around this historic and charming East Side abode. Or stay in with our grill and fire pit.

4.96 out of 5 average rating, 342 reviews

A vibrant yellow wreath adorns a red door, leading into a welcoming space. Inside, a dining area is visible, featuring a round table surrounded by wooden chairs. A circular mirror reflects the textured wall with blue floral patterns, creating a lively and inviting atmosphere.

Bungalow in Bay View

Our Cozy Bay View Bungalow Getaway

Our relaxing, clean, fully equipped Bay View bungalow delivers a perfect getaway. We are equipped with 1g wifi, 4K smart TV, dimmers, and a washer/dryer. Tastefully decorated, uncomplicated, and comfortable. There are cozy coffee shops, restaurants, and local bars just a few blocks from the house. The Bay View Dog Park is one block away. We have parking for two cars. We follow an Enhanced Cleaning Protocol, and are 100% smoke free without exception.

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.

4.94 out of 5 average rating, 132 reviews

Charming Bayview House, steps from MKE Merriment!

You will be in the heart of the Bayview neighborhood, centrally-located, three blocks from the vibrant restaurant and bar scene on historic Kinnickinnic Avenue. Enjoy a walk through Humboldt Park. Easily explore the eclectic, independent, and creative hub that makes Bayview so special. You are a 10-minute ride from the airport, and a 10-minute ride to the MKE Public market. Our cozy home and all-embracing neighborhood are waiting for you.

4.99 out of 5 average rating, 126 reviews

A cozy living room is centered around a modern fireplace framed by built-in shelves filled with decorative items and books. Light-colored sofas surround a glass coffee table atop a patterned rug. A ceiling fan provides airflow while natural light streams through nearby windows.

Home in Walker's Point

Barclay House in Walker's Point

Our Walker's Point house is recently renovated, nearly everything is new. Relax in this stylish space which includes a private backyard, w/rear & front decks. Located next to cafes and some of Milwaukee's best restaurants. It is also within walking distance to the Summerfest grounds. We are minutes from Downtown Milwaukee, bike trails and the pedal taverns are just a block away from the house. We just recently added a new hot tub!

4.95 out of 5 average rating, 118 reviews

A modern kitchen features sleek cabinetry and stainless-steel appliances. A spacious island with four bar stools offers ample seating, while a bowl of fresh fruit adds a pop of color. Natural light enhances the airy atmosphere, complemented by understated lighting fixtures.

Flat in Lower East Side

*FREE PARKING*Brady Street Private Residence

Welcome to your Milwaukee home-away-from-home! Located just a short stroll from the iconic Brady Street, this spacious and thoughtfully designed unit puts you right in the heart of the city’s energy—boutiques, cafes, restaurants, nightlife, and local flavor are all just steps away Book now and experience Milwaukee like a local—with all the comfort and convenience you need to relax, recharge, and explore.

Popular amenities for Milwaukee pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.94 out of 5 average rating, 204 reviews

The dining area features a wooden table with six black chairs, positioned on a decorative rug. A tall vase with dried flowers serves as a centerpiece. The kitchen area includes white cabinetry and bar stools at the counter, illuminated by pendant lighting above.

Home in Walker's Point

HGTV Renovated Home with GREAT backyard!

Superhost

A dining nook is highlighted, featuring two high-backed black bar stools surrounding a small round table. A wall-mounted sign lists several cities, and natural light filters in through nearby windows, illuminating the wood-like flooring and creating a bright atmosphere.

Home in Cudahy

4.91 out of 5 average rating, 106 reviews

Upgraded! 4BR in Milwaukee near Airport & Downtown

4.84 out of 5 average rating, 229 reviews

A comfortable living area features a gray sectional sofa adorned with decorative pillows. A round coffee table is situated in front, with a plant centerpiece. Light streams from the kitchen area, which includes modern appliances and a dining table in the background. Wall art adds a touch of character.

Home in Muskego

Lake Muskego House, Walk to Stores & Restaurants

4.98 out of 5 average rating, 63 reviews

A comfortable living area is showcased with a light grey sofa, complemented by natural wood armchairs. A flat-screen television is mounted on the wall across from the seating. Natural light filters in through a large window, highlighting the soft, neutral tones of the space.

Home in Milwaukee

Cozy Dog Friendly Home Near Airport & Downtown

4.88 out of 5 average rating, 117 reviews

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.

Home in Wauwatosa

Entire Wauwatosa Home!

4.99 out of 5 average rating, 148 reviews

Historic Brewery Tied-House in Bayview (Sleeps 12)

5 out of 5 average rating, 21 reviews

The modern home features a striking facade with a mix of dark brick and orange paneling. Spacious balconies are visible on each level, and a well-maintained landscape with shrubs and steps leads to the entrance. A rooftop deck adds to the home's outdoor space.

Home in Riverwest

Best View In Milwaukee Modern Home Rooftop Patio

4.98 out of 5 average rating, 59 reviews

The bathroom features warm-toned tile walls and a glass-enclosed rain shower, highlighted by gold fixtures. A green vanity contrasts with the tiles, offering storage space. Soft towels are neatly arranged on a wooden shelf, and natural light filters through a frosted glass window.

Home in Johnson's Woods

Cozy Wintery Stay @ The Ramble House

Pet-friendly home rentals with a pool

4.94 out of 5 average rating, 176 reviews

A historic Victorian-style home is showcased with a blue exterior and ornate architectural details. Bright green foliage frames the entrance, leading to the front steps. The sky is clear, enhancing the home's inviting appearance.

Home in Brewer's Hill

Brewers Hill Gem w/hot tub & seasonal shared pool

5 out of 5 average rating, 13 reviews

A spacious outdoor patio surrounds the inviting swimming pool, featuring lounge chairs, umbrellas, and shaded seating areas. Lush greenery and trees frame the scene, enhancing the tranquil atmosphere. The bright blue sky is dotted with clouds, offering a relaxing space for sunbathing or gathering.

Home in Mequon

Vacation home: heated inground pool on 4+ acres

The exterior of the two-story townhouse is visible, featuring a beige facade with dark brown trim. Large windows allow for natural light, while a patio area is accessible through a glass door. Lush greenery surrounds the property, adding a tranquil feel to the entrance.

Townhouse in Milwaukee

4.67 out of 5 average rating, 3 reviews

2 Story - 2Br Condo

4.78 out of 5 average rating, 157 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

Close to Lake with Great Ammenities & Breakfast!

4.97 out of 5 average rating, 217 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

Home in Milwaukee

Townhome Villa private oasis

Private, pet-friendly home rentals

4.97 out of 5 average rating, 65 reviews

A light-filled living area showcases a round black dining table with two wooden chairs. A cozy seating area features a simple beige couch, and a wooden shelf displays decorative baskets and glassware. Natural light illuminates the space through a large window, enhancing the minimalist design.

Flat in Wauwatosa

Cozy Renovated Retreat in Tosa

5 out of 5 average rating, 8 reviews

Flat in Riverwest

Turn of the century Modern Upstairs Apt

4.97 out of 5 average rating, 36 reviews

An open-plan living area showcases a modern kitchen with stainless steel appliances and a central island. A dining table for six is situated near a large flat-screen TV. Natural light floods the space through multiple windows, enhancing the sleek design and neutral tones.

Cottage in Riverwest

Private Cottage w/ Skyline Views

5 out of 5 average rating, 28 reviews

The kitchen features green cabinetry and a white backsplash, creating a modern aesthetic. A gas stove, microwave, and refrigerator are readily visible. Countertops are crafted from wood, and utensils are neatly organized, while a patterned floor adds a unique touch.

Flat in Shorewood

The Little Blue Bungelow

4.97 out of 5 average rating, 32 reviews

The spacious living room features a large sectional sofa adorned with blue and gray accent pillows. A round wooden coffee table sits on a plush gray rug, and large windows provide ample natural light. A tasteful piece of art and a side table are positioned against the wall.

Home in Lower East Side

Style and Luxury | Unbeatable Location

4.97 out of 5 average rating, 98 reviews

A warm dining room features a round wooden table surrounded by six chairs. Natural light filters through large windows adorned with light curtains. Original woodwork highlights the charm of the space, complemented by decorative wall sconces and a sideboard with stained glass details.

Flat in Bay View

Historic Bay View Home

5 out of 5 average rating, 75 reviews

A quaint dining nook features a circular table with a blue top, paired with a cozy, upholstered bench. Natural light filters through the window, illuminating a vase of fresh flowers. Shelves display decorative items, adding character to the warm, inviting space.

Flat in St. Francis

Cozy & Stylish Bayview Lower – Easy Parking