Pet-friendly holiday rentals in Madison

4.95 out of 5 average rating, 361 reviews

Gorgeous Eastside Home+Yard+Bikes+5 Star Hosts

This completely renovated, 100-year old home is in the Town of Blooming Grove, an enclave surrounded by Madison's near eastside. It has new heating & air conditioning and is sparkling clean with original hardwood floors, stairs & hardwood trim detail. There are 2 bedrooms (with ample closet & storage space), a living room, dining room, kitchen & bathroom. Please note the staircase is steep and may be difficult for some guests. Please inquire about e-bike availability for use during your stay.

WalkabilityOutdoor spacesBathroom

The photo captures a view of glowing light reflecting off the surface of Monona Bay during sunset. In the background, the illuminated Capitol building is visible, surrounded by city structures along the shoreline.

4.85 out of 5 average rating, 242 reviews

House on water! Near UW, Capital & Alliant Center

Enjoy a drink while sitting in the living room, looking out over Monona Bay & the Capital. What is better?--the view, or your proximity to downtown, UW campus, & the Alliant Center? Most mention the view. (Read some reviews!) Grill out and light the fire pit on the front lawn. Cross the street, and you're at the edge of Monona Bay. Parking is easy. Click “Show more” for things you might NOT like about the house: I'll be in the basement, pricing nuances, etc. Business travelers?--read on!

Outdoor spacesPetsSleep quality

4.97 out of 5 average rating, 114 reviews

Cottage gem: Spotless, secluded & bring the dog!

Bring the whole family - furry friends, too! - to relax beneath towering trees in our quiet cottage on Madison's west side. Cooks love the refreshed kitchen with all the tools! Enjoy a remodeled bathroom, Mid Mod furnishings & comfy beds. Grill & dine on a spacious deck and enjoy the wooded (unfenced) yard. Dog owners: Up to 2 well-behaved pooches are welcome with $125 pet fee at booking; please observe rules so we can keep hosting 4-legged friends and maintain a pristine home for all guests.

PetsOutdoor spacesNearby

4.92 out of 5 average rating, 155 reviews

The image displays a serene waterfront view showcasing a private pier extending over calm waters. A stylish three-story house is framed by lush greenery, offering a welcoming outdoor space. The interior features a spacious living room with comfortable seating and a modern kitchen visible in an open layout.

Home in Edgerton

4 Season Fun: Private Fish Pier, Cozy Decks, Grill

4Br/2.5bath, beds for 12 adults+, on water with Private Pier, fire pit, gas grill, covered decks, 2 acre yard + woods. 4 SEASONS OF FUN: Fall Fest Farms, Wineries, Ice Fishing, Snowmobiling & Skiing. Lake Koshkonong is one of WI’s largest, famous for boat-up restaurants/bars, Live Music & fishing. Located on 39/90hwy - 90 mins to Chicago, 30 min to Madison. Perfect for entertaining: fully stocked, professionally cleaned, open floorplan, 3-story outdoor living areas, playroom & more! Pets ok!

PetsOutdoor spacesRiver

4.98 out of 5 average rating, 280 reviews

Lakeview Loft - Downtown Madison

Stay in the heart of Madison, enjoying exclusive access to our 3rd floor suite with lake views. Located on a quiet street along the Lake Loop bike path/Lake Monona, and close to Willy Street (0.3 mi), the Sylvee (1.1 mi), the Capitol (1.7 mi), Monona Terrace (1.6 mi), and Camp Randall (3.3 mi). Self check-in with keypad and ample parking. Wifi is over 500 Mbps download/upload speeds. #ZTRHP1-2022-00022 Note: Loft is accessed by 3 flights of stairs! Space has coffee bar only (no kitchen).

Outdoor spacesPetsGetting around

4.91 out of 5 average rating, 103 reviews

A spacious studio area features a comfortable queen-sized Murphy bed dressed in white linens. An accent chair in a soft blue is positioned beside a wooden dresser. Natural light spills from a window above, and a room divider offers additional privacy options.

Flat in Madison

Camp Randall - FREE parking! Walk to everywhere!

Welcome! Steps from the UW, Camp Randall, Edgewood College, Vilas Zoo, the bike path system, EPIC, all 3 local hospitals, downtown, the Capitol, & the lakes. With a combined 80+ years living in Madison, we’re available to you & will do everything in our power to provide for anything you may need as our guest. We’ve raised our family in this home over the past 25 years & look forward to hosting you! We allow dogs, but I’m afraid no cats. PLEASE read the ENTIRE description before booking!

WalkabilityPetsCheck-in

The collage displays various sleeping arrangements within the home. The first image shows a spacious bedroom with a soft blue bedspread and neatly placed towels. Adjacent, a cozy room features a pink bedspread. The basement showcases three twin beds with muted plaid bedding, providing ample sleeping options.

4.91 out of 5 average rating, 221 reviews

Kid+Pet Friendly Entire Home No Clean/Service Fees

Our kid and pet friendly home on Madison's East Side is a short distance to some of the funkiest and most eclectic parts of the city, and just a short drive to the rest of what Madison has to offer! The house comes fully stocked with cooking essentials, a private workspace, free parking, and more. Whether you're in town for a Badger game, visiting friends or family, or exploring the city, this is an ideal home base to explore all of the city! The best part - NO CLEANING & SERVICE FEES!!!

PetsWalkabilityGetting around

4.96 out of 5 average rating, 665 reviews

The outdoor area of the home is visible, featuring a spiral staircase leading to a deck with a covered area. A hot tub is positioned on the patio below, surrounded by lush greenery and string lights hanging above, providing a relaxed and inviting ambiance.

Guest suite in Madison

Downtown Lake Monona Haven | SUPs, Hot Tub & Sauna

Stay in your private 3BR, 2BA section of our lakefront home. Paddle from the dock, relax in the hot tub or sauna and enjoy mornings on the balcony with coffee. You’re moments from Willy Street restaurants and right on the bike path. Inside, find a full kitchen, comfy living spaces. Two parking spots included. Spend days on the water or exploring the city and evenings grilling or roasting marshmallows by the fire. Paddleboards included. Pontoon rental available in warmer months.

Outdoor spacesWalkabilityBiking

4.91 out of 5 average rating, 114 reviews

A bright dining area is highlighted by a wooden table surrounded by chairs. A chandelier hangs above the table, while natural light enters through sliding glass doors leading to an outdoor space. A nearby console table displays decorative items, enhancing the open atmosphere.

Home in Cambridge

Quiet country retreat

Peaceful solitude or exciting sightseeing? You’ll have the best of both worlds at this quiet country home located just outside Madison on 10 magnificent acres. After, enjoying your morning coffee, take a stroll on the grounds and enjoy the sweeping views of the pastoral landscape. Then head into Wisconsin’s state capital (23 minutes by car) for an exciting day of sightseeing. Or visit the quaint town of Cambridge (8 minutes by car) to explore its unique pottery and antique shops.

WalkabilityOutdoor spacesShared spaces

4.98 out of 5 average rating, 107 reviews

Flat in Madison

The Wilson Unit F | Handcrafted Downtown Retreat

Located within The Wilson, this tucked-away third-floor corner studio offers a charming downtown stay. Historic charm meets handcrafted warmth, with woodworking details and cozy design touches. The unit faces the empty lot and may occasionally experience trucks moving gravel. Guests enjoy the shared rooftop deck overlooking nearby restaurants and nightlife. Hosted by a local husband-and-wife team passionate about thoughtful spaces. Third-floor walk-up and paid parking nearby.

WalkabilityPetsHospitality

4.94 out of 5 average rating, 126 reviews

A spacious living area is arranged with two red sofas flanking a central wooden coffee table. A patterned couch with black and white designs provides additional seating. Natural light enters through large windows, illuminating the warm wooden floors.

Home in Monona

It's called the Annex-right next door to us!

The house is located in a quiet and friendly neighborhood. Community parks and city pool within 2 blocks of of the home. Close to all schools, library, parks and bike paths. Very safe and enjoyable neighborhood. Many good restaurants in the area and lots of things to do in the area Two bedrooms are upstairs with its' own bathroom. House is air conditioned and has a full and complete kitchen. The washer/dryer are located in the basement and guest have full access to it

Outdoor spacesPetsFamily

4.98 out of 5 average rating, 180 reviews

A spacious living area features a modern design with two teal sofas and a round coffee table positioned on a geometric rug. Large windows allow natural light to fill the room, and a television is mounted on a wooden media console against the wall.

Flat in Madison

Mendota Lake View Flat

Mendota Lake View Flat is located in the heart of James Madison Park neighborhood of Downtown Madison - just a few blocks to State Street and the Wisconsin State Capitol square. Enjoy panoramic park views of the park with plenty of space to live and work. You will love the original 1920's charm with a mix of mid century and modern flavor throughout the flat. City of Madison Permit # ZTRHP2-2021-00010 7-night minimum for June 1 - Nov 28 30-night minimum for Dec - May

Outdoor spacesWalkabilityParking

Popular amenities for Madison pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.91 out of 5 average rating, 169 reviews

The exterior of the bungalow showcases a charming yellow facade, complemented by a welcoming front porch. Lush green grass and well-kept shrubs frame the entrance, while tall trees provide shade in the background. The overall setting reflects a peaceful neighborhood vibe.

Home in McFarland

Cozy Magnolia Style 2-Bedroom Home with Loft

Outdoor spacesWalkabilityCondition

4.93 out of 5 average rating, 357 reviews

Home in Edgerton

Vast Lake Koshkonong Views from Pier, Deck, & Home

Outdoor spacesWalkabilityGetting around

4.99 out of 5 average rating, 121 reviews

Home in Milton

HotTub/FirePit/Arcade Your Fall Escape Starts Here

WalkabilityPetsParking

4.94 out of 5 average rating, 131 reviews

An A-frame house with a sloped metal roof is set among trees, showcasing a spacious front balcony with wooden railing. Light is visible streaming from large windows, while a gravel pathway leads to the entrance and is bordered by small shrubs.

Home in Blanchardville

Coffee with a View

WalkabilityOutdoor spacesComfort

4.99 out of 5 average rating, 154 reviews

Home in Janesville

Fully Renovated 2BR 1BA Gorgeous Exec Home #8ma-R

PetsWalkabilityLaundry

4.84 out of 5 average rating, 181 reviews

Home in McFarland

The little Green Birdhouse-McFarland/Monona

WalkabilityOutdoor spacesHeating

4.9 out of 5 average rating, 125 reviews

A spacious countryside home is presented, featuring a wide porch with a railing and large windows. The exterior displays a light-colored facade complemented by a stone chimney. A manicured lawn with shrubs and trees frames the property, offering a welcoming appearance.

Home in Middleton

Countryside Home Minutes to Madison

PetsWalkabilityFamily

4.96 out of 5 average rating, 133 reviews

A living room features wood-paneled walls and a fireplace with a flat-screen TV above. Comfortable seating includes a blue sofa, a wooden armchair, and a side table. Natural light streams in through large windows, illuminating a decorative area rug.

Home in Spring Green

MCM Influenced Home- *Sauna*

PetsWalkabilityAccuracy

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 169 reviews

A two-story house is set on a spacious lawn, framed by trees exhibiting autumn colors. The exterior features a welcoming porch with white railings. A paved driveway leads to a garage, and a privacy fence encloses the backyard, contributing to a tranquil environment.

Home in Spring Green

5BR Oasis

Outdoor spacesPetsAccess

Apartment in Wisconsin Dells

Luxurious Chula Vista Retreat

WalkabilityOutdoor spacesTV

4.76 out of 5 average rating, 144 reviews

4.85 out of 5 average rating, 133 reviews

Home in Wisconsin Dells

Dells Retreat - Sleeps 8 + Jacuzzi

PetsParkingLaundry

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.

FUN-tana All Year Round Abbey Springs Fontana WI

PetsOutdoor spacesView

4.79 out of 5 average rating, 209 reviews

Cottage in Fontana-on-Geneva Lake

A vibrant pool area is surrounded by a spacious deck featuring lounge chairs and umbrellas. Guests can be seen enjoying the water, with the large building in the background showcasing expansive windows that invite natural light. The atmosphere is lively and welcoming.

Fontana, Wis, Lake Geneva 4bd 2.5ba Abbey Springs

Outdoor spacesPetsValue

4.98 out of 5 average rating, 116 reviews

4.85 out of 5 average rating, 48 reviews

A spacious bedroom features a large bed with white linens and decorative pillows. A comfortable chair sits beside a small side table. Soft lighting is provided by lamps on either side of the bed, and a window allows natural light to fill the room.

Flat in Middleton

Private yet close to everything!

PetsOutdoor spacesComfort

4.91 out of 5 average rating, 33 reviews

Home in Sun Prairie

Private Pool - Hot Tub - Game Room - 20 min DT

Outdoor spacesWalkabilityBathroom

4.94 out of 5 average rating, 50 reviews

Home in Sun Prairie

Private Pool - Hot Tub - Sauna - Game Room - Pets

WalkabilityOutdoor spacesTV

Private, pet-friendly home rentals

4.93 out of 5 average rating, 191 reviews

Cabin in Fort Atkinson

Cozy Lakefront Cottage With The Best View

WalkabilityPetsGetting around

4.81 out of 5 average rating, 334 reviews

A view from the breakfast nook captures a sunset over Lake Mendota. The serene water reflects hues of orange and gold, while a grassy area and few remnants of snow are visible. A coffee maker and glass kettle rest on the windowsill, enhancing the cozy setting.

Guest suite in Waunakee

Private guest suite on beautiful Lake Mendota

PetsOutdoor spacesCondition

4.88 out of 5 average rating, 101 reviews

A comfortable living room is showcased, featuring a blue sofa and two armchairs. A coffee table sits in the center, with a plant atop. A fireplace is visible, along with windows allowing natural light. A mirror and wall art enhance the room's décor.

Cottage in Monona

Cheerful 3-bedroom cottage 2 blocks from the lake

PetsOutdoor spacesBeach

4.99 out of 5 average rating, 175 reviews

Farm stay in Monroe

The Dairy at the Wegmueller Farm

Outdoor spacesWalkabilityCleanliness

4.91 out of 5 average rating, 127 reviews

A spacious seating area is highlighted by a large sectional sofa adorned with decorative pillows. A glass coffee table sits in the center, with a television positioned nearby. Natural light enters through large windows, complemented by greenery visible outside.

Flat in Deforest

Private DeForest Flat| *Walk to Parks*

WalkabilityPetsKitchen

4.98 out of 5 average rating, 278 reviews

Yurt in Cambridge

YurtSimple

Outdoor spacesPetsView

4.91 out of 5 average rating, 343 reviews

Guest suite in Madison

Downtown Condo, 5 blocks from Capital, Btn 2 Lakes

Outdoor spacesWalkabilityView