Family-friendly vacation rentals in Sun Prairie

Guest suite in Sun Prairie

A two-story home with a mix of stone and wood siding sits on a grassy lot. Large windows allow natural light inside. A paved driveway leads to the garage, with trees and a view of open land in the background.

4.89 out of 5 average rating, 394 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

4.95 out of 5 average rating, 408 reviews

A cozy outdoor space is featured with a wooden pergola providing shade, surrounded by blue siding. Seating includes two cushioned chairs and a swing chair, all arranged around a fire table set on a patterned rug, enhancing the inviting atmosphere.

Guest suite in Madison

Cottage Suite + Jacuzzi Tub & Sauna

This Suite is perfect for 1-4 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond/Bodywash

4.94 out of 5 average rating, 190 reviews

A spacious living area features a large brown leather sectional sofa, accented with decorative pillows. A glass-top coffee table sits on a plush rug. In the background, a dining area with a modern table and light fixture is visible.

Townhouse in Sun Prairie

1,650 sq ft, 3 bd, 2ba Ranch - All the comforts!

Centrally located just 15 minutes to the airport, 17 mins to downtown Madison, 45 minutes to Devil’s Lake, an hour to Milwaukee. Only a mile from dozens of restaurants, Costco, Target, and a Marcus Palace theater. Feel recharged when you sleep in the luxury hybrid beds. Be at home on the patio with a drink in hand while watching the fire table and cooking on the Weber gas grill. It work calls, no worries - plug into the docking station complete with keyboard, mouse and ultra wide monitor.

4.97 out of 5 average rating, 396 reviews

The bedroom features a queen bed with a patterned blanket, complemented by two bedside lamps. Natural light enters through a window adorned with plants. A simple piece of wall art adds a touch of decor, while a wooden chair is positioned nearby.

Guest suite in Eken Park

Private & Clean Apartment Near Downtown & Airport

Private, sunny basement unit with separate entry accessible by keycode. 1 bedroom (queen), full bath, sitting area (2 twins/king bed), desk, WI-FI, TV, mini fridge, microwave, & coffee/tea. On street parking. Kid friendly! Note: We live with kids above the apartment - you will hear us walking around & some water pipes. 2-4 mi from Airport, Capitol, & UW Campus. Walk to brunch, pub, jazz lounge, bubble tea, grocery store, park, & bike path. Licensed by City & State. Paying all taxes & fees.

4.94 out of 5 average rating, 469 reviews

A cozy log cabin is surrounded by a winter landscape, with a blanket of snow covering the ground. Several outdoor seating options, including a picnic table and benches, are visible amidst the snow. Firewood is stacked nearby, contributing to the inviting atmosphere.

Cabin in Adams

Cozy Log Cabin in the Woods

Adams County TRH License #7333 Welcome to the Lucky Dog Cabin! Nestled in the trees, our charming log cabin is located 25 minutes North of the Wisconsin Dells and less than 10 minutes from Castle Rock Lake, Wisconsin River, and Quincy Bluff State Park. Come relax, unplug, and get away from it all. Enjoy the fresh air, starry nights, and peaceful nature sounds. Our 9 acre property offers a beautiful trail that leads to gorgeous sunset views, through the forest. A true nature-lover's paradise!

4.88 out of 5 average rating, 389 reviews

A spacious living area features a mounted flatscreen TV above a mid-century modern stereo console. Two armchairs are positioned around a round coffee table, creating an inviting space. Natural light filters through large windows dressed with light curtains, enhancing the room's atmosphere.

Home in Madison

Grooviest | Quiet | Close | Upscale MCM | Records!

• NEWLY RENOVATED SPACE. • Two floor upper unit in a private home • Private backyard with patio & fire pit • Flatscreen TV in living room with Chromcast and Antenna. • Luxury Mid Century Modern Stereo Console bluetooth • 12+ classic albums to listen to (jazz, rock, classical) More Avail Locally! • Access to thousands of albums at several nearby vintage vinyl stores • Electric fireplace w/ multi heat settings • Full Size Kitchen, Full Size Appliances, Fully stocked, Keurig • Vintage Bar Cart

4.97 out of 5 average rating, 230 reviews

A spacious loft area features vaulted ceilings with exposed beams, allowing natural light from multiple skylights. The layout includes a designated sleeping area with a queen bed, a comfortable seating arrangement surrounding a smart TV, and a cozy nook with a pop of color from a yellow accessory.

Home in Marquette

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).

4.96 out of 5 average rating, 107 reviews

A cozy living room features a plush orange sofa paired with two gray armchairs. A wooden coffee table is positioned in front, displaying magazines. The room is illuminated by natural light through three windows, and a flat-screen TV is mounted above a decorative fireplace.

Apartment in Oregon

Downtown Apt - Steps to Coffee & Sushi!

* Be sure to check out our winter extended stay discounts for 3+ nights! * Welcome to historic downtown Oregon! Step into the past while enjoying modern comfort in this beautiful space, which once housed our 1st library! Just steps away from locally owned coffee and gift shops, a wine reserve, and amazing restaurants! With convenient access to Madison (14 mi), experience the best of both worlds – small-town tranquility and urban excitement. Whether for work or leisure, welcome home!

4.98 out of 5 average rating, 232 reviews

A spacious studio featuring two green upholstered benches arranged on a decorative area rug. Natural light floods the room through skylights, illuminating the cozy sleeping area with a large bed and a dining nook equipped with a small table and chairs.

Guest suite in Middleton

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

Guesthouse in Sun Prairie

A cozy living area features a white-bricked fireplace with an arch-shaped mirror above it. A round table with two chairs stands adjacent to the fireplace, while a light blue chair is positioned nearby. Soft natural light enters through the window, enhancing the serene atmosphere.

4.98 out of 5 average rating, 380 reviews

Charming Milkhouse Cottage, minutes from Madison!

Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!

4.99 out of 5 average rating, 233 reviews

A cozy seating area features a light gray sofa positioned in front of a mounted TV and an electric fireplace, which emits a calming glow. A decorative plant adds a touch of greenery, while a textured rug and a basket with a towel enhance the inviting ambiance.

Guest suite in Madison

Peaceful 2 BR/1 BA w/ patio, fireplace, pool table

• 1400 sq. ft. lower level suite • Private backyard with patio & gas fire pit • Two TVs • Electric Fireplace • Pool table • Stocked kitchenette w/ bar seating area • Workspace • Blackout shades and curtains • Onsite parking in the driveway for one vehicle • Ample street parking • 16-min drive to UW campus and downtown • 9-min drive to the airport • 6-min drive to shopping and restaurants • Extremely safe neighborhood • License No. LICHMD-2022-00079 • Zone Permit ZTRHP1-2022-00005

4.96 out of 5 average rating, 161 reviews

The image depicts a charming three-building arrangement situated on a cul-de-sac. The structures feature varying architectural styles with a mix of siding colors. Lush greenery is visible in the surrounding landscape, and an American flag is displayed on one of the buildings under a blue sky with scattered clouds.

Guest suite in Deerfield

Studio on the Prairie Fen

Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

Popular amenities for Sun Prairie family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A spacious living room features comfortable seating arrangements, including a sleeper sofa and armchair. Natural light filters through large sliding doors, leading to a balcony. A cozy gas fireplace adds warmth to the space, complemented by a round coffee table and a flat-screen TV mounted on the wall.

4.94 out of 5 average rating, 204 reviews

Beautiful Villa with Amenities Galore

4.94 out of 5 average rating, 186 reviews

The cozy sitting area features a mix of patterned sofas and an armchair, with warm ambient lighting from two table lamps. Rich green walls create a comfortable environment, while a view into the dining area is visible through an open doorway, adding to the home's vintage charm.

Home in Watertown

Beautiful Victorian in Historic District

Superhost

A unique A-frame exterior features a mix of black wooden siding and natural brown shingles. A small patio area is visible with a round table and four black chairs, surrounded by well-kept shrubs and landscaped gravel.

4.9 out of 5 average rating, 106 reviews

Dells Retreat - A Romantic Haven- Luxury Living

4.98 out of 5 average rating, 123 reviews

A sunroom features a vintage fireplace at the center, surrounded by a circular brick hearth. Soft seating is arranged nearby, and a large wooden table with white chairs is positioned to one side. String lights provide a warm glow, enhancing the inviting ambiance.

Home in Baraboo

Winter Getaway! Hot Tub! Game Room! Near Dells!

Apartment in Fort Atkinson

An antique-style treasure map illustrates the Southeast coastline of Florida, featuring intricate details such as a ship image and a compass rose. The map's aged parchment texture and faded ink enhance its vintage charm, with marked locations and routes guiding potential treasure seekers.

4.98 out of 5 average rating, 172 reviews

“Goonies Never Say Die” You found theTreasure!

4.85 out of 5 average rating, 280 reviews

The hot tub is positioned on a deck with two glasses of red wine placed on its edge. A sunset casts warm hues over the water, while the silhouette of trees frames the scene. The distant hills create a serene backdrop.

Home in Poynette

Quietwater Cottage-Hot Tub, Nearby Skiing, Nature!

4.95 out of 5 average rating, 103 reviews

The open living area features high ceilings and large windows that allow natural light to fill the space. A green sectional sofa and matching ottoman are arranged around a coffee table. A wooden dining table is visible in the background, along with a modern kitchen.

Cabin in Portage

Secluded WI River Getaway w/ Hot Tub near Skiing

The living area showcases a spacious layout with a leather pullout couch and armchair, complemented by a modern coffee table. A smart TV is mounted on one wall, while an electric fireplace adds warmth. The kitchen features a bar with three stools, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 188 reviews

The Wanderlust at the Sunset Cove

Family- and pet-friendly home rentals

5 out of 5 average rating, 117 reviews

A farmhouse is positioned centrally on a green lawn, surrounded by mature trees and shrubs. Rolling fields extend in the background, with distant farm structures visible. The scene is framed by a clear blue sky, suggesting a tranquil rural setting.

Farm stay in Cambria

Cambria Home with a View

4.96 out of 5 average rating, 109 reviews

A spacious guest suite showcases a queen-sized bed with soft linens and a decorative throw. A small sitting area features a dark leather chair and a round dining table. Natural light fills the room through large windows framed by light curtains.

Guest suite in Verona

Peaceful Guest Suite at The Retreat

4.94 out of 5 average rating, 390 reviews

A wooden outdoor sauna is shown, featuring a rounded shape and a glass door. The structure is set among leafless trees, with a wooden deck leading up to the entrance. Natural wood tones provide a harmonious appearance in the peaceful surroundings.

Guesthouse in Stoughton

Country cabin, birders paradise.

4.94 out of 5 average rating, 333 reviews

Two Adirondack chairs are positioned on a grassy area overlooking Lake Koshkongong. The bright blue sky complements the sunlight reflecting off the water, creating a serene waterfront setting.

Home in Edgerton

Vast Lake Koshkonong Views from Pier, Deck, & Home

Place to stay in Brodhead

The exterior of a historic one-room schoolhouse is shown, featuring a red front door and a fenced yard. Surrounding trees provide a natural backdrop, and a shed is visible nearby. Soft sunlight enhances the inviting outdoor space, contributing to a peaceful setting.

4.98 out of 5 average rating, 197 reviews

Historic Randall Schoolhouse

Guest suite in Monona Bay

A bedroom features a spacious bed adorned with a light blue coverlet. Framed artwork decorates the walls, and a bedside lamp provides soft lighting. A small desk and chair are positioned beside the bed, enhancing the room's functionality.

4.98 out of 5 average rating, 633 reviews

DT+Bikes+Pvt Suite+Jacuzzi+Parking+Near Campus

4.93 out of 5 average rating, 207 reviews

A wooden deck offers a view of the tranquil Sugar River, surrounded by lush greenery. Trees line the riverbank, and a bridge crosses over the water in the background. Natural sunlight enhances the serene atmosphere of the outdoor space.

Apartment in Albany

Sugar River Hideaway

4.88 out of 5 average rating, 139 reviews

A bright living area features a subtle color palette with natural light enhancing the space. A plush sofa is positioned near a small coffee table, complemented by an accent chair. A kitchenette is visible on one side, along with a decorative area rug that adds warmth to the hardwood floor.

Apartment in New Glarus

Süden Chalet - Trail-side, 1 Bdrm in New Glarus

Family-friendly home rentals with a pool

A sandy beach area stretches along the tranquil shore of Lake Delton. White lounge chairs are arranged in neat rows, facing the calm water. Gentle waves lap at the edge of the shore, bordered by lush greenery and a stone embankment.

4.9 out of 5 average rating, 116 reviews

Lakefront Condo - Private Beach | Boat Slip| Pool

The image displays a scenic view of a riverfront condo complex with balconies overlooking the water. A red boat is docked nearby, reflecting blue skies and clouds. Below, a cozy interior is showcased with a queen bed, a television, and a seating area featuring a fireplace and large windows for natural light.

4.92 out of 5 average rating, 286 reviews

1BR UpperDells Riverfront: Jacuzzi, Pool & Hot Tub

4.91 out of 5 average rating, 111 reviews

A cozy seating area features a blue sectional sofa complemented by two bedside tables with lamps. A vibrant green wall adorned with faux plants adds a natural element. A neon sign stating 'Wisconsin Dells' is prominently displayed above the sofa.

Home in Wisconsin Dells

Family-Friendly Dells Stay | Sleeps 8 + Jacuzzi

The living room features a velvet sofa and a matching armchair paired with a coffee table set on a patterned rug. A decorative sign reading 'River Life' is displayed on the wall, alongside pink flamingo decor. Soft lighting is provided by a floor lamp.

4.85 out of 5 average rating, 166 reviews

Mel’s Marina, on the River, walk downtown.

The family room features a comfortable sofa with decorative pillows facing a large 58" Roku TV mounted on a wooden accent wall. An electric fireplace adds warmth, while a coffee table occupies the center space. Large windows allow natural light and open to a door leading outside.

4.87 out of 5 average rating, 329 reviews

The Docksider for Couples & Young Families

A breathtaking view of the sunset over Lake Como is framed by large glass doors. The patio features comfortable seating, adorned with potted plants, while the tranquil lake and lush greenery create a serene backdrop.

4.97 out of 5 average rating, 190 reviews

Lakefront condo with magnificent view & fireplace

An open kitchen area is showcased with a wooden dining table and two white chairs. Modern appliances, including a microwave and a decorative wall with floral wallpaper, add a touch of charm. An oversized clock hangs above, contributing to the inviting ambiance.

4.91 out of 5 average rating, 108 reviews

LG Quaint Condo on Lakeshore Dr.

A spacious living area features a large sectional couch and a soft ottoman. A wooden table stands nearby, with a laptop resting on it. The kitchen area is visible, showcasing a bar with seating for four. Soft lighting enhances the neutral color palette.