Holiday rentals with a pool in Fitchburg

Guest suite in Spring Green

A well-maintained home exterior is surrounded by a lush garden, featuring a variety of plants and shrubs. The entrance is framed by a decorative archway, and a large tree provides shade. An inviting walkway leads up to the front door, enhancing the overall charm of the property.

4.91 out of 5 average rating, 172 reviews

Spring Green River Pines

Spend a few days in the beautiful countryside. A private entrance to the lower level of home (completely separate from our home) that includes a central room, 2 bedrooms with kitchenette, & 1 lg bath. WiFi >500 Mbps speed. Smart 60" TV, Bluetooth Airplay/stream compatible. Parking on sight. Great location 5 min from beautiful downtown Spring Green. Close to APT, Taliesin/Frank Lloyd Wrights Home/School, House on the Rock, WI River, Gov. Dodge State Park and 1/2 hr to Devils Lake State Park.

5 out of 5 average rating, 22 reviews

The image showcases a hot tub surrounded by a wooden deck, with a seating area featuring a cushioned sofa. In the background, a heated pool is visible, complemented by lush green trees and a serene sunset sky, enhancing the outdoor relaxation space.

Home in Sun Prairie

Private Pool - HOT TUB - Sauna - Game Room - Pets

🔹Private fenced-in backyard w/ heated pool, hot tub, sauna, deck & fire pit 🔸Outdoor living w/ lounge seating, pool toys, & outdoor dining 🔹Large families & groups - 2 King, 6 Queen 🔸Game room w/ pool table, ping pong & arcade games 🔹3 min to Sun Prairie restaurants & shopping 🔸Basement gym w/ free weights & equipment 🔹Pickleball court in the garage 🔸You'll find "The Kohl Center, UW-Madison, Camp Randall Stadium, State Street, The Capitol, & The Alliant Energy Center" within 20min

Home in Apple Canyon Lake

The lake house is situated on a sloping hillside, surrounded by trees. A stone pathway leads down to the water's edge, where a private dock can be seen. The calm lake reflects the blue sky and scattered clouds, creating a serene setting.

4.93 out of 5 average rating, 88 reviews

The Ho Hum East on Apple Canyon Lake

The Ho Hum East is a beautiful lake house with private dock on pristine Apple Canyon Lake! The house is named in honor of my grandparents who ran the Ho Hum Motel in Denison, Iowa :) A place to unwind, de-stress, and have some family fun! The house features all brand new mattresses in 3 bedrooms plus flex space; master bedroom with queen bed, guest bedroom with 1 queen and 1 twin, loft bedroom with 2 queens, pull out couch in living room, and 2 couches in the loft that pull out into twin beds.

4.98 out of 5 average rating, 91 reviews

Home in Janesville

*Family Retreat* *Indoor Pool* *Arcade*

The Pool House is the perfect family retreat for any group that wants quality time with quality amenities. Come enjoy everything our home has to offer and make all those wonderful memories with the ones you love. The indoor heated pool is perfect for that private party experience that can be followed up with the fully loaded arcade room. Enjoy the pinball machines and great classic arcade games then go off to the full size Golden Tee and Buck Hunter and see if you can get the new high score.

Guest house in Beloit

Spacious Delightful 2 Bedroom Home

Entering the front door you'll feel right at home. Full Bathroom with walk-in shower and amenities. Living Rm and separate Reading/Work Den with 60" HD Roku TV. Complete Fully Functional kitchen. An additional Twin or Queen size air bed, set up with bedding, is available by request to sleep a total of six. Conveniently close 2 min. from Beloit Hospital, Grocery Store, Drug/Convenience Stores, restaurants, bike/hiking paths along the scenic Rock River, Beloit College and Downtown activities.

4.92 out of 5 average rating, 36 reviews

A charming two-story house with a front porch is surrounded by lush green grass and trees. The property includes an additional structure to the right, showcasing a well-maintained landscape that enhances the serene atmosphere of the setting.

Home in Albany

Sunset retreat oasis Pool hot tub river fishngame

Take it easy at this unique and tranquil getaway. romantic dinners. tranquil evenings. pool and hot tub. big yard. Foosball . yard games. close to ice age trail and multiple parks dams and waterfalls. . neibors r cool. u should be too. available for tubing and kayaking thru snb or minihaha. sugar river raceway. New Gllarus brewery and Monroe shops. bonfires n cookouts. bands down the road on sat. parties available 4 rental of both houses. please enquire. extra or tenting available.

4.98 out of 5 average rating, 52 reviews

A spacious log home is showcased, featuring large floor-to-ceiling windows that illuminate the interior. The fenced-in pool area is surrounded by landscaped gardens, with lounge chairs positioned near the water. Lush greenery and trees create a serene backdrop for the property.

Cabin in Lodi

Modern Cabin with pool, hot tub and outdoor sauna

Forget your worries in this spacious and serene space. Secluded yet close to a big city (Maddison and Wisconsin Dells) and lots of entertainment! 20 min away from 2 ski resorts, an amazing winery and distillery, spas, restaurants, casino! 3 mile away from lake Wisconsin. Hiking trailers, 24 hour ferry service across the lake and more. This luxurious villa combines comfort and style, you won't want to leave it, but the area is full of enviting places to go to, so plan for a few extra days!

4.95 out of 5 average rating, 22 reviews

The exterior of the cabin features a modern design with a sloped roof, set in a lush green landscape. Tall grasses frame the building, and a deck with seating is visible, providing a peaceful spot to enjoy the surrounding nature.

Home in Dodgeville

Little Eden

A little Eden in the Town of Eden. This mod 1972 cabin is just four miles West of Dodgeville, nestled in a secluded glen with private pool, staggering views, 60 acres of hiking, hunting, or trout fishing, two decks, and access to all the Driftless Region is known for: hiking, biking, antiquing, thrifting, fine and regional dining, American Players Theater, Taliesen, House on the Rock, and Potosi Brewing Company. This place is perfect for two families or one big one, or a group of friends.

4.97 out of 5 average rating, 100 reviews

Home in Rockton

HD Jameson House at River’s Edge

Nestled on the Rock River, the HD Jameson House, a National Historic Register gem, blends historic charm with modern amenities. Enjoy river views and with quaint shops and restaurants exploring the Village of Rockton is a perfect family-friendly retreat. This haven is surrounded by nature but close to numerous attritions, ideal for a romantic getaway or peaceful escape. The HD Jameson House offers a heavenly retreat, blending past beauty with present allure for everyone in the family.

4.96 out of 5 average rating, 137 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

Hot Tub/$0 Cleaning Fee/Golf Course/The Hemlock

Our 4 bedroom, 2.5 bath home in downtown Spring Green, Home to Frank Lloyd Wright’s Taliesin, American Players Theater, the House on the Rock, and Tower Hill State Park, the vibrant village of Spring Green is a place where nature and art meet. Just 45 minutes from Madison, And the Dells Waterpark. Do You enjoy Golfing Or snow mobile Riding? Relax with the whole family at this peaceful place to stay. walk to downtown or the Rec Park with soft ball diamond and skate board Park.

4.96 out of 5 average rating, 27 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!

Our 900 sqft basement apartment features a master bedroom, connecting kitchenette/sitting room, and bathroom. We are a 20-minute drive to the UW campus, Capitol Square, and Dane County Airport—minutes from Middleton Pheasant Branch Conservancy for hiking and biking. Madison and Middleton consistently win "Best Places to Live" awards for quality of life. As past Superhosts, we are excited to start hosting again after COVID!

4.88 out of 5 average rating, 17 reviews

Home in Sun Prairie

New place to stay

Garden View Oasis – Pool – Near Madison – Family F

🔹 Peaceful Sun Prairie stay with serene garden views and a private pool 🔸 Modern, cozy, and close to shops, dining, and Madison attractions 🔹 Spacious 2,300 sq. ft. home with 3 bedrooms, 2 baths, and comfort for up to 6 guests 🔸 Ideal for families, couples, or professionals seeking a quiet yet connected retreat 🔹 Enjoy outdoor relaxation, indoor comfort, and the convenience of a central location

Popular amenities for Fitchburg rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene backyard scene features a clear blue swimming pool surrounded by a spacious patio. Comfortable seating arrangements, including lounge chairs and a patio table with chairs, are positioned nearby. A red patio umbrella provides shade, and lush greenery frames the area, enhancing the outdoor setting.

Home in Fitchburg

Country Living/Downtown Access

A spacious outdoor area features a sparkling swimming pool surrounded by stamped concrete. A covered seating area offers comfortable chairs. Lush greenery frames the space, and vibrant murals decorate the adjacent wall, creating a lively and inviting atmosphere. Colorful pool floats rest on the water.

Home in Edgerton

4.76 out of 5 average rating, 38 reviews

Boat Dock & Backyard: 'Rock River Retreat'

A two-story home is depicted, surrounded by a well-manicured lawn and various shrubs. The inviting entrance features a porch with white railings. A spacious driveway leads to a garage, and trees dot the landscape, offering a sense of openness in the rural setting.

Home in Poynette

4.81 out of 5 average rating, 47 reviews

Your Home Away From Home!

Home in Sun Prairie

New place to stay

Hot Tub - Pool - Game Room - Fire Pit - Pets

5 out of 5 average rating, 84 reviews

An outdoor balcony features a large table surrounded by six chairs, with a bright red umbrella providing shade. Green Adirondack chairs are positioned nearby, overlooking the grassy lawn that leads to the waterfront.

Home in Janesville

Family Home w/ Deck, Yard, Dock on Rock River

An expansive outdoor deck is revealed, featuring a canopy-covered dining area alongside several lounge chairs. Umbrellas provide shade over seating arrangements, surrounded by lush trees. A glimpse of a pool is visible in the background, enhancing the inviting outdoor space.

Home in Madison

4.89 out of 5 average rating, 285 reviews

Luxurious BBQ and Pool House

Home in Apple Canyon Lake

A spacious living area is highlighted by a wooden ceiling and large windows. A dining table with intricate carvings sits nearby, complemented by comfortable seating arranged for relaxation. Soft lighting from a chandelier adds to the inviting ambiance of the space.

4.31 out of 5 average rating, 13 reviews

Log Home near amenities

A cozy living area showcases a large wooden coffee table centered on a geometric-patterned rug. A plush armchair and a soft sofa are positioned nearby, while a decorative vase with greenery and modern accents adds a touch of style. Light enters through large windows, enhancing the space.

Home in Verona

Luxurious Bright Golfing Oasis!

Other holiday rentals with a pool

A rustic cabin is set amidst greenery, featuring a small porch with seating. A picnic table is positioned nearby, and a fire pit is located in front of the cabin's entrance, surrounded by a grassy area suitable for outdoor gatherings.

4.33 out of 5 average rating, 3 reviews

The Sleepy Cabin 37

A light blue cabin is nestled among the greenery, surrounded by trees that provide a natural setting. A small wooden deck is visible at the front, offering outdoor access. Large windows allow for ample daylight, creating a bright and welcoming atmosphere.

Sunset Hollow PM13

The rustic cabin, constructed from wood, is set within a natural garden, surrounded by greenery. A covered porch with a railing is visible at the entrance, leading to a white door. Picnic tables can be seen nearby on the well-maintained grounds.

Summit View Cabin 94DL

A rustic cabin is nestled among trees, featuring a welcoming porch with seating. A picnic table is positioned on the grassy area, accompanied by a fire pit. The natural surroundings provide a serene atmosphere for outdoor activities.

Tiny Retreat Cabin 33

A charming wooden cabin is nestled among trees, showcasing a simple front porch with two chairs. A rustic picnic table sits nearby on a gravel surface, surrounded by lush greenery, enhancing the serene and natural setting.

Cozy Cabin 80

A quaint red cottage is viewed from a distance, surrounded by lush greenery. A picnic table stands to one side, while a fire pit is positioned in front. The path leading to the entrance is lined with grass and dirt, creating a welcoming approach.

Charming Nook Cabin 97

Maplewood Retreat PM11

A round yurt with a tan canvas exterior is situated in a natural setting, surrounded by trees. A wooden door is visible at the front, with a small wooden deck leading to the entrance. Gravel paths and green foliage enhance the welcoming outdoor space.