Family-friendly holiday rentals in Delavan

4.89 out of 5 average rating, 140 reviews

Sweet retreat is waiting for you!

Sweet Retreat is ready for a cozy winter getaway. Come spend the weekend with friends and family or have a much needed vacation. Lake Geneva has something for everyone. Our Sweet Retreat is a perfect location for winter activities and is a short drive to downtown Lake Geneva. Tons of bars and restaurants to enjoy and explore . Three ski resorts, tons holiday festivities, Santa cruise and much more located around the area. Our home is fully decorated and ready for your friends and family.

Superhost

A spacious living area features high, wooden beams and large windows allowing natural light. A stone fireplace is positioned centrally, accompanied by a cozy seating arrangement. A dining table sits adjacent, surrounded by earthy decor, enhancing the rustic ambiance.

Cabin in Delavan

4.87 out of 5 average rating, 221 reviews

Cabin Outdoor HotTub Sleeps 7 Pet Friendly

Renovated cottage. Featuring a full bath, hot tub, stone stacked fireplace and much more. Bedrooms are cozy , with hand crafted log furniture & accessories, Master has a queen size bed and guest bedroom has full size. 2 sofa sleepers upstairs in the loft area. Centrally located on Delavan's north shore and in walking distance of multiple bars and restaurants including the world famous Inn Between Bar and Grill. Within 1 miles of the Lake Lawn resort which offers golf, dining, and boat rentals.

A manicured lawn gently slopes towards a serene body of water in the distance, framed by tall trees on either side. The landscape features lush greenery under a partly cloudy sky, creating an open and inviting outdoor space.

4.98 out of 5 average rating, 239 reviews

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

4.98 out of 5 average rating, 244 reviews

The entrance of the A-Frame cabin features a wooden door framed by large windows. Two black wire chairs sit on a wooden deck, complemented by potted plants. Natural surroundings enhance the welcoming feel of the entrance.

Cabin in Lake Geneva

Dog friendly - A-Frame adventure

Welcome to The River Birch Cabin, located in Lake Geneva, Wisconsin. Featured in Madison Magazine, this 1966 A-Frame is located two blocks from Lake Como and minutes from downtown Lake Geneva. It has many amenities including the Little Birch A-Frame playhouse for the kids and an outdoor firepit. The River Birch is just a 20 minute drive to Alpine Valley for snow skiing and summer concerts! It’s an ideal getaway for couples, families, or friends seeking relaxation and nature and dog friendly!

4.96 out of 5 average rating, 115 reviews

The welcoming entrance of the cabin is illuminated under a dusky sky, showcasing a broad front porch supported by intricately designed wooden beams. Stone accents frame the entryway, while landscaped paths lead to the steps, inviting guests into a cozy retreat.

Cabin in Delavan

The Hideaway: 8 Acre Resort

Welcome to The Hideaway, an eight-acre luxury log retreat near Whitewater Lake and Kettle Moraine State Park, offering year-round access to scenic parks and hiking. Outdoor amenities include a hot tub, fire pit with oversized Adirondack seating, and lighted pickleball and beach volleyball courts. Inside, enjoy a 16-foot shuffleboard table, foosball, air hockey, ping pong, and a private home theater. Six bedrooms, including a primary suite with jetted soaking bath, provide exceptional comfort.

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.

4.88 out of 5 average rating, 120 reviews

Lake Geneva relaxation!

4 mi to Downtown Lake Geneva, WI. Rent kayaks on Lake Como. New pool and tennis courts, amazing wildlife. Snowboard, cross country ski, sled on hills during our amazing Wisconsin winters. Dine at The Ridge restaurant CRAFTED or just buy a bottle of wine from the guest store and watch the sunset. Quiet corner of the condominium complex. Completely furnished. Beautiful comfortable King size bed, kitchen, cook and eat in! Balcony overlooking peaceful grounds. Private entry, laundry in building.

A bright and open living area features large windows allowing natural light to fill the space. A modern dining table with white chairs sits adjacent to a cozy seating arrangement with a gray sofa and decorative pillows. A stylish fireplace adds warmth to the ambiance.

4.96 out of 5 average rating, 195 reviews

Renovated Luxury Retreat Near Lake•Peaceful Escape

Luxury getaway close to private beaches, downtown Lake Geneva, and many area amenities. Relax in comfort in this newly renovated 3-bedroom. Enjoy all that the Lake Geneva area has to offer while unwinding in a modern, comfortable retreat. Conveniently located a 3-min walk to Lake Como and a 10-min drive to downtown Lake Geneva. Charming golf cart community with so much to do. Perfect for couples, families, and business travelers. Ideal space for up to 4 adults and great for families of 5.

4.9 out of 5 average rating, 147 reviews

The exterior of the home is showcased, featuring a welcoming red facade and a spacious wooden deck. Large windows allow for ample natural light, while lush greenery surrounds the property, enhancing the serene, natural environment.

Home in Delavan

Newly Remodeled Rustic Lakehouse Cabin

We are lovers of "Lake Life" and want to share our experiences of Turtle Lake with others who love tranquility and time to reflect, but also want to hike at the Kettle Morraine State Forest, enjoy camp fires, tour local historic towns such as Lake Geneva and other sites, fish (including the best ice fishing in the area!), canoeing, paddle boarding, swimming, reading, and simply enjoying conversations with friends and family. We recently remodeled the kitchen, bathroom and 2 lower bedrooms.

4.97 out of 5 average rating, 146 reviews

The cottage features a charming facade with a combination of blue siding and stonework. Two sets of double doors are framed by large windows, allowing natural light to fill the entrance. Flower beds line the pathway leading to the front door, enhancing the welcoming appearance.

Home in Elkhorn

Cozy Country Cottage near Lake Geneva, WI

Our Cozy Cottage features 3 comfortable bedrooms and nightly magnificent sunsets. Nestled on a country road, the house offers plenty of space to rest after visiting Lake Geneva, Lauderdale lakes, biking at Kettle Moraine or site seeing in the area. It’s close to Walworth County fair grounds where the flea market, Das Fest and Rib Fest are held. This is country living with plenty of opportunity to enjoy the beautiful outdoors or the peace and quiet of the countryside.

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, 195 reviews

Lakefront condo with magnificent view & fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

4.92 out of 5 average rating, 109 reviews

The home is set on a spacious lot surrounded by mature trees, showcasing a welcoming exterior design with light-colored siding and a gabled roof. Lush greenery and flowering plants create a natural border along the pathway, leading to an inviting front porch.

Cottage in Lake Geneva

The Peacock Cottage

Cozy, quiet, accessible Lake Geneva home with large open living area, vaulted ceilings, large 1-acre wooded lot. 3 minutes from beach, 5 minutes to both Lake Geneva and Williams Bay, 2 minutes to a local Wisconsin-style convenience store. Welcome to the Peacock Cottage! Located on a deep, private lot surrounded by woods, so it's great to let loose without any nearby traffic. We are super into cozy homes, and love creating spaces that are restful and fun.

A cozy living area features a dark sofa set against a textured wall, with a small decorative pillow. An open kitchen bar with four modern black stools invites gatherings, while greenery enhances the room's decor. Natural light is filtered through large windows.

4.97 out of 5 average rating, 225 reviews

Relaxing Villa with Amazing Amenities!

Resort day passes included with booking! Hot tub, indoor and outdoor pool, outdoor bar and fire pit, sauna, the list goes on! Only five minutes from downtown Lake Geneva, this second floor condo offers the best of both worlds. Enjoy the laid back Lake Como attractions, or have a blast in Lake Geneva! This hidden gem is perfect from golfers (only 5 minutes from Geneva National) to families. Give us a try, and enjoy a discount on your second stay!

Popular amenities for Delavan family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

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.

Apartment in Fontana-on-Geneva Lake

4.78 out of 5 average rating, 197 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

4.98 out of 5 average rating, 138 reviews

The great room features vaulted wood trusses and large windows that allow natural light to fill the space. A dining table is positioned centrally, surrounded by four chairs. Two rocking chairs are placed at opposite ends, with a decorative rug on the wooden floor.

Cabin in Twin Lakes

Secluded in the Woods, Hot Tub

4.93 out of 5 average rating, 381 reviews

A red cabin is nestled among large trees on a grassy slope, with a set of stone steps leading up to a spacious deck. Several seating areas and decorative plants are visible, blending harmoniously with the natural surroundings.

Cabin in Trevor

Living the Lakehouse Dream

4.95 out of 5 average rating, 242 reviews

Home in Woodstock

The Tailor House: 2BR w/ Hot Tub near Woodstock Sq

4.99 out of 5 average rating, 190 reviews

A spacious outdoor patio area features a circular arrangement of comfortable seating, including chairs and a table. A large umbrella provides shade, while lush green lawns and flowering plants create a serene backdrop. The space is designed for relaxation and social gatherings.

Home in Antioch

COUNTRY RETREAT / SPACIOUS GROUNDS / LARGE HOT TUB

4.86 out of 5 average rating, 119 reviews

A spacious driveway leads to a modern log cabin home surrounded by greenery. Flanking the driveway are several well-maintained evergreen trees. The cabin features a warm orange exterior, complementing the natural setting, with a stone accent wall visible on one side.

Cabin in Lake Geneva

Luxury Log Cabin retreat home

4.85 out of 5 average rating, 116 reviews

A serene lakeside view features calm waters surrounded by lush greenery. A paved patio is equipped with a dining table and several chairs, providing an inviting space to enjoy the scenery. A private dock with boats is visible in the background, enhancing the lakeside atmosphere.

Home in Bristol

Lakefront Home Sleeps 12 – Hot Tub/Boat/Pets/Ski

Superhost

A tranquil evening scene showcases a hot tub on the deck, with two glasses positioned on the edge. The vibrant sunset casts warm colors over the lake, reflecting off the water where a pier extends into the distance. Soft grassy areas are visible in the foreground.

Home in Ingleside

4.88 out of 5 average rating, 161 reviews

Chain O' Lakes Nautical 2/2 Lake House w/ Hot Tub

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 79 reviews

Tiny home in Delavan

Tiny Red House on Lake Delavan

4.98 out of 5 average rating, 159 reviews

The exterior of the blue house is complemented by white-framed windows featuring flower boxes with blooming red flowers. A small landscaped area with green plants lines the building, while dappled sunlight filters through the nearby trees.

Flat in Lake Geneva

Pedal Inn II

4.83 out of 5 average rating, 23 reviews

An aerial view showcases the property’s proximity to Lake Delavan, with a clear path marked towards the nearby boat launch. Lush greenery surrounds the area, providing a serene setting, while residential structures are visible along the tree-lined streets.

Cottage in Delavan

Cozy Lake-Area Gem: Master Suite + Loft Lounge

4.95 out of 5 average rating, 131 reviews

An open-concept living area features a cozy sectional sofa, wooden coffee table, and three barstools positioned at a breakfast bar. A modern kitchen with stainless steel appliances and stylish cabinetry is visible in the background, complemented by warm wood flooring and soft overhead lighting.

Flat in Whitewater

Pet-Friendly Industrial 2 Bedroom Near UWW Campus!

5 out of 5 average rating, 144 reviews

Home in Janesville

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

4.95 out of 5 average rating, 220 reviews

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

TheGlassCabin @ HackmatackRetreat

4.98 out of 5 average rating, 138 reviews

A living area features a stone fireplace and large windows providing views of Lake Beulah. Comfortable seating surrounds a wooden coffee table. A dining table is visible, alongside decor elements that create a cozy ambiance. Natural light floods the space, enhancing the connection to the outdoors.

Home in East Troy

Lakeside Getaway

4.96 out of 5 average rating, 67 reviews

The charming cottage displays a yellow exterior with white trim and a welcoming porch. An American flag is featured by the door, while a manicured lawn surrounds the house. Pathways guide visitors to the entrance, framed by greenery and landscaping.

Cottage in Williams Bay

A vintage charming 2-bedroom cottage!

Family-friendly home rentals with a pool

The spacious living area is illuminated by natural light from large windows. A leather sofa is paired with an accent chair, while a round rug centers the space. A modern coffee table sits atop the rug, and a dining counter with two bar stools is positioned nearby.

5 out of 5 average rating, 48 reviews

Chic Condo in Lake Geneva.

A refreshing pool surrounded by a wooden deck is visible, complemented by several loungers for relaxation. Lush greenery frames the area, providing a serene backdrop. Colorful flowers in the foreground add a touch of vibrancy to the peaceful outdoor setting.

4.98 out of 5 average rating, 42 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

Apartment in Fontana-on-Geneva Lake

The kitchen features dark cabinetry against a brick wall, complemented by a large island with seating for six. Pendant lights hang above, illuminating the cooking area which includes modern appliances and tasteful decor. A dining table is positioned in the background, promoting an open-concept feel.

4.91 out of 5 average rating, 23 reviews

Abbey Villas Condo Steps to Pool Near Beach

A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.

4.95 out of 5 average rating, 97 reviews

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

5 out of 5 average rating, 66 reviews

A two-story blue house is positioned on a spacious lawn, framed by green grass dotted with yellow flowers. A tree provides shade in the front yard, while a small porch with chairs welcomes visitors. The driveway leads to a single-car garage.

Home in Genoa City

Family Getaway near Lake Geneva Winterfest

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, 109 reviews

LG Quaint Condo on Lakeshore Dr.

An open living and dining area features a dark wooden dining table surrounded by black chairs. A light blue wall complements a cozy seating arrangement with armchairs and a sofa. Natural light enters through a large sliding door, with decorative elements and a chandelier enhancing the space.

4.9 out of 5 average rating, 208 reviews

Lakeview at CasaComo