Family-friendly vacation rentals in Twin Lakes

4.97 out of 5 average rating, 253 reviews

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!

Cabin in Fontana-on-Geneva Lake

An A-frame structure is nestled among lush green trees, showcasing large glass windows that allow for ample natural light. The contrasting wood siding complements the surrounding foliage, creating a harmonious blend with nature. A raised deck leads to the entrance, enhancing accessibility to the home.

4.93 out of 5 average rating, 182 reviews

Exquisite Modern A-frame all WithInnReach

An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

4.94 out of 5 average rating, 124 reviews

A cozy seating area is presented with two sofas adorned with decorative pillows. A large lamp with a blue shade complements the space, while light filters through the large windows, enhancing the bright atmosphere. A piece of wall art and natural accents are also visible.

Home in Salem

Center Lake View Cottage, near Camp&Silver Lakes

Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch boat in Center Lake at end of street or several nearby lakes. Camp Lake is 2 mins away, close to Silver Lake and many others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Lake Geneva, & Renaissance Faire. Ski at Alpine Valley or Wilmot Mountain. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base.

4.96 out of 5 average rating, 230 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

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

5 out of 5 average rating, 14 reviews

Twin Lakes Family Escape-NEW Home & Lake Access!

Welcome to the Twin Lakes Family Escape! You will be staying in a brand new (2025 construction), 2400 square foot home featuring 4 bedrooms and 2.5 bathrooms with space for up to 10 family and friends. We are a 3 minute walk to Lake Mary and the downtown area of Twin Lakes and a short drive to Lake Geneva, Wilmot Mountain, and many other local attractions. We aim to have a cozy and relaxing home where both you and your children can get a break and enjoy your time away from home.

A modern living area features a sleek fireplace and large glass doors opening to a deck with lounge chairs overlooking the water. Sunlight shines through, creating a bright and airy feel, while the serene lake and surrounding greenery are visible outside.

4.88 out of 5 average rating, 180 reviews

Cove at 420: Modern Lake Front Home near Chicago

Welcome to the Cove at 420. A modern vacation paradise where indoor and outdoor lines blur. Every space is designed for enjoyment. A short 75 minute drive from Chicago, this is a true retreat. Wake up to beautiful sunrise views or enjoy them from a kayak on the water. We offer kayaks, paddle boards, hot tub & sauna, Sonos sound system, a fire pit and plenty of yard games for our guests. Hidden on a cul-de-sac between Lake Mary and Lake Elizabeth, enjoy the best of lake life!

5 out of 5 average rating, 111 reviews

A grassy area features multiple wooden lounge chairs facing the lake. A small fire pit is positioned in the center. Behind, a light-colored shed and a dock can be seen, with boats and kayaks stored nearby. A vibrant sky with colorful clouds adds to the scene.

Home in Fox Lake

Wonderful Mineola Bay Lakefront Cottage 4adu+4kids

Book a romantic weekend or bring the whole family to this cozy, clean and well-appointed lake house that has plenty of room for fun. Embrace lake-life at its finest when you call this Fox Lake cottage on Mineola Bay your home away from home! We have a dock to park your boat, so bring it. Access to restaurants, bars, convenience and grocery stores, boat launches and more. Or hang out and soak in the sunshine while paddle boarding, boating, kayaking, swimming and nature hikes.

4.92 out of 5 average rating, 183 reviews

A spacious living area features a large wall of windows providing abundant natural light and views of the outdoors. The wooden walls and ceiling add warmth, complemented by cozy seating and a dining area. Doors lead out to a deck with seating options.

Cabin in Salem

A Frame Cabin located near multiple lakes

Experience the allure of Salem Lakes Chalet. featuring modern comforts nestled within a quaint 3-story log cabin. Relax in a fenced yard offering picturesque vistas of woods, and relish in the variety of nearby lakes. Enjoy the northern ambiance without the lengthy journey—be amazed by our expansive wall of windows! Whether you are in town to visit family or looking for a retrieve from the city we are conveniently located 10 mins from I-94. Brought to you by NCL Properties.

A modern house features an inviting front porch with landscaped gravel beds and well-maintained grass. A wooden garage door complements the green exterior walls. Surrounding trees and shrubs enhance the outdoor space, creating a welcoming entrance.

4.98 out of 5 average rating, 131 reviews

4Bd 3.5ba Cozy New Construction! Close to lake!

Welcome to our cozy home! Twin Lakes is quintessential small town America situated surrounding lakes Elizabeth and Mary in Wisconsin. Less than 15 minutes from downtown Lake Geneva and less than 5 minutes from Richmond, Illinois. During your stay you can experience much of what the area has to offer including boating and fishing on Lakes Elizabeth and Mary, access to the community beach, local shopping, and peaceful country nights in this small family-oriented community.

4.97 out of 5 average rating, 148 reviews

A private hot tub is set under a clear blue sky, surrounded by tall trees and lush greenery. Sunlight reflects off the water's surface, creating a serene and relaxing ambiance in this secluded outdoor space.

Cabin in Twin Lakes

Secluded in the Woods, Hot Tub

Owl's Rest Cabin is nestled in acres of fully wooded, peaceful forest. This is a cozy couple's retreat or small family getaway with a fireplace, hot tub, full kitchen, washer/dryer, located 4 minutes from Lake Mary and 15 min to Lake Geneva. Many activities nearby - festivals, hiking, boat rentals, golf, beach, downhill skiing, tubing, and snow shoeing. Eco conscious cabin, including Level 2 electric vehicle charging & more. Please message us with any questions.

4.95 out of 5 average rating, 166 reviews

A spacious bathroom features large skylights that illuminate a freestanding tub, set beneath an arched window overlooking greenery. Two modern lounge chairs are situated nearby, enhancing the tranquil ambiance. The glass-enclosed shower and soft neutral tones create a serene and relaxing environment.

Farm stay in Harvard

Eden Farm: Family Stays & Intimate Moments

Unwind and find your inspiration just 1.5 hours from Chicago at the Ten Acre Farmhouse Retreat. Designed for families, intimate moments, and retreats. High-speed Wi-Fi, Smart TVs, and workspaces enhance your stay. This 5,000 sq ft estate blends modern comfort with rustic charm on 10 peaceful acres near Lake Geneva. Luxurious bedrooms, a Jacuzzi, and premium entertainment await. Two outdoor cameras monitor the front yard and driveway. No indoor cameras. Book now.

4.96 out of 5 average rating, 50 reviews

Cabin in Twin Lakes

Fully Renovated | 15 Min to Lake Geneva

Welcome to The Green Door Cabin, a beautifully renovated 2024 retreat in a charming lake town just 15 minutes from Lake Geneva. Walk to Twin Lakes and Lake Mary while enjoying a peaceful neighborhood setting. This bright, sun-filled cabin features stylish furnishings, an open layout, and a spacious yard with patio lights, yard games, a fire pit, and propane grill—perfect for relaxing after a day on the lake.

Popular amenities for Twin Lakes family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 153 reviews

Cottage in Antioch

#4 Adorable Lake Cottage-Cypress Resort & Marine

4.95 out of 5 average rating, 152 reviews

A two-story home is set amidst a lush green lawn, featuring a welcoming entrance with a landscaped pathway. Large windows on the façade allow ample natural light, and a brick chimney adds character to the exterior. Trees and shrubs provide a natural backdrop.

Home in Lake Geneva

Walk 2 lake, HOT TUB, pool table, bikes & kayaks

Guest suite in Riverwoods

A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.

4.95 out of 5 average rating, 479 reviews

Master qtr close to nature & easy urban facilities

4.94 out of 5 average rating, 266 reviews

Home in Woodstock

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

4.87 out of 5 average rating, 132 reviews

Guest suite in Elkhorn

Lake Lovers Hideaway near Lake Geneva

A charming two-story house is set within a lush green lawn, featuring large trees that provide shade. The front porch is approachable and includes a railing, while an American flag gently waves. A fence encloses the backyard, creating a private outdoor space.

4.86 out of 5 average rating, 102 reviews

walk to beach, dog friendly yard hot tub sleeps 12

4.86 out of 5 average rating, 121 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

4.88 out of 5 average rating, 168 reviews

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

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

Family- and pet-friendly home rentals

4.82 out of 5 average rating, 225 reviews

An inviting living area features a wooden dining table with four chairs, complemented by a cozy chair and a side table. A decorative sign is mounted on the wall, while an air conditioning unit is visible near the window. A faux stove adds aesthetic charm to the room.

Home in Lake Geneva

Cozy Cottage 1.5 Blocks From The Lake

4.88 out of 5 average rating, 148 reviews

A spacious living area features a large, comfortable sectional sofa arranged to face large windows offering views of the lake. The warm wood flooring complements the modern kitchen visible in the background, which includes wooden cabinetry and a dining area for gatherings.

Home in Antioch

Lakefront, beautiful views, spacious and private.

This ranch home presents a welcoming exterior, featuring a light brick facade and a sloped roof. A manicured grass lawn is bordered by low shrubs, with a wooded area providing a natural backdrop. A spacious driveway leads to the garage, visible on the left side.

5 out of 5 average rating, 12 reviews

Hickory House

4.9 out of 5 average rating, 230 reviews

A charming two-story lake house is presented, featuring a prominent American flag and a large white flag. A spacious veranda overlooks the fenced yard, while bare trees frame the house against a bright blue sky with scattered clouds.

Home in Round Lake Beach

Corner Lakefront Property

4.92 out of 5 average rating, 13 reviews

Harrys Lake front, jacuzzi, sunset Dream Home!

4.94 out of 5 average rating, 173 reviews

Cottage in Wonder Lake

The Cozy Lake House, Dm me ?s Lake Front Property!

4.9 out of 5 average rating, 251 reviews

A rustic cabin with dark wooden logs is situated among tall green trees. The spacious porch features a railing and several chairs, inviting relaxation. Sunlight casts warm tones across the facade, while the surrounding grass and woods enhance the cabin's natural setting.

Guesthouse in Racine

Charming log cabin in the woods

5 out of 5 average rating, 68 reviews

Home in Genoa City

Getaway w/ POOL near Lake Geneva/Country Thunder

Family-friendly home rentals with a pool

4.85 out of 5 average rating, 136 reviews

A white motor yacht, named 'Irish Mist,' is docked at Reefpoint Marina. The boat features a spacious top deck with a black canopy and is surrounded by other yachts in the water, with a soft sunset glow illuminating the scene.

Boat in Racine

Vessel: Irish Mist V - 32' @ Reefpoint W1-3

A cozy bedroom features a plush king-sized bed with a light-colored duvet and decorative cushions. Natural light enters through large windows adorned with soft curtains. A comfortable bench sits at the foot of the bed, alongside a dark wood dresser and a small television.

4.97 out of 5 average rating, 145 reviews

The Landis, elegant condo w/ king bed & fireplace!

The living area features a dark leather sofa adorned with blue throw pillows, accompanied by a light gray couch. A round woven pouf and an antique-style trunk serve as accent furniture. Large glass doors provide access to a balcony, with lake-themed decor on the wall.

4.96 out of 5 average rating, 174 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

4.95 out of 5 average rating, 105 reviews

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.

Home in Lake Geneva

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

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.

4.9 out of 5 average rating, 124 reviews

LG Quaint Condo on Lakeshore Dr.

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, 232 reviews

Relaxing Villa with Amazing Amenities!

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, 125 reviews

Lake Geneva relaxation!

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.