Luxury Vacation Rentals for Families in Oconomowoc

Luxury Vacation Rentals for Families in Oconomowoc

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 2 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Oconomowoc

Sytlish Retreat Near Wedding Venues + Downtown property photo 1

Sytlish Retreat Near Wedding Venues + Downtown

3 bedrooms•2 baths
1,124 US dollars for 3 nights•

~$100 less than other sites

Charming Historic Upper Walk to Downtown & Lakes property photo 1

Charming Historic Upper Walk to Downtown & Lakes

3 bedrooms•2 baths
879 US dollars for 3 nights•

~$75 less than other sites

Welcome to family adventures in Oconomowoc

Welcome to family adventures in Oconomowoc

Bring the whole crew to Wisconsin’s Lake Country without sacrificing style. Wander pairs the polish of a five-star stay with the comfort of home in our luxury family vacation rentals in Oconomowoc. Every property is exactly as pictured, immaculately cleaned, and backed by 24/7 concierge support for an effortless arrival.
Spread out in bright, multi-bedroom layouts made for together time. Cook favorite meals in fully equipped kitchens, stream with ultra fast WiFi, and keep routines easy with in-home laundry. Child-friendly details, plush hotel-grade linens, and private outdoor spaces help everyone unwind, while inspiring views and modern tech let parents blend work and play with zero stress.

Available soon in Oconomowoc

Sytlish Retreat Near Wedding Venues + Downtown property photo 1

Sytlish Retreat Near Wedding Venues + Downtown

3 bedrooms•2 baths
1,124 US dollars for 3 nights•

~$100 less than other sites

Charming Historic Upper Walk to Downtown & Lakes property photo 1

Charming Historic Upper Walk to Downtown & Lakes

3 bedrooms•2 baths
879 US dollars for 3 nights•

~$75 less than other sites

All homes in Oconomowoc

Sytlish Retreat Near Wedding Venues + Downtown property photo 1

Sytlish Retreat Near Wedding Venues + Downtown

3 bedrooms•2 baths
1,124 US dollars for 3 nights•

~$100 less than other sites

Charming Historic Upper Walk to Downtown & Lakes property photo 1

Charming Historic Upper Walk to Downtown & Lakes

3 bedrooms•2 baths
879 US dollars for 3 nights•

~$75 less than other sites

View all homes

Highlights in Oconomowoc

Discover a vibrant lakeside getaway filled with inclusive playgrounds, sandy beaches, scenic state parks, and nostalgic family-friendly dining.
City Beach on Lac La Belle
Imagination Station at Roosevelt Park
Lapham Peak Observation Tower
Fowler Lake Park and Boardwalk
The Kiltie Drive-In

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for family vacation rentals in Oconomowoc

Lake access (1)
Beach access (1)
Sound system (1)
Hammock (1)
Fire pit (1)
Dryer (2)
Patio (1)
Oven (2)
Washer (2)
Garden (1)
Kitchen (2)
Tv (2)
Outdoor dining area (1)
Wifi (2)
Microwave (2)
Heating (2)
Discover more family fun in Oconomowoc

Discover more family fun in Oconomowoc

Surrounded by sparkling lakes and wooded shoreline, Oconomowoc anchors Wisconsin’s Lake Country. Lac La Belle and Fowler Lake set the scene for calm mornings on the water and golden-hour views, while the walkable downtown offers lakefront parks, summer concerts at the band shell, and kid-friendly festivals.
Bike or stroll the Lake Country Trail, find sandy swims at local beaches, and visit seasonal farms and markets nearby. Summer brings breezy boat days, autumn paints the hillsides, and winter invites skating and snow play. With Milwaukee and Madison an easy drive, variety is built in. This is why Wander’s luxury family vacation rentals in Oconomowoc are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Oconomowoc

Why should I book a Wander in Oconomowoc over other family vacation rentals?

Wander offers a level of consistency and quality you won’t find with most family vacation rentals.
Every home in Oconomowoc delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular family vacation rentals in Oconomowoc?

Some of our most popular family vacation rentals in Oconomowoc include Sytlish Retreat Near Wedding Venues + Downtown, Charming Historic Upper Walk to Downtown & Lakes, and Sytlish Retreat Near Wedding Venues + Downtown. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different family vacation rentals does Wander have available in Oconomowoc?

Wander offers 2 family vacation rentals in Oconomowoc, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s family vacation rentals in Oconomowoc?

You can check-in to Wander family vacation rentals in Oconomowoc after 4.00pm and check-out before 10.00am.

Do Wander’s family vacation rentals in Oconomowoc have WiFi access?

Yes. Every Wander home in Oconomowoc has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.