Our Results Speak for Themselves

At Wisconsin Getaways, success isn’t claimed — it’s measured.
Our homeowners consistently outperform the market with 2x higher revenue than regional competitors, thanks to our precise hospitality model and data-driven luxury positioning.

$1.4 M

Average home value across
our portfolio

$250,000+

Average annual gross revenue
per home

$400,000+

Top-performing property
annual revenue

Numbers don’t lie. Our expertise in pricing, marketing, and service excellence consistently yields unmatched return on investment.

Where Luxury
Meets Operational
Mastery

Our management approach blends five-star hospitality with precise operations. Each home is managed like a private luxury resort — ensuring peak performance and guest delight.

General Manager Model

A dedicated luxury-hotel caliber GM oversees a small
collection of properties.​

Internal Maintenance and Construction

Fast response, consistent quality, and brand-
standard excellence.

Smart Tech Integration

Real-time monitoring, automation, and AI-driven systems
ensure every home runs efficiently while delivering a seamless,
elevated guest experience.

Certified Pool Technicians

Ensuring every aquatic amenity meets resort-level
clarity and safety.

Superior Hospitality Training

We hire, train, and retain professionals who understand
true guest care.

A Partnership Built on
Selectivity & Success

We partner with a limited number of exceptional properties each year to ensure every home receives the focus and precision it deserves.
This is not a mass-market program — it’s a curated alliance built on mutual success.

Luxury-Caliber
Homes

Homes that reflect architectural distinction, design excellence, and unique guest appeal.

Shared Vision for Excellence

Owners who value elevated hospitality, quality, and long-term
partnership.

Premium Locations

Waterfronts, vineyard estates, or properties with exceptional experiential potential.

→ Applications are reviewed individually to ensure a mutual fit and shared commitment to excellence.

From Evaluation to Elevation

Consultation

We discuss your property’s potential and financial goals.

Property Audit

Our team conducts an in-depth revenue and design assessment.

Onboarding & Optimization

Branding, pricing strategy, and marketing alignment.

Launch

Your home joins the elite Wisconsin Getaways Collection.

Growth & Reporting

Transparent owner dashboards and continuous performance scaling.

“Partnership isn’t a service, it’s our shared pursuit of excellence.”

Tyler Le Roy

— Founder and CEO

We Don’t Just Manage.
We Maximize.

True Passive
Income

Hands-free, six-figure annual
returns.

Luxury Brand
Power

Your property elevated under Wisconsin’s most trusted name.

Full
Transparency

Real-time owner dashboards, maintenance logs, and revenue tracking.

We’re not just managing homes – we curating experiences that earn loyalty
and repeat bookings.

Request Access to Our
Partnership Guide

We accept only a select number of new homes each year — ensuring every property meets the standard of Midwest luxury hospitality that defines Wisconsin Getaways. Complete the short form below for instant access to our Partnership Guide, revealing how we deliver category-leading performance for luxury vacation rentals.

Inside, you’ll discover:

  • Real homeowner earnings and six-figure case studies
  • Our proven 5-step evaluation & onboarding process
  • Design, amenity, and branding strategies that maximize revenue
  • Exclusive insights into investment models and ROI projections

Your next chapter in luxury real estate begins here.

Submit your details below to access the Wisconsin Getaways Partnership Guide.

Sign Up For Your Free Guide Today!

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Together Let’s Transform Your Home Into a High-Powered Luxury Destination and Your Investment into a Legacy.

Join the region’s most exclusive collection of luxury vacation homes.

FOR EXCEPTIONAL WISCONSIN HOMES

A remarkable home.
A brand guests choose.

Luxury vacation-rental management. An established guest audience. A team to help your home reach its potential.

Get the Homeowner Guide

Real portfolio results. Property transformations.
The full partnership model.

The opportunity. The brand. The team. Tyler LeRoy introduces the Wisconsin Getaways approach.
Keep ownership and the major decisions. Let a specialist team coordinate the daily operation.

THE CALIBER OF THE COLLECTION

Exceptional homes.
A substantial opportunity.

$1.63M Average estimated
property value
$278K Average projected 2027
gross revenue per home
The Grand on Longtail
The Grand on Longtail
Baronwood Oasis
Baronwood Oasis
Gray Lake Villa
Gray Lake Villa
35 homes in the plan $57M estimated property value $9.7M projected 2027 gross

September 23, 2026 plan: 28 operating + 7 prelaunch homes. Averages include all 35. Management estimates, not appraisals, guaranteed revenue or owner income. Property-level results and definitions are in the guide.

A RECOGNIZABLE BRAND. DISTINCTIVE PRIVATE HOMES. A RECOGNIZABLE BRAND. DISTINCTIVE PRIVATE HOMES.

MORE THAN AN INDIVIDUAL LISTING

A name they seek out.
An audience you can join.

A RECOGNIZABLE BRAND. DISTINCTIVE PRIVATE HOMES.
“We will be looking at WG homes exclusively moving forward.”

SCOTT Guest who described two WG stays · August 2026

$1.35M
Direct gross booking value
for 2026 stays290 reservations · 23.4% of booked value

Your home joins a brand with existing guest relationships and a working direct-booking channel—not a marketing operation you have to build from zero.

See the brand advantage in the guide

September 22 snapshot, 28 operating homes; includes future stays. Reservations may change. Direct bookings are not all repeat or incremental. The quote reflects an individual guest's preference.

1,909 published guest reviews 4.94 / 5 average normalized rating Through September 24, 2026. Ten-point scores normalized to five.

REAL SPACES. A DIFFERENT GUEST EXPERIENCE.

The home is the foundation.
We help unlock the potential.

Guest insight. Professional vacation-rental design. Purposeful amenities. Approved work coordinated around a complete stay.

BEULAH HOUSE · EAST TROY
Before: Designed interiors
BEFORE
After: Designed interiors
AFTER

A suite designed for the stay.

Not every home needs a major renovation. Preserve what works. Evaluate improvements against guest appeal, installed cost and ongoing upkeep.

See the investment breakdown in the guide

Actual owner-supplied photographs; angles differ. Beulah is founder-affiliated. Images show physical changes, not measured financial returns. Owners fund readiness; design and startup execution are separately scoped.

THE COMPANY BEHIND YOUR HOME

One point of contact. A full team behind it.

Your assigned General Manager

Your primary operating contact: one person who knows your home, coordinates the team and keeps you informed.

Senior leadership

Supporting your General Manager and the wider team.

  • Tyler LeRoy

    Tyler LeRoy

    Founder & CEO

    Company strategy and owner partnerships.

  • Jerry Vogel

    Jerry Vogel

    Director of Operations

    Property operations and owner advocacy.

  • Brittney Munro

    Brittney Munro

    Director of Hospitality

    Guest experience and hospitality standards.

  • Guest hospitality & quality
  • Property care & pool/spa support
  • Pricing, marketing & reporting

You keep ownership and major capital decisions. We coordinate the day-to-day.

Ordinary management is included; physical labor, vendors and property expenses are separate. Support is property-specific.

THE OWNER PERSPECTIVE

“Handing the management off to Tyler and Wisconsin Getaways allows us to focus on running our own business and making family time a priority, while knowing that the STR is in good hands.”

DAN & AIMEE Owners, Riverwoods Retreat

THREE STARTING POINTS. ONE SHARED STANDARD.

A place in the collection
starts with the right fit.

01

A private home

Explore the opportunity alongside personal use, privacy and the character you want to preserve.

02

An existing rental

Keep the strong product. Evaluate better positioning, demand and a more complete operating relationship.

03

A purchase or build

Consider guest appeal and operating requirements before major decisions are locked in.

A strong partnership needs a distinctive home, a workable rental calendar, appropriate service support and an owner open to evaluating necessary improvements. No standard renovation budget. No need to have every answer today.

A FEW QUESTIONS, ANSWERED

Start with clarity.
Continue with confidence.

No need to decide to rent, switch managers or approve improvements before an introductory conversation.

Do I need to be renting already?

No. We work with owners considering rental use, existing rental owners, and serious buyers or builders. We assess the home, owner goals, rental calendar and local operating path together.

Will my home need a major renovation?

Not necessarily. Your home may need normal preparation, specific improvements or a broader repositioning. Owners fund required readiness; WG can coordinate additional execution through a separately agreed paid scope.

Can I still use my home?

Personal use is part of the agreed operating plan. Existing reservations are protected, and availability affects the rental opportunity. The guide explains owner-use provisions and responsibilities.

What will I learn about fees and owner costs?

The guide explains the management-fee structure, booking-channel deductions, owner-paid operating costs and separately scoped startup work. You receive those details before deciding whether to move forward.

SEE WHAT BELONGING LOOKS LIKE

Explore the collection.
Imagine your home's next chapter.

Distinctive homes. Thoughtful experiences. See the portfolio your property could join.

Malibu House
Malibu HouseLake Michigan
The Grand on Longtail
The Grand on LongtailSuamico
The Castle Vineyard
The Castle VineyardCleveland, Wisconsin
Explore Our Homes (opens in a new tab)

Opens in a new tab so your partnership inquiry stays here.

THE HOMEOWNER PARTNERSHIP GUIDE

See what your home
could become.

The numbers, property decisions and partnership details behind Wisconsin Getaways. Explore the opportunity before deciding your next step.

Cover of the approved Signature 2027 Homeowner Partnership Guide 28 PAGES
OF OWNER INSIGHT

Inside your guide

01Property-level performance and the 2027 outlook

02Beulah's transformation and initial capital breakdown

03Management fees, owner costs and how partnership works

Then take the next step: a focused conversation about your property, your goals and the right assessment.

GET YOUR HOMEOWNER PARTNERSHIP GUIDE

Explore Your Home's Potential

Get the guide after submitting. Then request a property-specific conversation when you are ready.

Enter your 10-digit mobile number (area code + number). Country code +1 is auto-populated.

Property to be considered, not your mailing address. Buying or building? Enter the target area where relevant.

No obligation to join or approve a project. Fees, owner expenses and startup responsibilities are explained in the guide before any commitment.

Own a home, planning a purchase, or building? Start here. Co-owners are welcome in the conversation.

The Wisconsin Getaways approach

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