Pirate Properties

Pirate Properties Contact information, map and directions, contact form, opening hours, services, ratings, photos, videos and announcements from Pirate Properties, Vacation Home Rental, Pewaukee, WI.

Airbnb / VRBO Property Management & Super Host
Waterfront Vacation Rentals in the Midwest & Florida
Host: 350+ Reviews, 4.95 Rating
5 Star Consulting & Coaching
Real Estate Investments Vacation Renal Property Manager & Investor.
*Growing portfolio in residential, commercial, long-term and short-term rentals, with an affinity for waterfront property.
*5 Star STR Superhost.
*Strong understanding o

f real estate financing, deal structuring, and municipality regulations.
*Creative ability to furnish and update properties with character on a tight budget and timeline.
*Experienced and detailed budgeting and financial management.

🎊First Guest Arrival Day! 🎉Our first guests check in at my newest listing on Okauchee Lake today! This marks my 15th pro...
05/22/2026

🎊First Guest Arrival Day! 🎉

Our first guests check in at my newest listing on Okauchee Lake today! This marks my 15th property launch- and somehow, the excitement (and nerves 😅) ahead of that first guest never go away.

The week before a launch is always a whirlwind:
✔️ Last-minute details
✔️ Random surprises to troubleshoot
✔️ Countless store runs
✔️ Double-checking every guest touchpoint
✔️ Hoping people walk in and instantly LOVE the space

The properties in my portfolio had never been vacation rentals before and almost all of my homeowners were brand new to the vacation rental world too. There’s something incredibly rewarding about transforming a home into a place where families and friends will gather, reconnect, celebrate, relax, and make memories together.

Here’s to another property launch done and dusted 🎉
Now time to wait for that first guest review ⭐️⭐️⭐️⭐️⭐️

Link in Bio for all our property listings!

✨NOW LIVE ✨ Introducing our newest premium vacation rental on Okauchee Lake, WI 🌊☀️This 4-bedroom lakefront retreat was ...
05/11/2026

✨NOW LIVE ✨ Introducing our newest premium vacation rental on Okauchee Lake, WI 🌊☀️

This 4-bedroom lakefront retreat was designed for unforgettable stays for multigenerational families and lifelong friends 👯‍♀️

Featured Amenities:
• a movie theater 🎬
• epic game room 🎯
• custom built-in bunk room
• hot tub under the stars ✨
• private pier + lake access 🚤
• all the lake toys
• 3 floors of beautifully designed living space

Whether your vibe is boating all day, cozying up for a REAL movie night, or swapping stories and cocktails while watching the sunset - this house was made for all the memories with your favorite people.

Summer dates are being snatched up FAST - but luckily this is a year round gem 💎 DM for booking info or check availability on our website.

Tag the group you’re bringing with you 👇

OkaucheeLake LakeHouseRental WisconsinGetaway LuxuryVacationRental LakeLife

Spring is one of Wisconsin’s best-kept secrets 🌿✨Our lake homes still have spring date openings -and a few summer dates ...
04/09/2026

Spring is one of Wisconsin’s best-kept secrets 🌿✨

Our lake homes still have spring date openings -and a few summer dates left—and now is the perfect time to escape and enjoy!

Think: peaceful mornings, uninterrupted water views (no boats yet!), crisp fresh air, and cozy, quiet nights around the fire overlooking the lake.
Plus… lower rates before peak season hits!

If you’ve been craving a reset, this is it. 💙

Message us or book now to grab one of the remaining dates before they’re gone 🌼

In the property management business, most of the messages we get are questions, requests, or the occasional problem to s...
03/05/2026

In the property management business, most of the messages we get are questions, requests, or the occasional problem to solve. That’s just part of taking care of people — and I truly love being able to help make sure your stay is terrific.

But every once in a while, a message like this comes through. A kind note from a guest who took a moment to say thank you.

These are the reminders of why we do this. The art of hospitality: Creating spaces where families can relax, make memories, and feel taken care of is what it’s all about. And hearing that it made a difference never gets old.

❄️ Wisconsin’s been 0 degrees for two weeks — but hey, there is a silver lining! 😂🎣All this cold means solid ice and a l...
01/28/2026

❄️ Wisconsin’s been 0 degrees for two weeks — but hey, there is a silver lining! 😂🎣

All this cold means solid ice and a longer ice fishing season, so you’ve got plenty of time to plan your winter getaway for winter fishin!
We have cozy homes on Pewaukee Lake which has great fishing and beautiful lake views you can enjoy all year round 😍

Book your winter stay with us now!

Nothing matters more to me than guests feeling truly cared for and genuinely enjoying their stay. Grateful for every gue...
01/25/2026

Nothing matters more to me than guests feeling truly cared for and genuinely enjoying their stay.
Grateful for every guest.

01/16/2026

Bloodies, Fish Fry’s, Boat Days, Fires- What’s not to Love in Wisconsin 🥰
We have a portfolio of Waterfront homes in Lake Country and Oxford just waiting for you to make vacation memories!

Book your stay with us today!

✨ Happy New Year! ✨As the year comes to a close, my heart is so full of gratitude. Thank you to every guest who trusted ...
12/31/2025

✨ Happy New Year! ✨

As the year comes to a close, my heart is so full of gratitude. Thank you to every guest who trusted us with their stay, every client who partnered with us, and every supporter who believed in our business.

Whether you booked a home with us, referred a friend, shared a post, or cheered us on behind the scenes — thank you from the bottom of my heart. I am truly grateful for each and every connection, lesson, and moment created along the way.

Here’s to another year of beautiful travels, memorable stays, and continued growth for us all. 🥂✨

We are taking on a limited number of new clients in 2026 - Lets Chat!
12/27/2025

We are taking on a limited number of new clients in 2026 - Lets Chat!

Traveling to Oconomowoc Wisconsin this winter? Book your stay with us at the Okauchee Fairway - a 4BR/ 4 BA new custom b...
12/27/2025

Traveling to Oconomowoc Wisconsin this winter? Book your stay with us at the Okauchee Fairway - a 4BR/ 4 BA new custom build with top of the line EVERYTHING, sky high ceilings, cozy amenities and a spacious layout for 8 guests.

Our recent Thanksgiving Guests loved it so much they returned for Christmas with family ❤️ and left us a lovely 5 Star Review :
"Kristen was an amazing host- communication was prompt and very friendly. The home worked out absolutely perfectly for our thanksgiving with the family. So much so, that we will be renting it again for Christmas this year. The kitchen is a dream kitchen! Top of the line appliances and everything you could need. A HUGE island for prep and just gathering around visiting, plenty of seating in the dining area, big comfy couch. All of this and it still felt very open and we were not all on top of one another. Bedroom set ups are flexible (2 twin or make it a king) which was amazing. Everything is up a large set of stairs so take note. (We knew this prior to renting) But once up, there was plenty of room for my daughter to maneuver her wheelchair around even in the bedroom and main bath. I can’t wait to stay again next month!"

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Pewaukee, WI
53072

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