Peak Season - Short Term Rentals & Management

Peak Season - Short Term Rentals & Management We provide top-notch management that ensure expert care for your property. Luxurious Vacation Rentals

This milestone hits differently 🤍High Point Hideaway was our very first short-term rental, the property that started Pea...
12/22/2025

This milestone hits differently 🤍

High Point Hideaway was our very first short-term rental, the property that started Peak Season STR and shaped how we do this business.

We’ve just reached 200 reviews with an overall 4.95-star rating.

Since the beginning of May 2023, this property has consistently maintained over 70% occupancy, while continuing to generate strong off-season revenue.

It’s not waterfront.
It’s not about trends.
It’s about systems, care, and knowing what actually works — year round.

We’re especially thankful this time of year for our guests, our team, and the journey that brought us here!





11/28/2025

We’re excited to partner with Cayo Loco, a stunning collection of 3 oceanfront villas on the quiet, breathtaking island of Eleuthera in The Bahamas, owned by fellow Canadians who built their dream getaway and are now sharing it with you.

Getting there has never been easier.
Air Canada and WestJet now fly direct to Nassau, and from there it’s just a quick 20-minute flight to Eleuthera. Warm beaches, turquoise water, and total relaxation are closer than you think.

To celebrate this new partnership, Canadians get an exclusive 15% off their stay.
Use promo code PEAKSEASON at checkout.

Escape the cold. Embrace the sun. Your oceanfront villa is waiting. 🌞🌊

Book now at mybahamasbeachhouse.com

Direct Booking Link in Bio

🎥 Video content created by .wander.on and .onwings

11/18/2025

Therapy comes in all forms, let this place be one of yours one day.

Nestles on the quiet waters of Lost Bay in Dunchurch, Ontario.

Check out the full listing on our website, link is located in our Bio.

11/13/2025

There’s something truly magical about winter in Ontario. The lakes freeze into glittering sheets, the forests transform into snow-covered wonderlands, and cozy evenings by the fire become the highlight of the day. Whether you’re planning a romantic getaway, a family ski trip, or a quiet weekend ...

10/22/2025

At Peak Season STR, we help Ontario cottage owners earn more while doing less. From bookings to guest care, we handle every detail—so you can sit back, relax, and actually enjoy your property again.
Let’s turn your rental into a top-performing investment this season.

📞 905-317-1861

👉 Book a free consultation today!

Welcome to KC’s Cottage. Huntsville, Ontario location. If you’re looking for a cozy modern cottage to getaway, this is t...
05/26/2025

Welcome to KC’s Cottage.

Huntsville, Ontario location.

If you’re looking for a cozy modern cottage to getaway, this is the spot.

Or

If you’re a cottage owner and are thinking about renting your space, and would like some guidance on the how to’s and how to get 5 ⭐️ reviews, give us a call.

📞 905 317-1861
Kyle Milani
Peak Season short term rentals & Management.

Check out all the features on our website.The link is located in our Bio!

.

Meet Samantha 👋 Love for family, friends , hair design & interior design are my passions✨ It’s an honour to be apart of...
04/14/2025

Meet Samantha 👋

Love for family, friends , hair design & interior design are my passions✨

It’s an honour to be apart of someone’s journey in the short term rental industry. I know first hand how much time and an investment it can be.

Im here to help you transform or simply refresh your property into the space you envision for you’re guest ✨

🌴 Dedicated mom of two girls.
🌴 Loving wife of 12 years
🌴Married my high school sweetheart
🌴love for all things creatively designed
🌴Hairstylist for over 18 years.
🌴Canadian 🇨🇦/ Mexican 🇲🇽

Come spoil yourself in Magnetawan!WEEKENDS & WEEKDAYS AVAILABLE!🏡Croft Cove 🏡📍 Magnetawan, ON 📍https://g.co/kgs/bhn4aaE...
04/07/2025

Come spoil yourself in Magnetawan!

WEEKENDS & WEEKDAYS AVAILABLE!

🏡Croft Cove 🏡

📍 Magnetawan, ON 📍https://g.co/kgs/bhn4aaE
🚗 3 Hours from Toronto 🚗
🛌 3 Bedrooms 🛌
🚿 1.5 Bathroom🚿
🛏️ Sleep 5 🛏️
🌊 Waterfront 🌊
📺 Smart TV 📺
📷 📷

TEXT OR CALL me to book! 905-317-1861

Direct Booking Link - https://peakseason.holidayfuture.com/

Airbnb Link - airbnb.ca/h/croftcovecottage

Come spoil yourself in Downtown Sundridge! APRIL & MAY 2025WEEKENDS & WEEKDAYS AVAILABLE.🏡Sundridge 🏡📍 Sundridge, ON 📍ht...
04/07/2025

Come spoil yourself in Downtown Sundridge!

APRIL & MAY 2025
WEEKENDS & WEEKDAYS AVAILABLE.

🏡Sundridge 🏡
📍 Sundridge, ON 📍https://g.co/kgs/GYYktZS
🦶 Steps to Downtown Sundridge 🦶
🚗 3 Hours from Toronto 🚗
🛌 3 Bedroom 🛌
🚿 2 Bathroom 🚿
🌊 Lakefront 🌊
Games room

***Call or Text me to book! 905-317-186***

Airbnb Link - airbnb.ca/h/mainstinn

Direct Booking Link - https://peakseason.holidayfuture.com/

“What’s the #1 feature you look for in an Airbnb—great views or cozy interiors? Croft Cove has both 🤍Comment below whic...
03/17/2025

“What’s the #1 feature you look for in an Airbnb—great views or cozy interiors?

Croft Cove has both 🤍

Comment below which you prefer?!! 👇

3 🛌
2 🚽
🏖️Lakefront
📍Magnetawan , Ontario
3 hours from Toronto.

Book Direct & Save!

Link in Bio to Book!

Is your rental truly “Guest Ready”?If you’re not getting repeat guests or glowing 5-star reviews, it’s time to step up y...
02/17/2025

Is your rental truly “Guest Ready”?

If you’re not getting repeat guests or glowing 5-star reviews, it’s time to step up your hosting game! Small upgrades can make a huge impact on guest satisfaction.

✨ 𝐇𝐞𝐫𝐞’𝐬 𝐡𝐨𝐰 𝐲𝐨𝐮 𝐜𝐚𝐧 𝐦𝐚𝐤𝐞 𝐲𝐨𝐮𝐫 𝐫𝐞𝐧𝐭𝐚𝐥 𝐮𝐧𝐟𝐨𝐫𝐠𝐞𝐭𝐭𝐚𝐛𝐥𝐞:

1️⃣ Make Check-in Seamless – Clear instructions and fast communication ensure an stress-free arrival.
2️⃣ Stock Up on Essentials – A well-equipped kitchen with quality cookware, coffee, olive oil, and pantry basics keeps guests happy.
3️⃣ Refresh the Space – Thoughtful décor, cozy throws, and warm lighting create a welcoming atmosphere.
4️⃣ Add a Luxury Touch – A hot tub, sauna, or stylish feature instantly elevates your rental.

At Peak Season, we transform short-term rentals into guest-loved stays that book faster and earn more!

💬 Drop a comment with your biggest hosting challenge!
�📩 DM us for personalized tips!�🌐 Explore our services: https://www.peakseasonstr.com
�📞 Call for a free consultation: +1 905-317-1861

Let us handle the details while you enjoy the rewards!From professional listings with high-quality photos to SEO-optimiz...
02/13/2025

Let us handle the details while you enjoy the rewards!

From professional listings with high-quality photos to SEO-optimized descriptions and strategic advertising on top platforms like Airbnb, Vrbo, and Cottages in Canada, we ensure your property stands out.

Ready to get more bookings? Send us a message today!

🔗link in BIO to book your next stay at one of our properties or get in touch with us on the website! https://www.peakseasonstr.com/contact
📞Call us at 905-317-1861

Address

Hamilton, ON

Opening Hours

Monday 9am - 9pm
Tuesday 9am - 9pm
Wednesday 9am - 9pm
Thursday 9am - 9pm
Friday 9am - 9pm
Saturday 9am - 9pm
Sunday 9am - 9pm

Telephone

+19053171861

Website

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