ITrip Colorado Springs

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ITrip Colorado Springs ✨ iTrip Colorado Springs ✨
We make short-term rental ownership simple and stress-free.

From Colorado Springs to Divide, we manage vacation homes with the perfect mix of tech, local expertise, and personal care.

Holiday travel plans require group coordination and planning well in advance.Let iTrip make sure your home is ready.
10/14/2026

Holiday travel plans require group coordination and planning well in advance.

Let iTrip make sure your home is ready.

Property Caretakers Wanted — iTrip Vacation Rentals (Colorado Springs Area)iTrip Vacations is looking for reliable local...
10/14/2026

Property Caretakers Wanted — iTrip Vacation Rentals (Colorado Springs Area)

iTrip Vacations is looking for reliable local caretakers (1099 independent contractors) for our vacation rental portfolio: 27 properties across three zones — Divide / Woodland Park, Colorado Springs / Manitou Springs, and Florence.

What the job involves:

Monthly property inspections (15 inspection stops across the portfolio)
On-call availability for on-site assistance (guest issues, check-ins, minor emergencies)
Light maintenance: replacing lightbulbs, breaker resets/troubleshooting, delivering supplies (toilet paper, etc.)
Pay:

$65 per inspection stop (flat $195 for the San Ayre Court building — 11 units in one stop)
$19/hour for on-call assistance and light maintenance work
You:

Live in or near the zone(s) you cover
Have reliable transportation
Are handy with basic home fixes (no licensed trade work required)
Available for one inspection round per month plus occasional on-call visits
This is 1099 contractor work with a flexible schedule — a great side income.

Interested? Email [email protected] with your name, phone number, and the zone(s) you're interested in covering.

10/13/2026

Every memorable property has something guests can't stop talking about. Let iTrip’s local owner operators help you decide what that feature is or should be, and then our national team makes sure the right people see it.

You're already making the trip.Spend another day exploring local cafés, scenic drives, farmers' markets, and those littl...
10/12/2026

You're already making the trip.

Spend another day exploring local cafés, scenic drives, farmers' markets, and those little shops you never would've found otherwise.

🌻 The wedding is just the beginning. Make the most of the trip with iTrip.

Some of the most important work happens long before the first holiday guest arrives.Preparing your property, adapting to...
10/09/2026

Some of the most important work happens long before the first holiday guest arrives.

Preparing your property, adapting to seasonal demand, and keeping everything running smoothly are all part of helping your home perform at its best.

See what proactive management looks like with iTrip.

10/08/2026

Everyone has their thing.

Maybe it's getting outside, trying something new, exploring the area, or taking over the kitchen with the whole crew.

The best trips leave room for everyone to enjoy them their own way and plenty of time to come back together.

🍂 Find your home base with iTrip.

Proactive management means keeping you informed while keeping your property moving forward.With a property owner dashboa...
10/08/2026

Proactive management means keeping you informed while keeping your property moving forward.

With a property owner dashboard and invested owner operators , we'll keep you in the loop every step of the way.

📍 Experience responsive management with iTrip.

Every season asks something different of your property. From preparing for colder weather to keeping guests comfortable ...
10/07/2026

Every season asks something different of your property. From preparing for colder weather to keeping guests comfortable throughout their stay, local management means the details are already in motion before winter arrives.

❄️ Let's get your property winter-ready together.

10/06/2026

The holidays are meant for gathering, celebrating, and spending time with the people who matter most.

Let iTrip's local team keep your property running smoothly while you enjoy the season.

🎄 Enjoy the holidays. We'll handle the details.

Fireplace. Big kitchen. Hot tub. Room for everyone.Finding the perfect home for your holiday escape can be overwhelming....
10/06/2026

Fireplace. Big kitchen. Hot tub. Room for everyone.

Finding the perfect home for your holiday escape can be overwhelming. iTrip can help.

🍂 Find your Thanksgiving home base now.

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Colorado Springs, CO
80902

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