The standard in short-term rental property management.

Experience the iTrip difference. World-class property management with total transparency, cutting-edge technology, and industry-leading rental revenue.

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iTrip Annapolis manages short-term rentals in Annapolis, Kent Island and St. Michaels in Maryland.

Affectionately known as the “Sailing Capital of the U.S.,” Annapolis is home to the U.S. Naval Academy and historical attractions. Kent Island ranks among the largest islands in Chesapeake Bay and has parks, beaches, distilleries and vineyards. St. Michaels is a pet-friendly community ideal for festivals and weddings, waterfront dining, and spas.

As local short-term rental property managers in Annapolis, we focus on building long-lasting relationships with homeowners, guests, and real estate investors, and offer a vacation guide to each guest to enhance their stay. Our portfolio of vacation rentals includes historic homes in downtown, waterfront homes on Chesapeake Bay, and show-stopping estates for the most luxurious stays. To make each stay a five-star experience, we also provide guest gift baskets and welcome pets in many homes.

Interested in earning more from your rental? Learn about us and our full-service Annapolis rental property management program and meet our team.

Short-Term Property Management with iTrip Annapolis, MD

What is the iTrip Difference?

Rental revenue that can exceed the industry average by 5x, while still allowing you the freedom to stay in your property when you want.

A hands-on property manager that treats your property as if it's their own.

If you're ready to work less, and earn more, contact iTrip Annapolis today.
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MARKET-LEADING INCOME

iTrip special sauce combines local expertise with extensive digital marketing - the result: top performing properties.

A SAFE PAIR OF HANDS

Experienced professionals care for your property like it was their own. Regular cleaning and inspections along with damage protection keeps your property in excellent condition.

HOSPITALITY FOCUSED

iTrip creates a warm & welcoming guest experience by showcasing your property’s unique features of a quality accommodation in a desirable location.

TRUST via TRANSPARENCY

Complete visibility to your property: see reservations as they happen! Easily reserve your place when you wish.

More Services from Us, 
More Revenue for You

Some property managers offer a few services, but still require too much work from you. Isn't it time your rental property started feeling less like a second job, and more like an investment? 

LOCAL BUSINESS OWNERS

Direct communication with ownership and decision makers.

MORE LISTINGS

See your property on 80+ vacation rental & travel sites.

EXTENSIVE DIGITAL MARKETING

Over 15 Million impressions per month across social media channels.

PAMPERED PROPERTY

Perfectionists care for your place as if it's their own.

A FELLOW INVESTOR

We deeply understand protecting & leveraging assets.

FULL GUEST EXPERIENCE

Warm & welcoming 24/7 guest services, responsive & knowledgeable.

PRIMARY BUSINESS

Focused on success in short-term rentals- not other business ventures.

ASSET SECURITY

Grade locks, noise monitoring, and other technology.

HIGHEST REVENUES

Results-oriented; Proven market-leading incomes.
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Request your personalized revenue forecast to see what you can earn.

Questions? Let's talk.

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(410) 571-4076

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sean@itrip.net

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iTrip Annapolis
626C Admiral Dr. #234
Annapolis, MD
21401

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