11 Best Maryland Vacation Rental Companies and Startups

May 25, 2023

This article showcases our top picks for the best Maryland based Vacation Rental companies. These startups and companies are taking a variety of approaches to innovating the Vacation Rental industry, but are all exceptional companies well worth a follow.

We tried to pick companies across the size spectrum from cutting edge startups to established brands.

We selected these startups and companies for exceptional performance in one of these categories:

  • Innovation
    • Innovative ideas
    • Innovative route to market
    • Innovative product
  • Growth
    • Exceptional growth
    • Exceptional growth strategy
  • Management
  • Societal impact

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Top Maryland Vacation Rental Startups

Data sourced from Crunchbase and SemRush.

Vintory

Vintory

Crunchbase Website Twitter Facebook Linkedin

Vintory is a marketing firm that operates in vacation rental sector and focuses on inventory acquisition.

Proper Insurance

Proper Insurance

Crunchbase Website Twitter Facebook Linkedin

Proper Insurance provides vacation rental insurance services.

Proper Insurance

Taylor-Made Deep Creek Vacation Rentals

Crunchbase Website Twitter Facebook Linkedin

Taylor-Made Deep Creek Vacations & Sales are the most innovative Real Estate & Property Management Company in the Deep Creek Lake area.

Proper Insurance

RAILEY VACATIONS

Crunchbase Website Twitter Facebook Linkedin

RAILEY VACATIONS is providing vacation rental homes.

Proper Insurance

Gotugo

Crunchbase Website Twitter Facebook Linkedin

Gotugo provides rental restroom service,

Proper Insurance

Railey Realty

Crunchbase Website Twitter Facebook Linkedin

Railey Realty is a real estate & management firm that provides buying & selling services of vacation rental homes & residential properties.

Proper Insurance

All Inclusive Resorts

Crunchbase Website Twitter Facebook Linkedin

All Inclusive Resorts is a vacation rental company that provides destination weddings, bachelorettes, reunions, and meeting venue services.

Proper Insurance

Sea Gate Sales & Rentals

Crunchbase Website Twitter Facebook Linkedin

Sea Gate Sales and Rentals provides sales and rentals services of vacation condos in Ocean City, Maryland.

Proper Insurance

Ocean City Maryland

Crunchbase Website Twitter Facebook Linkedin

Ocean City Maryland provides vacation rental, property management, and other real estate services.

Proper Insurance

Shoreline Properties

Crunchbase Website Twitter Facebook Linkedin

Shoreline Properties is a vacation home rental agency.

Proper Insurance

Holiday Real Estate

Crunchbase Website Twitter Facebook Linkedin

Holiday Real Estate is a real estate company.

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