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Discussion – 


Discussion – 


How to Invest & Crush It in Competitive STR Markets (EP 310)

Airbnb Superhost Rebecca Cramer lives by the philosophy that it’s better to regret something that you’ve tried than to regret something that you didn’t try at all. And that attitude has served her well, inspiring Rebecca to invest in short-term rental (STR) properties in highly competitive markets and absolutely crush it—proving that big risk, when done right, can reap big rewards.

Rebecca is the founder of Mad Men Vacation Rentals, a STR business with listings in Maryland and Florida. She invests in vacation spots she and her family love, creating the Mad Men Beach House listing in Ocean City, MD, and the Mad Men Magic Kingdom House near Disney World. Rebecca started hosting on Airbnb in January of 2018 and has quickly proven that newcomers can be successful in crowded STR markets.

On this episode of Get Paid for Your Pad, Rebecca is back to discuss her decision to invest in competitive locations like Maryland and Florida. She walks us through the process of finding, buying and renovating STR properties, explaining what she did to research profit potential and why her listings surpassed expectations. Listen in for Rebecca’s insight on furnishing your STR (without breaking the bank) and learn her top strategy for getting more bookings in the off-season!

Topics Covered

Rebecca’s STR portfolio

  • Start with Ocean City vacation home in 2018
  • Added Disney World property last year
  • Deep Creek Lake location will go live in 2020

How Rebecca found the Ocean City property

  • Discovered neighborhood on vacation there
  • Outdated house on Zillow (9 months on market)

How Rebecca researched STR profit potential in Ocean City

  • Look at similar listings in neighborhood on Airbnb
  • Talk to realtor, friends with vacation homes there

Why Rebecca’s listing surpassed profit projections

  • Renovations, updated furnishings and amenities
  • High level of customer service

What Rebecca did to command a higher price for her listing

  • Offer kayaks, pool and tennis courts
  • Made property dog friendly

How well the Ocean City property performed

  • Covers mortgage, updates and cleaning fees
  • Provide down payment for next investment

Why Rebecca chose to invest in Florida

  • Open to risk, confident in ability to recreate success
  • Family loves Disney + can escape there themselves

How Rebecca furnished her listings for less

  • Sold furniture that came with properties
  • Utilized Craigslist, Facebook Marketplace
  • Willing to paint/refinish distressed pieces

Rebecca’s strategy for getting more listings in the off-season

  • List property twice (e.g.: 3BD/2BA AND 1BR/1BA)
  • Fill booking gaps with solo travelers + small groups

Connect with Rebecca

Mad Men Vacation Rentals

Mad Men on Instagram

Mad Men on Facebook

Mad Men Beach House

Mad Men Magic Kingdom


Rebecca on GPFYP EP309


STR Profit Academy

STR Legends Mastermind

Email jasper@getpaidforyourpad.com

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