Strategies for Legacy Resorts Success: Short-Term Rental Focus
- Florida Custom Merch
- 2 hours ago
- 5 min read
In an era defined by rapid shifts in traveler behavior, legacy resorts face both an incredible opportunity and a significant challenge: how to remain relevant, profitable, and beloved in a marketplace increasingly dominated by short-term rental platforms like Airbnb, VRBO, and boutique vacation homes. The traditional resort model — heavily reliant on seasonal occupancy, package deals, and on‑site amenities — can feel rigid compared to the flexibility that today’s travelers crave. Yet with the right strategic focus, legacy resorts can not only compete but thrive by embracing short‑term rental dynamics while preserving the brand values that have sustained them for decades.
In this comprehensive guide, we’ll explore practical, forward‑thinking strategies that legacy resorts can implement to harness the power of short‑term rentals without losing their identity. Along the way, we’ll also touch on a powerful but often overlooked tool in the resort playbook: custom merchandise —a tactic that can deepen guest loyalty and extend your brand well beyond the guest’s stay. For more insights into the role of merchandise in guest engagement and revenue, check out this article on resort success strategies:
Understanding the Shift: Why Short‑Term Rentals Matter
Travelers today aren’t just booking a room — they’re booking an experience. Gone are the days when a standard hotel room and continental breakfast satisfied most guests. People want:
Flexibility in check‑in/out times and accommodations
Unique, local experiences
Privacy and space, particularly for families or group travel
Value and personalization
Short‑term rentals have grown in popularity precisely because they deliver these expectations at scale. Legacy resorts can harness this trend by adapting operational models and marketing strategies that resonate with this new class of traveler.
1. Develop a Short‑Term Rental Division Within Your Resort Portfolio
Rather than viewing short‑term rentals as competition, think of them as a complementary extension of your resort’s offerings.
A. Curate Resort‑Managed Villas and Homes
If your property includes spacious villas, cottages, or standalone homes, position them as resort‑managed short‑term rentals. Benefits of this approach include:
Standardized service quality
Inclusion of resort amenities
Enhanced control over pricing and guest experience
Guests can enjoy the space and privacy of a rental home while still benefiting from your resort’s reputation and service infrastructure.
B. Partner With Local Property Owners
In markets where resort‑owned inventory is limited, consider strategic partnerships with local homeowners. By managing these properties under your brand umbrella, you can ensure quality and consistency while increasing inventory without significant capital investment.
2. Implement Dynamic Pricing and Revenue Management
Legacy resorts have traditionally relied on fixed seasonal pricing. Short‑term rental markets take a more fluid approach, adjusting rates based on demand, local events, and competitor pricing.
A. Use Data‑Driven Tools
Invest in revenue management software that evaluates demand patterns in real time. This enables you to:
Adjust pricing dynamically
Maximize occupancy during slow periods
Increase rates during peak times without alienating guests
B. Incentivize Longer Stays
Short‑term rental guests often stay 3–7 nights or longer. Create tiered pricing and packages that reward multi‑night stays with discounts, resort credits, or complimentary services.
3. Enhance the Guest Experience With Personalization
One of the advantages short‑term rentals have historically held is the feeling of a “home away from home.” Resorts can blend that comfort with luxury service.
A. Concierge‑Level Check‑In
Offer flexible and contact‑free check‑in options, paired with concierge support. This mirrors the ease of short‑term rentals while showcasing the elevated service that resorts provide.
B. Localized Guides and Experiences
Guests increasingly seek authentic local experiences. Provide curated guides featuring:
Best local restaurants
Hidden gems in the area
Cultural and outdoor activities
Personalized recommendations make guests feel truly catered to, enhancing satisfaction and loyalty.
4. Reimagine On‑Property Amenities for Rentals
Traditional resort amenities like pools and spas remain valuable, but guests also love unique experiences that feel tailored to their stay.
A. Family & Group‑Focused Amenities
Create offerings that cater to longer stay guests — think:
In‑room dining kits
Family game packs
Outdoor grills or picnic setups
These kinds of experiences make stays more enjoyable and encourage repeat bookings.
B. Wellness and Recreation Packages
Partner with local fitness studios, wellness practitioners, or outdoor guides to create packages — such as yoga at sunrise, paddleboarding at sunset, or guided nature hikes — that speak to both leisure and experiential travelers.
5. Build an Integrated Marketing Strategy That Targets Short‑Term Renters
Marketing to a new kind of traveler requires an evolved strategy that blends traditional resort branding with short‑term rental sensibilities.
A. Direct Booking Incentives
Encourage guests to book directly through your resort’s website by offering:
Best price guarantees
Exclusive perks (e.g., free breakfast, resort credit, priority access)
Special merchandise or welcome gifts
Direct bookings reduce dependency on third‑party platforms and enhance your customer data insights.
B. Tailored Messaging for Different Guest Segments
Use targeted messaging that appeals to different traveler types:
Guest Segment | Messaging Focus |
Families | Space, comfort, and activities |
Remote workers | Wi‑Fi reliability, workspace comfort |
Couples | Romantic experiences and privacy |
Groups & reunions | Group activities and shared spaces |
Segmented email campaigns and social media ads can dramatically increase engagement and conversion.
6. Reinforce Your Brand With Custom Merchandise
One often underestimated avenue for strengthening guest loyalty — and generating incremental revenue — is branded merchandise. High‑quality resort merch serves multiple purposes:
Acts as a memory of the stay
Turns guests into brand ambassadors
Provides a tangible connection to your property
Items like branded towels, hats, beach gear, or apparel extend your resort’s presence into guests’ everyday lives. When done well, merchandise doesn’t just sell a logo — it tells a story about your resort’s values, aesthetics, and unique identity.
For deeper insights into how merchandise plays a role in overall resort strategy and guest engagement, this piece offers excellent context: https://www.insidehs.com/strategies-for-legacy-resorts-success-short-term-rental-focus/.
7. Leverage Guest Feedback to Refine Offerings
Short‑term rental platforms thrive on guest reviews, and resorts should too.
A. Make Feedback Easy
Encourage guests to provide feedback at multiple touchpoints:
Post‑stay emails
Quick in‑room surveys
Incentives for reviews (e.g., voucher for next stay)
B. Act on Feedback Quickly
Use insights to:
Improve amenities
Adjust pricing
Enhance service delivery
A resort that listens and evolves builds a reputation that drives bookings through both loyalty and positive word‑of‑mouth.
8. Build Loyalty Programs That Reward Repeat Stays
Finally, short‑term renters often become loyal travelers when provided with perks that matter. Legacy resorts are uniquely positioned to leverage deep customer histories to build meaningful loyalty programs.
A. Tiered Rewards
Create a multi‑level loyalty program offering benefits such as:
Free nights
Early check‑in/late check‑out
Exclusive amenities
B. Partner Offers
Collaborate with local businesses — restaurants, adventure tours, spa services — to create bundled rewards that add value to longer stays.
Conclusion
Legacy resorts have a solid foundation of brand heritage, service excellence, and memorable experiences. By intentionally integrating short‑term rental strategies — from dynamic pricing and diversified inventory to personalized guest services and branded merchandise — resorts can adapt to modern traveler expectations while preserving their core identity.
As the travel landscape continues to evolve, those resorts that embrace flexibility, listen to their guests, and invest in experiences that go beyond the room key will redefine what it means to be a timeless destination in a dynamic world.
With so many options available, choosing the right branded promotional item can be overwhelming. Since 2016, we, at Florida Custom Merch, have helped numerous businesses achieve success through the use of custom branded promotional merchandise. Hiring an expert can help you select the perfect item, save time and money, and, most importantly, maximize your results.
Thank you for reading! We hope you found this article helpful!
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