Alex and Annie: The Real Women of Vacation Rentals

A high-end vacation rental and a premium nightly rate don't always guarantee well-behaved guests.

And when a stay ends with serious property damage, getting the home back in shape can be only part of the headache.

In Episode 4 of Pour Decisions: When Stays Go Sideways, presented by Safely, Alex and Annie are joined by Alexandra “Ali” Chaney of 30A Beach Stays & Vacations, alongside Amanda Martins and Zach Grimes of Safely, for a candid conversation about the unpredictable side of vacation rental management.

Ali brings firsthand stories of unexpected guest incidents and the challenges of managing damage claims, while Amanda and Zach share insights from Safely's experience helping operators navigate these situations.

Together, they explore the realities of guest-related risks, the challenges of recovering costs through booking platforms, and how the right protection and processes can help property managers safeguard the homes entrusted to them.

We discuss:

12:55 - Why luxury properties are not immune to destructive guest behavior

14:53 - The challenges of recovering damage costs through booking platforms

21:52 - How the right protection can support homeowner confidence

24:08 - What operators can learn from real guest damage incidents

27:47 - Why documentation and a clear claims process matter

30:14 - How different types of insurance and damage protection work together

36:48 - Where guest waivers fit into a broader protection strategy

From shocking guest stories to practical insights on damage protection, this episode offers plenty for property managers to think about before the next stay goes sideways.

Connect with Ali: https://www.alexandanniepodcast.com/guests/alexandra-chaney/ 

Connect with Zach:

LinkedIn: https://www.linkedin.com/in/zach-grimes-9242b478/ 

Connect with Amanda:

LinkedIn: https://www.linkedin.com/in/amandakatmartins/ 

Learn more about Safely:

Website: https://safely.com/alex-and-annie
LinkedIn: https://www.linkedin.com/company/safely-stay/
Instagram: http://instagram.com/safely/
Facebook: https://www.facebook.com/safelyprotection 

This Episode's Cocktail: Ali's Special

A classic margarita with a fresh citrus twist.

Ingredients:

• Tequila
• Triple sec
• Sour mix
• Fresh lime juice, optional
• Fresh orange juice, optional
• Ice

How to make it:

Combine the tequila, triple sec, and sour mix in a shaker with ice. Add fresh orange and lime juice if desired. Shake well and pour into your favorite glass.

#vacationrentals #shorttermrentals #damageclaims

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A guest books a beautiful vacation rental, has an incredible stay, and leaves with memories worth sharing. But when they tell others about their experience, whose brand do they remember?

In this episode, Alex & Annie sit down with Michelle Gilliland, VP of Sales at Savvy, to explore what it takes to build a recognizable brand in a market where OTAs dominate traveler attention.

Drawing from nearly 15 years of experience in the vacation rental industry, Michelle brings a unique perspective on how brands can differentiate themselves, create stronger connections with travelers, and build lasting recognition.

The conversation offers a look at Savvy's approach to branding and distribution, along with insights that challenge property managers to think more intentionally about how their businesses are discovered, experienced, and remembered.

Episode Chapters:

03:06 - Michelle Gilliland's background at Vrbo, Expedia Group, and Savvy

03:43 - Why property managers deserve greater brand visibility

06:21 - Airbnb's direct booking links and what they mean for operators

12:33 - Why consistency matters throughout the guest experience

17:00 - Should the vacation rental industry establish clearer hospitality standards?

21:48 - Making it easier for travelers to connect directly with property managers

24:58 - Collaboration, community, and building local brand awareness

26:05 - Behind Savvy's unconventional "Death of the Middleman" marketing campaign

31:17 - How referral incentives can encourage more bookings

33:26 - Savvy's approach to brand visibility, distribution, and guest relationships

37:58 - Building a business that is less dependent on major OTAs

If you're looking to strengthen your vacation rental brand and stand out in an increasingly competitive market, this is a conversation worth tuning into.

Connect with Michelle:

LinkedIn: https://www.linkedin.com/in/michellegilliland/

✨ Exclusive Offers to Alex & Annie Listeners:

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

Learn more about dormakaba’s vacation & short-term rental access solutions:

👉 Website: https://dk.world/Vacation26 

#vacationrentals #shorttermrentals #directbookings

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The way travelers discover vacation rentals is changing.

Traditional Google search still matters, but discovery is increasingly expanding into tools like ChatGPT, Gemini, and Claude, where travelers can describe the kind of trip they want and receive recommendations based on that intent.

In this episode, Alex & Annie sit down with Gil Chan, Founder and CEO of CraftedStays, to explore what this shift means for vacation rental operators and the direct booking websites they have spent years building.

Gil shares how his experience as a property manager, combined with his background in e-commerce and product development, led him to build CraftedStays around a problem he saw firsthand: vacation rental websites often lack the infrastructure needed to support a seamless, measurable direct booking journey.

The conversation also dives into how AI search is changing website strategy, what CraftedStays has learned from its research into AI visibility, and why content, structured data, reviews, and strong local expertise may become even more important as the search journey evolves.

Episode Chapters:

05:39 - Why direct bookings are still complicated
06:56 - What vacation rental websites can learn from e-commerce
16:52 - Building a website platform that can evolve faster
18:55 - CraftedStays’ relationship with Google and the development of Aria
22:56 - From Google search to conversational travel discovery
28:34 - Reviews, structured data, and helping AI understand your business
32:07 - What CraftedStays learned from 24,000 AI search queries
36:53 - Using AI to create and optimize direct booking landing pages
48:13 - Where independent operators can compete with OTAs in AI search
50:12 - How to audit your visibility across AI search platforms
55:35 - Why there is no “page two” in AI search

Want to dig deeper into AI search?

CraftedStays has created a free AI Search Guide for vacation rental operators that breaks down what property managers should be paying attention to as search continues to evolve.

👉 Explore the guide: https://craftedstays.co/ai-search-for-vacation-rentals/

Connect with Gil:

LinkedIn: https://www.linkedin.com/in/thegilbertchan/

Learn more about CraftedStays:

Website: https://craftedstays.co/alexannie/

✨ Exclusive Offer to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with CraftedStays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/alexannie/

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

#vacationrentals #shorttermrentals #directbookingwebsite

Send us a message!

In this fourth episode of First of the Month Wrangle, presented by Lasoh, we are joined by Orlie Benjamin, Founder and CEO of Lasoh, and Eric Goldreyer, Founder and CEO of Savvy, to unpack one of the latest conversations surrounding Airbnb and direct booking.

Airbnb has been testing a program that allows some hosts and co-hosts to drive their own demand to an Airbnb listing in exchange for a reduced platform fee. The company may be calling it direct booking, but Orlie and Eric argue that the definition gets more complicated when the reservation still happens on Airbnb and the operator does not fully control the guest relationship.

That question opens the door to a much bigger conversation about what direct booking actually means, who owns the guest relationship, and what operators gain or give up depending on where that relationship lives.

Episode Chapters
00:57 - What Airbnb is testing with “direct booking”
05:53 - Is Airbnb’s direct booking link really direct?
08:30 - If you are doing the marketing, who owns the guest?
13:02 - Guest data, remarketing, and the customer relationship
23:30 - Why direct booking has a trust problem
26:23 - Why your guest list is part of the value of your business
29:05 - Owning versus renting the customer
30:02 - The opportunity in referrals and repeat guests
39:31 - Solving the discovery problem for direct booking
41:56 - How AI, AEO, and GEO are changing travel search
49:04 - Why there will never be only one booking channel
51:31 - Building around customer feedback and relationships

For vacation rental operators thinking seriously about reducing OTA dependence, strengthening guest relationships, and building more value beyond the next reservation, this episode offers a useful look at what “direct” really means and what it takes to build a business around the customer relationship. 

Learn more about Lasoh:

Website: https://tinyurl.com/52nvyw8t
LinkedIn: https://www.linkedin.com/company/lasoh/
Facebook: https://www.facebook.com/people/Lasohio/61575721958679/
Instagram: https://www.instagram.com/lasoh.io

Connect with Orlie:

LinkedIn: https://www.linkedin.com/in/orliebenjamin/
Facebook: https://www.facebook.com/profile.php?id=61585160391720
Instagram: https://www.instagram.com/orlie.benjamin/ 

Learn more about Savvy:

Website: https://www.savvy.com/
LinkedIn: https://www.linkedin.com/company/stay-savvy/
Instagram: https://www.instagram.com/savvy_stay
Facebook: https://www.facebook.com/savvystays 

Connect with Eric:

LinkedIn: https://www.linkedin.com/in/ericgoldreyer/ 

✨ Exclusive Offer to Alex & Annie Listeners: 

Turn every guest interaction into more revenue with Lasoh.

Get 20% off Lasoh products with code AlexandAnnie. Valid through November 30, 2026.

👉 Learn more: https://explore.lasoh.io/alex-annie

#vacationrentals #shorttermrentals #directbookings

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A guest can spend months planning a vacation, travel all day, arrive with tired kids and luggage in tow, and then have the entire experience unravel at one very important moment: the front door.

In this episode, Alex is joined by Dawn Keathley of Dormakaba and Matt Seyed of Secure Lodging Systems for a conversation about an often overlooked part of the vacation rental experience: guest access.

They explore why getting guests through the door reliably is about much more than choosing a lock. Access sits at the intersection of guest experience, property security, owner trust, and day-to-day operations.

Drawing from both the manufacturing and implementation sides of the industry, Dawn and Matt share what reliable access looks like in practice and why the right system needs to hold up to constant turnover while still making arrival simple for guests and manageable for teams.

Reliable access is easy to overlook precisely because guests should not have to think about it. A failure at the front door, however, can quickly become the moment they remember most.

Episode Chapters:

06:17 – What makes Dormakaba different in access control
08:18 – What makes vacation rental access different from other industries
09:30 – Working with homeowners, HOAs, and associations
10:51 – Managing access across complex condo and resort environments
17:20 – How vacation rental access control has evolved
18:20 – The challenges with hard keys and inconsistent lock systems
19:55 – Commercial-grade vs. residential-grade locks
21:43 – Phasing access-control upgrades across a portfolio
22:55 – Why the vacation starts at the front door
24:00 – Access control and the professionalization of vacation rentals
25:26 – What happens when operators cut corners on guest access
31:53 – Evaluating doors, common areas, pool gates, and guest workflows
33:14 – New access technology built for vacation rentals

Learn more about dormakaba’s vacation & short-term rental access solutions:

Website: https://dk.world/Vacation26 

Connect with Dawn:

LinkedIn: https://www.linkedin.com/in/dawnkeathley/ 

Connect with Matt:

LinkedIn: https://www.linkedin.com/in/matt-s-2a05751b6/ 

✨ Exclusive Offer to Alex & Annie Listeners:

Thinking about the next chapter for your vacation rental business? 

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/ 

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

#vacationrentals #shorttermrentals #guestexperience

Send us a message!

Alex & Annie are taking the podcast on the road for a special on-location episode from Montego Bay, Jamaica. 

This time, they’re stepping inside Call Center Solutions to see the operation firsthand, meet the people behind it, and get a closer look at what it takes to build a hospitality team that can support vacation rental businesses from hundreds of miles away.

Throughout the visit, Alex and Annie sit down with members of the CCS team across operations, HR, IT, and leadership to hear what the business looks like from the people running it every day. One theme keeps surfacing along the way: the importance of culture, connection, and making remote team members feel like a true extension of the companies they support.

Episode Chapters:

00:00 – Alex & Annie arrive at Call Center Solutions in Montego Bay

02:49 – How CCS started in Jamaica and grew beyond the original experiment

06:50 – What onboarding and training a remote hospitality team actually looks like

11:36 – Meet the operations team: culture, customer service, and what makes a great agent

20:47 – Inside HR: hiring, employee support, and building a team people want to stay with

29:42 – The IT and infrastructure keeping the operation running

34:21 – Beachside reflections on culture, connection, and hospitality

41:30 – Beyond reservations: how CCS supports more of the operation

45:16 – How property managers can get started with a CCS team

Come along for a behind-the-scenes look at Call Center Solutions, the team they've built in Montego Bay, and a few uniquely Jamaican moments along the way.

Connect with Call Center Solutions:

Website: https://www.ccssuccess.com/ 

LinkedIn: https://www.linkedin.com/company/my-call-center-solutions/ 

Instagram: https://www.instagram.com/call.center.solutions/ 

✨ Exclusive Offers to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with Crafted Stays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/alexannie/

Thinking about the next chapter for your vacation rental business? 

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/ 

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

#vacationrentals #shorttermrentals #guestexperience

Send us a message!

Alex & Annie are taking the podcast on the road for a special on-location episode from Montego Bay, Jamaica. 

This time, they’re stepping inside Call Center Solutions to see the operation firsthand, meet the people behind it, and get a closer look at what it takes to build a hospitality team that can support vacation rental businesses from hundreds of miles away.

Throughout the visit, Alex and Annie sit down with members of the CCS team across operations, HR, IT, and leadership to hear what the business looks like from the people running it every day. One theme keeps surfacing along the way: the importance of culture, connection, and making remote team members feel like a true extension of the companies they support.

Episode Chapters:

00:00 – Alex & Annie arrive at Call Center Solutions in Montego Bay

02:49 – How CCS started in Jamaica and grew beyond the original experiment

06:50 – What onboarding and training a remote hospitality team actually looks like

11:36 – Meet the operations team: culture, customer service, and what makes a great agent

20:47 – Inside HR: hiring, employee support, and building a team people want to stay with

29:42 – The IT and infrastructure keeping the operation running

34:21 – Beachside reflections on culture, connection, and hospitality

41:30 – Beyond reservations: how CCS supports more of the operation

45:16 – How property managers can get started with a CCS team

Come along for a behind-the-scenes look at Call Center Solutions, the team they've built in Montego Bay, and a few uniquely Jamaican moments along the way.

Connect with Call Center Solutions:

Website: https://www.ccssuccess.com/ 

LinkedIn: https://www.linkedin.com/company/my-call-center-solutions/ 

Instagram: https://www.instagram.com/call.center.solutions/ 

✨ Exclusive Offers to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with Crafted Stays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/alexannie/

Thinking about the next chapter for your vacation rental business? 

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/ 

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

#vacationrentals #shorttermrentals #guestexperience

Send us a message!

In this episode, Alex & Annie sit down with Vinny Dicarlo, CEO of Ciirus, and Josh Parry, Chief Product Officer, for a conversation about the philosophy that has shaped the company over nearly two decades.

Founded as a family business, Ciirus has taken a deliberately measured approach to growth. Rather than building around outside investment or pressure to scale at all costs, Vinny and Josh explain how the company has focused on long-term customer relationships, continued investment in its technology, and human support that keeps the team closely connected to the property managers it serves.

That approach opens up a broader conversation about what operators should expect from a technology partner today. Vinny and Josh share why they believe there are limits to how much vacation rental operations can be automated, where AI can genuinely help, and why human involvement still matters in an industry where every property, owner, guest, and stay can look different.

Episode Chapters:

11:14 - Building customer relationships designed to last

17:15 - Why Ciirus has chosen measured growth over growth at all costs

18:28 - How independent ownership shapes investment in customers and technology

22:38 - Why vacation rental operations cannot automate everything

27:39 - Building a global team around specialized talent

32:49 - Helping property managers get more from their technology

38:14 - Why customer and employee satisfaction matter together

39:55 - Ciirus’ new mobile app, owner tools, and Booking.com integration

46:03 - How LoveRentals helps property managers expand their capabilities

54:59 - Finding vacation rental demand beyond the major OTAs

57:55 - Reaching guests through travel agents, wholesalers, and international markets

1:02:24 - What is next for the Ciirus platform

If you are evaluating your tech stack, thinking about sustainable growth, or looking for new ways to reach guests, this episode offers a closer look at what a strong technology partnership can bring to your business.

Connect with Josh & Vinny

Josh Parry: https://www.linkedin.com/in/josh-parry-47165997/ 

Vinny Dicarlo: https://www.linkedin.com/in/vincenzo-dicarlo/ 

Connect with Ciirus

Website: https://ciirus.com/

✨ Exclusive Offers to Alex & Annie Listeners:

Alex & Annie listeners can receive their first three months of Ciirus subscription fees waived when joining the platform.

Visit https://ciirus.com/ and let the team know you heard about Ciirus through the Alex & Annie Podcast.

Thinking about the next chapter for your vacation rental business? 

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/ 

List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.

👉 Get started: https://partners.vacationfinder.com/alexandannie 

#vacationrentals #shorttermrentals #vacationrentaltechnology

Send us a message!

In this episode, Annie is joined by Jinnie Randolph for a conversation with Cristiana Carpini, founder of the Women in Vacation Rental European Conference (WVREC), and Neely Khan, founder of Kahani.

Together, they explore the value of creating spaces where women can build trust, share openly, and form meaningful relationships that support both personal and professional growth. Cristiana shares the thinking behind WVREC, while Neely reflects on what made the first gathering feel so different and why that environment gave her the confidence to share a deeply personal story publicly for the first time.

They also look ahead to WVREC 2026 in Barcelona, how the event is evolving, and the larger community Cristiana and Neely hope to continue building around it.

Episode Chapters:
02:20 - The story behind the Women in Vacation Rental European Conference
09:23 - Why trust and vulnerability shaped the first WVREC
16:19 - Why Cristiana is keeping the event women-focused
18:28 - How deeper connections can lead to collaboration and opportunity
21:52 - What to expect from WVREC 2026 in Barcelona
24:52 - Cristiana and Neely’s upcoming storytelling project
28:00 - Making the case for investing in professional development
34:27 - What surprised Cristiana most about the first conference
40:31 - Final details for WVREC 2026

Connect with Cristiana:

LinkedIn: https://www.linkedin.com/in/cristiana-carpini-hospitality/

Connect with Neely:

LinkedIn: https://www.linkedin.com/in/neelykhan/ 

Learn more about WVREC: https://wvrec.eu/ 

✨ Exclusive Offer to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with Crafted Stays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/alexannie/

Thinking about the next chapter for your vacation rental business? 

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/ 

List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.

👉 Get started: https://partners.vacationfinder.com/alexandannie 

#vacationrentals #shorttermrentals #hospitality

Send us a message!

Welcome to Episode 300 of the Alex & Annie Podcast! 🎉 

Three hundred conversations, countless aha moments, plenty of industry debates, and a front-row seat to some of the biggest shifts vacation rentals have seen over the last several years.

This is such a huge milestone for us ⭐

To celebrate, we knew we wanted to bring back someone who has been part of the Alex & Annie journey since the early days.

We’re fortunate to have several people who have supported us along the way, and for this milestone, longtime friend of the show Terry Whyte returns for a conversation about how far the vacation rental industry has come and where it may be headed next.

Terry revisits predictions from his past appearances, including his views on technology, all-in-one platforms, loyalty, and distribution. He shares what he got right, what he would revise today, and how AI has changed the conversation.

Through it all, Terry keeps coming back to the fundamentals: quality properties, strong technology, smart distribution, customer care, and real human hospitality.

And because this is Episode 300, Alex & Annie also reflect on the journey so far and share a glimpse of what comes next for the podcast.

Here’s to 300 episodes and the next chapter of Alex & Annie. 🥂

Episode Chapters

02:30 - Revisiting Terry’s past industry predictions
03:26 - How AI changed the vacation rental tech conversation
06:29 - Why technology is becoming more fragmented
08:29 - Where automation ends and human hospitality matters
16:31 - Why growth does not always mean adding more doors
18:35 - Why distribution matters more than ever
19:37 - Direct bookings, website traffic, and marketing
24:39 - Rethinking loyalty in vacation rentals
29:40 - Terry’s advice for operators today
30:39 - What will separate thriving property managers in the future
33:37 - The risk of relying on a single OTA
35:49 - Terry reflects on the Alex & Annie Podcast
39:44 - The industry shift that changed Terry’s business
41:23 - What comes next for Alex & Annie

Connect with Terry:

LinkedIn: https://www.linkedin.com/in/terry-whyte-4540633b/ 

✨ Exclusive Offer to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with Crafted Stays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/ 

Thinking about the next chapter for your vacation rental business? 

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/ 

List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.

👉 Get started: https://partners.vacationfinder.com/alexandannie 

#vacationrentals #shorttermrentals #hospitality

Send us a message!