This episode takes us to Anna Maria Island, FL to meet Nancy and Michael McAleer, of Anna Maria Island Beach Life and hosts of Anna Maria Island Home Rental “Sirenia by the Sea.” In this Episode we explore the challenges of hosting a vacation rental remotely, and go searching for ‘Old Florida’, that blue-water, green-palmetto, shrimp-and-crab kind of place that just might still exist on the Gulf Coast.

The Property

We felt cozy and at home at the enormous, water-front Sirenia By The Sea.  Perfect for multi-generation families and larger groups looking for a quiet getaway. Supremely located as close as you can get to the Gulf of Mexico while perched on a deep waterfront for boaters.  The pool and hot-tub are sublime.  We wish we were there, right now.


Key Takeaways

For us, Anna Maria Island was about how to experience 'Old Florida' as visitors, while still preserving it.  We had Cory, a local artist, turn our idea for a gift for Nancy into a reality now hanging in Sirenia by the Sea.

Read Matt's full essay, here.

Key Culinary Connection - Sean Murphy

Eating on Anna Maria Island meant a smorgasbord of fresh, gulf seafood.  While the colossal claw at the Cortez Stone Crab Festival  or the fried goodies at Starfish Company were tough to beat, it was Sean Murphy who became our ambassador to all that was fine wining and dining on the island.  Sean is a chef and owner of The Beach Bistro, an Anna Maria Island institution for more than 30 years and consistently the highest rated restaurant in the greater region.  We first met Sean at his bar, The Doctor's Office.  This place was simply happening, and we worked up an appetite over sips at an absinthe fountain and a peanut butter and jelly martini accompanied by a warm nut medley and spicy edamame.  From there it was a short golf-cart hop to the Beach Bistro, where the tasting menu lived up to it's reputation and then some.  This was the second to last day of our journey, and we took the opportunity to celebrate with Nancy and Michael, all the while regaled with Sean's tales.  Canadian born Sean has taken the Old Florida feeling of his adopted home and fused it with an old world cape-cod style dining experience to create something that simply cannot be missed when visitng the island.

 The Beach Bistro at sunset.

The Beach Bistro at sunset.

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Key Activity: Boating

We managed to get out on the water twice in five days while visiting Anna Maria Island and only scratched the surface of all there is to see and do.

First up was a direct recommendation from Nancy, to go meet Steve and Yetta of Anna Maria Island Outfitters.  This warm couple runs a shop that has everything you need for your outdoor adventures while on the island, from apparel to those coveted Yeti coldsters we have fallen in love with.  Steve is an avid fly fisherman, and once a week Yetta lets him out on the water with his shallow-water skiff.  Occasionally, he'll bring a client along, and this particular week, we got to join him for a masterclass in salt-water fly fishing, a spectacular lunch off the dock in Cortez, and some of the sharpest thoughts we'd yet heard on the balance of development and Old Florida feel in the area. 


A couple of days later, we linked up with Captain Dev, a fun, former Navy guy who spun us around to all of his childhood haunts, including a beach rope-swing and a sunken molasses vessel.  We spotted dolphins aplenty and chowed on fried fish sandwiches back over in Cortez.  Dev is the man to see for serious sports-fishing charters, or jaunts out to Edgemont key.  Anna Maria Island offers a lot of ways to get on the water, suitable for a variety of interests and budgets.  There are many freely accessible piers and beaches where fishing and exploring are also possible.  The key is to get into or on that water, by any means necessary.  Remember, asking your vacation rental host is one of the best ways to find the best people and ways to experience this sort of activity when you travel.


Welcome to the VRMB Learning Corner

A Sense of Place is first and foremost a travel show, so in the process of filming and editing we so often found ourselves unable to include industry tidbits that could help so many owners and managers grow. This section by VRMB, the top marketing resource in the vacation rental industry, is dedicated to sharing that valuable learning information with newcomers and veterans alike.

A Sense of Place Deconstructed: Anna Maria Island

Each destination and vacation rental host has multiple layers to its success. So we decided to pull back the curtain and watch, over Matt's shoulder, as he shares insider commentary on the people, places, and best industry practices that made this destination so unique. To record this video, we've used the Logitech c920 webcam, the Blue Snowball microphone, and Camtasia screen recording software.


Host Interviews

 You may have noticed a one-on-one interview with the host that ran through this episode in order to establish a narrative. But in the several hours we spent interviewing, there was way more valuable insight geared towards vacation rental industry professionals. Below are packaged nuggets of wisdom that you can use to improve your vacation rental business.


When considering investing in a vacation rental home, there are two layers of research that Nancy recommends: the first is to investigate city data such as crime, household income, taxes...etc. The second layer is the more granular vacation rental deep dive: browsing the major listing sites to gauge the supply (inventory) and demand (occupancy calendars) of the local market. This is an unusually helpful aspect of the major listing sites like VRBO and Airbnb: one can actually predict, with a fair degree of certitude, how an investment will perform based on comparables.
Recommended Research Tools: Airdna (data and insights), Inside Airbnb (data)


When getting started in the vacation rental industry, it's hard to know exactly what guests will expect to be in your home. Nancy found that the easiest way to equip a vacation rental is to assume the role of "high maintenance" vacationer: while it may be a more expensive investment upfront, the "high maintenance vacation home" leaves little room for disappointment and commands higher nightly rates.

A lot of vacation rental owners manage their properties from afar. And thanks to technology, remote hosting is easier today than ever before. But more than just Your Welcome Tablet and the internet, Nancy practices a preemptive style of management that begins way before the guests arrive. She combines that with simple phone/text correspondence to ensure that guests are taken care of as well (if not better) than if she was living next door.


When getting started, consider seriously the quality of items to put in your home. From a sheer investment standpoints, high-quality products that are durable end up costing you less in the long run: durable furnishings also generate 5-star reviews, which gives you the momentum and social proof needed to earn the investment back sooner rather than later.

What one single item gets featured the most in your reviews? Nancy says it's her towels. Splurging on extra comfortable towels is not just a way to generate 5-star's a way to command a higher nightly rate. Find "the little things" -- the items that don't cost an arm and a leg, but that really make a difference in the guest experience, and double-down.


This episode of A Sense of Place is brought to you by aBundle, a new e-commerce site that puts all the essentials in one place for vacation rental owners, managers and hosts. We first learned about aBundle through their parent company, the American Hotel Register, which for 150+ years has been supplying the hotel industry with the best supplies guests could ask for. Now aBundle is bringing things like soaps, shampoos, towels, and sheets to vacation rental hosts...and you don't have to buy a gazillion to try it out -- you can buy just one. We think that's important for an evolving industry looking to professionalize. 

To celebrate this perfect partnership, we invite you to save 20% on your first order at Use code SENSEOFPLACE through March 31st.


Key Additional Links from the Show

Cory Wright:

The Studio:


Eat Here:

AJ The Loft 5 catering:

The Waterfront Restaurant:


We would love to hear from you!

What was your biggest takeaway from this episode?  Do you have a question or comment about the show, or host, or destination?  Please write us below, or leave a comment on Youtube, Facebook, or hit us up on Instagram.

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