Revisiting idea of vacation condo

21 Replies

Good Day!

My wife and I keep getting the itch to buy a VRBO'able vacation condo, preferably on the Gulf coast. (MUST BE Ocean front or nothing) We already own 34 units here in our own town of Waterville Maine, but we plan to travel more and more. We are age 52 and are already semi retired and feeling the itch ... the VRBO condo would serve the purpose of A.) Having a warm place to fly off to at a moment's notice as long as it's not rented at the time, as well as a great place to hang out and travel FROM. Sort of a travelers "HQ" if you will. (Flying and cruising from Siesta Key will be pennies on the dollar vs. Portland Maine). 


What are some decent areas on Gulf Coast. We have friends that have condos in Venice but it's not a good place for VRBO's that I know of. 

Is this a good time?? My perspective is that we're again at the "peak" or at least certainly a seller's vs. buyer's market. 

What are the "best" places to buy a VRBO on the West Coast?

Thank you all!

While not on the gulf, I do quite well in Kauai. Shoot me a PM if this area is of interest to you and I’ll share my experience.

@Mike V.

Hey Mike,

Are you doing SFR, small multi or condos? I assuming you're using a PM that collects that short rental tax? About a year ago I considered trying to find something like a 4plex I could rent out some long term for stability and mortgage payment and some for short term higher rates and availability for family and I to visit.

Originally posted by @Bill Brandt :

@Mike Verna

Hey Mike,

Are you doing SFR, small multi or condos? I assuming you're using a PM that collects that short rental tax? About a year ago I considered trying to find something like a 4plex I could rent out some long term for stability and mortgage payment and some for short term higher rates and availability for family and I to visit.

Condos, walking distance to the beaches. Self manage everything from California.

@Mike V.


Only been to Hawaii once. Cruises the 4 main isles 2 years ago for 20th wedding anniversary. They didn’t impress me much (hard to live up to 40 years of hearing how magical they are I assume)  but Kauai was my favorite. I especially liked the colorful Waimea valley, even more than the Grand Canyon and I got a lot of gruff for saying I liked Poipu beach  the best. Reminded me of Aruba. Clear, sandy and shallow approach. 

PM me an example of what you’re doing if you have time in the future please. Everything I have now is in Vegas except a couple lake homes in MN. 

@Kenneth LaVoie We are also looking for a place in warmer climes. Basically in the same shape as you just not as many doors lol, 18 in Lewiston/Auburn area.

Planning on renting a place in the Fort Myers area for a year and scout around and either buy something or build something. We went down there for a vacation to see if we liked the area and we did. We would basically be there in the winter and here in Maine in the summer/fall (June-Octoberish).

It has a decent airport with lots of flights to Atlanta (my wife travels a lot for her job and uses Delta). 

Siesta Key was nice, have you been to Sanibel Island? Liked the Sarasota area and may end up there.

Good luck in your search and keep us posted!

Carl! A brother from Maine! Glad to meet you. I'd love to keep in touch with how you are finding being a snowbird. We also were thinking it might be a good idea to rent. We plan to travel the world. I'm semi fluent in spanish now, and have been practicing an hour or so a day 365 days a year, for 3 years so I'm anxious to immerse myself in a spanish speaking culture (I'm half deaf so it hasn't been easy!). 

We actually toyed with the idea of renting year round once we knew we'd spend a few months down there so that we had a place to run off too any time. I actually ran the numbers and it's FAR cheaper to rent year round than buy a 300K condo even factoring in VRBO'ing it to a certain extent. 

We anticipate domiciling in central or south america at some point but have dozens of places to venture to so we've resisted buying. As you know, we'll probably both make more money buying multi units in Central Maine vs. vacation rentals any day, so even buying a few VRBO's here and there for fun and to  have a place to crash doesn't really make alot of financial sense. We talk each other out of it about every 3 years! The "draw" is our personalities. We both love to have a place of our OWN vs. renting, regardless of how financially silly. 

Have not been to Sanibel, but heard great things about it. My Dad lived in KW but that's too expensive and too removed from everything else for our tastes. It is our first destination when we start traveling without our daughter (now 17). We have friends that have an "inland" condo in Venice and they absolutely love the area. So besides Cocoa Beach on the Atlantic side we're pretty sure we'd hang out somewhere between Sarasota and Naples! 

Let's keep in touch! I'll PM you with our websites as well. 

@Kenneth LaVoie now may not be the best time to invest in the Gulf coast area as we are in a sellers market. I’ve been kicking tires for a year on a vacation rental and have not found anything decent. An agent out of Florida told me that I would have to put down around 50% of purchase price if I wanted to cash flow on a beach front property!!!! Have you looked into Puerto Rico? Maybe there is opportunity due to the recent hurricanes.

Sounds like a great "problem" to have @Kenneth LaVoie ! I grew up in Winslow, so I am familiar with your market in central Maine. 

We spend a few weeks a year on Sanibel and we love it. I wouldn't stay anywhere else in Florida. We don't own property down there, but we do know people who have vacation properties on the island that they've owned since the early '80s. Anecdotally, it sounds like a mixed bag. Good news is that the high season clientele (Jan - Apr) are great... mostly retirees and families. The summer season (May - Aug) is a bit rougher crowd. You get party groups escaping the inland/Miami heat and hardcore fisherman who decide to clean their catch in your bathrooms. Our connections no longer rent in the summer season because it's just not worth it. On the upside, it's not uncommon to get more mid-term renters who want the place for the season (snowbirds), which drastically reduces your costs to manage.

Fort Myers and surrounding coastal towns are pretty nice in spots, but you do get more "party" types on the mainland. And I don't like Southwest Florida International at all. It's a bear to travel through there in the high season. I think if you're looking for a "jumping off point" for international travel, a larger airport like Tampa is a better bet. I've visited and enjoyed the Sarasota/Bradenton area and that is relatively close to Tampa, but also has a mid-sized airport locally (Elite Airways flies direct from PWM to Sarasota, as far as I know). 

Personally, I'm hesitant to buy beachfront or beach adjacent property in Florida. Climate change is coming for Florida in a big way and between beach erosion, sea level rise, and rising temperatures, I think more people will be looking to vacation north of Florida in the future. It may not be a concern if your long term strategy is 20 years or less. 

What what fantastic replies. It does verify for me that purchasing beachfront in Florida might not be the wisest thing to do. 

@katie magoun thank you for your thoughts on Sanibel Island. Heard so much good stuff about it I think we may consider renting there, if even for a quick jaunt down before the end of this summer the scope it out. I have entertained the thought of renting a house or condo year round that I could possibly sublet if I wanted with the thought that that would still end up being cheaper than purchasing a condo and would allow us to travel light and have a place to escape 2 at a moment's notice. This is not a typical thing to do, renting a place year-round only to visit it 30 days a year or so, but I will have to crunch the numbers a little more.

@rush wall I hadn't thought of dipping my toes into the post-hurricane market. I don't think I would like Puerto Rico although I shouldn't say that because I've never been... What instinctively I would lean more toward one of the other Caribbean islands.

It's not on the Gulf Coast but in Maui I had a great time in the town of Kihei. Maui to me feels like the undeveloped version of Florida but with awesome mountains and so much more to do. You can get from sea level to 10,000 feet in a little over an hour in the car, unreal! I would also love to be a snowbird sooner rather than later.

What's your reasoning for going with VRBO over Airbnb? How do we determine if the HOA will even allow for these hospitality services?

@Kenneth LaVoie I'm an investor with 3 vacation rentals on the Gulf Coast of FL on Okaloosa Island near Ft Walton/Destin. I love it here and my properties do really well. I'm also a real estate agent and sell and manage vacation rentals for others. I manage my rental units myself and market them on VRBO and Airbnb. I have occupancy of close to 90% annually, which is not uncommon here since we have year-round visitors (including many people from up North in the winter). My units definitely cash-flow, so I know it is possible to have that here. I know a number of other people who have very good success with profitable vacation rentals here. If you have any questions about the area, etc, feel free to message me. I can also send you links of my personal properties so you can see my VRBO listings with pictures and current bookings, prices and occupancy for yourself.

@Kenneth LaVoie I know what you mean by the term "the itch to buy a VRBO'able vacation condo" my husband & I have experienced the same thing! And I appreciate you using the term "VRBO" instead of "Airbnb"...both seem to be interchangeable these days. But as a former employee of VRBO (when the original founders owned the company and I was part of the team that helped build the site to what it is today) I obviously am proud that "VRBO" has become a noun as well as a verb in this industry. :-)

We purchased our 1st STR in Summit County, CO in 2012 and since then have bought a new STR property every 2 years since, with the exception of 2017 when we bought a home in the city in VA where our alma mater is located. We now own 5 STRs: one in CO, three in FL and one in VA.

When we wanted to buy a beachfront condo in FL we took 2 exploratory trips because neither one of us had ever been to the Gulf Coast before. Our first trip we flew into Tampa and then drove down the coast all the way to Marco Island. We visited many of the cities that have been mentioned in this thread (Siesta Key, Fort Myers, Sarasota, Sanibel, Naples, etc.) 

Be careful to research each location's restrictions regarding STRs. We discovered that very many of those locations had really strict restrictions for STRs, such as can only rent one time per year and must be at least 30 days. Because we want our investment properties to basically pay for themselves (after the initial purchase & cash outlay to furnish it & get it ready to rent) we knew that buying a property in one of those locations was not going to work for us.

That is why we ended up in the Panhandle. We own 3 units in the same beachfront building on Okaloosa Island (in Fort Walton Beach, next door to Destin). Those locations in the Panhandle do not seem to have as many strict restrictions as the cities on the southern Gulf Coast.

Good luck!

@Kenneth LaVoie

Hey fellow Mainer (and Mainers)! Born in Maine, living in exile in Fort Myers, FL and love it. I’m a Realtor here so if I can help shoot me a PM. I own apt units in Los Angeles and also flip here. 

You get a lot of bang for your buck for waterfront condos in SW Florida especially parts of Fort Myers and Cape Coral. Higher HOA fees can kill cash flow but for building equity and having a place to launch from, here might be a good fit.

I did just read another article on Belize. Not spanish speaking but I love the area. Might visit Placencia soon..this winter maybe. 

@Kenneth LaVoie I love Belize and more specifically Placencia. It has been a few years since I have visited, I’ve heard that development has really taken off in Placencia. A couple other places you could look would be Hopkins Bay, Dangriga and Punta Gorda. 

How about Jamaica? The real estate market is booming, as foreigners continue to purchase private homes and private properties near to the beach like crazy. Resorts keep going up and the influx of visitors-turn-investors continue to spike each month. There are literally no barriers to foreigners owning real estate and it is relatively cheap to build in Jamaica. While it may cost 400K USD upward to cop a good property in the US, one can purchase land for near $150K and build a 10 room dwelling or a townhouse type apartment complex for around $200-250K USD. Not to mention - the climate being warm all year round - hello winters on the beach!

Let me know your thoughts - i have some connections in this regard.