Florida Keys? Anybody Have Firsthand Experience?

[Craig T]

Has anybody lived in the Florida Keys?…Or spent significant time vacationing there? What are the pros and cons? (Hurricanes are obvious cons, so let's skip that).

My sister loves Key West and asked me to go half on a vacation home. She found something nice, with short term rental potential. I love saltwater fishing, paddle boarding, free-diving, and all water sports, so Key West might be fun. Plus, my wife's family is spread across the south eastern seaboard. The Keys might be close enough to satisfy her (and far enough away to satisfy me).

I appreciate Pelican advice. I only have about 10 days to make a decision.

[Porsche-O-Phile]

If you're south of the clock...

A good friend lives in KW. Loves it. It's expensive and crazy (lots of tourists / drunks, not as bad outside of KW on the "other" keys). Jobs are scarce unless you tend bar or... tend bar.

It's kind of lonely from what he tells me (he's single). Most people are tourists or seasonal. Not as many locals as you'd think. Hard to cultivate relationships / friends sometimes.

[Craig T]

Originally Posted by Porsche-O-Phile

If you're south of the clock...

A good friend lives in KW. Loves it. It's expensive and crazy (lots of tourists / drunks, not as bad outside of KW on the "other" keys). Jobs are scarce unless you tend bar or... tend bar.

It's kind of lonely from what he tells me (he's single). Most people are tourists or seasonal. Not as many locals as you'd think. Hard to cultivate relationships / friends sometimes.

We're retiring soon, so no need to look for work. We won't live there permanently, and my sister will be using it too. With a new grand baby in CA, we'll downsize and keep a condo in Ventura Co. The house we're looking at is in Ramrod Key, so a ways from the crazy tourism. I have no idea how far we'd have to drive for groceries, restaurants, etc. I'm doing the research now….but the lack of social interaction could be a problem…especially if Ramrod Key has no business district.

[dad911]

I've had a place in KW since 2007, love it. pros & cons to the other keys, and some areas in KW. I have a good friend that's a broker there, straight shooter, PM me if you want his contact info.

Think twice about partnerships. Make sure you have an exit plan in writing if one of you wants out. Cost us 6 figures get my brother-in-law out of a partnership, and haven't spoken to my sister in 10 years. (They lawyered up first, instead of talking)

[Eric 951]

Ramrod Key is nice--I have spent a lot of vacations on Summerland (next key down). There isn't a "business district" on Ramrod--but Big Pine is right over the bridge and has everything you would need--drug stores, supermarket, liquor store, etc.

The nicest beach in the Keys is nearby too--Bahia Honda state park(you probably know the keys don't really have miles of "beaches" like some expect)--but Bahia is an actual sand beach and ahs some good snorkeling.

There are plenty of small restaurants, shops, etc. throughout the middle keys--part of the fun of living there would be finding your favorites--I'm partial to the Galley for breakfast, and the Square Grouper on Cudjoe for dinner.

Since you are retiring there--the job situation won't matter--your biggest worries would be hurricanes--as you can imagine US 1 gets jammed if there is an evacuation. Speaking of 1--it can get jammed anytime--esp with RVs, boat trailers, etc.

If you want to mix it up--Key West is an easy drive--I would rather be exactly where you are than in Key West proper--less crowded, cleaner, no huge influx of cruise ship passengers--but you are close enough to visit for special events, or if you feel the need.

Speaking of--Miami isn't a bad drive either--not quite my scene though.

You should check the local laws regarding renting the place out--unless you are just renting to friends and family--there are some permit procedures and inspections the place needs to pass to be considered a rental if you are listing it or using an agent, etc.

You will be on "Keys time" when there--as will most people you will be dealing with, and possibly hiring--(contractors, etc.) but if you can adjust there are no issues.

Based upon your interest and the location, I would definitely do it. The middle keys is the only place I have on the radar for a part-time retirement location.

Before you know it, you will be relaxing on the deck with a beer reading the Keynoter crime blotter (for laughs--lots of odd/funny crimes), and the letters to the editor about mosquito spraying, possibly dredging the channels for larger cruise ships, and the Red Humvee which parks down near Pepes - these were always the majority of the topics regardless of year visiting.

[Craig T]

Originally Posted by dad911

Think twice about partnerships. Make sure you have an exit plan in writing if one of you wants out.

Thanks dad911, but my sister and I would do fine as partners. Her husband and I share a room at races and play golf together regularly. Little chance of a separation ending in litigation. I'll put something in writing that I can buy her out at FMV anytime if my wife and I decide to retire there full time. My sister can always stay for free. She's a proffessor in the Cal State system and isn't going anywhere often or permanently.

Originally Posted by Eric 951

Ramrod Key is nice--I have spent a lot of vacations on Summerland (next key down). There isn't a "business district" on Ramrod--but Big Pine is right over the bridge and has everything you would need--drug stores, supermarket, liquor store, etc.

The nicest beach in the Keys is nearby too--Bahia Honda state park(you probably know the keys don't really have miles of "beaches" like some expect)--but Bahia is an actual sand beach and ahs some good snorkeling.

There are plenty of small restaurants, shops, etc. throughout the middle keys--part of the fun of living there would be finding your favorites--I'm partial to the Galley for breakfast, and the Square Grouper on Cudjoe for dinner.

Since you are retiring there--the job situation won't matter--your biggest worries would be hurricanes--as you can imagine US 1 gets jammed if there is an evacuation. Speaking of 1--it can get jammed anytime--esp with RVs, boat trailers, etc.

If you want to mix it up--Key West is an easy drive--I would rather be exactly where you are than in Key West proper--less crowded, cleaner, no huge influx of cruise ship passengers--but you are close enough to visit for special events, or if you feel the need.

Speaking of--Miami isn't a bad drive either--not quite my scene though.

You should check the local laws regarding renting the place out--unless you are just renting to friends and family--there are some permit procedures and inspections the place needs to pass to be considered a rental if you are listing it or using an agent, etc.

You will be on "Keys time" when there--as will most people you will be dealing with, and possibly hiring--(contractors, etc.) but if you can adjust there are no issues.

Based upon your interest and the location, I would definitely do it. The middle keys is the only place I have on the radar for a part-time retirement location.

Before you know it, you will be relaxing on the deck with a beer reading the Keynoter crime blotter (for laughs--lots of odd/funny crimes), and the letters to the editor about mosquito spraying, possibly dredging the channels for larger cruise ships, and the Red Humvee which parks down near Pepes - these were always the majority of the topics regardless of year visiting.

Great info, thanks Eric! I certainly need to do my due diligence on the short-term rental qualification. I don't think it makes sense prior to retirement if we can't get some subsidy from rental income. For the next three years, it'll sit vacant a LOT. I'm getting excited now.

I see now from Google Earth there are not many sand beaches. We're not people to sit on a beach anyway. It's fishing and watersports I'm after.

[Hugh R]

Craig T. I knew I hated you. How much? I love KW. I was in Boise last week and it was a lot colder. I'd also consider keeping my Ventura (Hollywood Beach condo) for six months, minus one day so I don't pay CA income taxes.

[Craig T]

Originally Posted by Hugh R

Craig T. I knew I hated you. How much? I love KW. I was in Boise last week and it was a lot colder. I'd also consider keeping my Ventura (Hollywood Beach condo) for six months, minus one day so I don't pay CA income taxes.

Hey Hugh! Don't hate me yet. I have a lot of research to do. If we can't rent it, I can't do it for a couple more years.

The house we're considering is right at $539K and split two ways (WAY less than a condo in Ventura). It's only 1,760 sf and three bedrooms, but it's only two of us…with occasional family visitors.

I've been watching your Boise thread closely. I did a deal in Boise in a couple years ago that took 6 months. My wife and I went a couple times and really liked it…Then I had to go to a closing dinner in January and it was 8 degrees! That fantasy was broker quickly.

We're doing the same as you. Likely sell this house and buy a condo in Camarillo Springs to be close to my daughter and grandson when in town. We'll buy something better in Florida to split time, but keep FL as address of residency for tax purposes. NO STATE TAXES!

[Hugh R]

Craig, just kidding. I'd love the Keys, been there a few times. I'm thinking the same thing, six months plus one day out of CA for taxes and keep the Hollywood Beach condo. $539K is doable from me. You're right, Boise is nice, but it was 4 degrees and it was only Thanksgiving.! I don't need a big place, and 1,7xx sq. ft. is more than enough for Donna and I.

[MBAtarga]

Craig - let's go thirds! I won't even have a hard time talking my wife into the deal!

[Paul_Heery]

Craig,

My wife and I will be down in that area in just over a week. Let me know if you would like us to check anything out for you.

The house that you are looking at is in Breezeswept Beach Estates. The Breezeswept Beach Estates Civic Association website has some history & background on the area.

Paul

[HardDrive]

My parents live on Big Pine Key for 4 months during the winter. They love it. They have an RV and stay in a place called Big Pine Fish Lodge. It's in the key deer preserve, grandfathered in. Definitely on the rustic side, but also incredibly beautiful. My dad is steps away from his boat. Camp management is very competent and puts up with 0% BS.

Pretty amazing to be sitting there having a drink at night around a campfire, and have an 8 point buck that's only 3 feet high come up and beg for a bit of lettuce.

www.bpkfl.com

[Eric 951]

Craig,

Some extra incentive.

view from Summerland Key


view from sunset Key (off KW)

[Seahawk]

I couldn't do more than what HardDrives parents do - 3/4 moths in the winter.

I have flown there quite a bit as a Navy pilot - a few of the NAS Key West base CO's were good friends of mine. I have also known a few folks that were stationed there.

I get the vibe and the life style since I am a water guy...but (there is always a but) the Keys are a lot more remote than you think. They are the last stop on the trolley line.

Everybody I know who lived there loved it for the first year or so, but with few exceptions were ready to leave when their tour was up.

Remoteness was part of the problem - it is a few hours to get anywhere to then go somewhere

Again, I like the Keys but just not for more than an extended stay a few times. I'll come and visit!

[Craig T]

Originally Posted by Paul_Heery

Craig,

My wife and I will be down in that area in just over a week. Let me know if you would like us to check anything out for you.

The house that you are looking at is in Breezeswept Beach Estates. The Breezeswept Beach Estates Civic Association website has some history & background on the area.

Paul

Thanks for the info, and the offer Paul, but I slowed things down. We're flying out on December 27th to take a look. My sister found another she likes a little better. Smaller, but facing open water.

We're taking a hop up to Charleston right after. I'm getting a little resistance from my wife on the Keys. She wants to do this closer to her mother and sister, who live in Johns Island, SC. She'd prefer Hilton Head, Edisto Island, or Kiawah. I'm hoping she falls in love with the Keys. We can't afford Kiawah, and Edisto is too close to her family.

[Crowbob]

Sorry for the deflection here but does anyone have info/advice on parking a tiny (16') travel trailer down there somewhere for a couple weeks?

[Paul_Heery]

Originally Posted by Craig T

We're flying out on December 27th to take a look. My sister found another she likes a little better. Smaller, but facing open water.

Even though it is smaller, since it faces open water I expect the new one that your sister likes is also a bump in price.

Christmas week is a very busy time for Key West. It should give you a good feel for some things you will experience when the tourists come flocking in. Hopefully, it will not turn off your wife to the Keys.

[seanratpel]

Just so you know, from around june to late sept you can fry an egg on your forehead! Half the restaurants on duvall close shop because its too friggin' hot. Can't really hang at outside restaurants and bars when you're on the verge of a stroke. Beautiful place but there's the ungodly heat and bums (well mannered and tanned though everywhere. Even after a month when I was there (2013-14) KW starts to close in on you, remember about 4 miles long 1 mile wide, not enough greenery for me!!

[Craig T]

Originally Posted by seanratpel

Just so you know, from around june to late sept you can fry an egg on your forehead! Half the restaurants on duvall close shop because its too friggin' hot. Can't really hang at outside restaurants and bars when you're on the verge of a stroke. Beautiful place but there's the ungodly heat and bums (well mannered and tanned though everywhere. Even after a month when I was there (2013-14) KW starts to close in on you, remember about 4 miles long 1 mile wide, not enough greenery for me!!

These exact topics come up at the breakfast table this morning. I'm not so worried about heat. Give me a paddle or fishing pole and some sunscreen and I'm happy as an Iguana on the rocks. We'll always keep something here due to my daughter and grandson, even if it's just a small condo, so summers can be spent in Ventura. ...But, We know some people who even went "island crazy" on Maui. After 18 months they couldn't stand it and moved back. I can guess KW would be even worse. I just Google-mapped it, and it's over 2 hours to Miami by car. That is pretty isolated, particularly if few live there full-time. Maybe it'll never be more than a vacation house. We'll see in a few weeks.

[HardDrive]

Originally Posted by Crowbob

Sorry for the deflection here but does anyone have info/advice on parking a tiny (16') travel trailer down there somewhere for a couple weeks?

You could call the Big Pine Key Fishing Lodge and ask them. My parents store a 5th wheel trailer there during the summer. Not sure if you need to stay there to store there. Worth a shot.

Big Pine Key Fishing Lodge

305-872-2351