Transient vs Monthly Rentals: What’s the difference??

The number one question we get at Last Key Realty, from both our vacation rental guests and our real estate clients, is what’s the difference between transient and monthly rentals?  We’ve put together this quick informational guide to help you better understand how renting a home in Key West works.

What’s the difference between rental types? Read on to find out!

What is a transient license?

The answer is pretty straightforward – properties with a transient license are authorized by the city to be rented for less than 29 nights; those without this license are restricted to be rented by the month.  That’s it, one piece of paper that makes a big difference.

Why can’t I rent this property for less than 29 nights?

If a property isn’t fortunate enough to have one of these highly coveted transient licenses, then according to strict Key West ordinances, the property legally can’t be rented for less than 29 nights — under any circumstance.  If we were to write a lease for a monthly property for less than 29 nights, that would be illegal and we could lose our license.  We like what we do, and want to keep doing it, so we have to adhere to these ordinances.

And before you ask, there are no exceptions to this rule.  Ever.  If a property doesn’t have a transient license (aka a monthly rental) it legally can’t be rented for less than 29 nights.

We wish we were able to rent out the Polynesian House for less than a month!

Why such a big price difference?

Transient rentals on average generate about 3x more income per month than a monthly rental.  This is due to their higher nightly rates. As a result, a monthly home might actually cost less for a month than a transient home of the same size for just two weeks!

Homeowner Associations (HOAs)

While we’re talking transient rentals, we have to touch on the various HOAs with transient rental licenses that exist around the island.  These HOAs can have their own requirements, and the majority of them do.  Most only allow for weekly rentals, but some have their own special rules altogether – like Truman Annex.

View from the widow’s walk at Noona’s Mansion in Truman Annex

Truman Annex

Let’s talk Truman Annex – the Truman Annex HOA regulations are stricter than most, they require rental properties to be rented for a minimum of 6 nights, have no more than 8 guests occupying a rental (no matter the size of the property) and can only be rented for a maximum of 26 weeks a year.  This is why these rentals are usually more costly, since they can only be legally rented for half the year. Explore our Truman Annex Rentals.

*** Ask us about the monthly rental discount in Truman Annex!  Must be booked direct to receive these significant savings ***

How can I get a Transient License?

Decades ago, the city of Key West issued a limited number of transient licenses. And they haven’t issued anymore since.  And probably won’t issue them ever again. 

These coveted licenses currently sell for $300,000 to $400,000, and that’s if you can find one.  (That’s just the price of the license, no property attached to it!)

Whether you’re looking to rent or buy, knowing how to navigate the unique Key West market is the difference between success and failure.  Having folks you can trust and rely on is vitally important, which is why you have us. 😀

View all of our beautiful Key West Vacation Rentals by Last Key Realty.

Success Stories: Keeping Up with the Joneses

So you’ve been to Key West and fell in love with the island, and now you’re considering purchasing an investment property in paradise.  It’s very likely this idea has popped into your head more than once.  If you’re like most people reading this, it’s probably the second or third (or more!) time you’ve entertained this thought.  Let’s be honest, there’s a reason you’re reading a premiere boutique real estate companies blog 😉

In this series, lovingly dubbed Success Stories, we’ll share a few inspirational stories to help nudge you in the right direction and help solidify that gut feeling you’ve had about owning a vacation rental in Key West.  Our first success story stars Mr. & Mrs. Emil Jones:

The Joneses, a family from Virginia, fell in love with Key West while vacationing on the island in 2014 and considered purchasing a vacation rental of their own.  The Joneses are well aware of how lucrative the vacation rental industry is, they own several successful vacation rentals in North Carolina and decided they would explore purchase options in Key West. This decision was made much easier as they knew and trusted Last Key, having stayed with us as vacation rental guests for many years.

Gulfside Vistas – The favorite Last Key Realty property the Joneses stayed in

During their most recent stay at Gulfside Vistas, the Joneses were introduced to Rodney Culiver – Last Key’s Marketing Director and one of our fabulous Realtors. Rodney got to know this family well and guided them through the purchase process – educated them on the Key West vacation rental market, provided extensive financials, and established expectations for owner operations. After discussing their goals and needs, they identified a home to operate as an income-generating vacation rental (and to stay in with their family a few times a year) that would be a perfect fit… The home they chose was our very own Seventh Heaven at 62 Front Street in Truman Annex.

Seventh Heaven – The Joneses amazing new property at 62 Front St

This home has been operating as a successful vacation rental with Last Key Realty for a number of years, with dozens of 5-star reviews and a jam-packed calendar of confirmed future reservations. Helping the Joneses realize the equity they would be stepping into and the immediate return on investment they would see was an integral part of this transaction. The fact that the home is beautifully maintained and located in the most exclusive gated community on the island didn’t hurt either 😉 The Joneses successfully closed on 62 Front Street and have already hosted a few guests!  We’re happy to welcome them to the Last Key family.

2020 taught us many things, but the most apparent in Key West is that hotel demand is being replaced by vacation rentals.  The demand for vacation rentals is sky high and based on our reservations already on the books for next year, it’s not looking to slow down anytime soon.  Look at the Online Travel Agent business as a whole, AirBnB and VRBO have increased their market share year after year, growing in popularity as vacation rentals become more of the norm.  When the last recession hit, people still flocked to Key West.  And they will continue to come to Key West. 

We’ve also noticed another positive trend, more and more of our past guests are becoming vacation rental homeowners themselves.  And Last Key has helped them every step of the way.  It makes perfect sense if you think about it, who better to help you purchase an investment property than the people who will be managing that very investment?  We know the market, we know our clientele, and we know what makes a successful rental.  Last Key Realty will be with you from your first stay as our guest, to help with your home purchase, and for years to come profitably managing your rental. Experience the Last Key difference.

Fall 2021 – A Better Value For A Beautiful Time of Year

The Fall is actually a great time to be in Key West, there’s less traffic and the island is much quieter, allowing you to enjoy all of your Key West favorites without having to deal with the crowds. The Fall is also when you’ll find the best rate values of the year, your favorite Key West vacation homes can be booked for nearly 20% less than the cost of on-season rates!


Get ready for Fantasy Fest! An experience you have to see to believe. Fantasy Fest is an annual 10-day party for grown-ups including costumes, parades and excitement! This year’s event will be held from October 22, 2021 to October 31, 2021. Put on your most extraordinary costume and get ready for all the fun!  While it’s true the parade is cancelled this year, 95% of the festivities are still going on, so honestly, no one will even notice! Find a Key West vacation rental near Fantasy Festival.


Planning a getaway to Key West?  Fall is a perfect time! Temperatures start to cool down slightly in September. Key West averages a daily maximum temperature for September that’s between 87 and 89 degrees Fahrenheit (30 to 32 degrees Celsius).  October averages a high of 85 degrees and a low of 78 degrees (25 – 29 degrees Celsius). 

You can also enjoy less crowded beaches and attractions.  With kids going back to school, your Key West vacation experience can be a bit more relaxed and slow-paced.

Your time in Key West can be as action-packed or as relaxed as you desire. Adventure-seekers can book a fishing charter, snorkel trip, or dive to explore a shipwreck. Or, simply relax and unwind at the beach, at your vacation rental’s private pool, or strolling the downtown area. 

Last Key Realty… The Accidental Business

It’s no secret Last Key Realty has set the standard for luxury vacation rentals in Key West.  The thousands of guests that have stayed with us over the years, along with our happy homeowners, will be the first to tell you that.  But few know the story of how this titan of real estate came to be.  Until now.

Founder Chris Santry & COO Alex O’Donnell celebrating Alex’s 3rd (!!!) baby on the way

A Retirement Cut Short

If you ask our founder Chris Santry how Last Key came into being he’ll tell you just like he told me in my job interview, it was completely by accident.  He had no intention of creating a vacation rental company, the island demanded it of him.

Chris and his wife Sharon retired to Key West in 1999 and planned on renting out several properties they’d acquired… doing little more than floating in their pool and hanging out at La Te Da.  After dealing with another vacation rental company in Key West for a couple of years, Chris decided he would be better off renting his homes himself.  So that’s exactly what he did.

Conch Casa Grande – One of the 1st homes under the Last Key umbrella, and still with us!

Last Key Realty is Born

Over the next few years, Chris and Sharon did so well with their homes that other homeowners asked if they could be a part of the program. By 2008, they were managing a dozen homes, and the couple decided they needed to actually be a company. Thus, Last Key Realty was born.

The next decade was a period of steady growth and expansion. And we’re happy to report that many of those original owners are still part of Last Key Realty’s rental program.

The view from the living room at Noona’s Mansion, a long time Last Key favorite

Key West Awesomeness

So what sets LKR apart?  There are plenty of vacation rental companies in Key West, either locally based or part of a worldwide conglomerate.  With so much competition how have we grown so steadily?  The answer is simple – we care about our guest’s experience, that’s what it’s always been about.

We do everything we can to ensure our guests get a taste of the Key West Awesomeness we’ve grown to love.

Last Key Realty has the largest vacation rental staff, at least triple any competitor in Key West. Each member of our staff is dedicated to enhancing our guest’s experience.  We love Key West and want to show off the Key West Awesomeness that keeps drawing people to our little island year after year.  And we do everything in our power to ensure our guests find that awesomeness, whatever their idea of it may be.

The Polynesian House is a great representation of Key West Awesomeness…

It’s no coincidence the most notable luxury vacation homes in Key West are with Last Key.  We have a strict set of standards for our homes and we ensure those standards are met for every single guest staying with us.  You read that correctly, we check our properties before every stay to make sure everything is top-notch for you.  One of the most common phrases guests use in their reviews is “nicer than the photos.”

Buy Key West

We’ve even helped a bunch of our guests become locals.  The reason our guests trust us in the search for their own vacation home is because we don’t simply sell them a house… We act as consultants to help them find their dream home. 

Whether you’re looking to stay for a week, or a month… or the rest of your days, look no further than Last Key Realty to ensure you find that Key West awesomeness you’ve always desired.

Investing In Key West

As Key West’s premier Vacation Home Asset Manager, when it comes to Real Estate our priority isn’t production. When we venture into Real Estate our priority is the best possible outcome for our clients, period. This may not sound like a typical Real Estate Agency’s motto, that’s because we’re not your typical Real Estate Agency.

Because our bread and butter is vacation rentals, we have a unique understanding of what makes a successful vacation rental home. From identifying Key West’s leading investment opportunities to producing a high performing vacation rental, we are ready to help make your Key West investment dreams a reality.

If you are ready to embark on the journey of purchasing an investment home in Key West, start with the ones who will be mutually invested in the long term success of your investment. Schedule a personal consultation with our team today to discuss your investment goals and how we can help make those a reality.

March 2018 Review/Photo of the Month

We received a multitude of excellent guest reviews and photo submissions this month! Each month we select the most memorable review/photo received as our monthly contest winner of a $100 cash card.

Our March 2018 Review/Photo of the Month Winner is The DeFelice Family, who stayed with us at << AVALYNN HOUSE >> and submitted a glowing 5-star review for their stay and shared some fun photos of themselves enjoying their vacation home and celebrating St. Patty’s Day!

The DeFelice Family celebrated St. Patty’s Day in true Key West style during their stay!

The 5-star review submitted from their stay at Avalynn House.

The whole gang posing by the pool.

It never gets old seeing moments like these of our guests enjoying their vacation homes and time in Key West. We take full pride in providing them with a memorable vacation experience.

Future guests: Be sure to send us a photo or video of your time on vacation and/or submit your memorable review for your stay to be automatically entered for a chance to win a $100 cash card. You could be April’s winner!

February 2018 Review/Photo of the Month

We love receiving reviews and photos from our guests. Each month we select a memorable guest review or photo to win a $100 cash card. The Chambliss Family is our February 2018 “Review/Photo of the Month” Winner for the review and photo submitted for their stay at << COASTAL CABANA >> for the outstanding 5-star review and this adorable photo they submitted from their stay!

Pets need a vacation too, ya know…

5-star review from the Chambliss Family

We thoroughly enjoy seeing these amazing moments of our guests’ vacations. It reminds us how lucky we are to do what we do and to live in such a magical place!

For future guests, send us a photo/video of your time on vacation and/or submit your memorable review for your stay to be entered for a chance to win a $100 cash card.

January 2018 Review/Photo of the Month

We received lots of wonderful review and photo submissions this month, but there can only be one winner! Our January 2019 “Review/Photo of the Month” Winner is The Manzler Family,  guests of << HAVANA HOUSE >> for the month. We received such a flattering 5-star review on Google from them, as well as these fun photos!






The Manzlers review from their stay at Havana House

Where else can you enjoy the pool in January?! We love seeing our guests enjoying their vacation homes and time in Key West. It is a reminder of how lucky we are to do what we do and the fact that we live in such a magical place.

Future guests are encouraged to send us a fun photo or video of your time on vacation and to submit a memorable review of you stay to be automatically entered for a chance to win a $100 cash card.

December 2017 Review/Photo of the Month

It’s again time to announce our Monthly “Review/Photo of the Month” winner. Each month we select a memorable guest review or photo to win a $100 cash card.

Our December 2017 winner is the Gansner Family, holiday guests of ours at << PLANTATION TROPICALE >> who submitted an excellent 5-sar review for their stay, and shared a fun photo of the whole group enjoying the home’s spacious outdoor pool area!

The Gansner’s review of their stay at Plantation Tropicale

The family celebrated their holidays ‘Key West’ style this year.

Receiving such a flattering review and seeing these amazing moments of our guests’ vacations reminds us how lucky we are to be doing what we do in such a magical place.

For our future guests, send us a photo or video of your time on vacation and submit your memorable review for your stay to be automatically entered in our Monthly contest for a chance to win a $100 cash card.

Time to Kick Start Key West – Post Hurricane Irma Update

Six weeks have passed since Hurricane Irma showed her ugly face in the Florida Keys, primarily impacting the middle and lower Keys about 20 miles North of Key West. Magically (see more on the mystical Grotto here), Key West was spared from much of the devastation and is now back to normal… which if you know Key West, is not normal at all.

Last week many Key West lovers flocked down to take part in the annual Halloween celebrations known as Fantasy Fest. It was such a fine sight to see so many people enjoying our glorious island again! If you weren’t able to make it to Fantasy Fest, don’t worry: There are a great number of fun events on the calendar for the rest of the year, including next week’s 37th Annual Super Boat Races, where guests can witness exciting power boat races right from the Truman Annex waterfont.

Now that Irma is in our rear-view, we need your help in bringing the activity back to our island! Despite the media’s portrayal of Irma’s impact, Key West was mostly spared – but what is now hitting us the hardest is the misconception that we are not yet open for tourism.  The island opened back up for tourism on October 1 and is back in full swing at this point. If you love Key West, it’s time you escaped all of your worries and took a relaxing vacation to our beautiful island. The weather is literally perfect, the beaches are glistening and you couldn’t pick a better time of year! Support your favorite vacation destination AND do your quality of life a favor by making a plan to spend a few nights, a week, or a month in the Conch Republic!


To make the deal even sweeter, we are offering some AMAZING specials that you will not want to pass up like our Procrastinator’s Discount, Snowbird Special, and Kick Start Key West.  See our specials page for details. Discounts included in online quoting.

Should you have additional questions about the impact of Hurricane Irma, the state of the island or our properties, please do not hesitate to call us directly at 305-292-6266.

Long live the Conch Republic!  #keysstrong