Key West Real Estate Success Stories 3

We’re not in Springfield anymore…

We’ve had such positive feedback with our Success Stories Series that we had to keep the love going!  For those just finding our little blog, we’ve decided to showcase a few success stories from our happy Key West real estate clients turned Key West vacation rental homeowners.  We’re hoping to inspire you to take that step you’ve contemplated how many times now when you see that others have successfully achieved this dream.  The same dream you’ve had.  No matter your reason, the time to invest in Key West real estate, and capitalize on this booming industry, is now. Still not convinced?  Read on…

For our latest success story, we look at The Simpson Family:

The Simpson Family + Key West = Love at First Sight

The Simpsons fell in love with Key West on their New Year’s 2018 vacation. The family stayed in a luxury property (check out Good Vibrations!) managed by us, Last Key Realty. They were so impressed with the quality of the property and the level of guest services received that they began considering an investment property for themselves. The Simpsons needed a home that would house their large family and could also be rented when they weren’t using it. The family knew what they were hunting for. Now they just had to find it.

Photo of Key West real estate property named Good Vibrations. The living space features color matching couch and two chairs, a television mounted to the wall, and four chairs at a dining room table.
The Simpsons stayed at Good Vibrations in 2018 – still a guest favorite today!

Fast forward a year later, they were under contract on a beautiful newly built 5 bedroom home in Old Town. Thanks to the help of Last Key’s very own Rodney Culiver. Rodney helped guide the Simpsons through the entire buying process. Educating them on the vacation rental market, providing rental income projections for the homes on their shortlist, and negotiating a favorable deal below the asking price. The house they bought was 317 Angela Street, better known as Envy of The Island, a monthly vacation rental home that checked ALL of their boxes.

Success Through Adversity and Change

The Simpsons couldn’t have been happier with their decision to “get in” when they did. In the first year of ownership, Envy of The Island rented 10 out of 12 months and generated over $100k in gross rental income. The Simpsons were happy homeowners. When COVID happened, there was a huge question mark hanging over the future of vacation rentals. Which prompted the Simpsons to sell their beautiful rental home after only a year and a half of ownership. Who better to list it than their go-to Key West Real Estate guru, Rodney?

Photo of an outdoor pool at a residence in Key West, Florida. The rectangular pool is in the foreground which leads into the background that shows the open floor plan of a porch and living room area of the main house.
Envy of the Island – The Simpsons’ first Key West real estate purchase with Last Key Realty

Within a few months, the home was sold at a price well above what they had paid just 18 months before. One caveat of Rodney selling their beloved Key West investment home was that he promised to help them find a new Key West investment property when they were ready. It didn’t take long for them to be prepared to purchase a new property. (On a sidebar, the new owners of Envy of The Island purchased the home and left it in our rental program; with their house’s booming success, they’re delighted they did!)

Key West Real Estate Success Round Two

Back to the Simpsons… The following spring, the search began for their next Key West real estate investment property. Rodney guided the Simpsons through the buying process. He helped them land a property that met the needs of their large family and one that offered monthly vacation rental potential. Shortly after closing on their new home, located at 2718 Harris Ave, it was ready for monthly vacation rental. And so, Island Opulence was born. Today, the Simpsons are once again happy homeowners of a successful vacation rental home. And Last Key is grateful to have played such a prominent role in making their Key West investment dreams come true.

Photo of the front of a Key West real estate property. The angle is several feet back from the main entrance, there is a stone path that leads up to the house, and is framed on the right and left by lawn and palm trees.
Island Opulence – One of Last Key’s largest luxury monthly rentals!

This success story spanned 3 years, across 3 transactions and lots of rental income and equity made along the way. It just shows how sound an investment Key West Real Estate is. Who better to help facilitate that investment purchase than Last Key Realty? From purchase to renting, the Last Key Realty team is with you every step of the way. Call Last Key Realty today and speak with one of our talented real estate agents at 305-292-6266.

Key West Real Estate Success Stories #2

Investing in Key West & Don’t It Feel Good!

Christie came to Key West and was walking on Sunshine in no time…

It was a warm summer evening, the refreshing breeze rolled off the Atlantic as Christie took in the breathtaking view from Neptune’s Penthouse, a condo managed by Last Key Realty in the 1800 Atlantic building. Christie had come to Key West to enjoy some fun in the sun and to look at real estate around the island. Upon seeing this stunning view she knew that 1800 Atlantic is where she wanted to be.

A wide angle picture of a condo's porch in Key West. A table and chairs are in the foreground, and the view looks out to the ocean.
The view from Neptune’s Penthouse…

A Tailored Approach to Key West Real Estate

While the purpose of Christie’s visit to Key West was to find a piece of property that she could use for both investment purposes and her family’s personal use, she could not have found her condo without the help of Last Key’s Andrea Leskova Otava, a fresh-faced Realtor at the time. Andrea’s expertise in the vacation rental Real Estate market paved the way for Christie to confidently pursue, and ultimately purchase, her Key West investment condo.

Prior to Christie’s arrival in town, her and Andrea had a few conversations about the tricky Key West Real Estate market. They determined what Christie’s investment goals were and how Last Key could help her achieve those financial goals. Andrea helped Christie narrow down her search to a few choice properties with a transient license. This included an available unit at 1800 Atlantic.

Picture of a condo living room in Key West, Florida. A flat screen television on the left handside above a cupboard and on the right are a brown chair and a white couch.
The living area of Christie’s unit, Walking on Sunshine

The first property they looked at turned out to be the only one Christie needed to see. “When I saw the view, I was sold.” 2 days later, they were under contract on the condo that would become known as Walking on Sunshine.

Over the years Andrea and Christie’s relationship has grown. Andrea has even recently helped Christie acquire her second investment property at 1800 Atlantic. “I love working with Christie,” Andrea said with a big smile. “I had the pleasure of meeting her kids and her parents too. I love seeing a family come together to work on a property.”  Christie’s new penthouse unit will surely be another jewel in Last Key’s collection!

The stunning view from Walking on Sunshine!

You can be Last Key’s next Success Story! Reach out to us at 305-292-6266 to speak with one of our knowledgeable and friendly agents today.

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.

Key West Real Estate Success Stories #1

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.