Fall 2018 – 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 vacation homes can be booked for nearly 20% less than the cost of on-season rates!

Fantasy Fest 2018 dates are October 19-28th

Get ready for Fantasy Fest! An experience you have to see to believe, this weeklong event features the Bahama Village Goombay Festival, the Zombie Bike Ride, WomanKind’s BraZaar Presented by Last Key Realty, the Pet Masquerade, the 36th Annual Headdress Ball, the famous Fantasy Fest Parade, and much, much more! Get your most extraordinary costume ready and come join us for a week of Halloween shenanigans! For complete details, check out the official Fantasy Fest website. We still have nightly & weekly rental homes available for the week of Fantasy Fest, including: Villa Cubana, Saltwater Harmony, Gulfside Vistas, Brisa Fresca, and Avalynn House.

Be the first to experience the newest additions to the Last Key rental program this Fall! Our newest homes are fully furnished, fully stocked, and fully equipped with everything you’ll need to enjoy a relaxing vacation in Paradise!



“Southernmost Soul” is a tastefully decorated 2-story townhome in Truman Annex that offers all of the comforts of home – a private pool, off-street parking, and spacious indoor and outdoor living spaces.




“Good Vibrations” is a 4 bedroom, 4.5 bathroom private home with a location that simply cannot be beat, on a quiet lane just half a block from the world-famous Duval Street. This home paired with Last Key Realty’s unrivaled Guest Services will have you feeling those “Good Vibrations” for your entire stay in Paradise!




“Southernmost Palms” is a beautifully renovated 3-story townhome with 2 bedrooms and 2.5 bathrooms, located at The Foundry in Truman Annex. You’ll be just steps from Mallory Square, Duval Street and all of the attractions Old Town, Key West has to offer.




“2 Cool Fish” is a quaint 2 bedroom, 1.5 bathroom townhome located in Truman Annex. This home is tucked away down a quiet pedestrian lane where you’ll have the peace and quiet that comes with a gated community, yet you’ll only be steps away from all of the action of Old Town, Key West.

May 2018 Review/Photo of the Month

It’s that time again… when we announce our Review/Photo of the Month winner. The Greenwood Family, guests of  << VILLA CUBANA >> in May are our $100 cash card winners! They submitted a fantastic review of their week long stay with us, read it below:

The Greenwood Family’s 5 star review from their stay at Villa Cubana.

We thoroughly enjoy reading each of our guest reviews. It’s a humbling reminder of how lucky we are to be able to provide guests with a memorable vacation experience and how lucky we are to live in such a magical place like Key West.

Want to be next month’s Review/Photo of the Month winner? Be sure to 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.

April 2018 Review/Photo of the Month

Each month we receive dozens of fabulous reviews and photos from our guests following their stays with us. We then choose the most memorable review and or photo for that month to win a $100 cash card. Our April 2018 Review/Photo of the Month Winner is Dr. Lentini’s chiropractic group that stayed with us at << THE COMMODORE’S MANOR >> for a long weekend. The group submitted a terrific review and awesome photo from their stay.

This fun group of Chiropractors enjoyed a day of jet skiing on the Gulf during their stay.
5-star review from the group.

We love hearing about our guests’ vacation experiences and seeing these amazing moments. It reminds us how lucky we are to do what we do everyday and to live in such a magical place.

We ask our future guests to send us a photo/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.

A DAY IN CUBA: The newest adventure from Last Key Concierge

Thinking about adding Cuba to your passport stamps, but not ready to make a commitment to an extended vacation just yet?  Our concierge has designed the perfect day trip to add “visit Cuba” to your Key West vacation itinerary, allowing you to get a taste of Havana but returning you to Key West by sunset.

A fully guided exploration through Cuba including Cuban cuisine, historical sites, art…

Wake up in your Last Key vacation home in Key West, hop on your semi-private charter flight to Cuba, spend the day exploring and be back in time to enjoy dinner and drinks on Duval St.

A Day in Havana

TRAVEL:  Your day will begin at 7 AM for check-in at the Key West airport. The flight for Havana departs at 8 AM and takes approximately 50 minutes to fly the 90 miles south.

EXPLORE HEMINGWAY’S ESTATE:  Once you’ve cleared customs, you’ll be met by the local guide and will begin exploring La Finca Vigia (Hemingway’s Country Estate). This is your chance to take a glimpse back in time and see where the famed author withdrew to during his years living between Cuba and Key West – and if you’ve ever visited The Hemingway House in Key West – compare the two monumental properties. Spoiler alert: Hemingway’s famous boat “Pilar” is on site.

LUNCH:  When lunch time rolls around, you’ll take a pleasant ride into the fishing village of Cojimar for a mid-day meal at Ajiaco for an authentic Cuban meal. While here, get a glimpse of the “Hemingway Bust” the village people erected.

EXPLORE OLD HAVANA:  Once you’ve satisfied your appetite, it’s time to explore Old Havana. You’ll have a chance to visit some of Hemingway’s old hangouts: Hotel Ambos, Mundos, La Floridita, the Cathederal, Parque Central, and La Bodeguita del Medio. 

SHOP:  Stop for souvenirs (maybe some authentic Cuban cigars or rum) on your way back to the airport. The returning flight to Key West departs at 5 PM and you’re home by 6 PM.

Ready to experience the Key West and Cuban cultural connection for yourself?  Contact Last Key Concierge – 305.290.2522 to make a reservation or for additional details.

The Insider Guide to Prime Season Key West Vacation Home Booking

The keys to scoring the best Last Key vacation home fit for your prime season stay are: educate yourself on our policies ahead of time, let us help you find a match, and be prepared to secure your rental. For those prime season Key West vacationers who brave the vacation rental market each year, this is your insider’s guide, created for you by our Director of Marketing & Reservations, so that once next year’s dates become available for rental you are ready to pounce on that vacation home you’ve been crushing on.

**Insider Tip** Understanding Right of First Refusal

In order to properly prepare for prime season rentals, it is best to start with the pre-booking policy of Right of First Refusal. We offer the Right of First Refusal to our prime season monthly guests (Jan-April months in relevant homes.) “Right of First Refusal” simply means we try to give current guests the first crack at renting the same home for the same dates the following year before it is made available to the public. Our timeline for this shifts each year, but typically seasonal guests are contacted the December prior to their stays to exercise their bookings for the following season. As an example, in December 2018, guests for season 2019 will be contacted regarding Jan-Apr 2020.

What this means for prime season vacation home shoppers is the day following the right of first refusal deadline is the best opportunity to jump on a reservation for the home you have your sights on. Mark your calendar for the right of first refusal deadline and call our office on that day.

Let Us Help You Find a Match

Our goal is to host you as our guest in the home that fits your needs. Help us do this by thoroughly communicating what you do and do not like about various homes we discuss in the booking process. New homes join our inventory all year long, so the more we know about you and your search, the better. Just in case the home you’ve been eyeing is unavailable, it’s always a good idea to have other homes in mind. Rank your top choices (1-4) and communicate why you do or do not like options we share, and we can best match you with the right home for your dates.

Tour The Home In Person

Although our homes are very true to the photos here on our website, we appreciate that many guests prefer to personally view a home prior to confirming a rental. We are available to walk you through any of our rental homes free of charge, as long as the home is not occupied by guests at that time.

Not able to come tour a home for yourself? We encourage vacation home “shoppers” to take a look at the reviews past guests have entered on our website, on HomeAway/VRBO/AIRBNB listings, and on Google.

Be Prepared to Secure Your Rental

Provide our team with as many details as you can about your needs so that we can best consult on the homes in our inventory that may match your search. On the day that homes become available for rental, be prepared to secure yours by knowing what you need – we require a signed contract and a 50% deposit in order to confirm your reservation. Be ready to sign and put down your deposit to lock in your dates as quickly as possible.

There you have it, the recipe for how to get the vacation home you want! The prime season months always book up the fastest (a year or so in advance) so do not hesitate to make your plans early. Remember we’re always here to help you plan your next Key West adventure – contact us at rentals@lastkeyrealty.com or call our Office at (305) 292-6266 to speak with a reservationist directly.



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

Slow Down, This ain’t the Mainland: Your Guide to Getting Around Key West Without A Car

Getting around Key West isn’t too difficult, after all it is an island. Speed limits are low, people are friendly and you’ll probably see a few bumper stickers with the tagline “Slow Down, this ain’t the mainland.” We’ve come up with a guide – for those vacationing without a vehicle or for those that want to ditch their vehicle – to get you around Key West in the style that best fits your island experience.

Ride A Bike

The quintessential mode of island life transportation is biking. Most streets in Key West have designated bike lanes, making cycle commutes safe and easy. However, be sure to keep your wits about you and watch out for traffic. Key West has a long history of being a bike-friendly community. Many locals take pride in dressing up their “conch cruisers” and rig them with distinct character, flair and fabulousness. Just remember to always use bike lights at night, and to lock up your bike when making a pit stop downtown. Renting a home without parking for a vehicle? Bike racks are located all around Key West, and most LKR vacation homes have designated space for locking up your bicycle when you aren’t out cruising around. If your bike won’t fit nicely in the overhead bin or safely under the seat in front of you, don’t worry, our Concierge Team will be happy to help you secure two wheels during your time in paradise. They can even arrange for bike delivery to your vacation home, so that you won’t have to waste valuable vacation time. Not the most confident on a bike? You can always snag a three-wheeled adult beach cruiser for an easy ride around town, plus these tri-cycles feature ample basket space. This set-up is perfect for a “beverage” run or a quick trip to the local grocer, Faustos, for the essentials.

Hop on a Scooter

There’s nothing like scootin’ around town with your hair blowing in the wind. Driving a scooter is quicker than riding a bike, yet more convenient than driving a car. Key West is very scooter-friendly and scooter/moped parking is a breeze – especially in Old Town. Plus, you really get to see more of the island up close when riding a scooter compared to driving a car. Reserve a scooter for your stay through our Concierge Team, who will offer to shuttle you to your scooter pick-up location.

On Foot

Get your steps in! Nothing is “too far” to walk in Key West. At only 2-miles by 4-miles, walking the entire island can be accomplished in a single day. Walking is a safe option (especially after you’ve hit a few happy hours) and it allows you to soak in and marvel the island’s beautiful architecture.

Ride Sharing

Now that Uber, Lyft, and other Ride Sharing Services have made their way to Key West, enjoy the convenience of a quick ride around town just by using your smartphone. Ride sharing is a great option after hitting the bars on Duval Street or for a prompt fast trip to and from the airport. Ride sharing is the perfect option for reaching locations that may be a bit far for a bike ride or a walk without having to rent a vehicle for your entire stay.

Duval Loop

As of August 31st, Key West will offer a circulator bus ride to your favorite stops on and around Duval Street. Tentatively called the “Duval Loop,” this complimentary bus service consists of a sixteen stop route. The Duval Loop is part of the city’s “Car Free Key West” initiative to eliminate cars and ease congestion in the heart of Old Town Key West. Check out the official Duval Loop website for pickup times and stops.


Pedicabs are three-wheeled vehicles that seat two passengers in a hooded cab behind the driver, who operates it using pedals. You will see them riding up, down, and around Duval Street constantly, and hopping in one to get from one bar or attraction to the next is a relaxing and fun way to get around. It’s also a great way to see the island while letting the pedicab driver do all the work.

July 2017 Review/Photo of the Month

Another month has come and gone, and with it we’ve received a number of excellent reviews and fun photos from our guests from their adventures in Key West. Each month we select one of these memorable guest reviews and/or photos to win a $100 cash card.

Our July 2017 winner is The Bakewell Family who stayed with us at :: LA BONNE VIE :: and submitted an excellent 5-star review and shared fun photos of their vacation in Key West!















We love seeing photos of our guests enjoying their vacations and receiving feedback about the properties they stayed in and the service they received.

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

June 2017 Review/Photo of the Month

Each month we choose our favorite guest Review and/or Photo submission received during that month to win a $100 cash card. Our June 2017 winner is the Shepherd Family who stayed with us at :: VILLA CUBANA :: and submitted an outstanding 5 star review, as well as shared some lovely photos of their time in Key West with us! It looks like they got to enjoy some time on the water…

Villa Cubana Guests Last Key Realty Guests

Last Key Realty Guest Photo

Seeing these amazing moments of our guests’ vacations just reminds us how lucky we are to be doing 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. July’s winner might be you!

Neighborhoods of Key West

The Southernmost City of the U.S. is a 2 by 4-mile island, which features distinct neighborhoods that offer their own unique personalities and charm. While the island is very small, where you stay during your time here plays a huge role in shaping your Key West experience.  Knowing more about the various neighborhoods on the island will help you to choose the best fit for your family or group.  Read on to get a feel for which Key West neighborhood is right for you.


Historic Old Town

Old Town Key West is the heart of the island and is widely considered by visitors to be the most desirable neighborhood. The world famous Duval Street runs right through the center of Old Town. Here, you’ll find many of Key West’s top restaurants and attractions. If you want to experience what it’s like to really live in the “Conch Republic”, Old Town is where you’ll want to be.

Recommended for groups and families who want to be close to the vivacious nightlife, bars, restaurants and attractions of Key West. Groups looking to ride scooters, bike or walk as their main mode of transportation are perfect for Old Town, as parking is often limited. Enjoy being near the best restaurants, close to beautiful historic architecture and the Historic Seaport.


Truman Annex

Truman Annex is an exclusive gated community on the ocean and in the heart of Old Town. President Harry Truman spent his winters here at his home, famously known as “The Little White House” and often joked about relocating America’s Capital to Key West. In Truman Annex, you’ll find impeccably maintained grounds, white picket fences alongside quiet streets and sidewalks. It’s a quieter part of Old Town, but still within walking distance to Duval Street and many downtown restaurants and attractions. Truman Annex is appealing for both its Key West charm and modern comforts. Just out the gate towards the ocean is Fort Zachary Taylor State Park, featuring one of the nicest beaches on the island.

Recommended for groups and families that want to spend a week or longer in a vacation home that is close to Duval Street, yet “away from it all”. Truman Annex is a desirable quiet residence where you are just a couple minutes from Duval Street, the center of downtown, and the Mallory Square Sunset Celebration. However, if you’re a group coming to Key West for the party atmosphere, this may not be the best location for you. This neighborhood closely monitors noise and security issues in order to keep the community nice and quiet for residents.


Smathers Beach

Even though Key West is an island, a common misconception is that there is plenty of beachfront property. In reality, there are not many beachfront properties in Key West, as much of the beachfront land is either public beach, Navy land, or hotels. The primary beachfront property in Key West is located near Smathers Beach. Smathers Beach is one of four beaches in Key West, and is located on the north Atlantic Ocean side of the island. The Smathers Beach neighborhood is home to the Key West International Airport, as well as a handful of restaurants and attractions. The accommodations in this area include multiple hotel options, private homes, condos and apartment complexes. The majority of our properties in this neighborhood are located at The 1800 Atlantic Condominium Complex and at The Key West Beach Club.


The 1800 Atlantic Condominium Complex is an upscale private community featuring picturesque balcony views, modern amenities and is located within a short bike or Uber ride to many favorite Key West sites. The residence offers a Resort-Style Community Pool, an oversized Jacuzzi, a cabana with restrooms, picnic tables and BBQ grills. When you stay at 1800 Atlantic you have direct beach access and are steps away from Smathers Beach which is located around the corner.

The Key West Beach Club is a quiet residential condominium complex located right on the Atlantic Ocean. This property offers two pools, a fitness center and incredible ocean views. It is in a great location, perfect for biking or walking to town and to restaurants.

Recommended for groups and families who love the beach, sun, value great views, and dig modern amenities. This quiet tropical paradise is perfect for R&R, in a great location that avoids downtown noise. You will only be a short bike or Uber ride from all the action of Old Town.


Casa Marina/Casa East

The Casa Marina neighborhood is the southern area of the island running along the Atlantic Ocean. This neighborhood is close to Old Town, but is not technically considered “Old Town” by those who apply that definition strictly. This unique area is laidback, quiet, and beautiful. At Casa Marina, you will enjoy exclusivity – a quiet residential feel with generally larger homes. They often feature more spacious properties than in Old Town. Dog lovers will also love this area for the “Dog Beach” and for the popular community dog park.

Recommended for groups and families looking for a quiet residential neighborhood with spacious homes on typically larger lots all located just a quick bike ride or walk to Higgs beach / White Street Pier and a short Uber ride to Duval.


MidTown/New Town

MidTown/New Town is a neighborhood primarily known as home to many locals, although you will find plenty of shopping centers, grocery stores, restaurants, etc. Several canals allow access to open water, something you won’t find – except at the marinas – in any other part of Key West. Over the years, homeowners have updated and renovated these sometimes larger Mid-Century homes which are now upscale villas featuring private pools, larger lots, and private gardens. 20 minutes in a scooter or car gets you to the heart of Old Town.

Recommended for groups and families who have a boat and desire canal access. Great for those interested in homes that can be a little larger offering ample parking, larger properties and are away from the busy streets of Old Town. Not recommended for those looking to stick strictly to walking, as many of the homes in these areas require a car ride to get downtown.


Stock Island

Stock Island is located just outside the entrance to Key West and is what you may consider a ‘suburb’ of the main island. It is quickly growing with residential areas and commercial businesses, including many fishing and water adventure companies. Many of our rentals in this neighborhood have the perk of being near the water, whether that is on a canal or with a view of the Gulf or Ocean.

Sunset Marina is private condo complex is about 5 miles from Old Town directly on the Florida Bay. This gated community has a large community pool, a clubhouse and boat slips. All of these two and three-bedroom condos feature balconies with direct water views. The condos are available for monthly rental, many with their own boat slips. If you are renting for a month or more, and don’t mind a 10-minute Uber ride or 20-minute bike ride into town, this quiet, gated, waterfront community is the right place for you.

Recommended for nautical focused groups who have a boat and want to rent a slip. Sunset Marina is great for fishing enthusiasts, couples and families who like peace and quiet, boating, and amazing sunset views from your own private balcony.

The Key West Golf Club sits right at the entrance to Key West. This planned gated community offers 24-hour security, with tropical town homes and private residences surrounding an 18-hole 6500-yard Rees Jones golf course. Enjoy one of the largest resort-style pools in Key West and a fitness room. The Key West Golf Club area has an inviting, polished, suburb vibe.

Recommended for groups and families seeking a quiet neighborhood and don’t mind being a 10-15 minute drive or Uber ride from Old Town. This area is ideal for golf enthusiasts and vacationers who enjoy the quiet and local feeling of a less commercialized area.