Preferred Properties Key West

Experiencia fantástica: What a wonderful month we had in Key West staying at Corazón. The home is lovely warm cozy has everything you need and more. Property managers are always available if there’s any questions or issues and they are amazing. Can’t wait till next year.

Experiencia fantástica: We couldn’t have asked for a better stay at 527 Fleming Street. The house itself is fantastic, but the private backyard and pool truly set it apart. Having our own secluded, tropical pool area to cool off and unwind in complete privacy made the trip feel like a true retreat. A special shoutout to the property team, too—we ran into a minor maintenance issue during our stay, and they addressed it immediately without missing a beat. They even brought us a fresh propane tank for the grill so we could cook dinner outside and enjoy an evening around the pool, which was a huge highlight of our trip. The location in Old Town is practically unbeatable: Duval Street: Just a quick, easy stroll away. You’re close enough to enjoy all the action, dining, and nightlife in minutes, but far enough off the main drag that the house stays peaceful and quiet at night. Provisions: Having Fausto’s Food Palace directly across the street was an absolute game-changer. Grabbing grilling supplies, drinks, and pool snacks took under two minutes—no car or long trek needed. Dining: You can't beat having Café Marquesa right across the street. We had an incredible dinner there—easily one of the best meals on the island. Definitely book a reservation in advance! Clean, comfortable, perfectly situated, and backed by attentive hosts. We would book this property again in a heartbeat!

Experiencia fantástica: We recently stayed at Jasmine Place for a vacation. The location is terrific, an easy bike ride or walk to most Old Town locations. The house is very clean and comfortable and has everything you need. The backyard pool is delightful. We will be back again next year!

Experiencia fantástica: This is our third time staying in the Conch Cabin. We absolutely love it! It is perfect for a couples getaway and enjoyed staying for our 34th anniversary! We walked to everything. Perfect long anniversary weekend!

Experiencia fantástica: Wonderful place to stay! Close to everything you want to do in Key West!!!

Experiencia fantástica: We throughly enjoyed our vacation here. Your place is absolutely beautiful. Very welcoming and immaculate. The pool was truly enjoyable. We highly recommend this property. Thank you so much!

Experiencia fantástica: We had such a great stay here at the Airbnb on Fleming Street. It could not be a better location and in the home offers great amenities. Would highly recommend this property. The property is immaculate and super comfortable.

Experiencia fantástica: Our rental was beautiful, very clean and everything advertised! The management company was very responsive and professional.

Experiencia fantástica: Excellent location just a block off of Duvall Street. Perfect size cottage for 2 people. Staff was accommodating with every need. We would stay there again. Highly recommended!!!

Experiencia fantástica: Everything about this property was awesome. The location, the layout, and the staff, made for great trip to Key West. Will definitely book again.

Experiencia fantástica: The house was clean, comfortable, and well furnished. The host was vey helpful. Lovely pool and easy walking distance to many Key West attractions. MoonDog cafe just down the street is great. Would book this place again!

Experiencia fantástica: Very nice, clean, comfortable townhome and lush property. Great location; walkable to many restaurants and shops.

Experiencia fantástica: Wonderful stay at Shady Palms. Private pool was exquisite. Very clean and comfortable. Lighting and plantings were beautiful. Highly recommend!!!

Experiencia fantástica: The property was clean and perfect for us inside and out. We spent most afternoons by or in the pool, and nearly every evening we spent some time on the balcony. The off street parking was a big plus. We like to walk to the various attractions in Old Town, and this location was the best of any place we've stayed in the past. The host, Angela, was totally on top of everything we needed throughout our stay. We had a wonderful vacation, and this property was a big reason why. We definitely will be back next year!

Experiencia fantástica: We had a wonderful time staying at this fantastic property! It is in a great location, and Preferred Properties was attentive to all of our needs! I would highly recommend this company and property to anyone looking to rent in Key West!

Experiencia fantástica: Great stay at Island Pearls. Wonderful home with a beautiful interior. 2 masters with modern kitchen. Lounging in the pool made for a relaxing end of the day. Preferred Properties was a pleasure to deal with. Immediate response to the one and only issue we had was impressive. Their commitment to customer satisfaction was obvious. Wouldn’t hesitate to book with them again.

Experiencia negativa: DO NOT RENT FROM THIS PROPERTY MANAGEMENT COMPANY. Beware, they do not honor their rental contracts. Paid a deposit and had a contract for a week long rental in Key West for our Anniversary. Flights and rental car booked, then they abruptly cancelled the reservation and said the property was no longer for rent that week, but relisted it at ALMOST TWICE THE PRICE for the exact same dates. Complete lack of integrity and selfish greed.

Experiencia fantástica: Loved this place. Close to everything and private.

Experiencia fantástica: Everything about this cozy little cottage was meticulously done. Absolutely perfect for a romantic retreat for two! The communication from the property manager was fantastic, answered all of my questions along the way. This is everything anybody could ever hope for when traveling. Fantastic lodging, Responsive post, Great experience!

Experiencia fantástica: Beautiful home with great location! We had a great week of relaxing, touring and decompressing here with a perfect set up for 4 people!

Experiencia fantástica: Very easy to deal with. Friendly and professional.

Experiencia fantástica: Preferred Properties KW is our go-to for vacationing in Key West. Angela is very helpful and quick to answer any questions or concerns we have. The houses and cottages that Preferred Properties has in their inventory always meet our needs and exceed our expectations.

Experiencia fantástica: Lovely property, Amenities were very nice, terrific location, An amazing vacation retreat. Quiet except for the few days of construction at a neighboring condo. I will definitely want to return.

Experiencia fantástica: Wonderful house in a great location.

Experiencia fantástica: Property management was very good. The rental is next door to their Key West location. The best thing about the rental is that it is extremely private even though you're on the heart of the Key West action. Property was clean and exactly as described. Parking spot was great, but grocery and drug stores were minutes away by foot. Would definitely consider renting it again.

Experiencia fantástica: We stayed at the Island Pearls, and had a lovely time. The "cottage" is beautiful! The owners have spared no expense in renovations and upscale appliances and furnishings. It is so private and yet so convenient to all the happenings. We can't wait to come back!

Experiencia negativa: Rented a lovely home in Key West the month of December. Honestly, Preferred Properties was a good and responsive management company UNTIL we checked out and discovered what our utility charges were. Initially we were told that our $670 utility deposit would only be used if the actual charges were above normal/usual averages. Well as it turns out that average ($135) didn't cover us and we were charged an additional $193. Crazy right? Just two people in a small house (way less than 1,000 square feet) and they say we went over the normal/usual averages. Furthermore, it was December and the outside temperature never got hot. I can only assume this is a money-maker for these guys so beware your deposit may turn into their profit!

Experiencia fantástica: Our stay at Island Pearl was fantastic! Great location and walking distance to all things. Beautifully done inside, modern and plenty of room for 4 people to move around and relax comfortably. Outdoor area is cute and the pool is nice for cooling off. Would definitely stay here again. Highly recommend this property.

Experiencia fantástica: We stayed at Green Goddess for our wedding and couldn’t have been happier! We could tell it was important to Preferred Properties that our stay be enjoyable, and when we ran into a hiccup or two they went above and beyond to make our stay comfortable and aligned to our vision for the week.

Experiencia fantástica: I have been renting houses in Key West for a long time and Peachy Keen is truly one of the best! It is minutes from Green Parrot and Blue Heaven. I could walk everywhere easily so I left my car parked in the driveway. The house had a beautiful pool and lots of space for everyone to spread out. It was equipped with everything we needed for a month stay. The property managers were outstanding. They responded quickly to anything we needed. Phil was exceptional along with Angela and John. I hope that I can rent this property next year! Thanks for everything!

Experiencia fantástica: I’m a repeat customer and love working with this company! My rental is always clean & beautiful and the service keeps me coming back! Thanks to the team at Preferred Properties Key West!

Experiencia negativa: HORRIBLE MANAGEMENT COMPANY. LITERALLY DID NOTHING WHEN THE ENTIRE HOUSE VIBRATED FROM EAR SPLITTING MACHINE NOISE DAY AFTER DAY FROM A NEIGHBOR. WE MOVED OUT AFTER OUR COMPLAINTS WERE IGNORED AND WE CURRENTLY HAVE HIRED A FLORIDA ATTORNEY TO SUE THEM AND THE RENTAL OWNER FOR DAMAGES EXCEEDING $50,000 AND THEY ARE STILL TRYING TO COLLECT ONE MONTH'S RENT FROM US. HORRIBLE HUMANS.. LOOK ELSEWHERE!!!

Experiencia fantástica: We stayed in the Conch Cottage, this is a great property in the middle of everything in Key West! Would definitely stay again! House was clean and had everything we needed to make the trip memorable! There is limited street parking but is located only about 15min walk from paid parking.

Experiencia fantástica: Thank you Frank and Laurie! I so appreciate your knowledge, professionalism and patience (I may have toured 200 properties ). I could not be happier with the outcome - love this house, happy to be in my happy place. Your guidance was invaluable and I thank you for continuing to check in on me post-transaction. ☀️

Experiencia positiva: Not exactly ideal sleeping quarters with having to climb a ladder to get to the fairly uncomfortable bed. Woke up with a sore back every morning. Fridge is tiny and can’t fit a bag of ice in freezer. The only amenity worth noting was the pool, it was wonderful after a hot day of walking around! Be very careful of the rotten wood on the deck! Splinter city!! This place is definitely not for people in their 50’s but would probably work for younger people in their 20’s!

Experiencia fantástica: Love Such a lovely home Perfectly located, waking distance to everything We had an amazing time here Highly recommend!

Experiencia fantástica: We had a wonderful stay at Jasmine Place. Perfect location to everything. The pool was so nice to relax in after being in the hot sun. We walked to breakfast each day - Moon Dog or Banana Cafe. Loved having a driving for our car and golf cart. We will come back for sure!

Experiencia fantástica: We often visit the Florida Keys and this is the best place we have ever stayed at in terms of location and amenities. This is a beautiful home , just blocks away from Key West main attractions including Mallory square and Duval st. The Beach at Fort Zachary (hidden gem) is just about 10 minutes away!

Experiencia fantástica: Great customer service! Really enjoyed our stay and definitely will use Preferred Properties again.

Experiencia fantástica: Excellent communication regarding the property. Was so helpful with scheduling activities! Will definitely use Preferred Properties for our next visit to Key West.

Experiencia fantástica: We stayed at Love is in the Air for 5 weeks (end of Sept to beginning of Nov 2022). Everything was great! The house, the pool, the location.......we had absolutely NO complaints! Whenever we did have questions, we had easy access to Preferred Properties. Thank you Preferred for making our stay wonderful!

Experiencia fantástica: Pineapple Cottage was amazing! It had everything we needed for the week. The pool was wonderful and very private! Preferred properties was great to deal with and very helpful! We’ll definitely be back!

Experiencia fantástica: Beautiful house, great location. You have a lot of privacy but it is close to EVERYTHING you want to do in Key West! Grocery store is one block away. Staff at rental agency are very helpful and pleasant to deal with. We couldn’t have asked for more. Thank you!!

Experiencia fantástica: I’ve been coming to Key West for 40 years and this is the first property that was perfection. From start to finish, the experience that my husband and I had, was truly amazing. The property manager was helpful and thoughtful, and communicating with them was effortless. The unit itself was nicely appointed and spotless. Every detail was thought of. The outdoor area was an oasis away from the hustle and bustle of Duval. So if this property remains a rental, we have found our go to place!

Experiencia fantástica: We absolutely loved this house…especially the outside shower! The location was perfect. We walked everywhere. I highly recommend checking it out!!!

Experiencia positiva: Cozy little place on Simonton called Conch Cottage about a half mile from the southern most point & half mile from the north marina & a couple blocks from Duval where all the action is. We mostly walked & an Uber was typically just over $10. The outside shower is private & had better water pressure than the indoor one & the hot tub was a great way to unwind during the day. There isn’t parking available at the Conch Cottage & public parking runs $4 per hour, so you may want to consider that if you plan on bringing a vehicle. The area is very walkable with plenty of bike, scooter & golf cart rentals nearby.

Experiencia fantástica: Excellent experience. Elizabeth secret was beautiful. We enjoyed the pool every day after walking around in the hot weather. Excellent communication from the perfered property. Question were answered very fast definitely recommend

Experiencia fantástica: We truly enjoyed our stay at Jasmine Place. The pictures provided online are exactly what the house and property look like. The location is perfect for anyone wanting to explore Key West. The home is very close to historical sights like the Hemingway House (next door), the Lighthouse (across the street), and Truman’s Little White House. It is also within walking distance of some excellent eateries and watering holes like Blue Heaven, Rams Head, Hogs Breath Saloon, and Papa’s Pilar Rum Distillery. We really appreciated the pool after our long days of exploring and shopping. The pool was well maintained and there was plenty of lounge seating. Preferred Properties was kind, friendly, and responsive to our texts and inquiries. These accommodations were perfect for our Key West adventure and we highly recommend Jasmine Place. We plan on staying here again!

Experiencia fantástica: This was our third time at the Conch Cottage, a beautiful 1-bedroom cottage with a wonderful and private outdoor patio. Everything we could ask for in a central, historic Key West location. Cottage is well-maintained and very clean. The folks at Preferred Properties are fantastic to deal with and always immediately responsive. We can't wait to return!

Experiencia fantástica: We've been with Preferred Properties for over 20 years. They're the best.

Experiencia fantástica: Preferred Properties is a locally owned, full service real estate company. Vacation Rentals, Home Sales, Long-term rentals, commercial properties, absentee owner management. They will get it done!

Experiencia fantástica: Anytime I come to Key West I always try and book with Preferred Properties. They have some of the most beautiful rentals in some of the best locations. The Pineapple Cottage is my absolute favorite. It's located down a quiet little secluded street but still walking distance to all the fun of Duval Street. The staff are so friendly and accomodating. I can't recommend them enough! Looking forward to my next trip!

Experiencia fantástica: Was lucky enough to stay with Preferred Properties a while back and what a treat it was. With things hopefully on the right path back to normal can't wait to stay with them again!

Experiencia negativa: I strongly recommend staying away from this rental property group. Unfortunately, We had a member of our party catch Covid-19 and we thought it would be best to cancel to help protect others in the keys and not take a chance to get anyone sick or even spread germs at the rental. Please be advised our trip was still 20 days out and within the cancellation policy. Upon conversation with the management group, which was handled extremally poorly. We explained the situation and Preferred Properties cancelled us without a refund of our trip OR even a chance to re-book for another time. This is an action of theft. As someone that personally works in the hospitality industry and deals with a high volume of bookings, you would think they would accommodate any guest within the proper cancellation time frame. Instead, they kept our money and said "oh well" During a Global Pandemic - especially from another person from another area of Florida, you should be ashamed of yourself of the way business is practiced here. You stole from us and you know it. We would appreciate if you call us to make things right. I will be writing a letter to city of Monroe county explaining this situation.

Experiencia negativa: We had an exciting trip planned to the keys and someone in our group caught the global pandemic virus. We thought it would be best to not travel and we were not refunded. Please tell me how this makes sense? I guess we were wrong? By doing right thing? I advise to not book here. Simple as that.

Experiencia fantástica: Stayed at one of their properties in Old Town for a week with my parents. Had an absolute wonderful time - the house was perfect and had everything we needed. We barely had to leave! Angela was extremely responsive and helpful - especially with navigating potenital travel restrictions, etc. Will be booking direct with them again soon!

Experiencia fantástica: If you want a memorable experience while in Key West, trust the staff here to go above and beyond to find you the perfect accommodations.

Experiencia fantástica: Worked with us for over 20 years. Great people AND they are very philanthropic in our community!❤️❤️

Experiencia fantástica: Great people, lovely homes.

Experiencia fantástica: I rented a house in key west, old town, from these folks... first house I've rented... premium experience. Way beyond a rental... Angela... told me she was my concierge too... and I tested her several times.. needing simple referrals for local eateries to making arrangements for a golf cart rental... as well as finding last minute seats on a sold out seaplane excursion (per the website)... like a friend... nothing less.

Experiencia fantástica: Found a property on VRBO which disappeared when I went to book it but found it here!! Renting Jasmine Place for our wedding week was beyond easy and Angela was awesome! We even stopped at their office a few months prior to our stay just to make sure they were “legit” as only used vrbo and Airbnb before. They were more than legitimate and beyond helpful!! We didn’t have an appointment and they sat us down and showed us our rental and answered any questions we had. Property was clean and was glad to have a texting number if we needed anything during our stay. I cannot wait to go back and use Preferred Properties again! Thank you guys for making our wedding week stay wonderful!!

Experiencia fantástica: Frank Kirwin's gentle tenacity over the years in showing us real estate finally paid off in the form of a wonderful condo with a gorgeous Key West sunset view each evening! Frank was always a pleasure to deal with, and he kept all of us on our toes during the closing process so that everything went off without a hitch. Many times, Frank went above and beyond the call of duty to make sure our transaction was a smooth one. Not an easy thing to do when the buyers (us) were in Chicago, and the seller was in South Dakota.

Experiencia fantástica: Frank Kirwin sold two family properties each of which had several owners in the past several years. One of the properties had been in the family since 1938, and the sale was emotional for all. Frank was calm, patient, and negotiated with care for all. We got the price we had agreed we wanted, and the process was smooth. We all left the table feeling that we had accomplished a lot for the family, the houses, and the neighborhood, all of which were important things to us. I cannot recommend Frank highly enough for his expertise in real estate, his knowledge of the community, and his great concern for both buyers and sellers. I would certainly recommend Frank, and he is the only real estate person I would use in Key West.

Experiencia fantástica: Frank Kirwin has handled our rental property for several years. He is always responsive and reliable. He has handled everything from getting our tenants in to occasionally getting a tenant out. Frank is easy to work with and keeps us informed about any issues that arise. We appreciate and value his efforts on our behalf.

Experiencia fantástica: My husband and I have known Frank Kirwin for many years, first as fishing captain, then as a realtor. Frank has the patience of a saint and worked side by side with us over the last three years to help us find our 'final dream home' as well as sell our existing home here in town. Settlement went without a hitch on both properties and we are happily settled in to our new home. Couldn't be more pleased.

Experiencia fantástica: The Preferred Properties team has managed the home we rented for the past two years and during this time any maintenance issues were handled quickly and properly. When we began searching for a home to purchase, Angela McChesney went above and beyond to find our perfect home. Through closing she was always available to discuss our questions and concerns. We are very happy with both our leasing and sales experiences with Preferred Properties.

Experiencia fantástica: Have owned many homes and rental properties over the past 40 years but Preferred Properties Key West and realtor Corry Held exceeded not only all previous experiences but all my expectations. Ms Held's knowledge of the market, dedication to detail and follow up are second to none. From my experience I wasn't surprised when Ms Held was named realtor of the year for 2015.

Experiencia fantástica: I have bought and sold several properties with Cory Held and Jeffrey Grosky over the past six years and every transaction has always been handled very professionally. They also have a knack for making sure it's all done in a pleasant, friendly way too. These guys really know their stuff, nothing is too much trouble. I would have no hesitation in recommending them to anyone.

Experiencia fantástica: I originally contact Preferred Properties and Angela McChesney based on their reputations. Having her by my side was a plus as she is extremely knowledgeable about the Florida Keys market and her experience showed. It took me almost a year to find my perfect first home. Buying a house can be extremely frustrating. I don’t think I really understood the full process of what it took until I watched Angela smoothly navigate me though the varying paths of this journey from beginning til end. She was always available to see homes on short notice, gave me good advice (without being pushy) and always understood what I was in the market for. With so many online resources available, there is no excuse for not doing your research. Hiring the best agent and agency who knows the market and the neighborhood whether buying or selling your home is a plus and Preferred Properties (and Angela) is that and more.

Experiencia fantástica: We bought our first business with the help of Preferred Properties. They ease the process of an otherwise stressful endeavor. Our realtor was Angela McChesney, and she was absolutely wonderful!. She constantly followed up on items and helped us stay on track, along with the bank and seller. We never had to worry that something was slipping through the cracks on her end. She worked hard to get the job done and was extremely responsive and easy to work with. We look forward to using her services in the future!

Experiencia fantástica: Captain Frank Kirwin worked with us for several months to find the perfect home for our family. We couldn't have asked for better in our experience moving to Key West. Loved them so much that once we settled in I decided to join Preferred Properties Key West as one of their own Sales Associates. One Human Family (This is it)

Experiencia fantástica: Angela McChesney and Preferred Properties could not have been more professional and easy to work with. Angela took all the stress out of purchasing my home. I can't explain how grateful I am for her hard work and persistence during the entire process. Highly Recommended.

Experiencia negativa: Not recommended!!! Very poor occupancy rate--less than 20%, poor house-keeping staff--unable to operate W/D without damaging, hidden fees--cleaning outside entry, a 6x6 ft area, $35.00--owners charged the credit card fee when guests paid with a credit card, etc etc etc even though they collected 29%. There are better rental agents in Key West. Watch out!!!!

Experiencia negativa: STAY AWAY!!!!! Al leader is like a used car salesman!!! He will sell you a house and make you all kinds of promises and when you ask him for them he can't seem to make them happen. Al and Preferred Properties were also my property managers. I bought a separate warranty on my home for any repairs that may need to be made. Al was to contact me if something would go wrong with the house so I could call my warranty company and get it fixed. Well!!!! Al evidently could not remember that so he would get it fixed and I would be stuck with the entire bill. The warranty company would not reimburse me because they were not notified. There were many other problems that I had with his lack of professionalism. I contacted Laurie McChesney, THE OWNER, and tried to cancel my rental agreement because of all the problems I had. I had been with Preferred Properties for about 17 months. There was about 6-7 months left on my contract when I asked to cancel. I explained to Laurie McChesney all of the problems I had. She told me Al was meaning well and that I could cancel the contract but, I still had to pay them their 15% fee. I tried to contact Laurie McChesney, THE OWNER, many times. She would not return my calls!!! Not VERY PROFESSIONAL!!! I could go on and on but it is long now.