My family and I rented a home in Key West over the holidays. First of all, the house was nothing…read moreshort of outstanding! Everything was perfect...the house itself was gorgeous, the location was ideal, and the personal service we received from the staff at Vacation Homes of Key West was nothing short of amazing! We were so well cared for, and we could not possibly have asked for a better experience. Among other wonderful things I could say about the house, the kitchen stands out in particular. Some rental houses have the bare minimum when it comes to pots, pans and cooking utensils. Not this house! We had everything we needed to make excellent meals. And, of course, the pool was a wonderful extra...even though the beach is only a block away, we enjoyed the pool every day! Oh, and one more thing...the outdoor shower! That's the only place we showered for our entire stay. So fun! When we come back to Key West, we will rent again from Vacation Homes of Key West. In fact, we wouldn't want to go anywhere else! Thanks again to the staff. We love you!

We got 4 bedrooms house rented for 5 night. We use it for our work visit to Key West. We search the…read moreentire area during the winter time in Key West is expansive if we have each room for person. The house renting make sense for cost and close proximity in downtown and a street away the Duval. Pro One spot parking assign to a house. 4 individuals bedrooms, two kitchen, one swimming pool, courtyard, secure entry way. It is affordable during high season. Con The shower room cannot be open in one of bedrooms. The problem reported but they cannot fix till we move out 5 days later. The security alarm across the street court house sound every night. They cannot do about it. Carpet is a bit dirty in some room. We have to take the garbage out when we vacated with we paid extra for the cleaning fees. The best thing of this location is located right at the mile marker zero of US1. Very close to downtown for food. Central location for attractions.

Been renting from last key for years. We rent expensive, luxury homes and they come through with…read moreEVERY request. Well worth it. Rodney is your person.

If I could put 0 stars... I would…read more Aggressive, unprofessional, and completely unacceptable management. We stayed here during Fantasy Fest, paying over $10,000 for what was supposed to be a premium property -- instead, it turned into a nightmare. There was major construction directly across the street that we were never informed about, waking us up every morning at 7 AM and blocking our entrance with work vehicles. Their excessive power use caused multiple electrical outages, forcing us to relocate our staff for an entire day. We reached out to Alina, our assigned representative, multiple times and never received a single call back -- there was zero communication the entire stay. Then on checkout morning, exactly at 10:00 AM, Alena, the property manager, stormed into the home unannounced, banging on every door like she was the police, yelling for us to get up, and threatening to call law enforcement. She was extremely aggressive and confrontational, giving major attitude while we were still half-asleep after working 18-hour days all week. Moments later, she brought in her manager Joyce, who escalated the situation even further -- yelling, pointing her fingers in our faces, refusing to let us close the door, and repeatedly threatening that she "knows the PD" and would make sure we go to jail. This was harassment, intimidation, and a complete violation of our privacy and safety. For the amount we paid, the lack of professionalism, communication, and respect was appalling. We will be filing a formal report with Airbnb and strongly urge anyone considering this property to stay far away until the management is replaced.

My brother died as the result of covid -19 he lived in an apt managed by compass. I called the…read moreoffice and advised them of the situation but the information never got to the owner, then they sent a repair person without notifying me that someone was coming, they gave them keys to the apt. then when I left they held the security and last months rent (almost $5000) for over a month even though the apartment was already in contract to be sold. The manager Megan was argumentative and defensive but really didn't acknowledge any problem. This is not a company I would want to deal with again.

Their agent Monica meskyte is by far one of the sneakiest, dishonest, and unprofessional agents…read moreI've ever come into contact with. As someone who grew up with real estate professionals and is familiar with the processes, she is clearly uneducated, and lacks basic morals and ethics. I am in no way finished with this review nor am I am finished with compass realty. Again, I am extremely familiar with how real estate works and I feel sorry for anyone who has to work with her.

I didn't break the lease I was told If you gonna be able to find a new tenant I'm gonna be able to…read morewalk away from the lease. And I paid the difference after I moved out and the new tenant moved in. I'm outraged by the fees they charged me...people be aware there is a lot of hidden fees before you sign the lease read carefully! They gonna charge you for this and that....This company also overcharged me for maintenance fees! its making money by ripping off people. I replaced the a/c filter and there was no damaged smoking detector or missing bulbs. And they charged me $198 for nothing! For hidden damages! And the yard yes I agree I didn't cut the grass so they charged me $179.30 for 10×10 townhouse yard cleaning for cutting the grass basically there us nothing to clean there. And the garbage what garbage I put everything in the trash can and what i supposed to do take the trash with me??? If garbage day is Monday and i moved out on Sunday. So basically they charged me for taking the trash cans out! I will never recommend to rent from this company for all my friends and anybody!

I lived in one of their properties for 3 years. Paid rent on time (actually early). Everything…read moreseemed fine until it came to maintenance. They take the cheap option. Ex: the dishwasher flooded underneath the flooring so some of the wood panels had to be replaced. They went with a cheaper wood that didn't match the rest of the flooring and didn't even run flush with the cabinets. Another ex: the AC kept kicking off. Mechanics would come to "fix" the issue. We later found out, they were putting a bandaid on the problem. Our AC went out again for over 5 days in the summer. We asked if they would pay to relocate us temporarily until the AC was fixed. They said no- it was my spouse, cat and myself living in a space that was 90°! As they were fixing the AC, construction took over the living room making it uninhabitable- no compensation, just an experience of cleaning up after the repair. As we moved out, they came up with ridiculous fees (processing, admin, cleaning). When we moved out, the unit was cleaner than moving in. This company does not care for their tenants. I've heard horror stories of how they have treated others but I was being hopeful. This company is full of inconsiderate managers, often with attitude problems, as well as hidden and made up fees. Would not recommend. Rent if you dare.

We have rented through Historic Hideaways over 20 times in the last 15 years. We keep coming back…read morebecause their properties are terrific, they are well located in safe areas, and Tim and the staff are responsive when a problem arises (which is almost never). We have rented large properties for the whole family for a month or more and small condos for short trips. Every experience has been perfect for the occasion. One of the best things about working with Historic Hideaways is that there are no hidden fees. When you request a booking, the cleaning fees are already included. We recommend Historic Hideaways to friends and family. My brother's family is now a regular Historic Hideaways customer, as well.

We went with Historic Hideaways to rent a large house in the Truman Annex. Their website is easy to…read moresearch and the people are easy to work with. The house was very clean and we had no problems with it. I would rent with them again.

First time visiting Key West, and we booked an Airbnb managed through Rent Key West Vacations…read more The service throughout our stay was very good. We had a couple of minor issues, including a broken chair and a shower faucet handle. After notifying the staff, both were addressed promptly. That level of responsiveness was appreciated. As for the rental unit itself, it was clean and stocked with the expected amenities. However, it had a noticeably worn appearance. Nothing major or disruptive, just a collection of small maintenance items that added up. Things like cracked tiles, wobbly faucet handles, and missing electrical face plates. Staying in Key West is expensive, and I may have assumed that the quality of the accommodations would closely match the cost. That wasn't necessarily the case here. None of these issues were showstoppers for us. We spent most of our time out exploring anyway. Still, the overall condition gave the impression of deferred maintenance and perhaps a lack of attention to detail. Overall, solid service from the management team, but the unit itself could benefit from some updates and general upkeep.

Beware of this company. We reserved a condo with them in October of 2025 for June 2026. In April of…read more2026 we received an email from them telling us the owner had decided not to rent the condo anymore. They wanted to move us to another condo that was not to our liking. We spent many hours researching condos and we chose the one that would fit our needs. We asked for a discount if we had to take the other condo and all of a sudden they said the owners decided to rent to us. When we arrived at our condo in June the key code did not work. After traveling all day we were forced to sit outside for 2 hours before they got us a code that would work. We asked for compensation and they told us that it was our fault because we wouldn't move to the other condo. Come to find out the owners were changing rental companies. They also quit communicating with us, they would not answer our texts or answer the phone. Stay away from this company.

We rented Mangrove Lagoon for two weeks starting on Christmas Day. We will get this exact condo…read moreagain.... It was beautiful and provided everything you could want for the comfort of hanging out at home. We didn't have any maintenance issues at all so I can't speak to their attentiveness but we did call about a couple minor things and had an immediate response. The price was very reasonable for the location and how much space this condo provides, including a covered parking spot. I do hope they will consider making a gate key available.... Having to use the Southard entrance to TA after 6:00 was a bit of a hassle... We rent in TA so we can walk everywhere and this adds 6 blocks or more additional to the walk home at the end of the night.

The rental from this place was a BIG OOF. My party had arrived 30 minutes after the agreed upon…read moretime for check in of 4pm. When we parked the car we heard people inside the house, which we thought was weird. Well the door was wide open because the cleaners had just arrived and were setting up. We contacted the office and they said yes the cleaners have to clean. Ummm...as a business charging over $800/night are you not supposed to have the rental property ready by the agreed upon time at a minimum? They were not willing to give us anything for not having their rental property ready. Well here's a list of everything else wrong (other than the condescending office who tries to gaslight you when you ask them about the property being ready at the contracted time?? Why is it not ready at 430 when you told me Check in was at 4??) There is a hot tub in the back but half the jets aren't working and it's infested with mosquitos. There is no bug spray provided so I suggest you bring some. The carpet looks raggedy. They might vacuum it but I don't know how often they really clean it. The place looks like it needs renovations like 8 years ago. The laundry machine outside is nice to have. Just make sure your shots are all up to date. It's ruiuuuusssty. And if you have any issues with the place...too bad. The front office will do anything but own up to their mistake. We stayed at "Hemingway's View".

Just got back from staying in one of the properties Cindy Dolberry manages. There had not been any…read moremaintenance on this property in years. It was in Venture Out, a gated community. The grounds in Venture Out were good, nice place, There were a list of things a mile long that were broken in the rental. It took a little while to realize because the place was so dirty. We called Cindy's office and her husband Ken was rude and combative with us. I would not recommend this Realtor for property management or rentals. They just don't care and I can't believe they are even licensed to do any kind of business. I wouldn't let her manage my dog house.

This is a fantastic company. Goes above and beyond to get you exactly what you want. Wouldn't use…read moreanyone else. Kudos!

Tomorrow we finish packing and will be leaving Conch Bar South. Over the past five winters, we…read morehave vacationed in this home a total of 178 days. The first time we entered the property we were overwhelmed with its beauty and amenities. That feeling has never left us. The home is clean, tastefully decorated, with attention to details that assure our stay will be pleasant. Every single year we notice that the owners invest in improvements that provide the most enjoyable experience possible. Friends have joined us for a week at a time and often leave saying this is the best vacation ever. Our daughter's family stays with us during their children's Christmas vacation. When mom suggested to the children that they fly down here the day after Christmas rather than travel on Christmas day, there was near mutiny. Understandable. We can fish off the dock, bicycle anywhere we want, enjoy beautiful sunsets over the bay from the observation tower, kayak to mangroves, or play games on the porch. We appreciate the owners who have made this experience possible. We appreciate the professionalism of the Keys Holiday Rentals staff who is always available should a need arise. We are already booked for next winter. Janet & Rob Coombs

This company and the customer service is wonderful. They are very responsive by phone and email…read more Booking our rental home was easy. Our issues with the home were addressed immediately however we would not rent this particular home again known as Lyon's Landing. We loved the home, its pool, and grounds but found ourselves fighting against German cockroaches the entire month (mostly in the kitchen and living area). Two visits from an exterminator did very little. the situation put a huge "damper" on our vacation. Think twice before renting this particular property. It can take months, if ever, to eradicate these pests.