Cancel

    Open app

    Search

    Rent Key West Vacations

    2.4 (14 reviews)
    Open 9:00 am - 6:00 pm

    Rent Key West Vacations Photos

    You might also consider

    Recommended Reviews - Rent Key West Vacations

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration

    6 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    2 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    11 months ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    5 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    2 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    2 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Sigena S.
    1
    99
    190

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    6 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    13 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    11 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    15 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of C Z.
    0
    22
    0

    10 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 1

    Ask the Community - Rent Key West Vacations

    You might also consider

    Verify this business for free

    Get access to customer & competitor insights.

    Verify this business

    Vacation Homes of Key West - Sunset Key private 2BR/3BA vacation rental.

    Vacation Homes of Key West

    4.2(70 reviews)
    0.5 mi

    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.

    Photos
    Vacation Homes of Key West - The Key West Dreamin 2BR vacation rental.

    The Key West Dreamin 2BR vacation rental.

    Vacation Homes of Key West - The porch at our Sunset Key Monthly Vacation Rental.

    The porch at our Sunset Key Monthly Vacation Rental.

    Vacation Homes of Key West - A classic Key West Style Vacation Rental.

    See all

    A classic Key West Style Vacation Rental.

    Last Key Realty - Towels used by workers

    Last Key Realty

    3.5(44 reviews)
    0.1 mi

    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.

    Photos
    Last Key Realty - Tools left on shower floor, screws in soap ledge and supplied towel used and left on floor

    Tools left on shower floor, screws in soap ledge and supplied towel used and left on floor

    Last Key Realty - Tool on shower floor

    Tool on shower floor

    Last Key Realty - Luxury Key West Vacation Rentals by Last Key Realty

    See all

    Luxury Key West Vacation Rentals by Last Key Realty

    At Home In Key West - Rooms with a view

    At Home In Key West

    2.9(27 reviews)
    0.3 mi

    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.

    Photos
    At Home In Key West - Spacious homes with private pool

    Spacious homes with private pool

    At Home In Key West - Charming city scenes

    Charming city scenes

    At Home In Key West - Historic homes

    See all

    Historic homes

    Key West Vacation Rentals - Sticky remote

    Key West Vacation Rentals

    3.0(63 reviews)
    0.1 mi

    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".

    Photos
    Key West Vacation Rentals - Tv with "cable". It says central AC. I'm not familiar with AC terms but if window units are central ac. They have that

    Tv with "cable". It says central AC. I'm not familiar with AC terms but if window units are central ac. They have that

    Key West Vacation Rentals - Rusty door hinges

    Rusty door hinges

    Key West Vacation Rentals - Floor is beat up and that carpet needs to be cleaned

    See all

    Floor is beat up and that carpet needs to be cleaned

    Keys Holiday Rentals - Kathy 
Manager at Keys Holiday Rentals

    Keys Holiday Rentals

    4.8(4 reviews)
    77.3 mi

    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.

    Photos
    Keys Holiday Rentals
    Keys Holiday Rentals
    Keys Holiday Rentals - Perfect for the whole family! Plantation Adventure offers something for everyone...

    See all

    Perfect for the whole family! Plantation Adventure offers something for everyone...

    Rent Key West Vacations - vacationrentalagents - Updated September 2026

    Loading...
    Loading...
    Loading...