Keys Holiday Rentals - Representing vacation rental properties in the captivating Islands of the Upper Florida Keys!

Keys Holiday

Welcome to Keys Holiday Rentals. Established in 2007 we have grown our vacation rental management business due to our reputation for guest satisfaction. The properties we represent offer a variety of amenities in a variety of price ranges. We have experienced rental specialists who know Islamorada Area and the Upper Keys Rental Market. Let us put our knowledge, experience, and dedication to work for you. Give us a call today and we will immediately get to work for you. We represent properties in Key Largo, Plantation Key, Tavernier and Islamorada!


Company Overview

Keys Holiday Rentals
In Business Since 2007
83247 Old Highway
PO Box 257
Islamorada Florida 33036

* Trusted Find Rentals Member Since April 2010

Interested in Booking a Vacation Rental with Keys Holiday Rentals?


Vacation Rentals from Keys Holiday Rentals

Gorgeous Bay Views
$3,800/week
Cottage in Islamorada Florida
4 Beds • 3 Full Baths • Sleeps 12
Keys Holiday Rentals
Aerial View 1
$30,000/month
Home in Plantation Key Florida
4 Beds • 4 Full Baths • Sleeps 10
Keys Holiday Rentals
Back of Home
$8,750/month
Home in Key Largo Florida
4 Beds • 4 Full Baths • Sleeps 10
Keys Holiday Rentals
Front of Home
$7,850/month
Home in Islamorada Florida
4 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals
Front of Home
$5,500/month
Home in Key Largo Florida
4 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals
Outdoor Area
$6,500/month
Home in Plantation Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Keys Holiday Rentals


Need a Company to Manage Your Vacation Property?

Get Vacation Property Managed

Looking to have your vacation property managed by a professional rental management company? You have come to the right place.

If you own a vacation property in Key Largo, Islamorada, Tavernier, Plantation Key or the surrounding areas and are interested in hiring a professional management company , you can contact Keys Holiday Rentals to help you.


Looking to Buy a Vacation Property?

Buy a Vacation Home

Owning a home in a great location is a great investment opportunity. Whether you're buying your first rental property or adding to your fleet, Keys Holiday Rentals has what you're looking for.

If you're in the market to purchase a vacation property in Key Largo, Islamorada, Tavernier, Plantation Key or the surrounding areas, contact Keys Holiday Rentals using the button below.


Want to Sell Your Vacation Property?

Sell Your Vacation Property

Selling your vacation property is a big decision. Why not sell it to a professional property management company like Keys Holiday Rentals?

If you own a vacation property in Key Largo, Islamorada, Tavernier, Plantation Key or the surrounding areas and are looking to sell it to a reputable property management company, please contact Keys Holiday Rentals by clicking the button below.


Keys Holiday Rentals Reviews

Have you rented with Keys Holiday Rentals?
Let other travelers know your experience by submitting a review!

We really noticed the extra attention to detail your office does. - from Dave M. on May 22, 2017
Overall Rating  

We have rented in Futura for 3 years through a different management office and really noticed the extra attention to detail your office does. From the binder with everything we might want to know and the cleanliness. Thanks for all the extras we did notice. We will want to return with Keys Holiday Rentals again. Also, should this owner want to sell we would be interested. Again Thanks Dave M. 4-1-17