Eating in The Florida Keys
The laid back Caribbean feel to the Keys is portrayed in its abundance
Florida · The Florida Keys
The Florida Keys
The Florida Keys
vacation rentals
Explore privately owned The Florida Keys vacation rentals, professionally managed with a destination specialist available to help you compare the options.
539 homes listed
113 beachfront
Up to 12 bedrooms
Sleeps up to 36
539Homes listed
113Beachfront
440Houses & villas
96Condos
About The Florida Keys vacation rentals
Choosing a vacation rental in The Florida Keys
Emerald Kite currently represents 539 professionally managed The Florida Keys vacation rentals. The collection includes houses, villas and condos, including layouts with up to 12 bedrooms, homes sleeping up to 36 guests and 113 beachfront options. Each property is privately owned and represented by an established property-management company responsible for guest support during the stay.
Visitors to the Florida Keys are all about embracing the laid back beaches and wonderful Crystal green ocean. For some unique excitement visit Jules Undersea
Lodge in Key Largo where guests can actually scuba dive 21 feet and
Beachfront
Villas & houses
Condos
Pet-friendly
539homes listed here
Your destination specialist
Call our local agents
An Emerald Kite specialist for The Florida Keys, 7 days a week, 9 a.m. to 10 p.m. EST.
Find the right fit
Explore The Florida Keys vacation rentals by size & style
Start with the space your group needs, then use the available property and experience links to narrow the collection. Each direct link opens matching The Florida Keys vacation rentals, with the closest bedroom and guest-capacity matches shown first.
The Florida Keys rentals by bedroom count
Property types and featured collections
Handpicked in The Florida Keys
Search all 539 homes →
Featured The Florida Keys vacation rentals
Compare a rotating selection of professionally managed houses, villas and condos in The Florida Keys. Each card shows bedrooms, bathrooms, sleeping capacity and a starting rate where one has been supplied.
Platinum 
The Florida Keys
Beachfront Escape with 4 Bedroom, Private Pool & Dock
From $53,993 / night
Gold 
The Florida Keys
Key Largo Vacation Condo 4 BR & Access to Magnificent Resort
From $882 / night
Around The Florida Keys
Ways to spend the week
Shopping in The Florida Keys
are some great shops along the Florida Keys that have exceptional,
Good to know
Planning your trip to The Florida Keys
Getting around The Florida Keys
Key West International Airport (EYW / KEYW) is the closest major airport
House or condo?
Of the homes represented here, 440 are houses and 96 are condos. A private house may offer more outdoor space and separation between generations; a condo may offer a convenient position or shared amenities.
Why book with us
Booking The Florida Keys with Emerald Kite
Every home on this page is privately owned and represented by an established property-management company, with a destination specialist available to help you compare the options.
- Privately owned homes, each represented by an established management company
- Vetted on location, quality, amenities and the manager’s responsiveness — and removed if that slips
- A destination specialist helps compare the homes that fit your trip
- Payment, cancellation and check-in terms supplied before you book
- Villa Specialists available by phone
- A complimentary concierge service for dining, activities and directions
Guest stories
What guests wrote after staying in The Florida Keys
Unedited notes sent to the Emerald Kite team after their stay.
“Jacklyn: First let me Thank you for doing an excellent job finding our vacation rental. Every suggestions you made was excellent, and feel within out budget, time constraints, and personal likes. I look forward to working with you again as you made our trip...”
The Florida KeysJune 2017
Good to know
The Florida Keys vacation rental FAQs
Answers to common questions about choosing and booking a professionally managed stay in The Florida Keys.
Are these The Florida Keys homes professionally managed?
Yes. Every home is privately owned but represented by an established property-management company responsible for cleaning, maintenance and guest support during your stay. Before a property joins the portfolio it is assessed on location, the quality of the accommodation, access to amenities and the reputation and responsiveness of the management company, and it is removed if it stops meeting that standard.
Can we bring a dog?
It varies by property rather than by destination. Ask your agent to identify homes that currently accept pets, then confirm the type, number and size limits before booking. Property rules, including smoking policies, are supplied for the individual home.
How is my payment protected?
Payment schedules, cancellation terms and any protections vary by property manager and destination. Your agent will identify the contracting property manager and provide the applicable rental agreement and payment terms for review before you book.
What do Platinum, Gold and Silver mean on a listing?
They are our own rankings and they describe the interior furnishings only - not the price, the view or the location. A Platinum or Gold home can cost less than a Silver one in a better position. Rankings move up when a home is upgraded and down when it has not been refreshed in a while.
How much does a rental cost, and when do we check in?
Where a manager has supplied a starting rate you will see it on the listing; where they have not, rates are quoted on request because they change with season and length of stay. Check-in and checkout times vary by property and manager, and your agent will confirm both for the home you choose.
Need help choosing?
Tell us who is travelling and when, and a destination specialist will shortlist the homes that suit you.