Things to do in Siesta Key
Siesta Key has more outdoor activities than many of the beach resort
Florida · South Central Gulf Coast
Siesta Key
Siesta Key
vacation rentals
Explore privately owned Siesta Key vacation rentals, professionally managed with a destination specialist available to help you compare the options.
1,198 homes listed
507 beachfront
Up to 12 bedrooms
Sleeps up to 40
1,198Homes listed
507Beachfront
216Houses & villas
981Condos
About Siesta Key vacation rentals
Choosing a vacation rental in Siesta Key
Emerald Kite currently represents 1,198 professionally managed Siesta Key vacation rentals. The collection includes houses, villas and condos, including layouts with up to 12 bedrooms, homes sleeping up to 40 guests and 507 beachfront options. Each property is privately owned and represented by an established property-management company responsible for guest support during the stay.
Siesta Key Luxury Vacation Homes are what we specialize in. Siesta Key is considered the number one beach destination in sunny south Florida. Visitors flock from around the world to enjoy our incredible weather and amazing beaches. Imagine vacationing on one of the world's top 10 beaches! We invite you to view the largest selection of luxury vacation rental homes and speak with a local agent who will strive to ensure you experience a five star vacation experience.
Beachfront
Villas & houses
Condos
Pet-friendly
1,198homes listed here
Your destination specialist
Speak to Jacklyn
Jacklyn looks after Siesta Key for Emerald Kite. Lines are open 7 days a week, 9 a.m. to 10 p.m. EST.
Find the right fit
Explore Siesta Key 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 Siesta Key vacation rentals, with the closest bedroom and guest-capacity matches shown first.
Siesta Key rentals by bedroom count
Property types and featured collections
Handpicked in Siesta Key
Search all 1,198 homes →
Featured Siesta Key vacation rentals
Compare a rotating selection of professionally managed houses, villas and condos in Siesta Key. Each card shows bedrooms, bathrooms, sleeping capacity and a starting rate where one has been supplied.
Gold 
Siesta Key
Siesta Key Luxury Vacation Rental - Four-Bedroom Private Pool Home
From $827 / night
Around Siesta Key
Ways to spend the week
Eating in Siesta Key
Siesta Key has an abundance of heavenly dining experiences to suit all
Shopping in Siesta Key
Siesta Keys has a spiritual quirkiness most likely inspired by its rare
Good to know
Planning your trip to Siesta Key
Getting around Siesta Key
KSRQ) is an exceptional airport that has wide selection of international
House or condo?
Of the homes represented here, 216 are houses and 981 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 Siesta Key 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 Siesta Key
Unedited notes sent to the Emerald Kite team after their stay.
“I want to say how pleased I am with our stay and your customer service! I cannot thank you enough and will most definitely use you all each time I look to book a trip!!! Thanks, Brittany, Ohio”
Siesta KeyJune 2020
“I have been searching for a vacation rental in Siesta Key for July for at least 2 months now. I contacted just a few places and nearly went insane! One of the websites was yours. Jamil was one of the agents from your office that helped me. He took the time...”
Siesta KeyJune 2019
“Hello Marni Thank you for your e-mail. Everything at the property was absolutely wonderful and we all had a lovely time. Thank you for all the help regarding booking the home for us. I am not sure what plans we have for next year but I will certainly use...”
Siesta KeyJuly 2016
Good to know
Siesta Key vacation rental FAQs
Answers to common questions about choosing and booking a professionally managed stay in Siesta Key.
Are these Siesta Key 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.