Things to do in Longboat Key
Longboat Key is considered one of the most upscale beach communities on
Florida · South Central Gulf Coast
Longboat Key
Longboat Key
vacation rentals
Explore privately owned Longboat Key vacation rentals, professionally managed with a destination specialist available to help you compare the options.
576 homes listed
354 beachfront
Up to 6 bedrooms
Sleeps up to 16
576Homes listed
354Beachfront
91Houses & villas
483Condos
About Longboat Key vacation rentals
Choosing a vacation rental in Longboat Key
Emerald Kite currently represents 576 professionally managed Longboat Key vacation rentals. The collection includes houses, villas and condos, including layouts with up to 6 bedrooms, homes sleeping up to 16 guests and 354 beachfront options. Each property is privately owned and represented by an established property-management company responsible for guest support during the stay.
Discover the Smarter Way to Book Longboat Key Vacation Rentals
At Emerald Kite, we’re not just another online booking site — we’re your personal travel brokers for Longboat Key vacation rentals. When you call our on-call accommodation specialists, you’ll get real, one-on-one service from experts who know the island inside and out.
Beachfront
Villas & houses
Condos
Pet-friendly
576homes listed here
Your destination specialist
Speak to Marni
Marni looks after Longboat Key for Emerald Kite. Lines are open 7 days a week, 9 a.m. to 10 p.m. EST.
Find the right fit
Explore Longboat 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 Longboat Key vacation rentals, with the closest bedroom and guest-capacity matches shown first.
Longboat Key rentals by bedroom count
Property types and featured collections
Handpicked in Longboat Key
Search all 576 homes →
Featured Longboat Key vacation rentals
Compare a rotating selection of professionally managed houses, villas and condos in Longboat Key. Each card shows bedrooms, bathrooms, sleeping capacity and a starting rate where one has been supplied.
Gold 
Longboat Key
Luxury Waterfront Property in Longboat Key - Your Dream Home Awaits
Call for rates
Platinum 
Longboat Key
Luxury Longboat Key Residences - Gulf Coast Beachfront Property
Call for rates
Around Longboat Key
Ways to spend the week
Eating in Longboat Key
Longboat Key Luxury Vacation Rentals are our specialty.
Shopping in Longboat Key
Guests that stay at Emerald Kites Vacation Rentals on posh Longboat Key love the on Island Publix Grocery Store .
Grocery Stores
Longboat Key has a wonderful Publix grocery store located on the southern end of Longboat Key next to the Longboat Key Club bayside.
St Armand’s Circle
St Armand’s Circle, referred to as the “circle” by the locals is a charming, European style outdoor plaza which provides the best of dining as well as designer shops, local art galleries and spectacular jewelry stores.
Sarasota Malls
Sarasota has a number of good Malls all within a thirty min drive of Longboat Key.
Good to know
Planning your trip to Longboat Key
Getting around Longboat Key
Longboat Key and Anna Maria Island are serviced by the Island Trolley which start at on Anna Maria to downtown Sarasota via Longboat Key and St. Armand’s Circle. Daily service runs from 5:30 a.m. to 8 p.m. every 60 minutes.
Nearest airports
There are no airports on Longboat Key the 12-mile barrier island can be reached by using several nearby airports.
Commercial Airports
The closest commercial airport, Sarasota Bradenton International Airport, is located about 7 miles east of Longboat Key.
House or condo?
Of the homes represented here, 91 are houses and 483 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 Longboat 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 Longboat Key
Unedited notes sent to the Emerald Kite team after their stay.
“Hi Shelly, the condo is perfect. Great location right on the beach. It is exactly what we were looking for. Thank you for finding us this condo for us! Ann Gumkowski, IL October 2017”
Longboat KeyOctober 2017
“Hello Shelly, Thank you for your help in getting us a place to stay in Long Boat Key on short notice. You did a great job understanding what kind of place we wanted to stay at and giving us various options to pick from. Ann Gumkowski”
Longboat KeySeptember 2017
“My wife and I have been making reservations through Sally over the past six or so years. Her service is consistently outstanding . She has always been polite, professional, responsive and exceptionally efficient. Sally is a true pleasure to work with. Bob...”
Longboat KeyMarch 2017
Good to know
Longboat Key vacation rental FAQs
Answers to common questions about choosing and booking a professionally managed stay in Longboat Key.
Are these Longboat 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.