Longboat Key Vacation Rentals - Privately Owned Professionally Managed®

Luxury Longboat Key vacation rental homes and condos is our specialty.  Whether you are looking for a luxury beachfront vacation home or a bayside condo we have them all!  Monthly and weekly rentals are available.  Call your local Longboat Key Emerald Kite Destination agent and reserve your vacation home or condo today. 

Marni - Emerald Kite Destination Agent

Call Our Local Agents 7 Days a Week from 9am - 10pm EST

USA Toll Free: (866) 922-0572

International: +1 305-425-1750

Our Most Popular 5+ Bedroom Longboat Key Rentals

Longboat Key Luxury Beach Front rental Home Five Bedrooms

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 6 Bathrooms
  • Property #892086
  • Available
  • Average $1271 per Night plus taxes and fees
  • Map Request Quote

Beach front Estate Gulf Views California Style Living

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 5 Bathrooms
  • Property #6889
  • Available
  • Average $1799 per Night plus taxes and fees
  • Map Request Quote

Exclusive Longboat Key Rental in Queens Harbour - Bay Views

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 5 Bathrooms

Our Most Popular 4 Bedroom Longboat Key Rentals

Luxury Vacation Rental Home /Estate for Rent

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms
  • Property #2218
  • Available
  • Average $14078 per Month plus taxes and fees
  • Map Request Quote

Luxury Longboat Key Vacation Rental Home with Pool

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms
  • Property #6720
  • Available
  • Average $8512 per Month plus taxes and fees
  • Map Request Quote

One of the Very Few Beach Houses for Rent on Longboat Key

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms
  • Property #6714
  • Available
  • Average $1298 per Night plus taxes and fees
  • Map Request Quote

Our Most Popular 3 Bedroom Longboat Key Rentals

Luxury Country Club Villa South Longboat Key

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Direct Walk Out With Gulf Views

  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms
  • Property #911716
  • Available
  • Average $6854 per Month plus taxes and fees
  • Map Request Quote

Longboat Key Homes with Pools to Rent in Country Club Shores

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms
  • Property #6511
  • Available
  • Average $8993 per Month plus taxes and fees
  • Map Request Quote

Our Most Popular 2 Bedroom Longboat Key Rentals

Luxurious Longboat Key Club Vacation Rentals - All Year Round

  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms
  • Property #6741
  • Available
  • Average $600 per Night plus taxes and fees
  • Map Request Quote

Longboat Key Full Gulf View Vacation Rental Condo South End

  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms
  • Property #1413
  • Available
  • Average $5656 per Month plus taxes and fees
  • Map Request Quote

Longboat Key Luxury Vacation Condo Sleeps 4 Guests

  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms
  • Property #885091
  • Available
  • Average $7995 per Month plus taxes and fees
  • Map Request Quote

Our Most Popular 1 Bedroom Longboat Key Rentals

A Rare One Bedroom with Views- Condo

  • Gold
  • Condo
  • Pool
  • Max Occupancy: 2
  • 1 Bedroom
  • 1 Bathroom
  • Property #6554
  • Available
  • Average $198 per Night plus taxes and fees
  • Map Request Quote

Boutique Beach Resort One Bedroom Rental Weekly

  • Gold
  • Condo
  • Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom
  • Property #6584
  • Available
  • Average $184 per Night plus taxes and fees
  • Map Request Quote

Walk Out Beachfront One Bedroom Walk from Living room to Beach

  • Gold
  • Condo
  • Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom
  • Property #6586
  • Available
  • Average $184 per Night plus taxes and fees
  • Map Request Quote
Marni - Emerald Kite Destination Agent

Call Our Local Agents 7 Days a Week from 9am - 10pm EST

USA Toll Free: (866) 922-0572

International: +1 305-425-1750

Longboat Key is considered one of the most upscale beach communities on the South Central Gulf Coast of Florida. Only a few miles from sophisticated Sarasota, Longboat Key offers visitors a high-end beach destination connected to one of the most cosmopolitan of Florida’s cities. This barrier island is ideal for those who love the beach and want easy accessibility to the culture, world-class shopping and fine dining that both Longboat Key and Sarasota provide. 

The Island is small but offers a multitude of leisure, sporting and entertainment activities. It’s only 11 miles long, so it’s possible to traverse the entire length of the Island in one trip - now that’s a beach walk!  The Island spans a mere quarter of a mile at its widest point, with the Gulf of Mexico on one side and Sarasota Bay on the other.  Both beach and bay activities will always be nearby, no matter where you stay on the Key. 

 

Longboat Key vacation rentals are located on both the beach side and bay side, however even bayside rentals are incredibly close to the beach, and can typically be reached by simply walking across Gulf of Mexico Drive, the main two-lane road on the Island. Many of the bayside vacation homes have docks and boast spectacular views of Sarasota Bay and the gorgeous Sarasota skyline, simply perfect for those renting or bringing a boat. It is important for visitors to note that Longboat Key has less than a thousand rental properties, and demand significantly outweighs supply. Only a small percentage of rentals permit weekly stays, so call your Emerald Kite agent as soon as you are planning on visiting. 

 

Our pristine beaches are beautifully groomed, and there are only a small number of public parking areas, creating an almost private beach community feel. There are no true private beaches along the South Florida coast, however the atmosphere on Longboat Key’s shores is exclusive and uncrowded.  Regular visitors and residents refer to the Island as having a North and South end, with the unofficial border being the Publix grocery store. The sophisticated South end of the Island is where the high-rise condos frame the shoreline, and its bayside homes enjoy beach access as well. The South end of the Island is also close to neighboring Lido Key’s famous St Armand’s Circle, known for its fine dining and fabulous shopping. The more Key West-style vacation homes and traditional beach or bayside vacation cottages tend to be located on the pretty North end of the Key, where you will also find a small bridge that takes you onto the beautiful sister Island of Anna Maria. There is a free island trolley that travels between Anna Maria Island, Longboat and Lido Keys 7 days a week, making local transportation a breeze.

 

Boasting two championship golf courses at the Longboat Key Club, and with dozens more located in nearby Bradenton and Sarasota, Longboat Key is a golfer’s paradise.  There is also a stunning ten-mile bike path that winds along beautiful Gulf of Mexico Drive and provides breathtaking scenery for joggers and cyclists alike.  Whether you enjoy tennis, watersports, rollerblading, fishing or swimming, you are sure to find the outdoor activity you are seeking when staying on Longboat Key. The New York Times recently wrote an exceptional article highlighting this cultural mecca on the Gulf!

 

The vast majority of vacation rentals on Longboat Key are monthly minimum stays, with some exceptions. Call your Emerald Kite Longboat Key local agent, who will work to secure a weekly or winter vacation home or condo for you. Longboat Key is considered one of the ultimate beach destinations in Florida, with Lido Key and St Armand's Circle at its base providing the ultimate in designer shopping and upscale dining and entertainment. You will want to book early, as the Island attracts regular visitors from all over the world eager to secure those limited short term/weekly accommodations. 

 

On sophisticated, upscale Longboat Key you won’t find a MacDonald’s or any other fast food chain, but there are several locally owned burger joints and seafood “shacks” for more casual fare that both children and adults will enjoy on relaxed days at the beach.  If your kids love sailing, swimming, tennis and building sandcastles on the shore, they will have a fabulous vacation experience. There is also great fishing and Motts Marina on the South end of the Island for the whole family to enjoy. 

 

Longboat Key & Lido Key are connected and only 10 miles apart

Longboat to Siesta Key - 18 Miles  

Longboat Key to Casey Key - 27 Miles

Longboat Key to Clearwater - 61 Miles

Longboat Key to Indian Shores - 53 Miles

Longboat Key to Indian Rocks - 62 miles

Longboat Key to St Petersburg - 42 Miles

Longboat Key to Venice - 31 Miles

Longboat Key to Boca Grande - 64 miles

Longboat Key to Cape Coral - 94 Miles

Longboat Key to Orlando - 131 Miles

Longboat Key to Naples -129 Miles

Longboat Key to Marco Island - 142 Miles

Longboat Key to Captiva Island - 128 Miles

Longboat Key to Key West - 387 Miles

 

 

 

Gym/Workout Facilities

Good News! We are pleased to announce a fantastic new fitness studio on Longboat Key. Located right next to the Publix supermarket, Longboat Key Fitness offers seasonal, weekly or day passes for state-of-the-art fitness and personal training, http://longboatkeyfitness.com/.  Some of the same instructors from the exclusive private (and somewhat costly) Longboat Key Club are now offering their Personal Fitness Services at the facility.

 

Golf

The Longboat Key Club boasts two exceptional golf courses, and for guests staying at the Club, this private course offers a unique beachside golfing experience. The club has strict members- or resort guest-only policy, and as such is not open to the public. However, Sarasota has an abundance of world class golf courses within minutes of the Island. 

Tennis

Longboat Key is home to the Longboat Key Club, a private club which has tennis courts available for resort guests and members. If you are staying in a private vacation rental, it’s worth a call to the tennis desk at the Club to see if they are in need of any tennis partners for their guests.  In addition, the Island’s public tennis courts at the North end of Longboat  are exceptional.  Offering 10 tennis courts as well as adult player programs, USTA leagues and tournaments, ladders, round-robins and seniors 50+ events.  The Longboat Key Tennis Center is one of the better public facilities in Florida. For more information, contact (941) 316-8367, Longboat Key Public Tennis Center, 590 Bay Isles Rd., Longboat Key, FL 34228.

Longboat Key Luxury Vacation Rentals are our specialty.  Home to some of the most superb dining establishments in South Florida Longboat Key visitors will enjoy selecting from an abundant array of elegant multi-cultural cuisine as well as local fresh seafood restaurants located on the bay or at the beach.  Down town Sarasota is home to a wide variety of wonderful restaurants and St Armand’s Circle, located at the Islands south end provides Café style dining and a European ambiance. Casual or formal, Longboat Key & St Armand’s circle can guarantee you a world class dining experience.

 

Dining on Longboat Key


The 2018 Emeralds Kite Award for Excellent Casual Dining on Longboat Key deservedly goes to the tucked away Mar Vista Pub & Dockside Grill   This gem of a waterside outdoor dining establishment is frequented by locals and those in the know. When arriving at the restaurant guests are somewhat taken aback by the ramshackle exterior,but bite the bullet, and walk through to the outdoor area... A romantic bay side setting awaits where guests dine under twinkling fairy lights late into the evening. Lunch time guests dine bayside watching  the fishing boats anchor and if your lucky the occasional manatee and dolphins will swim by  This special restaurant does not take reservations and the wait can be long. We recommend ordering a bottle of wine from their extensive and impressive wine list and sitting out on the dock until your table is (eventually)ready. Emerald Kite Vacation Rentals on Longboat Key offer accommodations within close access to some of the finest dining establishments on the Island and Mar Vista should be right at the top of your list! 


In 2017 we had to award our Emerald Kite Fine Dining Award of Excellence to Euphemia Haye. This Posh, dining establishment is nestled mid Island and across from the beach!  Its exterior and interior decor is somewhat  reminiscent of a upscale,charming French countryside Inn with twinkling lighting, richly colored flowers and tropical plantings. A stunning, cozy, romantic environment with superb fusion cuisine to match! Prices here are not cheap but Emerald Kite guests looking for East Coast quality cuisine will not be disappointed. Check the Euphemia Haye menu and  if you are seeking a more casual environment the Haye Room upstairs offers an exceptional desert room with excellent apetizers and lighter plates   Call for reservations & open 7 days per week.


Dont even think about leaving Longboat Key without stopping off at the fun and best outdoor hamburger joint in South Florida. New Pass Grill  located on Longboat Key, just half a mile north of St Armand's Circle and if it had walls would be described as a hole in the wall hangout where the workers on the Island go for a hearty lunch. The burgers are world class and a glass of imported beer or a just ok chilled white served up in plastic glass makes a great accompaniment. The burgers are excellent and the casual out door environment is simply world class. Watch the fisherman come in and the pelicans gracefully swooping up their own catch of the day. Super value, super food, and super casual dining a combination not easy to find on Longboat Key!


Book a Table at a Longboat Key Restaurant.


Dining on Lido Key


Longboat Key and Lido Key are connected by a small bridge and Lido Key is home to world famous St Armand's Circle. This European plaza community is home to over 80 chic shops and local dining establishments. Dining outside and people watching is what Lido Key is all about. Art galleries, boutiques with exceptional restaurants dotted throughout makes for a special vacation experience.


Tommy Bahamas 

Without question, no exception the best fish tacos you will find anywhere. We kid you not. Emerald Kite staff are asked to sample fish taco's and compare them to Lidos Tommy Bahamas and so far Tommy's gets the gold!  A really fun Tommy Bahama Florida interior (naturally) with great food and cocktails. Best drinks are their Margaritas. Open for lunch and dinner this terrific venue also has limited out side dining. Our suggestion, skip dessert and head next door to Kilwins, the best Ice cream store in America and Emerald Kites top flavor? Hands down the toasted coconut! 


Lido Beach Grille

The Lido Beach resort has a really great dinner spot where you can dine on the water and really get into the swing of your vacation. the Lido Beach Grille specializes in fresh seafood with a Caribbean twist.  This great restaurant is worth a visit and prices are affordable with really good service.  

Guests that stay at Emerald Kites Vacation Rentals on posh Longboat Key love the on Island Publix Grocery Store . This exceptional grocery store sits at the heart of this exclusive Island and locals and visitors congregate in the Bay Isles shopping area to not only obtain their grocery shopping but meet for coffee, visit the boutique specialty stores or pop for lunch and drinks at Amores Italian eatery conveniently situated right next to the flagship grocery store.   At the South end of Longboat Key you will arrive at Lido Key which is home to world class St Armands Circle, a European outdoor plaza with designer shops, restaurants, galleries and jewelry stores. Take short drive and visit one of the many Sarasota Malls where you will find premier stores.

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. This grocery store has an amazing assortment of fresh seafood, fine European cheeses and one of the largest and best selections of wines in the area. A Wholefoods is located in Sarasota however Publix is ever bit its equal and right there on the Island.

525 Bay Isles Parkway, Longboat Key, FL (941) 383-1326

 

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. Visitors can enjoy a leisurely lunch or dinner at one of the twenty restaurants and cafes and later explore the shopping delights at the Circle.

 

Sarasota Malls

Sarasota has a number of good Malls all within a thirty min drive of Longboat Key. In October 2014 the grand opening of the $315 million mall at Interstate 75 and University Parkway will include premier stores such as Apple, H&M, Crate & Barrel and Brooks Brothers, Macys, Saks Fifth Avenue .

 

Poshe

8201 S Tamiami Trail,Sarasota, FL

(941) 925-2161

 

Westfield Southgate

westfield.com, 3501 S Tamiami Trail, Sarasota, FL

(941) 955-0900

 

DeSoto Square Mall

303 301 Blvd, West  Bradenton, FL, (941) 747-5868

 

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. Trolleys offer both indoor and open-air seating. The fare is $.75 (discounted rates available for senior citizens). The trolley does not operate during major holidays including New Year’s Day, Memorial Day, the Fourth of July, Labor Day, Thanksgiving and Christmas Day.

 

View the map and schedule of the Longboat Key Trolley.

 

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. This local airport handles both domestic and international carriers, including US Airways, Delta, Jet Blue and Air Canada. Tampa International Airport, located 40 miles from longboat offers over 30 major airlines with hundreds of national and International flights arriving daily.  St. Petersburg-Clearwater International is located just over 30 miles North of Long Boat with limited carriers and a good choice If you can get direct flights.   Orlando International is routinely forgotten and yet typically offers the best priced airfares for those willing to drive the two hours to Longboat Key.

Emerald Kite is proud to endorse Cheap O Air who have one of the best on line calendars offering an abundance of inexpensive flights into Tampa and Sarasota Airports. 

Municipal Airports

There are two Municipal airports, catering to private-jet travelers one 25 mile away is Airport Manatee in Palmetto and St Petersburg’s Albert Whited Airport located 24 miles from Longboat Key.


Car rental

Car rental is needed for those visitors to Longboat Key who want to visit Sarasota and explore our area. Car rental should be booked early to ensure the best prices.