Siesta Key Vacation Rentals - Privately Owned Professionally Managed®

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.   
Jacklyn - 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 Siesta Key Rentals

Close to Siesta Key Village A great Town House Luxury

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 6 Bathrooms
  • Property #887184
  • Available
  • Average $908 per Night plus taxes and fees
  • Map Request Quote

A Siesta Luxury 5 Bedroom Condo with Communal Pool.

  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 11
  • 5 Bedrooms
  • 4 Bathrooms
  • Property #895505
  • Available
  • Average $599 per Night plus taxes and fees
  • Map Request Quote

This Vacation Home Sleeps 22 Walk to Siesta Key Beaches

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 22
  • 8 Bedrooms
  • 6 Bathrooms
  • Property #895509
  • Available
  • Average $2170 per Night plus taxes and fees
  • Map Request Quote

Our Most Popular 4 Bedroom Siesta Key Rentals

Four Bedroom Home with Private Pool and Hot Tub Sleeps 12

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms
  • Property #892405
  • Available
  • Average $633 per Night plus taxes and fees
  • Map Request Quote

Luxury Vacation Rental Estate Walk Siesta Key Beach

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms
  • Property #6670
  • Available
  • Average $479 per Night plus taxes and fees
  • Map Request Quote

One of Siesta Keys Best Rental Homes with Pool

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms
  • Property #887128
  • Available
  • Average $500 per Night plus taxes and fees
  • Map Request Quote

Our Most Popular 3 Bedroom Siesta Key Rentals

The Most Amazing Luxury Vacation Rental with Pool Sleeps 10

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 3 Bathrooms
  • Property #877305
  • Available
  • Average $797 per Night plus taxes and fees
  • Map Request Quote

Gulf Views from the this stunning 3 bedroom plus BONUS ROOM

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 9
  • 3 Bedrooms
  • 3 Bathrooms
  • Property #877306
  • Available
  • Average $455 per Night plus taxes and fees
  • Map Request Quote

Newly Renovated three bedroom on Siesta Key

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms
  • Property #896568
  • Available
  • Average $15539 per Month plus taxes and fees
  • Map Request Quote

Our Most Popular 2 Bedroom Siesta Key Rentals

Two Bedroom Condo Across From Beach

  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 5
  • 2 Bedrooms
  • 2 Bathrooms
  • Property #877251
  • Available
  • Average $439 per Night plus taxes and fees
  • Map Request Quote

Stunning inside and Out Quite Simply the Best! Upscale Home

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 2 Bedrooms
  • 2 Bathrooms
  • Property #895496
  • Available
  • Average $664 per Night plus taxes and fees
  • Map Request Quote

2 Bed 2 Bath Condominium with Gulf Front Views Sleeps 6

  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms
  • Property #878904
  • Available
  • Average $455 per Night plus taxes and fees
  • Map Request Quote

Our Most Popular 1 Bedroom Siesta Key Rentals

One Bedroom View of the Gulf of Mexico Two Big Beds !

  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom
  • Property #878870
  • Available
  • Average $290 per Night plus taxes and fees
  • Map Request Quote

One Bedroom Siesta Key Vacation Rental

  • Gold
  • Condo
  • No Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom
  • Property #887943
  • Available
  • Average $161 per Night plus taxes and fees
  • Map Request Quote

Siesta Key One Bedroom Rental at a Value Price

  • Gold
  • Condo
  • No Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom
Jacklyn - 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

Siesta Key has more outdoor activities than many of the beach resort areas of Sarasota.  Due to the younger crowd this beach town attracts Jet Skiing, hand gliding, surfing, paddle boarding and parasailing are all available year round and the beaches have volley ball nets strung up along selected beach areas. The bohemian atmosphere of this funky beach town is prevalent everywhere but peaks just before sunset every Sunday night when locals and visitors bring their drums and percussion instruments to the public beach for an impromptu performance of exotic dance and music.

Siesta Key has an abundance of heavenly dining experiences to suit all of our visitor’s tastes and expectations. Whether you are looking for casual, laid back, casual fare or fine, world class gourmet dining then Siesta Key certainly has it all. St Armand’s Circle, located on Lido Key has some of the best award winning restaurants in South Florida as well as a European Plaza environment with designer stores, horse and buggy rides and Jazz music.  The aesthetically beautiful City of Sarasota is home to some of the country’s best dining establishments as well as the theater, ballet, and opera and should most certainly be on your list of top places to visit during your stay.

Some of Emerald kite Vacation Rentals top dining options in Siesta Key include


This fine dining establishment boasts high end cuisine while enjoying spectacular views of the Sarasota bay. Open for lunch and dinner we recommend an early dinner to enjoy those to die for views!  The butter poached pink shrimp and Key Lime pie is fabulous. 


Great fine dining restaurant and ideal for those with a more discriminating palette. A little posh yet Siesta Key comfortable and the extensive menu enjoys an American Asian fusion! Dont be shy ask the chef to create something unique and off the menu! You will make his day. Our favorite appetizer the creamy lobster bisque! 


We were all down in Siesta Key Village this weekend and had a blast at the Oyster Bar. A down home casual bar type atmosphere complimented by upscale casual food. Ideal for true foodies that love a laid back, casual interior with no need to dress up!  The oysters were great but my personal favorite was the amazing craw fish and my son gobbled down their award winning wings. 

Siesta Keys has a spiritual quirkiness most likely inspired by its rare quartz sand beach considered by many to possess healing qualities. Many of the quaint charming shops in the village sell quartz trinkets, scented candles and an array of local, hand crafted jewelry and specialty gifts items. For high end designer shopping take a short 15 minuet drive to the world famous St Armand’s Circle where you can enjoy outdoor café dining and visit over forty designer boutiques, art galleries and designer jewelry stores.

Sarasota-Bradenton International Airport (SRQ / KSRQ) is an exceptional airport that has wide selection of international and domestic carriers. Located only 8 miles from Siesta Key. An exceptional first option. Many flights into SRQ are not direct and some airlines cut flights during low season.

Another major airport is Charlotte County Airport (PGD / KPGD), which has domestic flights from Punta Gorda, Florida and is 56 miles from Siesta Key, FL. A great little airport if you can get the flights you are looking for.

St. Petersburg-Clearwater International Airport (PIE / KPIE) has domestic flights from Saint Petersburg, Florida and is 60 miles from Siesta Key, FL. A great easy to access airport and fewer lines than you will find at Tampa and Orlando.

Tampa International Airport (TPA / KTPA) has international and domestic and is located 70 miles from Siesta Key, FL and often has the best direct flights and price options. For departing flights out of Tampa International we recommend arriving early as the lines can be long and the terminals can be a significant distance.

Orlando International Airport, (MCO) offers an additional airport a mere two hour drive from Siesta Key. For international guests and particularly European guests, MCO offers direct flights from most international European cities.