Lido Islander

Siesta Key. Our large and luxurious three-story holiday residence and boating home is the perfect place where you and your loved ones can get away and unwind together. We also have a fitness center, private tennis court, bicycles, boat dock, beach equipment, outdoor grilling along with a beautiful outdoor pool and spa you can enjoy! In minutes, you can boat, kayak, or paddleboard to Big Pass or Sarasota Bay to enjoy the open water or one of many nearby sandbars.

Welcome to The Cottages on the Key, an exclusive vacation rental management company with a boutique collection of luxury vacation homes located in Siesta Key, Lido Key, Anna Maria Island and the mainland of Sarasota, Florida. We offer complete vacation rental management and asset preservation services for owners/investors and our guest services are offered 24/7.

Vaaraway is the go to destination for discerning travelers seeking amazing vacation rentals and unique experiences. We live by our mantra, “The generous and friendly treatment of visitors and guests,” and believe that every guest and homeowner deserves to experience the “WOW” factor. We hand select every vacation home and guarantee to provide personal service and hospitality that is generally considered a lost art in the world today.

Luxe coastal vacation experiences | You dream about | Praised by Travel + Leisure | Reserve Your Escape!

5049 Ocean Blvd

303 Canal Rd

16 S Orange Ave

With nearly 40 years of combined experience in rental management, we pride ourselves on providing a personalized, boutique-style approach to customer care, ensuring both owners and guests receive exceptional service. We offer a variety of rental accommodations, from cozy one-bedroom condos to spacious family retreats and luxurious private pool homes. Our properties are located in some of the most sought-after destinations along the Gulf Coast, including Siesta Key, the Fort Myers – Bonita Beach area, Englewood – Manasota Key, and the Venice Beach area.