Vacation Rentals
Not sure if you want a condo or a house? Want to consider a variety of locations across Siesta Key? Are you flexible on where but need a place next week? Consider one of Siesta Key’s countless vacation rental properties. A local vacation rental management company can help you find the exact property and amenity package you need, be it now or next year.
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Vacation with Sunnyside Properties
We offer a collection of vacation rentals at 8 locations up and down Siesta Key.
Jennette Properties
Welcome to Jennette Properties, the premier site to discover the most desirable, luxury seasonal vacation properties, along with luxury long-term …
Argus Property Management
Argus can make all your vacation dreams come true! We have more than 300 Siesta Key rental condominiums ... all …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
Home & Condo Rentals and Property Management
For your next vacation or seasonal rental on Siesta Key we offer many types of lodging including luxury waterfront condos, …
The Cottages on the Key
Here at The Cottages on the Key, we understand what makes a luxury vacation home right for you. We make …
Rent Siesta Now
A family owned and operated collection of thirteen luxury vacation properties. Providing an exceptionally clean and fully stocked home …
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
Cunningham Property Management
Whether you're looking for the the world famous white-sand of Crescent Beach on Siesta Key, love the serenity of Longboat …
Siesta Key Vacations
At Siesta Key Vacatons Rentals we understand what makes a luxury vacation home right for you.
Siesta Home and Condo Rentals
Carve out a piece of paradise with your very own affordable, seaside rental property. Roomy and stylish, our properties feature …
Altez Vacations
Every vacation should be unique, dynamic and distinct. Find our homes in the sugar sands of Siesta Key, and beyond. …
Tivoli by the Sea
Welcome to Tivoli by the Sea Resort...your ultimate vacation getaway. Tivoli is a luxurious condominium on beautiful Siesta Key. As …
All Sunnyside Properties
Sunnyside Properties is a family-owned and operated full service property Management Company specializing in vacation rentals on Siesta Key. We …
Ascendia Group | Real Estate | Property Management | Insurance
Ascendia Group is an award-winning one-stop for real estate (buying and selling), property management (vacation homes, annual & seasonal rentals), …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers affordable vacation home rentals at lower prices than competitors, saving you time and money.
Siesta 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …