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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iTrip Vacations Sarasota & Venice
iTrip Vacations offers affordable vacation home rentals at lower prices than competitors, saving you time and money.
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
All Sunnyside Properties
Sunnyside Properties is a family-owned and operated full service property Management Company specializing in vacation rentals on Siesta Key. We …
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 …
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), …
Tropical Siesta Vacations
Vacation Rentals and Property Management Services
Jennette Properties
Welcome to Jennette Properties, the premier site to discover the most desirable, luxury seasonal vacation properties, along with luxury long-term …
Altez Vacations
Every vacation should be unique, dynamic and distinct. Find our homes in the sugar sands of Siesta Key, and beyond. …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
Siesta Key Vacations
At Siesta Key Vacatons Rentals we understand what makes a luxury vacation home right for you.
Sarasota Timeshare Resales & Rentals
Find an affordable timeshare resale or rental on Siesta Key within resorts like the Calini Beach Club. Timeshares are the …
Home & Condo Rentals and Property Management
We offer many types of lodging including luxury waterfront condos, beach resort accommodations, private homes, villas and more.
Argus Property Management
Argus can make all your vacation dreams come true! We have more than 300 Siesta Key rental condominiums ... all …
Rent Siesta Now
A family owned and operated collection of thirteen luxury vacation properties. Providing an exceptionally clean and fully stocked home …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
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 …
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 …
Midnight Cove II
Siesta Key's Midnight Cove II has bayside condos located on 14 lush acres with access to Crescent Beach. We're just …
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
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 …
Siesta 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …

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