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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Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
Tropical Siesta Vacations
Vacation Rentals and Property Management Services
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
Siesta 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
The Cottages on the Key
We understand what makes a luxury vacation home right for you. We make it our business to find a vacation …
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, …
Rent Siesta Now
A family owned and operated collection of thirteen luxury vacation properties. Providing an exceptionally clean and fully stocked home …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers affordable vacation home rentals at lower prices than competitors, saving you time and money.
Ascendia Group | Real Estate | Rentals | Property Management
Ascendia Group is an award-winning one-stop for real estate (buying and selling), property management (vacation homes, annual & seasonal rentals), …
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 …
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 …
Cunningham Property Management
Whether you're looking for the world famous white-sand of Crescent Beach on Siesta Key, love the serenity of Longboat Key …
Argus Vacation Rentals
Whether you want a quiet spot to enjoy the tropical weather or a vacation spot to drop into between fun …
Altez Vacations
Every vacation should be unique, dynamic, and distinctive. Find our homes on the sugar sands of Siesta Key, and beyond. …
Beachside Management, LLC
Let us assist with your Siesta Key vacation rental. Whether you prefer a condo, bungalow, studio villa, or 5 bedroom …
Rent Siesta Key
We offer an unrivaled selection of vacation rentals throughout Siesta Key and the Sarasota/Bradenton Gulf Coast. Discover a spectacular paradise …
All Sunnyside Properties
Sunnyside Properties is a family-owned and operated full-service property Management Company specializing in vacation rentals on Siesta Key. We have …
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
Vacasa
Our Siesta Key vacation homes are listed so you can easily find exactly what you’re looking for, and know exactly …
Siesta Key Vacations
At Siesta Key Vacations Rentals, we understand what makes a luxury vacation home right for you.

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