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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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 …
FloridaRentals.com
We offer the highest quality vacation rentals in Siesta Key: romantic beachfront condos, expansive homes and everything in between. Trusted …
SkyRun Sarasota
SkyRun Vacation Rentals is the premier short-term rental property management company serving Sarasota and surrounding beaches, including Siesta Key, Lido …
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 …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
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 …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers affordable vacation home rentals at lower prices than competitors, saving you time and money.
Beachside Management, LLC
Let us assist with your Siesta Key vacation rental. Whether you prefer a condo, bungalow, studio villa, or 5 bedroom …
Siesta 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
Rent Siesta Key
We offer an unrivaled selection of vacation rentals throughout Siesta Key and the Sarasota/Bradenton Gulf Coast. Discover a spectacular paradise …
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
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 …
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, …
Hyatt Residence Club Sarasota, Siesta Key Beach
An oasis of island calm just feet from the Gulf of Mexico, our spacious condo-style accommodations range from 1800 to …
Altez Vacations
Every vacation should be unique, dynamic, and distinctive. Find our homes on the sugar sands of Siesta Key, and beyond. …
Vacasa
Our Siesta Key vacation homes are listed so you can easily find exactly what you’re looking for, and know exactly …
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), …
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 …
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
Argus Vacation Rentals
Whether you want a quiet spot to enjoy the tropical weather or a vacation spot to drop into between fun …

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