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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Meet Sea Shell Condominium's backyard!
We offer 5 floors and 49 units for a most relaxing vacation, steps to the beach.
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Find Your Escape with Altez Vacations
Every vacation should be unique, dynamic and distinctive. Find yours with Altez.
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Vacation with Sunnyside Properties
We offer a collection of vacation rentals at 8 locations up and down Siesta Key.
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
Argus Vacation Rentals
Whether you want a quiet spot to enjoy the tropical weather or a vacation spot to drop into between fun …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers a variety of vacation home rentals from homes to condos 5 star service
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
Siesta 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
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 …
Siesta Key Luxury Rental Properties
What sets our vacation rentals in Siesta Key, FL apart from other houses to rent? From spacious, gourmet kitchens to …
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 …
SkyRun Sarasota
SkyRun Vacation Rentals is the premier short-term rental property management company serving Sarasota and surrounding beaches, including Siesta Key, Lido …
FloridaRentals.com
We offer the highest quality vacation rentals in Siesta Key: romantic beachfront condos, expansive homes and everything in between. Trusted …
Beachside Management, LLC
Let us assist with your Siesta Key vacation rental. Whether condo, bungalow, studio villa or 5 bedroom home we have …
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 …
Rent Siesta Key
We offer an unrivaled selection of vacation rentals throughout Siesta Key and the Sarasota/Bradenton Gulf Coast. Discover a spectacular paradise …
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), …
Florida Rental By Owners
Discover the freedom of vacationing on your terms with Florida Rental By Owners. As the premier vacation rental listing site, …
Sunset Royale
Sunset Royale offers one and two bedroom condos fully equipped with all the amenities, including a full kitchen to make …
Altez Vacations
Altez Vacations is a family owned and operated vacation rental management company on Siesta Key. As natives of Sarasota we …
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 …
Siesta Palms by the Beach
If you’re looking for a vacation rental on Siesta Key, consider the unique charm and big condo accommodations at Siesta …
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 …
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 …
Vacasa
Our Siesta Key vacation homes are listed so you can easily find exactly what you’re looking for, and know exactly …
Lido Key Vacations
Lido Key is a cozy island vacation getaway in Sarasota that remains a bit of a hidden gem. For travelers …