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.
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 …
FloridaRentals.com
We offer the highest quality vacation rentals in Siesta Key: romantic beachfront condos, expansive homes and everything in between. Trusted …
Turtle Beach Campground
We're Sarasota County's premier beachfront campground. From sunrise to sunset, there's nothing like camping next to the Gulf of Mexico. …
SkyRun Vacation Rentals
SkyRun Vacation Rentals is the premier short-term rental property management company serving Sarasota and surrounding beaches, including Siesta Key, Lido …
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, …
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 …
Gulf & Bay Club
Gulf & Bay Club offers two and three bedroom/two bath units on the beautiful award winning white sand beach of …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers a variety of vacation home rentals from homes to condos 5-star service
Our House At The Beach
Our House at the Beach is a two bedroom/two bath condominium complex with 106 units total. Condos are fully furnished …
Siesta Key Island Rentals
Siesta Key Island Rentals is a collection of professionally managed properties and units. Our vacation rentals are convenient to restaurants …
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 …
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 …
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
Horizons West
Located on top-rated Crescent Beach on beautiful Siesta Key. Beach to bay, 1, 2 & 3 bedroom Gulf front apartments …
Gulf Coast Property Management
Our homes are near main attractions, such as award-winning beaches, beautiful golf courses, a lively shopping and entertainment scene and …
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 …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
Siesta 4 Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
Florida Rental By Owners
Discover the freedom of vacationing on your terms with Florida Rental By Owners. As the premier vacation rental listing site, …
Lido Key Vacations
Lido Key is a cozy island vacation getaway in Sarasota that remains a bit of a hidden gem. For travelers …
Altez Vacations
Altez Vacations is a family owned and operated vacation rental management company on Siesta Key. As natives of Sarasota we …
Beachside Management
Beachside Management opened in 2015 with the goal of providing wonderful vacation experiences to Siesta Key travelers. We offer a …
Sunset Royale
Sunset Royale offers one and two bedroom condos fully equipped with all the amenities, including a full kitchen to make …
Siesta Key Inn
Welcome to Siesta Key Inn, your ideal Siesta Key vacation rental for a memorable getaway. Nestled just a short 5-minute …
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 …
Gulf Coast Vacations
Offering comfort, style and unbeatable access to Florida's stunning coastline. Properties professionally managed to ensure a seamless experience, with top-tier …
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 …
Pinkie Flamingo & Friends
With 20+ years of marketing and management experience, exceptional attention to detail, and a love for the boutique experience, we …
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 …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …