Siesta Key Vacation Rentals
Condos, pool homes and lagoon bungalows. Book direct with Siesta Key Dreams.
Featured Siesta Key Properties
The owners hand-pick every home in our collection. Browse a few favorites below, or enter your dates in the search bar for live availability and rates per night.
Beach Road Complex
12 bedrooms · Sleeps 35
Siesta Key Bungalows Resort
10 bedrooms · Sleeps 30
5239–5241 Village Complex
8 bedrooms · Sleeps 28
Building 228
6 bedrooms · Sleeps 20
5316 Private Pool Complex
5 bedrooms · Sleeps 18
Avenida
6 bedrooms · Sleeps 16
Siesta Key Vacation Rentals on the Florida Gulf Coast
Siesta Key is a barrier island just off Sarasota, and its sandy shoreline of powdery white quartz is why most people come. Our homes keep you close to it, whether you want a quiet getaway for two or a whole building for a family reunion.
Condos, Beach Houses & Bungalows
Choose a studio or one-bedroom condo, a multi-level beach house like Avenida with Gulf views, or a bungalow on the lagoon. Larger groups can book an entire complex for up to 35 people.
Pools, Pets & Everyday Comforts
Many homes share a heated pool, and the 5316 complex has a private one. Select pet-friendly units are available on request. Most homes include a fully equipped kitchen, and all have air conditioning and parking.
Explore Siesta Key by Location
Siesta Key Village & Siesta Key Beach
Our Beach Road condos are 300 feet from a public access and 500 feet from Siesta Key Village, with plenty of shops and restaurants just down the street. Building 228 has a rooftop sundeck with partial ocean views, a lovely spot for sunset. The 5316 complex is 100 steps from a beach access, and the 5239 and 5241 units are a four-minute walk away.
Siesta Key Bungalows near Crescent Beach
On the quieter side of the key, Siesta Key Bungalows are located on Heron Lagoon with a pool, a private dock and kayaks. You’re about a mile from Turtle Beach and two miles from Crescent Beach and the snorkeling at Point of Rocks.
Why Book Direct with Siesta Key Dreams
Booking here skips the service fees that booking sites add, and puts you in touch with the team that runs the homes. A local Guest Experience Manager handles your stay, the owners stay involved in every home, and keyless smart-lock entry means no waiting for a key. You can also add a golf cart rental once you book.
Frequently Asked Questions
How far are your homes from the water?
Most are a one- to five-minute walk from a public access. The Bungalows sit on the lagoon, about a mile from Turtle Beach.
What does a stay cost per night?
Rates change by season, home size and length of stay. Enter your dates in the search bar at the top of the page for an exact total.
Can we book a whole building for a group?
Yes. Beach Road, 228, 5239–5241, 5316 and the Bungalows can each be booked as one property for reunions, celebrations and retreats. See all of our large-group homes.