White sand beaches on Siesta Key
A Siesta Key vacation rental with ocean views
Ocean view from a Siesta Key vacation rental
A dining table in a Siesta Key rental
A beach chair on a white sand beach

Vacation Forever - Vacation With Gertrude

Experience Siesta Key

Soak up Siesta Key with a stay in one of our beach vacation rentals! Choose between a variety of different coastal communities including the Siesta Key Bungalows, Crescent Beach, and Siesta Village. Our vacation rentals feature cozy, coastal décor as well as proximity to Siesta Key’s gorgeous, white sand beaches and activities. Browse our Siesta Key short-term rentals and start planning a vacation to this island paradise!


Looking to swap out the beach for the ski slopes? We also feature properties in Vermont's Green Mountains. Check out our Vermont vacation rentals when you want a cozy home for Vermont's ski season! 

Waves crashing on a beach