Siesta Key Vacation Rentals

Siesta Key offers a wide variety of accommodations. Choices range from cottages to townhouses, beach houses to high-rise condos. All of the properties listed below are bookable online. If you are looking for a hotel or want to shop by complex, check our Siesta Key vacations page for complexes and hotels in the area. Many of those listings have a link so you can book directly with the management company or front desk. You can also call a friendly BeachGuide vacation planner seven days a week, and most evenings, at 888-404-2602 for help finding the perfect vacation rental. Check availability and book your stay on BeachGuide. 

Over 85% of our properties that match your search are booked!
Default Sort

Siesta Key Beach Hideaway

1-4 BD

1-3 BA

Sleeps 2-12

Beachfront

Beach View

Oceanfront

Ocean View

Waterfront

Water View

Pet Friendly

Pet Friendly

Washer/Dryer

Washer/Dryer

King bed(s)

Deck/Patio

Patio/Balcony

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Sombrero Siesta Retreat

2-4 BD

2-3 BA

Sleeps 4-10

Beachfront

Beach View

Oceanfront

Ocean View

Waterfront

Water View

Pet Friendly

Pet Friendly

Washer/Dryer

Washer/Dryer

King bed(s)

Deck/Patio

Patio/Balcony

Courtyard

Non-Metered Parking

Private Parking

Private Pool