To reserve one of our Siesta Key vacation rentals, we require a 50% deposit at booking, with the remaining balance due 60 days before arrival. Our homes are among the most sought-after vacation rentals in Siesta Key, Florida so we recommend booking early—especially for peak season.
We accept all major credit cards.
We understand plans change when booking Siesta Key beach rentals:
- Refund for cancellations made 60+ days in advance (minus the cancellation fee and the 3% for credit card processing fee)
- No refunds apply within 60 days
- Travel insurance is highly recommended for all vacation rentals.
- Typically Check-in: 4:00 PM
- Specific entry requirements will be provided prior to your arrival.
- Typically Check-out: 10:00 AM
- Specific check out procedures will be provided upon arrival.
Our streamlined process makes arriving at your Siesta Key vacation home rental simple and stress free.
All StaytheKey properties offer contactless check-in, so you can go straight to your Siesta Key rental home —no office visits required.
Our Siesta Key house rentals and condos include:
- Fully equipped kitchens
- High-speed Wi-Fi
- Smart TVs
- Washer & dryer (in most)
- Linens & towels
- Beach gear for enjoying Siesta Key Beach
These features make our homes ideal for anyone searching for family-friendly Siesta Key vacation rentals or luxury beach rentals in Siesta Key.
Yes, each Siesta Key rental property includes starter supplies. Guests staying longer in our weekly or monthly Siesta Key rentals may need to restock.
Our properties are located on or near Siesta Key, the beaches around are consistently ranked among the top beaches in the U.S. If you’re searching for Siesta Key beachfront rentals or walking-distance beach rentals in Siesta Key, you’re in the right place.
Guests staying in our Siesta Key vacation rentals can enjoy:
- Free trolley service
- Bike rentals
- Golf cart rentals
Most visitors find they don’t need a car when staying in a centrally located Siesta Key beach rental.
Sarasota Bradenton (SRQ) -20 minutes, Tampa (TPA) is 60 minutes and Orlando (MCO) is 2 hrs.
Yes—our Siesta Key rental homes include designated parking. Availability varies by property, especially for beachfront Siesta Key condos and rentals.
Yes—you must be 25+ to book our Siesta Key vacation rentals.
Most of our Siesta Key condo rentals are not pet-friendly, but we do offer select pet-friendly Siesta Key vacation rentals—just ask for availability.
All properties are non-smoking, including patios and balconies.
No—our family-friendly Siesta Key rentals are designed for relaxing getaways. Parties and events are not permitted.
When staying in one of our Siesta Key beach house rentals, bring:
- Groceries & personal items
- Beachwear & sunscreen
- Any specialty items for extended stays
Everything else is ready for your perfect Siesta Key Florida vacation.
We provide responsive, local support with an emergency 24-hour contact number 941-400-1266 for all guests staying in our Siesta Key vacation homes, ensuring a smooth and enjoyable experience.
Guests choose Stay the Key when searching for:
- Best Siesta Key vacation rentals near the beach
- Luxury Siesta Key beach rentals
- Family-friendly Siesta Key condo rentals
- Prime locations near Siesta Key Beach
- Professionally cleaned and managed homes
- Easy booking + contactless check-in
- Local, responsive guest support