Rent Siesta Key

10/13/2026

⚔️ Sarasota Medieval Fair 2026 ⚔️

Step back in time and experience the magic of the Sarasota Medieval Fair 2026! Enjoy jousting, live entertainment, artisan vendors, delicious food, and so much more. It's a fun-filled event for the whole family!

📅 October 2026 | 📍 Sarasota, FL

Read more about this exciting event on our blog:
👉 https://rentthekeys.com/sarasota-medieval-fair-2026/

Planning a trip to Siesta Key for the fair? We have the perfect vacation rentals waiting for you! 🏖️

https://rentthekeys.com/sarasota-medieval-fair-2026/

09/01/2026

🎉 BayFest 2026 Anna Maria Island Guide is here!

Get ready for one of Anna Maria Island's most exciting annual events — BayFest 2026! Whether you're a local or planning your vacation around this incredible festival, our latest guide has everything you need to know.

🌊 Live music, local food, fun on the bay, and so much more await you on beautiful Anna Maria Island.

Read our full guide and start planning your trip today! 👇
https://rentthekeys.com/bayfest-2026-anna-maria-island-guide/

https://rentthekeys.com/bayfest-2026-anna-maria-island-guide/

07/09/2026

🌴☀️ Your Florida vacation awaits! Avenida De Cortez – a stunning short term rental on Siesta Key with a private pool, steps from the beach! 🏖️ The ultimate Beach vacation rental experience!
👉 Book now: https://www.rentsiestakey.com/avenida-de-cortez/
🎉 Use code FB005 for 5% OFF!
*Promotion applies to select properties only.

https://www.rentsiestakey.com/avenida-de-cortez/

07/08/2026

🏆 Airbnb Superhost!

We’re honored to have earned Airbnb Superhost status.

This award recognizes hosts who consistently provide outstanding guest experiences—and that’s exactly what our team strives to deliver every single stay.

Thank you to all of our amazing guests for your reviews, support, and trust.

We can’t wait to welcome many more of you to beautiful Siesta Key!

☀️ Beachfront & beach-access vacation rentals
⭐ Exceptional guest service
🏆 Airbnb Superhost

Book your stay:
🔗 www.RentSiestaKey.com

07/02/2026

🌊☀️ Your dream Florida vacation awaits at Bayside Pointe - Siesta Key! This stunning 3BR/2BA vacation rental is steps from the beach, with a pool & sports courts. The perfect short term rental for your Beach getaway! 🏖️🌴 Book now & save 5% OFF with code FB005 👉 https://www.rentsiestakey.com/bayside-pointe-1232/
*Promotion applies to select properties only.*

https://www.rentsiestakey.com/bayside-pointe-1232/

06/25/2026

🎌 Sarasota Anime-Fest 2026: A Cool, Air-Conditioned Saturday at Robarts Arena

Escape the August heat! Sarasota Anime-Fest hits Robarts Arena on Saturday, August 15, 2026, from 10:00 AM to 5:00 PM. 🌟

Spend the day surrounded by anime, gaming, cosplay, vendors, artists, and pop culture — all indoors and air-conditioned. It's a fantastic outing for families, teens, and anime fans of all ages!

📍 Robarts Arena, Sarasota Fairgrounds — just 15–25 minutes from Siesta Key, Lido Key, and Longboat Key.

🏖️ Make it a full beach vacation day: morning on the beach, afternoon at Anime-Fest, and dinner on St. Armands Circle on the way back.

👉 Browse our vacation rentals and plan your stay: https://rentthekeys.com/sarasota-anime-fest-2026/

https://rentthekeys.com/sarasota-anime-fest-2026/

06/25/2026

🎶 Music on Main 2026 – Lakewood Ranch | August 7, 2026

Looking for the perfect way to kick off a Gulf Coast beach weekend? Music on Main is a FREE, family-friendly block party on Main Street in Lakewood Ranch — happening the first Friday of every month!

📅 Next Event: August 7, 2026
🕕 6:00 PM – 9:00 PM
🎵 Live music, food vendors, drink trucks & a kids' zone
🐾 Dogs welcome (on leash)!

Best of all? No tickets, no cover — just show up and enjoy the night.

Lakewood Ranch is only 20–30 minutes from our beach rentals on Siesta Key, Lido Key, Longboat Key, and Anna Maria Island. Spend the day on the sand, then head over for the music! 🌊🎶

👉 Read more & browse Gulf Coast vacation rentals:

Music on Main is a free first-Friday block party in Lakewood Ranch on Aug 7, 2026. Plan a Gulf Coast beach weekend around it and book your stay today.

06/25/2026

🌟 Laser Light Nights 2026 at The Bishop Museum: A Cool Bradenton Night Under the Dome 🌟

Laser Light Nights at The Bishop Museum of Science and Nature in Bradenton is back for 2026! The planetarium dome transforms into a full-sensory laser-and-music concert featuring Queen, Pink Floyd, Taylor Swift, The Beatles, and more.

📅 Season runs through September 6, 2026
🕕 Thursdays at 6 PM | Fridays & Saturdays at 6 & 7 PM

It's the perfect evening escape after a long beach day on the Gulf Coast! Come early to explore the museum, then stay for the show. Popular nights sell out — book your tickets in advance!

🏖️ Staying nearby? Browse our Anna Maria Island & Bradenton vacation rentals and make a night of it!

👉 Read more:

Laser Light Nights at The Bishop Museum runs through Sep 6, 2026. Cap a Gulf Coast beach day under the dome — book your Bradenton-area rental today.

06/25/2026

🌴☀️ Your dream Florida vacation awaits! Bay Oaks E53 is a beautifully renovated 2BR/2BA vacation rental on Siesta Key — steps from the beach! 🏖️ Heated pool, beach essentials included & near Siesta Key Village. Perfect short term rental for your Beach getaway! 🌊

Use code FB005 for 5% OFF! Book now 👉 https://www.rentsiestakey.com/bay-oaks-e53/

*Promotion applies to select properties only.*

https://www.rentsiestakey.com/bay-oaks-e53/

06/23/2026

🎪 Summer Circus Spectacular 2026 is HERE! 🎪

World-class circus arts come to Sarasota's Historic Asolo Theater, running June 23 – August 8, 2026! Experience breathtaking aerial acrobats, jugglers, clowns, and internationally acclaimed performers — all under one roof at The Ringling.

🎟️ Tickets: $20 adults | $15 kids (12 & under)
📍 Historic Asolo Theater, 5401 Bay Shore Road, Sarasota, FL
📅 June 23 – August 8, 2026

After the show, make it a full Gulf Coast getaway — stay on beautiful Siesta Key! 🌊☀️

Read more & book your stay 👇
https://rentthekeys.com/summer-circus-spectacular-2026-world-class-circus-arts-come-to-sarasotas-historic-asolo-theater/

https://rentthekeys.com/summer-circus-spectacular-2026-world-class-circus-arts-come-to-sarasotas-historic-asolo-theater/