Rent Siesta Key

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/

06/18/2026

🌴☀️ Escape to paradise at Bay Oaks E01 — a stunning beach vacation rental on Siesta Key, FL! 🏖️ This 2BR/2BA short term rental sleeps 6, features intercoastal views, a heated pool & is just steps from Florida's best beaches! 🌊 Use code FB005 for 5% OFF your stay! Book now 👉 https://www.rentsiestakey.com/bay-oaks-e01/
*Promotion applies to select properties only.*

https://www.rentsiestakey.com/bay-oaks-e01/

06/11/2026

🌴☀️ Your dream Florida vacation awaits! Sandy Cove Unit 401 on Siesta Key is the perfect beach short term rental — luxury 2BR/2BA condo, private beach access & heated pool! 🏖️ Book your vacation rental today & save 5% OFF with code FB005! 👉 https://www.rentsiestakey.com/sandy-cove-unit-401/

*Promotion applies to select properties only.

https://www.rentsiestakey.com/sandy-cove-unit-401/

06/04/2026

🌴 Your dream Florida vacation awaits at Oxford Oasis! 🏖️ This stunning Siesta Key vacation rental features a private heated pool, sleeps 10, & is just mins from the beach! Perfect short term rental for groups & families. 🌊☀️ Use code FB005 for 5% OFF! Book now 👉 https://www.rentsiestakey.com/oxford-oasis/
*Promotion applies to select properties only.

https://www.rentsiestakey.com/oxford-oasis/

05/31/2026

🥁 Siesta Key Drum Circle 2026: The Sunset Ritual Worth Driving Over For

Every Sunday at sunset on Siesta Beach, dozens of drummers gather south of the main pavilion for a free, informal drum circle that's been running for over 20 years. Dancers, hula-hoopers, fire performers, and the slow Gulf sky make it one of the most magical rituals on the Gulf Coast — and it costs nothing to attend.

🗓️ Sundays through Summer 2026:
• July 5 · sunset ~8:25 PM
• July 12 · sunset ~8:24 PM
• July 19 · sunset ~8:21 PM
• July 26 · sunset ~8:17 PM

Stay close enough to walk back when the rhythm winds down. Browse our Siesta Key vacation rentals and make a weekend of it! 🌅

👉 https://rentthekeys.com/siesta-key-drum-circle-2026/

https://rentthekeys.com/siesta-key-drum-circle-2026/

05/31/2026

🎪 Summer Circus Spectacular 2026 at The Ringling: Sarasota's Coolest Hour of the Summer!

Sarasota's Summer Circus Spectacular runs June 13 – August 8, 2026 at the Historic Asolo Theater — a one-hour, air-conditioned escape from the summer heat. The perfect outing during your Siesta Key vacation!

🗓️ June 13 – August 8, 2026
📍 The Ringling, Historic Asolo Theater, Sarasota, FL

Plan your stay with us and catch this incredible show! 🎡✨

👉 Read more:

Sarasota's Summer Circus Spectacular runs June 13 – August 8, 2026 at the Historic Asolo Theater — a one-hour, A/C escape from the July heat. Plan a stay.

05/31/2026

🎉🇺🇸 Anna Maria Privateers 4th of July Parade 2026: The Gulf Coast's Most Patriotic Saturday!

The Anna Maria Privateers are rolling out their beloved annual 4th of July Parade on Saturday, July 4, 2026! The parade kicks off at 10:00 AM at Coquina Beach and winds 3 miles north up Gulf Drive through Bradenton Beach and Holmes Beach, wrapping up around 1:00 PM at City Pier Park.

✅ It's FREE
🔫 You WILL get wet (wear your beach clothes!)
🎊 Beads, candy, floats, fire trucks & classic cars
🎶 Followed by the Anna Maria City Picnic with live music & fireworks over the Gulf after sunset

Make it a long weekend — the Fourth falls on a Saturday in 2026! Browse our Anna Maria Island vacation rentals and lock in your dates before they're gone. 🏖️

👉

Watch the Anna Maria Island Privateers' beloved 4th of July Parade on Saturday, July 4, 2026 — three miles, free, family-friendly. Plan the long weekend now.

05/28/2026

🌴 Escape to The Treehouse on Siesta Key, FL! 🏖️ This stunning 4BR/3.5BA vacation rental sleeps 8 w/ private pool, hot tub & outdoor kitchen. Perfect Florida vacation short term rental for families! 🐾 Pet friendly too! Use code FB005 for 5% OFF! Book now 👇
https://www.rentsiestakey.com/the-treehouse/
*Promotion applies to select properties only.

https://www.rentsiestakey.com/the-treehouse/

05/21/2026

🌴☀️ Escape to Siesta Key, FL! Vista Hermosa 302C is a stunning vacation rental steps from Crescent Beach 🏖️ — 2BR/2BA, pool, & beach gear included! Perfect Florida vacation short term rental. Use code FB005 for 5% OFF! Book now 👉 https://www.rentsiestakey.com/vista-hermosa-302c/

*Promo applies to select properties only.

https://www.rentsiestakey.com/vista-hermosa-302c/

05/19/2026

🍜🌏 Sarasota Downtown Foodie World Asian Food Festival 2026: A Taste of Asia on the Bayfront!

Get ready, Sarasota! One of Florida's most exciting culinary celebrations is heading to J.D. Hamel Park from June 5–7, 2026. Enjoy 80+ food vendors, live entertainment, cultural performances, and a dazzling night market experience — all with FREE admission!

From sizzling ramen bowls and Korean corn dogs to boba drinks and mochi donuts, there's something for every palate. Plus, night market shopping, games, and stunning waterfront views make this a must-attend weekend event.

📅 June 5–7, 2026 | 2:00 PM – 11:00 PM
📍 J.D. Hamel Park, 199 Bayfront Drive, Sarasota, FL
🎟️ FREE Admission

Planning to make a full weekend of it? Stay nearby in a Siesta Key or Sarasota vacation rental! 🏖️
👉 https://rentthekeys.com/sarasota-downtown-foodie-world-asian-food-festival-2026-a-taste-of-asia-on-the-bayfront/

https://rentthekeys.com/sarasota-downtown-foodie-world-asian-food-festival-2026-a-taste-of-asia-on-the-bayfront/