Rent Siesta Key

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/

05/19/2026

🥭 MangoMania 2026: Pine Island's Tropical Fruit Festival Returns July 11!

The MangoMania Tropical Fruit Festival is back at 9940 Stringfellow Road in St. James City on Saturday, July 11, 2026 — 9:00 AM to 5:00 PM!

Enjoy live music all day, mango recipe contests, the Biggest Mango Contest, tropical plants & fruit for sale, mango games for kids, food & beverages, planting seminars, and arts & crafts booths. Family-friendly and dog-friendly!

The festival is just 20 minutes from our Cape Coral villas — the perfect excuse for a July getaway! 🌴

👉 Read more & plan your stay: https://rentthekeys.com/mango-mania-pine-island-2026/

Pine Island's annual MangoMania festival returns Saturday, July 11, 2026 with live music, mango games, recipe contests, and fresh tropical fruit. Plan a stay.

05/14/2026

🌴☀️ Escape to Edgemere Escape – a stunning 4BR vacation rental in Siesta Key, FL! Private heated pool, modern luxury & steps from the world-famous Beach. Your perfect Florida vacation awaits! 🏖️ Use code FB005 for 5% OFF! Book now 👉 https://www.rentsiestakey.com/edgemere-escape/
*Promotion applies to select properties only.*

https://www.rentsiestakey.com/edgemere-escape/

05/07/2026

🌴☀️ Escape to paradise at Siesta Heron 3 – Captiva! This charming vacation rental on Siesta Key, FL is your perfect Florida vacation getaway! 🏖️ Steps from the beach, heated pool, bikes & beach gear included! Book this short term rental today & save 5% OFF with code FB005 👉 https://www.rentsiestakey.com/siesta-heron-3-captiva/
*Promotion applies to select properties only.*

https://www.rentsiestakey.com/siesta-heron-3-captiva/