The Cottages on the Key

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Siesta Key, FL
The Cottages on the Key

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We provide a hospitality & concierge service to a boutique collection of luxury vacation rental homes The Cottages on the Key, Inc.

provides hospitality & concierge service to a boutique collection of specially chosen luxurious vacation rentals in Sarasota.

10/20/2026

The Perfect Siesta Key Getaway!

Introducing The Coastal Collection, featuring two charming side-by-side units, Siesta Sands and Siesta Sunrise, just steps from Siesta Key Beach and a short stroll to the Village! ☀️

Enjoy the convenience of separate living spaces, fully equipped kitchens, and private entrances, plus access to a heated community pool and outdoor dining area.

🏡 Traveling together or separately? Both units can be booked individually or combined as The Coastal Collection, accommodating up to 8 guests!

With beach access just 0.1 miles away and Siesta Key Village only a 7-minute walk, this is island living made easy.

https://www.thecottagesonthekey.com/vacation-rentals/rental/the-coastal-collection-73/

10/16/2026

🎃 A spooky good time awaits at Marie Selby Gardens!

Lights at Spooky Point is back at the Historic Spanish Point campus, bringing Halloween magic to life with a dazzling, Halloween-inspired light show you won't want to miss!

Enjoy face painting, balloon creations, and delicious bites and treats from Michael's On East, c***r, and ice cream food trucks.

🗓️ Going Until October 31, 2026
🕡 Entry times: 6:30 PM & 7:45 PM

Whether you're visiting Sarasota or enjoying a local night out, this is a festive fall experience worth adding to your calendar!

Selby Gardens - Marie Selby Botanical Gardens

10/15/2026

🌴 Casa Junonia | Steps to Crescent Beach

Just 400 feet from Crescent Beach and Point of Rocks, Casa Junonia is perfect for beach days, snorkeling adventures, and laid-back island living.

With 4 bedrooms, room for up to 12 guests, and Crescent Village just a short walk away, it's an ideal island retreat!

🏡 Traveling with a larger group? Casa Junonia is part of a duplex, giving you the flexibility to book this side, the neighboring unit, or the entire duplex together! ☀️

https://www.thecottagesonthekey.com/vacation-rentals/rental/casa-junonia-1032l/

10/13/2026

We took our own advice and spent the day at Ananda Farms Fall Festival, and what a fabulous time we had

From pick-your-own flowers and the pumpkin patch to the giant bouncy pillow, trike track, playground, and plenty of fresh food and delicious treats, there was something for everyone to enjoy! 🌻

If you’re visiting Sarasota this fall, we highly recommend adding this family-friendly festival to your itinerary. It’s the perfect way to embrace the season while still soaking up that Florida sunshine ☀️🌴

10/09/2026

Your Siesta Key getaway, with the water right in your backyard.
At Blu Sky Cottage, mornings can start by launching a complimentary kayak straight from the dock, followed by an afternoon floating in the private saltwater pool or relaxing in the spa overlooking the canal.

Grill outside, play a round of co****le, or simply enjoy the waterfront views before heading into Siesta Key Village, just 0.5 miles away. 🌴

With 3 bedrooms, room for up to 8, and Siesta Key Beach only a mile away, this is island living done right. ☀️

https://www.thecottagesonthekey.com/vacation-rentals/rental/blu-sky-cottage-5037/

10/08/2026

🎃 Fall fun, Florida style! Who says you need cooler weather to get into the fall spirit? Sarasota has plenty of seasonal fun to enjoy, including pumpkin picking, festive photo ops, family activities, and delicious fall treats.

🍂 Spend an afternoon exploring the pumpkin festivals at Fruitville Grove, Hunsader Farms, or Ananda Farms, then head back to the coast for a sunset to finish the perfect fall day.

Pumpkins, palm trees, and Gulf Coast sunshine, fall looks a little different here, and we love it!

09/30/2026

🌅 There’s still time for a Beach Fanta Sea getaway before the year ends!

Gather the whole crew at this spacious 9-bedroom Lido Key retreat, where days can start with a 5-minute walk to the beach and end with sunset views from your private rooftop deck.

In between, enjoy the heated pool & spa with swim-up seating, relax on the Baja shelf, gather for dinner under the outdoor gazebo, or stroll over to St. Armands Circle. 🌴

✨ Beach Fanta Sea still has select openings before the end of the year, your Lido Key escape could be closer than you think!

https://www.thecottagesonthekey.com/vacation-rentals/rental/beach-fanta-sea-149/

09/29/2026

Your stay just got even better. ✨ We're thrilled to introduce our new concierge experience.

Our guide to making the most out of your stay. From booking local experiences to arranging transportation, getting restaurant recommendations, and more, our dedicated concierge team is here for you before and during your trip.

Because exceptional stays deserve exceptional service. 🌴

09/28/2026

✨ A Fresh Look at Beachside Bungalow!

This Siesta Key favorite recently got even better with new hot tubs, cozy fire tables, and outdoor games the whole family can enjoy. Spend the day just 0.1 miles away at Crescent Beach, then come home for a soak, some friendly competition, and an evening around the fire.

With two adjoining private bungalows, Beachside Bungalow is perfect for families and groups who want to vacation together while still having their own space.

Beach days, backyard fun, and plenty of room for the whole crew, it’s all waiting at Beachside Bungalow.

https://www.thecottagesonthekey.com/vacation-rentals/rental/beachside-bungalow-1136/

09/24/2026

Featured Properties. Exclusive Savings.

Each month, we handpick a collection of incredible vacation homes and give you 10% OFF your stay! 🌴

From private pools to unbeatable beach locations, it’s the perfect opportunity to discover a new favorite, and save while you do it. 🏖️

Explore this month’s featured properties and start planning your next Gulf Coast escape!
https://www.thecottagesonthekey.com/featured-properties/

Address

5016 Calle Minorga
Siesta Key, FL
34242

Telephone

+18003851499

Website

https://thecottagesonthekey.com/

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