The Cottages on the Key

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The Cottages on the Key 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.

NEW TO THE COLLECTION | Treasure on the Canal!We're excited to welcome Treasure on the Canal, a stunning Mediterranean-s...
11/09/2026

NEW TO THE COLLECTION | Treasure on the Canal!

We're excited to welcome Treasure on the Canal, a stunning Mediterranean-style waterfront estate, to The Cottages on the Key! With beautiful canal views, luxurious interiors, and plenty of space to unwind, this Siesta Key retreat has everything you need for an unforgettable getaway.

Property Highlights:
🏡 3 Bedrooms + Bonus Room | Sleeps 8
🏊 Private Heated Pool & Spa
🛶 Private Dock & 2 Kayaks
🍹 Covered Outdoor Kitchen & Multiple Wet Bars
🌴 Just 0.7 Miles to Siesta Key Village

NEW PROPERTY SPECIAL! Enjoy 10% OFF when you book Treasure on the Canal directly with us this November

https://www.thecottagesonthekey.com/vacation-rentals/rental/treasure-on-the-canal-701/

The Siesta Key Crystal Classic is Almost Here!From November 13–16, Siesta Key Beach will transform into an incredible ou...
11/06/2026

The Siesta Key Crystal Classic is Almost Here!

From November 13–16, Siesta Key Beach will transform into an incredible outdoor art gallery as master sand sculptors from around the world create breathtaking works of art right on our famous white sands! 🌟

Enjoy multiple days of stunning sand sculptures, live music, local food and drinks, shopping, and family-friendly fun.

🏡 Still looking for a place to stay near the action? The Cottages on the Key has plenty of beautiful vacation rentals just an easy walk from the festival, so you can enjoy every moment without worrying about parking or transportation!

https://www.siestakeycrystalclassic.com/

Fiesta Playa | Your Siesta Key Escape Awaits!Just steps from Crescent Beach, Fiesta Playa brings together beachside rela...
11/02/2026

Fiesta Playa | Your Siesta Key Escape Awaits!

Just steps from Crescent Beach, Fiesta Playa brings together beachside relaxation and plenty of fun for the whole family! ☀️

Property Highlights:
🏡 3 Bedrooms | 3 Bathrooms | Sleeps 8
🌊 Just 0.1 miles to Crescent Beach
🏊 Access to a heated semi-private community pool
🏓 Siesta Key-themed tiki lounge with ping pong and TV
🌴 Spacious balconies and private elevator
🍹 Less than 0.5 miles to South Siesta Key Village

Beach days, poolside afternoons, and island evenings are all waiting at Fiesta Playa!
https://www.thecottagesonthekey.com/vacation-rentals/rental/fiesta-playa-1027/

Happy Halloween time from The Cottages on the Key! 🎃If you’re in town visiting, be sure to check out this wonderful even...
10/30/2026

Happy Halloween time from The Cottages on the Key! 🎃

If you’re in town visiting, be sure to check out this wonderful event tomorrow, hosted by the Siesta Key Chamber.

Halloween Safe Treats for children and families, Saturday, October 31, 4pm - 6pm. Bring your little ones to trick-or-treat with Siesta Key businesses. Look for participating businesses displaying their Safe Treats Signs across Siesta Key. 👻

Check out Crescent Cottage! Just 0.2 miles from Crescent Beach, this beautifully renovated 4-bedroom retreat has everyth...
10/27/2026

Check out Crescent Cottage! Just 0.2 miles from Crescent Beach, this beautifully renovated 4-bedroom retreat has everything you need for a laid-back Siesta Key getaway! ☀️

Spend your mornings strolling along the white sand, afternoons lounging by your private heated pool, and evenings grilling outdoors or gathering around the fire pit. Best of all, your four-legged family members are welcome too! 🐾

With room for up to 10 guests, beautiful coastal interiors, and a peaceful location on the south end of Siesta Key, Crescent Cottage is ready for your next island escape!

https://www.thecottagesonthekey.com/vacation-rentals/rental/crescent-cottage-1034/

☕ One of our favorite spots on St. Armands Circle!If you're exploring St. Armands Circle, Cafe on St. Armands is a must-...
10/26/2026

☕ One of our favorite spots on St. Armands Circle!

If you're exploring St. Armands Circle, Cafe on St. Armands is a must-visit. With its charming ambiance, beautiful indoor and outdoor seating areas, and views of the Circle, it's the perfect place to slow down and enjoy the atmosphere.

From morning coffee at their coffee bar to delicious brunch options and afternoon happy hour, there's something to enjoy any time of day. 🥂

Definitely a spot worth adding to your Lido Key itinerary!

🌴 A Little Holiday Cheer, Beachside! We're spreading a little extra holiday cheer with 10% OFF stays from November 14 – ...
10/23/2026

🌴 A Little Holiday Cheer, Beachside! We're spreading a little extra holiday cheer with 10% OFF stays from November 14 – December 31, 2026!

Whether you're planning a Thanksgiving escape, a coastal Christmas, or ringing in the New Year by the water, we want to give everyone a chance to save on a gorgeous beach vacation this holiday season. ✨

🎁 Enjoy 10% OFF your holiday stay with promo code HOLIDAY26!

There's no better way to celebrate the season than making memories by the coast.

Book direct and use code HOLIDAY26 at checkout to save!
https://www.thecottagesonthekey.com/

The Perfect Siesta Key Getaway!Introducing The Coastal Collection, featuring two charming side-by-side units, Siesta San...
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/

🎃 A spooky good time awaits at Marie Selby Gardens!Lights at Spooky Point is back at the Historic Spanish Point campus, ...
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

🌴 Casa Junonia | Steps to Crescent Beach Just 400 feet from Crescent Beach and Point of Rocks, Casa Junonia is perfect f...
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/

Address

5016 Calle Minorga
Siesta Key, FL
34242

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