*This quote was created on 08/11/2026. Booking total includes taxes & fees; Pricing and availability subject to change.
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Exclusive Amenities Include: ↑↓
• Private Heated Pool & Hot Tub
• Less than 3 Miles to Siesta Key Village and Beach
• 4 Bedrooms, 3 Full Baths (Sleeps 10) with Linens Provided
• Outdoor Lounge Area Including Private Putting Green, Dining Area, and Pool Loungers
• Private 2 Car Garage & Ping Pong Table
• Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided
• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipes
• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes
• Beach Towels, Chairs, Cooler, & Caddy Provided
• Screened Outdoor Dining Area & Gas Grill
• Enhanced Cleaning Protocols Provided by our CottageClean Team
• Dog-Friendly with a Fee (2 Small Dogs up to 25lbs)
Overview ↑↓
Casa Leone | Heated Pool & Spa, Pet Friendly, Putting Green
Why You'll Love This Home
Tucked on the northern end of Siesta Key, Casa Leone is a four-bedroom retreat where polished interiors meet a private outdoor oasis. The heated pool and spa, screened lanai, putting green, and upper deck lounge area give everyone plenty of ways to fill the day, with Siesta Key's world-famous beach and village just a short drive away!
Perfect For
Families, multi-generational groups, or friend gatherings looking for a well-appointed Siesta Key home with private outdoor amenities and room for up to 10 guests.
Imagine This
Morning starts in the open-concept kitchen, coffee brewing while sunlight fills the living room just off the pool. Slide open the door and the screened lanai becomes your breakfast spot, island breezes drifting through while the kids claim their pool floats. Afternoons shift between the putting green, a spirited ping pong match, and the upper deck lounge chairs where the breeze picks up and the neighborhood stretches out below. When dinner rolls around, Siesta Key Village is a short drive away, grab a table or bring something back to enjoy al fresco. Evenings settle into movie nights on the flat-screen or quiet time on the king suite's private balcony, the neighborhood still and cool around you.
Where You'll Sleep
• Bonus Room: Sleeper Sofa, 1st Floor, Full Bath, TV
• Bedroom 1: Queen Bed, 1st Floor, Bonus Room Bath, TV
• Bedroom 2: Queen Bed, 2nd Floor, Hallway Bath, TV
• Bedroom 3: Queen Bed + Twin/Twin Bunk Bed, 2nd Floor, Hallway Bath, TV
• Bedroom 4: King Bed, 3rd Floor, Ensuite Bath, Private Balcony, TV
Explore the Area
• 2.2 Miles to Siesta Key Village — Dining, Shopping, and Nightlife
• 3.0 Miles to Siesta Key Beach — Powdery Quartz Sand and Crystal-Clear Water
• 3.5 Miles to Downtown Sarasota — Arts, Culture, and Waterfront Dining
• 6.4 Miles to St. Armands Circle — Upscale Boutiques and Waterfront Dining
Don't wait
From the putting green to the screened lanai, Casa Leone is designed for days that feel effortlessly unhurried — and every stay is backed by our CottageClean™ program: a 6-hour deep clean and 35-point inspection.
Please Note
This property is registered as a vacation rental with the City of Sarasota, Registration No. VR22-00008. Per City of Sarasota code, this property may only be rented once per seven-day period with a maximum occupancy of 10 guests. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. We happily welcome up to 2 small dogs (up to 25 lbs) with a $250 fee per pet — breed guidelines apply to ensure a safe and comfortable stay for everyone.
"very great people to work with. kitchen had all the cookware we needed!
Reviewed By: Melissa Keathley
Perfect property for our family vacation!
Review Date: April 8, 2025
"Perfect property for our family vacation!
Reviewed By: Cody Mckay
We loved staying at The Cottages on the Key!
Review Date: September 3, 2024
"We loved staying at The Cottages on the Key! Amazing house with great amenities and in an amazing location! Host was responsive and took great care of us whenever we had any questions or concerns. Our family had a peaceful and relaxing vacation here, we would definitely stay here again!
Reviewed By: Inna Skots
Great house - short drive to the beach!
Review Date: July 8, 2024
"Great house - short drive to the beach! THe kitchen had everything we needed and was super clean / organized. The pool was so nice. We loved being a short drive to the beach.
Reviewed By: Rachel Mazur
It's a little drive to the beach but the golf cart was a major bonus!
Review Date: April 25, 2024
"The house is three levels. Very outdated small kitchen appliances. Everything else was OK. I wouldn't suggest having a girls trip here because the neighbor behind us got angry when we were playing our music at night around 830-9pm. It's a little drive to the beach but the golf cart was a major bonus! I can see where a family with children would love this house! Suggested for families vs girls trip
Reviewed By: Casey Shipp
Would definitely rent with this company again.
Review Date: April 16, 2024
"Management Company was very helpful and responsive. Everything at the house was clean and well kept. Would definitely rent with this company again.
Reviewed By: Teresa Gibson
April School Family Vacation
Review Date: April 27, 2023
"“Instead of. Christmas presents….Let's make a Family Memory”…… We Sure Did!!' Our family memory was over April School Vacation. The house was simply perfect! Plenty of room….the kids Loved the Pool!'m. The area was charming….The Beaches were fabulous…..Our only complaint was the vacation went by too quickly!!!!!
Reviewed By: Steven Doughty
Stayed with 4 couples ….perfect! Great location and wonderful private backyard and pool area!
Review Date: November 22, 2022
"Everything was great! Had groceries delivered early in the week and this was so convenient too!