Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony
A serene Siesta Key weekly retreat designed for relaxed gathering and coastal living. Located on one of the island’s most coveted streets, this 3-story home offers peekaboo views of Sarasota Bay, steady ocean breezes, and easy trolley access to Siesta Beach - one of the top-ranked beaches in the U.S. - perfect for families, weekly getaways, and refined island escapes.
Set on Flamingo Avenue, this three-story coastal home offers privacy, space, and quiet luxury in a well-established residential enclave accompanied by the island’s most iconic estates. Sarasota Bay sits at the end of the street, and peekaboo water views can be enjoyed from the balconies, along with steady ocean breezes throughout the home.
Siesta Key Beach is just minutes away, and the home is conveniently located in close proximity to a Siesta Key Breeze Trolley stop, making beach days effortless - no driving or parking required.
THE HOME 3-Story Key West–Style Residence Private swimming pool (unheated) 8-person hot tub 2-car garage + long private driveway Basketball hoop Wi-Fi Brand-new Samsung TVs throughout Fully equipped kitchen + family games
The home is thoughtfully laid out across three levels, offering both generous gathering spaces and private retreats.
TOP FLOOR - PRIVATE FAMILY SUITE LEVEL A peaceful, light-filled retreat at the top of the home. Two Queen beds 65” Samsung TV Spa-style bathroom with his-and-hers sinks, walk-in shower, and Jacuzzi tub beneath a skylight Private balcony with peekaboo water views - ideal for sunrise coffee or quiet dusk moments
SECOND FLOOR - MAIN LIVING LEVEL The heart of the home, designed for connection and flow. Spacious living room with fireplace (non-operational) + 75” Samsung Frame TV Dining room seating for up to 8 guests Fully equipped kitchen stocked with cookware, prep tools, and essentials Large front porch - doors open directly from living and dining areas Jack-and-Jill bathroom with shower-tub Bedrooms on this level: Bedroom 1: King bed + 43” Samsung TV Bedroom 2: Two Twin beds + 43” Samsung TV
GROUND FLOOR - INDOOR/OUTDOOR FAMILY LIVING Designed for relaxed evenings and family downtime. Additional flex space with 65” Samsung TV Sliding glass doors leading to the patio 8-person hot tub just steps away Direct access to the pool and outdoor oasis, creating seamless indoor-outdoor flow
OUTDOOR SPACE From the moment you arrive, the walled-in pool and patio create a private island escape - perfect for long afternoons, evening swims, and easy family time.
LOCATION Located on Siesta Key Ocean breezes and a relaxed island setting Quick access to Siesta Beach, dining, and shopping Easy drive to downtown Sarasota via the north bridge
IDEAL FOR: Families and multi-generational stays Weekly beach escapes Creative retreats and island living Guests seeking privacy, space, and a calm residential atmosphere
We are excited to host you as a weekly, 7-day rental. If you'd like to book for longer, please message us to discuss.
License Number: 25-VR-000060
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Casa Leone | Pet Friendly 🐶 on Siesta Key w/ Private Heated Pool, Golf Cart, & Putting Green!
Bay Island
Casa Leone | Pet Friendly 🐶 on Siesta Key w/ Private Heated Pool, Golf Cart, & Putting Green!
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Siesta Key
Bay Island, a neighbourhood in Siesta Key, is home to this holiday home. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Mote Marine Laboratory & Aquarium and St. Boniface Episcopal Church Labyrinth are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Mote Marine Laboratory & Aquarium - 20 min drive - 14.3 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 24 min drive
Restaurants
McDonald's - 3 min drive
Walt's Fish Market - 4 min drive
CinéBistro - 3 min drive
Connors - 3 min drive
Sonny's BBQ - 3 min drive
Frequently asked questions
Does Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony have a pool?
Yes, this property has an outdoor pool.
How much does it cost to stay at Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony?
As of 21 Apr 2026, prices found for a 1-night stay for 2 adults at Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony on 25 Apr 2026 start from AU$487, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony pet-friendly?
No, pets are not allowed at this property.
How much is parking at Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony?
On-site parking is available at the property.
What time is check-in at Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony?
Check-in begins at 4:00 PM.
What time is check-out at Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony?
Checkout is at 10:00 AM.
Where is Siesta Key 3-Story Retreat - Pool, Hot Tub, Balcony located?
Located in Bay Island, this holiday home is 0.5 mi (0.9 km) from Shell Beach and 2.4 mi (3.8 km) from Siesta Key Beach. Irma Beach and Siesta Key Farmers Market are also within 3 miles (5 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This home is lovely inside and out. We really enjoyed our stay. There is plenty of space if you are traveling with friends or family and the amenities are really great. The location is also ideal, very quiet area, and you can catch the Breeze trolly to go out on the town right at the end of the street. During our stay it was a bit chilly so were able to use the awesome hot tub that is adjacent to the pool. Great home - would definitely stay here again.
Michelle T.
Stayed 7 nights in Feb 2026
Response from VrboOwner on 6 Apr 2026
Thank you so much for your kind words! We’re so glad you were able to enjoy the hot tub during the cooler weather and that the quiet location and trolley access worked well for your stay. We would love to welcome you back anytime.