A Private Siesta Key Waterfront Estate with Extraordinary Indoor/Outdoor Pool

Welcome to Casa Flamingo, a one-of-a-kind private waterfront estate set on nearly an acre at the coveted north end of Siesta Key.
Many guests arrive planning to spend most of their vacation exploring Siesta Key, only to discover that Casa Flamingo itself becomes the destination.
At Casa Flamingo
- The Pool Floor — The Heart of Casa Flamingo
- The Sandy Waterfront Retreat
- Waterfront Recreation & Sarasota Bay Access
- Recreation Equipment Right on the Estate
- The Guest House & Estate-Style Living
- Outdoor Kitchen and Dining Patio
- Nearly an Acre of Tropical Grounds
- Variety of Indoor and & Outdoor Gathering Spaces
Casa Flamingo accommodates up to 14 overnight guests. Max 10 adult guests (over 7 years old per City code*)

Explore Siesta Key — or Stay Right Where You Are
Casa Flamingo offers something very different from a traditional vacation rental. Recreation is built into the property itself, with private waterfront access and kayaks, paddleboards, and a six-passenger golf cart included for guests. Step outside to launch directly from the property, fish from the private dock, or bring a boat and keep it at the estate with prior approval.
A sandy waterfront retreat, outdoor kitchen and dining for up to ten, resort-style pool, billiard area, dry bar, dedicated kids’ play area, and multiple indoor and outdoor living spaces offer plenty of ways to play, relax, dine, and enjoy time together. At the same time, accommodations are thoughtfully distributed throughout the estate, giving guests room to retreat and recharge when they want a little space of their own.
From the moment you arrive, you know you've entered somewhere special. Drive through the gated tunnel entrance beneath the guest house and continue along the Royal Palm-lined driveway toward an elegant iron-and-glass front door framed by a hand-carved Cantera stone entrance. The arrival is your first glimpse of the distinctive architecture and resort-like setting that await inside.
The Pool Floor — The Heart of Casa Flamingo
Step through the front door and you'll immediately be drawn to the heart of the estate: an extraordinary indoor/outdoor pool setting unlike a typical Siesta Key vacation home.
The pool is centered within a dramatic architectural space occupying much of the home's main level. Stone columns, soaring arches, covered seating areas, and floor-to-ceiling iron-and-glass doors surround the water, blurring the distinction between indoors and out.
Directly above the pool, the roof opens to the Florida sky. At the far end, a grand archway leads to the outdoor infinity-edge portion of the pool and more than 3,000 square feet of patio and outdoor living space beyond.
Float beneath the open sky, relax in one of the covered seating areas, play a game of billiards, or move effortlessly between the pool, patio, and waterfront.
More than an amenity, the Pool Floor is the centerpiece of Casa Flamingo—the place where everyone naturally seems to find one another.
The Sandy Waterfront Retreat
Beyond the pool and patio, the property opens to one of Casa Flamingo's newest and most distinctive features: an expansive sandy waterfront retreat stretching across much of the backyard.
Settle into an Adirondack chair overlooking the water. Enjoy morning coffee beneath the palms, read in the sunshine, watch the children play in the sand, or gather at the end of the day as the light changes over the waterfront.
The combination of sand, palms, water, and generous space gives this part of the property the relaxed feeling of a private tropical resort—without ever leaving home.
Waterfront Recreation & Sarasota Bay Access
Here, the waterfront isn't simply something to look at. It's part of the vacation.
A private dock and sandy launch area put the water just steps away, with four pedal kayaks and two paddleboards provided with your stay. Launch directly from the property and within minutes you can be exploring the open waters of Big Sarasota Bay or heading toward a popular nearby sandbar.
Guests also enjoy fishing from the private dock and keeping watch for dolphins and manatees frequently seen in the surrounding waters.
For guests who prefer to explore by boat, dock use may be available with prior approval. (Boat not provided.)
Whether it's an early-morning paddle, an afternoon fishing from the dock, or simply sitting by the water, Casa Flamingo makes enjoying Sarasota's waterfront part of everyday life at the estate.
The Guest House & Estate-Style Living
One of Casa Flamingo's greatest advantages for larger groups is its estate-style layout.
Rather than placing everyone under one roof in conventional vacation-home quarters, bedrooms and living spaces are distributed throughout the property, including a detached private guest house.
This creates a valuable balance: everyone can spend the day together while still having places to retreat for privacy and quiet.
The guest house is particularly appreciated by grandparents, adult children, two families vacationing together, retreat participants, or anyone who values additional independence while remaining just steps from the estate's shared amenities.
That flexibility makes Casa Flamingo particularly well suited for multigenerational vacations, multiple families traveling together, reunions, milestone celebrations, groups of friends, and executive or leadership retreats.
Outdoor Kitchen & Gathering Areas
More than 3,000 square feet of patio space wraps around three sides of the home, creating several distinct outdoor areas rather than one large patio.
Just outside the Pool Floor, the outdoor kitchen and dining area seats up to ten, making it easy to prepare a meal without leaving the activity around the pool. Another gathering area overlooks the sandy waterfront retreat and backyard, while a quieter shaded area along the north side offers a comfortable place to read, talk, or simply get away from the activity for a while.
As evening arrives, backyard Edison lights transform the outdoor spaces into an inviting setting for dinner, conversation, and relaxed evenings under the Florida sky.
Nearly an Acre of Tropical Grounds
With nearly an acre to enjoy, Casa Flamingo offers something increasingly unusual on Siesta Key: space.
Beyond the pool, patios, sandy waterfront, and dock, spacious lawn areas provide room for games and family activities, while mature palms and tropical landscaping create a sense of privacy throughout the estate.
Children can play, adults can find a quiet corner, and different generations can enjoy different activities without everyone having to occupy the same space.
The Great Room & Indoor Gathering Spaces
When it's time to come inside, the expansive Great Room provides another natural gathering place.
The open-concept kitchen, dining area, and living space allow everyone to remain connected while cooking, eating, talking, playing games, or celebrating a special occasion.
Together with the Pool Floor and extensive outdoor living areas, the Great Room gives larger groups something that's often difficult to find in a vacation property: multiple places where everyone can comfortably be together.
Explore Siesta Key — or Stay Right Where You Are
Although guests often discover they don't want to leave Casa Flamingo, its north Siesta Key location makes exploring the island easy.
A six-passenger street-legal golf cart is included with your stay, giving you another way to head out for Siesta Key Village, world-famous Siesta Key Beach, restaurants, shopping, and other nearby attractions.
Spend the morning at the beach, have lunch in the Village, and return to your own waterfront retreat for an afternoon paddle, time by the pool, fishing from the dock, or dinner outdoors.
At Casa Flamingo, you don't have to choose between experiencing Siesta Key and enjoying your vacation home. You can do both!

*Occupancy & Important Information
Casa Flamingo comfortably accommodates up to 14 overnight guests.
Per City of Sarasota regulations, occupancy is limited to a maximum of 10 guests age 7 and older. Additional guests, up to the 14-person maximum, must be children age 6 or younger. City of Sarasota VR22-00127.

Events and special gatherings require prior approval and may be subject to additional fees.
A signed liability waiver is required for use of recreational equipment provided at the property, including pedal kayaks and paddleboards. Guests wishing to bring a boat and use the private dock must receive prior approval and complete the required liability waiver.

We look forward to welcoming you to Casa Flamingo—and to sharing a place where some of the best vacation days may turn out to be the ones when you never leave the property.