Not listings scraped from a feed — these are properties Tracy personally manages, minutes from Siesta Key's #1-ranked beach. Book direct on Airbnb, or ask Tracy anything about a stay.
Siesta Key
1 Bed · 1 Bath
"The Point" — Siesta Key Resort Condo
Discover "The Point" on Siesta Key — a fully furnished 1-bedroom, 1-bath unit on a 5-acre resort property offering comfort, style, and every amenity you need for a relaxing stay.
Kayak or paddleboard from Turtle Beach, sink your toes into Siesta Key Beach’s powdery white quartz sand, and finish the day at Ophelia’s on the Bay or the Village favorites — all minutes away.
Take a break and unwind at this peaceful retreat on a .75-acre lot just steps from Nokomis Beach — roughly 3,873 sq ft of living space with an elevated terrace overlooking the Gulf.
The lower-level suite adds 2 bedrooms, 2 bathrooms, a full kitchen, laundry, and office space — ideal for remote work, extended stays, or multi-generation family gatherings. Casey Key Fish House and Deep Lagoon Seafood are minutes away.
Stay in this beautifully renovated 2-bedroom, 1.5-bath home (2020) featuring a Tesla Solar Roof & Generator, just 10 minutes to #1-ranked Siesta Key Beach and close to downtown Sarasota.
Outside: a heated in-ground pool with screened enclosure, hot tub, outdoor shower, fire pit, and a fenced backyard that’s perfect for pets. Inside: a bright sunroom with desk, Smart TVs, full kitchen, and washer/dryer.
Welcome to your renovated 2-bedroom, 2-bath condo in the heart of Siesta Key Village. Whispering Sands combines modern comfort with resort-style amenities — including private Gulf-front beach access to Siesta Key’s world-famous quartz sand.
Two swimming pools, a fitness center, and the Village’s dining, shopping, and nightlife just steps away make this the ultimate Florida getaway.
Situated in central Sarasota, this spacious, thoughtfully updated home is designed for indoor/outdoor living — 5.7 miles to Siesta Key Beach and 3.4 miles to downtown.
The private backyard retreat features a heated saltwater pool (Dec–March), ping pong, a grill, and outdoor games. Inside, an open floor plan fills with natural light, and a pool table plus provided beach equipment round out the fun.
Crystal white quartz beaches. Sparkling Gulf waters. Endless sunshine. Base yourself within reach of Siesta Key and fill your days with paddleboarding, kayaking, jet skiing, snorkeling, fishing, and charter cruises.
Off the water: golf, boutique shopping, Sarasota’s best restaurants, the Ringling Museum of Art, and Mote Marine Laboratory & Aquarium.
Be among the first to stay at this freshly remodeled waterfront home near the south Siesta Key bridge. Your private backyard oasis features a saltwater pool with baja shelf, fire pit, covered lanai with grilling area, and 100 feet of canal frontage with a 40-ft Azek dock and direct Gulf access.
Sleeps up to 9 across a king primary suite, a king guest room, and a queen-plus-bunk third bedroom — all in a bright, open plan with water views throughout. Bring your boat: fenced trailer parking is on-site, and Turtle Beach boat ramp is minutes away.
Escape to this family-friendly coastal retreat just 0.9 miles from Siesta Key Beach. The 3-bed/2-bath main house pairs with a private guest house (queen Murphy bed + full bath) — ideal for large families or groups of up to 12.
Relax by the sparkling pool, cook in the fully equipped outdoor kitchen with seating and TV, and enjoy washer/dryer convenience in both houses. Dogs up to 60 lbs and cats welcome (fee; breed restrictions apply).
Nestled in a quiet Gulf Gate neighborhood, this pet-friendly coastal retreat is 8 minutes from Siesta Key Beach, minutes from shopping and dining, and 15 minutes to downtown Sarasota.
The screened lanai holds a heated pool, spa, grill, and outdoor dining with a 43" TV; a firepit with Adirondack chairs and a hammock sit just outside. Inside: a 75" Smart TV, a stocked kitchen, a dedicated Florida-room workspace, and beach gear for the whole crew.
Tracy operates these rentals himself — pricing, guest communication, turnovers, and the
local rules that make or break short-term rentals in Sarasota County. If you’re weighing a
vacation-rental purchase or wondering what your current home could earn, get advice from
someone who actually runs them.
Siesta Key 
