My Office's Listings

Some or all of the listings below are provided by the Sarasota Downtown office.
$7,000 / mo (USD)
Active

Longboat Key Area Rental

Active

4780 Gulf Of Mexico Dr. Villa 5 Longboat Key, FL 34228

2 Bed
2 Baths
1325 sqft
MLS# A4668115
Virtual Tour
Booking Now for the 2027 Season! Completely Booked for the remainder of the 2026 season. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access. Appreciate the convenience of pulling directly into your private carport with no steps or elevators and relish the peace and privacy of having no neighbors above or below during your stay. This beautifully appointed coastal villa features two bedrooms, two bathrooms, a spacious open concept living area, and an opulent interior design that is soaked in sunlight. The brand new remodeled and fully equipped kitchen is ideal for preparing meals with fresh local ingredients from nearby farmers' markets or head out to dine at one of the delectable nearby restaurants. Windward Bay is a low-density, wildlife-rich community nestled mid-Longboat Key on 26 acres, offering resort-style amenities including two heated pools, two tennis/pickleball courts, two marinas, kayak racks, shuffleboard, a clubhouse with kitchen, library, fitness room, two saunas, and multiple fire pits and barbecue areas throughout the property. Enjoy half a mile of scenic waterfront trails and direct access to the Gulf or Bay for boating, fishing, or simply soaking up the sun. Located just minutes from Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and vibrant cultural attractions. This is a rare opportunity to create lasting memories in a home that guests return to year after year. This villa is more than a vacation rental — it’s a tradition. One couple has returned every March and April for over a decade, drawn by the comfort, beauty, and unbeatable location.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Deborah "Debby" McCaig
$6,500 / mo (USD)
Active

Longboat Key Area Rental

Active

3330 Gulf Of Mexico Drive 104D Longboat Key, FL 34228

2 Bed
2 Baths
1106 sqft
MLS# A4690993
Virtual Tour
Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease. Groceries are carried in with ease, morning coffee is enjoyed on your lanai, and just beyond, a nearly private lawn stretches out like your own backyard retreat. Only sixty feet away, the tranquil waters of Cranes Bayou create a breathtaking backdrop along with the Sarasota Bay. From your windows and lanai, the view feels intimate and serene as dolphins surface in the distance, manatees glide through calm waters, and coastal birds fill the sky. Just outside, an eagle’s nest tucked within a Spanish pine offers a daily reminder that nature is not something you visit here; it’s something you live beside. The lifestyle extends beyond the view. A deeded private walkway leads you directly to the soft sands of the beach, inviting spontaneous sunset strolls, morning shell hunts, and afternoons spent with your toes in the sand. For boaters, a private slip just steps from your front door makes life on the water feel effortless, ready for quiet cruises or sunset rides along the coast. Recently refreshed with a 2025 community pool upgrade and lush landscaping, the setting feels nature-filled with peacefulness. Inside, the residence reflects a thoughtful balance of high-end furnishings, warm textures, and a blend of contemporary design and classic Old-Florida charm, creating a space that feels both elevated and inviting. Carefully curated lighting, including modern fixtures and Frank Lloyd Wright–inspired sconces, lets you shape the atmosphere, whether you're hosting friends, unwinding with a book, or enjoying a quiet evening at home. This is more than a seasonal escape; it’s a place where mornings feel slower, evenings feel softer, and everyday moments carry the calm of island living. For those looking for a coastal rental that blends privacy, tranquility, and a seamless connection to the water, this inviting retreat delivers an island lifestyle you’ll appreciate the moment you step inside. ANNUAL RATE $4,000 / month. SEASONAL RATE $6,500 / month.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / John Schafer