Longboat Key Listings

Some or all of the listings below are provided by the Longboat Key office.
$12,500 / mo (USD)
Active

Sarasota Area Rental

Active

2231 Wood Street Sarasota, FL 34237

4 Bed
4 Baths
2731 sqft
MLS# A4663908
Virtual Tour
Experience the perfect blend of comfort, elegance, and convenience in this stunning turnkey furnished 4-bedroom, 3.5-bath modern vacation home. Thoughtfully designed to accommodate up to 10 guests, this property offers the ideal setting for families, friends, and luxury vacationers seeking a private oasis close to everything Sarasota has to offer. Step inside to find a spacious open floor plan with sleek finishes and top-of-the-line appliances, including a Subzero refrigerator and Wolf induction cooktop—perfect for creating memorable meals. Multiple indoor and outdoor dining spaces make entertaining effortless, while the comfortable living areas provide plenty of room to unwind. Outdoors, enjoy resort-style living on a double lot with a large fenced yard. Spend your days lounging by the sparkling pool and spa, grilling, rinsing off in the outdoor shower, or soaking up the Florida sunshine on the chaise lounge chairs. This home is ideally located—just steps to the Legacy Trail for biking and walking, only 1 mile from vibrant Main Street with its shops, cafes, and nightlife, and a short drive to Sarasota’s award-winning white sand beaches. Whether you’re looking for adventure, relaxation, or world-class dining, this home offers it all. Make your stay unforgettable in this modern luxury retreat designed for both relaxation and connection. *weekly rates available* Not Available Dec 27 2025- Jan 03 2026. Not Available Jan 13 2026- April 16 2026
Listing Courtesy of STELLAR / Coldwell Banker Realty / Rinat Sikdar
$10,500 / mo (USD)
Active

Longboat Key Area Rental

Active

4485 Gulf Of Mexico Drive Ph2 Longboat Key, FL 34228

3 Bed
2 Baths
1576 sqft
MLS# A4622055
Virtual Tour
**BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease JANUARY and FEBRUARY 2026 with the option to include APRIL 2026** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly on the beach, offering you breathtaking full views of the shimmering turquoise waters, sparkling sand, and those iconic Florida sunsets. This is the perfect opportunity to immerse yourself in the serenity of beachfront living during the best time of year. Imagine waking up each morning to the calming sound of waves and enjoying your morning coffee on the balcony as the sun rises over the Gulf. Step inside and be welcomed by the calm coastal colors and casual elegance that make this condo the ideal beach retreat. The community of Arbomar offers amenities that ensure your stay is as relaxing as possible. Take a dip in the heated community pool, stay active in the fitness room, or gather with friends in the community kitchen and lounge. Additional conveniences include climate-controlled storage lockers, a kayak rack, beach chair storage, and laundry rooms on each floor. With all-new Miami Dade certified high-impact windows, including turtle-tinted beachside windows to protect our local sea turtles, you can enjoy the view and feel secure. This spectacular Penthouse condo fresh on the market emphasizes the exclusivity and appeal of spending winter in a beachfront condo, encouraging potential renters to secure their spot for the popular January to March/April 2026 period as soon as possible!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Norma Mladineo
$9,400 / mo (USD)
Active

Sarasota Area Rental

Active

1750 Benjamin Franklin Drive 9B Sarasota, FL 34236

2 Bed
2 Baths
1364 sqft
MLS# A4674245
Virtual Tour
Gulf-Front Lido Key Rental — Available December 15, 2025 through June 2026 (30-day minimum stay). Seasonal Lease $9,400/mo. Off Season Lease $7,000/mo. Wake up to the sound of waves and end each day with a show-stopping Lido Key Beach sunset — this ninth-floor beachfront condo delivers front-row Gulf views that never get old. Located in the distinguished Key Towers South on Lido Key, this fully furnished retreat places the beach at your doorstep and luxury at your fingertips. Designed for comfort and ease, the open-concept layout flows effortlessly throughout the home. The kitchen features granite counters, stainless steel appliances, and a built-in desk space perfect for quick morning tasks or cocktail-recipe Googling. A dedicated office/den offers the ideal setup for remote work — because if you must email, at least do it from paradise. The real showpiece? The enclosed Gulf-front balcony — a breezy, bright extension of your living space where the shoreline becomes your daily backdrop. Coffee tastes better here. So do sunsets. The primary suite provides a serene coastal hideaway with ample closets and a private bath. A separate guest suite ensures your favorite company can enjoy comfortably. Additional conveniences include: Impact-rated windows throughout, Multiple storage closets, Access to a shared utility room with washers & dryers on the same floor and a dedicated storage locker. Residents of Key Towers South enjoy recently updated amenities, including:
Refreshed lobby and first-floor social spaces (renovated 2025), Fitness room, library, and social room with catering kitchen, Sauna & shower facilities, Bike storage ,Gulf-front pool and lounge deck with spectacular sunsets. Perfectly positioned between the Gulf of Mexico and Sarasota Bay, this condo places you in the heart of Lido Key’s coastal playground. Stroll to the beach — it’s literally your backyard — or explore: South Lido Park just a quarter mile away. St. Armand's Circle one mile north — boutiques, dining, nightlife. Downtown Sarasota only four miles over the Ringling Bridge. Prefer not to drive? Hop on the free Sarasota Bay Runner trolley with convenient stops from south Lido to downtown Sarasota.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Norma Mladineo