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PRIVATEER SOUTH - A4698869 - 1000 LONGBOAT CLUB RD #903, LONGBOAT KEY, FL 34228 Just Added on 07/16/2026 5:27PM
$11,500 | Condo | 2 beds | 2.0 baths | 1 car
Experience the best of Longboat Key living in this beautifully updated, turnkey furnished 2-bedroom, 2-bath residence located behind the gates of the sought after Longboat Key Club. This light-filled condominium features brand-new countertops, new appliances, and an open, inviting floor plan designed for effortless coastal living. Enjoy partial Gulf views and beautiful bay vistas from two private balconies—the perfect setting for morning coffee or evening sunsets. Both bedrooms are generously sized, including a spacious primary suite with an en-suite bath, making this an ideal seasonal getaway or extended stay. Residents enjoy an exceptional resort-style lifestyle with outstanding amenities, including a heated pool, hot tub, fitness center, tennis and pickleball courts, private beach access complete with beach chairs and umbrellas, and beautifully maintained grounds. Ideally located behind the gates of the prestigious Longboat Key Club, this residence offers the perfect blend of luxury, convenience, and island living, just moments from world-class dining, shopping, golf, and pristine Gulf beaches. **Available seasonally for $11,500 per month or for a 6-month lease at $8,500 per month.**
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S
SPANISH MAIN YACHT CLUB CONDO - A4699680 - 706 SPANISH DR S, LONGBOAT KEY, FL 34228 7 Days on yellowkey
$4,000 | Condo | 2 beds | 2.0 baths | 1 car
Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after, active 55+ community of Spanish Main Yacht Club! Ideally situated just steps from the marina, this 2-bedroom, 2-bathroom villa features a bright Florida room and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. It is the perfect spot for peaceful mornings, frequent dolphin and manatee sightings, and stunning bayfront sunrises, with Gulf-side beach access just a short stroll away. Residents enjoy unparalleled community amenities, including a private marina with boat docks a kayak launch, deeded beach access, a heated community pool, shuffleboard courts, and a vibrant social calendar. Perfectly located just minutes from the upscale dining and boutiques of St. Armands Circle and a short drive to Anna Maria Island, this property offers the perfect blend of coastal tranquility and accessibility. This turnkey property is offered at $6,500 per month for the in-season months of December through May (with a $2,500 security deposit) and $4,000 per month for the off-season months of August through November (with a $2,000 security deposit). For your ultimate convenience, the rental price is all-inclusive, covering all utilities and fees including internet, water, sewer, electric, and TV, so you can move right in without any extra hassle. Move-in requires the first month's rent and the corresponding security deposit,. There is convenient online tenant screening via RentSpree. In accordance with association requirements, at least one tenant must be age 55 or older. Whether you're boating, fishing, or simply relaxing, this is a rare opportunity to experience the ultimate Longboat Key lifestyle—schedule your viewing today!
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC
FAIRWAY BAY 1 - A4699659 - 1928 HARBOURSIDE DR #1402, LONGBOAT KEY, FL 34228 7 Days on yellowkey
$3,500 | Townhouse | 2 beds | 2.5 baths | 1 gar
Experience furnished island living in this turnkey, two-level Fairway Bay townhome offering 2 bedrooms, 2 full bathrooms, 1 half bathroom and 1,626 square feet of thoughtfully arranged living space. The open living and dining area is enhanced by cathedral and vaulted ceilings and offers views of the tropical landscaping and community pool. A split-bedroom layout provides separation between the sleeping areas, while the kitchen includes a built-in oven, cooktop, microwave, refrigerator, dishwasher and disposal. Additional features include ceiling fans, window treatments, an interior laundry area with washer and dryer, central heating and air conditioning, a covered deck and patio, and an attached one-car garage with tandem parking. Located within gated Bay Isles along Sarasota Bay, Fairway Bay offers beautifully landscaped grounds, on-site maintenance, pool and spa facilities, two cushioned mixed-use courts for tennis and pickleball, a clubhouse with a full kitchen, exercise facilities, a shell walking path bordering the bay and multiple kayak launches. Community activities include yoga, bridge, mahjong, book clubs and social gatherings. Bay Isles residents also enjoy access to the private Gulf-front Bay Isles Beach Club, featuring a beautiful stretch of beach, covered picnic and entertaining areas, tiki huts, barbecue facilities, restrooms, changing areas and showers. Nearby shopping, dining, golf, marina options, St. Armands Circle and downtown Sarasota provide convenient access to the many attractions of Longboat Key and Sarasota. Golf club and marina privileges are separate and are not included unless specifically stated in the lease. This furnished residence brings together comfort, recreation, coastal surroundings and the convenience of a gated island community.
FAIRWAY BAY 2 PH 2 & 3 - A4699651 - 2012 HARBOURSIDE DR #2102, LONGBOAT KEY, FL 34228 7 Days on yellowkey
$3,500 | Condo | 2 beds | 2.5 baths | 1 gar
Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural hubs of St. Armands Circle and downtown Sarasota, this property is ideal for those seeking a refined retreat with convenience to fine dining, shopping, and the arts. Don’t miss the opportunity to experience Longboat Key living at its finest.
- A4699467 - 691 RUSSELL ST, LONGBOAT KEY, FL 34228 9 Days on yellowkey
$9,500 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Experience luxury coastal living in this completely renovated annual rental on the desirable north end of Longboat Key. Situated on an oversized double lot just minutes from the pristine Gulf beaches, this exceptional pool home offers the perfect blend of style, comfort, and convenience. Thoughtfully redesigned from top to bottom, the home features a bright, open-concept floor plan with wide-plank oak flooring, hurricane-impact windows and doors, recessed lighting, and premium finishes throughout. The chef's kitchen is the centerpiece of the home, showcasing custom Campbell cabinetry, elegant quartz countertops, an oversized island, and commercial-grade KitchenAid appliances—ideal for everyday living and entertaining. The spacious sunroom opens to a spectacular backyard retreat with panoramic views of the private outdoor living space. Enjoy a heated 8-foot-deep saltwater pool, an expansive paver patio, hookups for two outdoor kitchens, premium artificial turf, and lush tropical landscaping, creating the ultimate setting for year-round Florida living. The owner's suite is a private sanctuary featuring two custom walk-in closets and a spa-inspired en-suite bathroom with a marble vanity, custom cabinetry, and a luxurious soaking tub with a frameless glass enclosure. A centrally located den/office provides the perfect space for working remotely or enjoying a quiet reading room. This home has been extensively updated with new plumbing, electrical, natural gas lines, HVAC and central air conditioning, and a new roof, offering modern comfort and peace of mind. Ideally located just minutes from Longboat Key's beautiful beaches, public boat ramps, waterfront dining, boutique shopping, salons, marinas, fishing charters, paddleboarding, kayaking, jet skiing, parasailing, and everything the island lifestyle has to offer. Don't miss this rare opportunity to enjoy luxury living on Longboat Key in an exceptional annual rental. Small Dogs welcome. First, Last and Security will be collected.
Listing is courtesy of: GULF COAST REALTY & MANAGEMENT
PROMENADE - A4698785 - 1211 GULF OF MEXICO DR #302, LONGBOAT KEY, FL 34228 15 Days on yellowkey
$13,500 | Condo | 2 beds | 3.0 baths
**Prime Location – Luxurious Waterfront Living at Promenade, Longboat Key** This absolutely gorgeous condo is located in the prestigious Promenade on Longboat Key, offering breathtaking water views from every room. The residence features 2 bedrooms plus a den and 2 bathrooms. The spacious master suite includes a king-size bed and an elegant en-suite bathroom with a separate bathtub, walk-in shower, and bidet for added convenience. The second bedroom is ideal for guests, offering two twin beds that can be converted into a king-size bed. The versatile den can be used as a home office or additional sleeping space, featuring a sofa that converts into a bed for unexpected guests. The well-appointed contemporary kitchen makes entertaining effortless, while electric motorized shades in the family room, master bedroom, and kitchen provide added comfort and convenience. Step outside to your private terrace and enjoy stunning sunrises and sunsets over the water—true Florida coastal living at its finest. Residents of The Promenade enjoy world-class amenities, including a private beach, 24-hour manned gated security, full concierge services, on-site management, two social rooms, fitness center, men’s and women’s health clubs, four Har-Tru tennis courts, a Gulf-side heated resort-style swimming pool and spa, and a beautifully landscaped gazebo area surrounded by lush tropical grounds. The unit includes one assigned parking space, with additional guest parking available. This is the perfect destination to experience luxury Florida vacation living at its finest. Available December 1, 2026. Tenant must pay a $75.00 Broker Fee.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE
BEACHES OF LONGBOAT KEY PH-1 - A4698769 - 775 LONGBOAT CLUB RD #904, LONGBOAT KEY, FL 34228 16 Days on yellowkey
$11,000 | Condo | 2 beds | 2.0 baths | 1 gar
AVAILABLE DEC. '26 THROUGH FEB.'27. Beautiful 9th floor, 1600 sq. ft. 2 bedroom 2 bath at the sort after Beaches condominium which is within the gates of the Longboat Key Club. Updated kitchen and bathrooms. Fabulous bay, and Longboat Key Club golf views. Wrap around balcony with partial Gulf view. Washer/dryer in the unit, pool, fitness center and tennis courts plus 24 hr. Concierge and garage parking. Short distance to St. Armand Circle with upscale shopping and restaurants or drive downtown and enjoy the symphony, opera, ballet, live theater and a variety of restaurants to suit most palates.
Listing is courtesy of: COLDWELL BANKER REALTY
FAIRWAY BAY 1 - A4698059 - 1930 HARBOURSIDE DR #122, LONGBOAT KEY, FL 34228 23 Days on yellowkey
$3,500 | Condo | 2 beds | 2.0 baths
Wonderful 2 bedroom 2 bath condo in Fairway Bay community on Longboat Key. Condo is being rented fully furnished and is available at a 2 month minimum rental. this is totally updated and ready to move in. amazing Bay views to enjoy and community has lots of amenities from Tennis, pool, spa, beach access and 24/7 security. All renters need to be approved by association, and application fee is required.
SEAPLACE III - A4697063 - 1975 GULF OF MEXICO DR #G4-401, LONGBOAT KEY, FL 34228 33 Days on yellowkey
$6,900 Reduced | Condo | 3 beds | 2.0 baths | 1 car
Perched on the top floor with nothing between you & the water, this fully furnished beachfront retreat at Seaplace offers unobstructed Gulf of America views from every room. Living, dining & kitchen face the Gulf; the king primary suite opens to a private beachfront balcony, the second bedroom (two twins) has its own, and a flexible 3rd room with a Murphy bed works as a bedroom, media room, or office. Crown molding, flat-screens, ADA-friendly primary bath & storm-ready shutters. Every utility & condo fee included, plus covered carport & elevator. Seaplace spans 42 gated acres beside the new St. Regis: half-mile private beach (chairs & umbrellas), two heated pools, two spas, three Har-Tru tennis courts, one-mile trail & renovated clubhouse w/ fitness center, sauna & Gulf-view grilling patio. Minutes to Publix, St. Armands Circle & downtown Sarasota. 2-mo min w/ approval; $6,900/mo May–Nov, $9,500/mo Dec–Apr; annual considered. Refundable deposit $5,000. Available for showings.
Listing is courtesy of: THE AGENCY SARASOTA