Location: Longboat Key
Do Not Show Listings
1000 LONGBOAT CLUB RD #903, LONGBOAT KEY, FL 34228
$11,500Listed 07/16/2026 5:27PM MLS ID: A4698869
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972Community: Privateer SouthCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: 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 (941-803-7522)
Listing Agent: Jenna Genovese (860-575-0088)
540 NEPTUNE AVE #7, LONGBOAT KEY, FL 34228
$5,700249 Days on yellowkey MLS ID: A4671262
REDUCED by $295 (4.9%) on 07/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1032 Built: 1972Condo
Remarks: Enchanting, Iconic…Gulf Key Discover Relaxation and Island Charm Just Steps from the Beach Unwind at Gulf Key Welcome to Gulf Key, a truly iconic villa community where the spirit of “old Florida” meets modern comfort. This immaculate, newly renovated 2-bedroom, 2-bath villa is perfectly situated just a 5-minute walk from the beach, making it an ideal destination for anyone seeking a tranquil coastal getaway. Classic Elegance and Timeless Appeal Gulf Key’s classic tile roof and stucco exterior evoke understated elegance and the relaxed lifestyle synonymous with Florida's historic coast. The community consists of just 10 units, ensuring exceptional peace, privacy, and charm for every guest. Premier Location Everything you need is at your fingertips - from a grocery store and pharmacy to the local library and unique boutique shops, Gulf Key’s premier location means you can walk or drive to all the essentials. Whether you are planning a beach adventure or a leisurely stroll, convenience is always a part of your stay. Amenities for Ultimate Comfort · Private patio: Enjoy your morning coffee or wind down with evening cocktails in your private outdoor space. · Beautifully maintained grounds: Experience the tropical natural beauty and serene atmosphere of the property. · Designated parking: Hassle-free parking for your peace of mind. · Complementary Wi-Fi: Stay connected throughout your stay. · Nearby spa, golf, tennis, shopping, and restaurants: Indulge in pampering, play, and local dining… all within minutes. · 5-minute walk to the beach: The highlight of Gulf key, offering quick and easy access to sun, sand, and surf. Experience the Best of Island Living Gulf Key blends the tranquility of a small, private community with easy access to the vibrant experiences and amenities of island life. Whether you are seeking relaxation, adventure or a mix of both, Gulf Key is a perfect setting to slow down, breathe in the salt air, and truly unwind. … your relaxing coastal getaway awaits
Listing is courtesy of: CASEY REALTY CORPORATION (941-922-3391)
Listing Agent: Pamala Casey (941-922-3391)
706 SPANISH DR S, LONGBOAT KEY, FL 34228
$4,0007 Days on yellowkey MLS ID: A4699680
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1423 Built: 1971Community: Spanish Main Yacht Club CondoCondo
Remarks: 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 (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228
$5,95062 Days on yellowkey MLS ID: A4693849
0 Days Off yellowkey (back on 7/12/2026)
REDUCED by $50 (0.8%) on 06/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970Community: Islander Club Of LongboatCondo
Elementary School: Southside Elementary
High School: Riverview High
Middle School: Booker Middle
Remarks: Now available FOR LEASE at The Islander Club on Longboat Key, this updated 2-bedroom, 2-bath residence offers exceptional value in a true beachfront community. Turnkey and move-in ready, the unit features an open layout with quality finishes, an updated kitchen with stainless steel appliances, wood flooring, refreshed bathrooms, and a spacious 38-foot terrace for outdoor living. The primary suite includes an ensuite bath and walk-in closet, while the guest bedroom offers comfort and privacy for visitors. Residents at THE ISLANDER on LONGBOAT KEY enjoy direct BEACHFRONT access along with resort-style amenities including a private beach, heated pool, fitness center, sauna, tennis, pickleball, and on-site management. Offered at $6,000/month May through December and $10,000/month January through April. AVAILABLE NOW for immediate occupancy. Contact listing agent for showing requests. OPEN FOR 2027 SEASON RESERVATIONS - 3 MONTH MINIMUM
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Richard Ivan (941-800-8891)
2012 HARBOURSIDE DR #2102, LONGBOAT KEY, FL 34228
$3,5007 Days on yellowkey MLS ID: A4699651
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1590 Built: 1985Community: Fairway Bay 2 Ph 2 & 3Condo
Remarks: 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.
Listing Agent: Alex Larchenko (224-628-8478)
1975 GULF OF MEXICO DR #G4-401, LONGBOAT KEY, FL 34228
$6,90033 Days on yellowkey MLS ID: A4697063
REDUCED by $2,600 (27.4%) on 07/09/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1977Community: Seaplace IiiCondo
Remarks: 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 (941-500-5150)
Listing Agent: Robert Hildreth (941-326-0278)
2109 GULF OF MEXICO DR #1203, LONGBOAT KEY, FL 34228
$10,0001005 Days on yellowkey MLS ID: A4584050
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1463 Built: 1984Community: Sunset BeachSpa: YesCondo
Remarks: Booked Dec 1st 2026-March 31st 2027. **Beachfront Bliss with Stunning Gulf Views** Experience coastal living at its finest in this beautifully updated beachfront condo. The bright, open living area flows seamlessly onto a spacious private balcony where you can enjoy panoramic Gulf views, sea breezes, and unforgettable sunsets. The renovated kitchen features sleek countertops, stainless steel appliances, and everything needed for effortless meal preparation. Wake each morning to sparkling water views and unwind in a comfortable, stylish setting designed for relaxation. Guests enjoy access to a resort-style pool, spa, and direct beach access, creating the perfect seaside escape. Just minutes to St Armand’s Circle or Lido Beach for shopping, fine dining or laying at the public beach with all your favorite people. Longboat is known for their waterfront golf, fine dining and luxury resorts. In fact, its 12 miles of white sand beaches have helped to make this a luxury Gulf Coast resort community. There are numerous Activities and Attractions in the Sarasota/Bradenton/Siesta area. -Just a few of the many treasures and cultural events are Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, fishing charters out of Marina Jack's, Florida's Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, and the Van Wezel. The $10,000 is for base rent only. There are taxes, refundable damage deposit, cleaning fees, and credit card fee. Plus the $125 application fee.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
655 CEDARS CT #655, LONGBOAT KEY, FL 34228
$6,5002114 Days on yellowkey MLS ID: A4478968
Bed: 1 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1244 Built: 1988 Tax: $3,991 (2021)Community: Cedars East Sec 1Spa: YesCondo
Taxes:$3,991
Tax Year: 2021
Remarks: AVAILABLE. 2027 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located in Cedars East. Cedars East has all the amenities you desire including tennis, fitness center, beach access, swimming, community activities, tiki bar and restaurant on site. The unit has been fully upgraded and has a full gourmet kitchen with breakfast bar. Enjoy sweeping bay views from the master lanai. Unit has a washer/dryer and 2 full baths. Feel free to bring your small dog as well. Easy access to St. Armands Circle and Bradenton Beach.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Brenda Cozy (941-350-4889)
455 LONGBOAT CLUB RD #401, LONGBOAT KEY, FL 34228
$7,0002671 Days on yellowkey MLS ID: A4431350
REDUCED by $1,000 (12.5%) on 07/07/2026
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2780 Built: 1990 Tax: $12,481 (2021)Community: PierreSpa: YesCondo
Taxes:$12,481
Remarks: Welcome to Paradise! Beautiful 3 bedroom 3.5 baths, luxury split floor plan condo on LONGBOAT KEY. Behind the gates of Longboat Key Club, known for its privacy and yet close to St. Armand's Circle for dining, shopping, entertainment & cultural offerings of downtown Sarasota. Located on the south end of Longboat Key, this tastefully furnished 4th floor updated unit offers a partial view of the sparkling blue waters of the Gulf of Mexico from rear balcony with access from master bedroom and living room. Master bedroom includes king size bed, walk in shower, & dual sinks. Guest bedroom with two twin beds & a King Bed in the 3rd bedroom. Kitchen includes stainless steel appliances & granite countertops. Side balcony access is from dining room and kitchen with a golf course view! Enjoy the amenities of this luxury condo resort, which includes a fitness center, a tennis court, private beach access, heated pool/spa, a gazebo with complimentary grills, 24 concierge/security, and within a golf course community. Rent includes water, sewer, basic cable, and internet. Electric will be a shared expense. Call now for more details!
Listing is courtesy of: ROSSI & COMPANY INC (941-955-7368)
Listing Agent: Deserea Hardy (941-960-6480)
1591 GULF OF MEXICO DR #619, LONGBOAT KEY, FL 34228
$65,00044 Days on yellowkey MLS ID: A4695816
REDUCED by $13,000 (16.7%) on 07/07/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5334 Built: 2024Community: St. RegisCondo
Remarks: Imagine taking in this view from your private balcony pool! An exceptionally rare opportunity to lease one of the most exclusive waterfront residences ever offered on Florida’s Gulf Coast. Positioned within the iconic St. Regis Residences on Longboat Key, this extraordinary four-bedroom, four-and-a-half-bath condominium redefines annual luxury living with an unrivaled level of privacy, sophistication, and world-class service. Arrive via private elevator entry that opens directly into your personal residence, where breathtaking panoramic Gulf and Sarasota Bay views unfold from nearly every room. Designed for the most discerning resident, this one-of-a-kind home seamlessly blends contemporary elegance with resort-inspired comfort across expansive indoor and outdoor living spaces. A spectacular wraparound terrace serves as a true extension of the residence, complete with a private pool overlooking turquoise Gulf waters, dramatic sunsets, and sparkling bay vistas — creating an unparalleled setting for entertaining or quiet relaxation. Inside, every detail has been thoughtfully curated to deliver an uncompromising luxury experience. A state-of-the-art integrated sound system flows throughout the residence, while a hidden speakeasy and private wine room offer an unforgettable level of exclusivity rarely found in condominium living. The grand primary suite is a private sanctuary featuring floor-to-ceiling windows with sweeping water views, a spa-inspired ensuite bath, and an extraordinary dressing room designed to function as a dedicated walk-in closet suite unto itself. Residents enjoy full-time concierge and butler service, delivering the legendary St. Regis standard directly to your door. In addition to exclusive resident amenities, tenants also enjoy access to the world-renowned hotel amenities, creating a seamless five-star lifestyle unlike anything else available on the market today. Close Proximity to IMG Academy. This is more than a residence — it is a statement of prestige, privacy, and elevated waterfront living. Opportunities of this caliber are exceedingly rare. There is simply no comparable product currently available on Longboat Key. Experience the absolute pinnacle of luxury coastal living at the St. Regis Residences Longboat Key.
Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)
Listing Agent: Jaime Barcelo (941-275-3233)
1211 GULF OF MEXICO DR #302, LONGBOAT KEY, FL 34228
$13,50015 Days on yellowkey MLS ID: A4698785
Bed: 2 Bath: 3.0 Liv Area Sq Ft: 2100 Built: 1985Community: PromenadeCondo
Remarks: **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 (941-907-2000)
Listing Agent: Elsie Salazar (941-284-7645)
2020 HARBOURSIDE DR #446, LONGBOAT KEY, FL 34228
$4,99550 Days on yellowkey MLS ID: A4695127
REDUCED by $500 (9.1%) on 06/25/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1984Community: Fairway Bay 2 Ph 1Condo
Remarks: Experience luxury island living in this beautifully remodeled 2-bedroom, 2-bath residence located in the highly sought-after Fairway Bay community within Bay Isles on Longboat Key. Available for immediate occupancy, this turnkey furnished coastal retreat offers flexible lease terms from 6 to 12 months. Step inside to discover a bright and open floor plan featuring upscale contemporary finishes, , updated flooring, a stunning modern kitchen with premium appliances, and elegantly renovated bathrooms. The spacious primary suite provides a peaceful retreat, while the second bedroom offers comfortable accommodations for guests or an ideal home office. Expansive living spaces and a private balcony create the perfect setting to relax and enjoy the Florida lifestyle. Residents of Fairway Bay enjoy an exceptional array of resort-style amenities, including a heated community pool, a beautifully maintained clubhouse, and a fully equipped fitness center. Tennis and pickleball enthusiasts will appreciate access to two regulation tennis courts that can also be configured into four pickleball courts, offering year-round recreation just steps from home. As part of the exclusive Bay Isles community, residents also enjoy access to the private Bay Isles Beach Club, featuring deeded Gulf-front beach access with some of Longboat Key's most beautiful sand beaches. The Beach Club offers gated parking, picnic areas, grills, restrooms, and the perfect setting to enjoy spectacular Gulf sunsets. Outdoor enthusiasts will also appreciate access to the Bay Isles marina area and kayak launch with direct access to Sarasota Bay. Ideally situated on Longboat Key, this residence is just minutes from St. Armands Circle, Longboat Key Club, championship golf courses, waterfront dining, marinas, boutique shopping, and the cultural attractions of downtown Sarasota. Whether you're seeking a seasonal retreat or an extended island stay, this residence offers the perfect combination of luxury, convenience, and coastal living. Available immediately with lease terms ranging from 6 to 12 months.
Listing is courtesy of: VIVE REALTY (941-600-8162)
Listing Agent: Jeffrey Swanson (248-938-1775)
775 LONGBOAT CLUB RD #904, LONGBOAT KEY, FL 34228
$11,00016 Days on yellowkey MLS ID: A4698769
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1602 Built: 1984Community: Beaches Of Longboat Key Ph-1Condo
Remarks: 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.
750 BAYPORT WAY #750, LONGBOAT KEY, FL 34228
$3,8001473 Days on yellowkey MLS ID: A4540609
REDUCED by $450 (10.6%) on 06/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1983Community: Bayport Bch & Ten Ph DCondo
Remarks: AVAILABLE IN JULY FOR 6-MONTHS OR MORE! Turnkey Furnished Rental at Bayport Beach and Tennis Club. You will fall in love with this wonderful Longboat Key Community, featuring one of the most beautiful beach fronts, and Bay front locations on Longboat Key. This well-appointed and tastefully furnished, updated home welcomes you with its understated elegance. Everything inside is new, from the flooring to the kitchen and baths, the decor is neutral with pops of color, giving the home a coastal urban vibe. The primary bedroom offers a king bed, walk-in closet with built-ins, smart TV and a desk. The primary bath has dual sinks and shower. The guest bedroom boasts queen sleeping accommodations and a smart TV. New luxury vinyl flooring throughout and gorgeous kitchen with stainless appliances, stone counters and lovely wood cabinetry. Outside your door you will find a bonus deck with chaises for sunbathing. This popular, Tim Siebert designed Gulf-to Bay community features 27 lushly landscaped acres, 4 Har-Tru Tennis Courts, a Jr. Olympic pool, kayak launch, bocce ball and fitness room in the clubhouse, and a gorgeous beach, located just across Gulf of Mexico Drive. St. Armands Circle is a short drive away, just over the Ringling Causeway you will find the vibrant downtown Sarasota arts and culture, as well as the many unique shopping and dining venues. Leases less than 6+ months subject to additional taxes and fees.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)
Listing Agent: Stephanie Deshaies (941-780-3229)
1511 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$24,750128 Days on yellowkey MLS ID: A4685769
REDUCED by $750 (2.9%) on 06/30/2026
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2940 Built: 1978Community: Tencon BeachCondo
Remarks: Offered at $24,750 per month for 3 months in 2027! - Come be on the beach! Rarely available on the south end of Longboat Key, a 3 bedroom + den, 3 1/2 bath DIRECT Beachfront 3-month (90 days total) rental is now available for this coming 2027 winter and spring season. This large 2940 +/- sq ft beachfront retreat is situated on the south side of this building which offers stunning 180-degree beach views along with unobstructed long southerly beach and island views from your front lanai. Tencon on Longboat Key is a true beachfront treasure located directly adjacent to the new St Regis Resort where one can walk right next door to enjoy a wonderful dining experience or sip cocktails on the beach! Situated on 3 beautifully manicured acres with a private gated entrance, gorgeous and recently built resort style pool and spa w covered gazebo area, firepit and tennis court. With only 10 units in this building and just 2 units per floor, each floorplan flows from front to back with a unique indoor-outdoor lifestyle that offers multiple outdoor lanais from each major room. From your semiprivate elevator you enter the residence to an open and bright living room and kitchen dining area with a large wall of windows and sliders while stepping out onto your large front lanai with stunning 180-degree views up and down the beach and coastline. Two nicely sized gracious guest bedrooms are privately situated away from the large owners retreat that includes a luxurious spa like bath w separate soaking tub and shower and dual vanities along with a large walk-in closet. The den/office is located right next to the owner's suite which all provides a wonderful sanctuary away from the main living area. You are located on the desirable south end of Longboat Key where one is a short drive to world famous St Armands Circle w all of its fabulous shops and restaurants or you can pop right over the bridge from St Armands and be right in the heart of downtown Sarasota and all it has to offer. Publix grocery, CVS pharmacy and other shops and restaurants are located on Longboat Key and close by along with city parks and a wonderful biking and walking trail all the way up and down the island. This small intimate complex is private and gated with a secured lobby entrance. With only 10 units in this building this tranquil condominium feels and lives almost like a house on the beach! A hidden treasure for someone who wants to be directly on the beach on the south end of Longboat Key this winter or spring. A great value at $24,750 per month in season which includes all utilities. Tenant is responsible for security deposit and all applicable taxes along with a $250 application fee, tenant approval is required by the association.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Carol Aviles (941-356-6777)
1211 GULF OF MEXICO DR #1005, LONGBOAT KEY, FL 34228
$15,000374 Days on yellowkey MLS ID: A4658115
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2135 Built: 1985Community: PromenadeCondo
Remarks: Gorgeous gulf front vacation rental available now through 2027!! You will love this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the open floor plan with a gourmet kitchen featuring quartz countertops, a breakfast bar, custom glass front cabinets, a glass front refrigerator and custom light fixtures. The flooring is luxury vinyl throughout, the main living area has a wet bar, electric fireplace, flat screen TV and lots of comfortable seating. The primary bedroom has a king bed, wall-mounted flat screen TV, built-in vanity and two walk-in closets, and the primary bath has a spacious shower with built-in seating and dual sinks. The guest bedroom and bath can be closed off for privacy and have a queen bed, wall-mounted flat screen TV and gorgeous water views! The Promenade is an upscale community with recently updated amenities, they have two areas to grill, a wonderful pool and spa, fitness, tennis and private beach access. The property is just five minutes to Publix, CVS and St Armands Circle. Please note the building has scheduled work on all elevators starting in Decmber of 2026, estimated to take at least a year. There will be noise and some minor inconvenience.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)
1930 HARBOURSIDE DR #122, LONGBOAT KEY, FL 34228
$3,50023 Days on yellowkey MLS ID: A4698059
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1192 Built: 1982Community: Fairway Bay 1Condo
Remarks: 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.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: David Leventhal (941-518-7694)
2425 GULF OF MEXICO DR #7C, LONGBOAT KEY, FL 34228
$12,0003026 Days on yellowkey MLS ID: A4215382
INCREASED by $1,000 (9.1%) on 05/25/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $7,896 (2021)Community: Sea Gate ClubSpa: YesCondo
Taxes:$7,896
High School: Booker High
Remarks: SEASONAL: 90 day minimum. No damages sustained in Hurricane. Beautiful unit from floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is beautifully renovated with professionally designed interior. Sip your morning coffee on the balcony with new glass railings as you plan your daily adventures. The light and bright living room features exquisite leather recliners and fabric sofas, one of which is a sleeper for an extra guest. Thoughtfully planned, you'll enjoy state of the art digital components including 85-inch TV and DVR while relaxing.Entertaining is a delight in the gourmet kitchen with stainless appliances. Escape to the tranquil master bedroom retreat with exquisite bedding overlooking azure waters with 65 inch smart TV, sitting area and ensuite master bath. For added comfort during your stay there’s a dedicated desk, stacked washer and dryer, built-in closet systems, wifi and 65' large smart tv in guest suite. Parking is conveniently located at the building's front door. Live the life you’ve always imagined with resort-style amenities that include Gulf-side heated pool, har-tru tennis court, updated social room, state of the art fitness area and kayak, paddle board & bike storage. Conveniently located to shopping, dining, St. Armand’s Circle and downtown Sarasota and the Arts. No pets or smoking permitted. Owners update every year...new flooring, dish washer and A/C system! BOOKED JAN - MAR 2027.
Listing is courtesy of: GULF COAST RENTAL HOMES&CONDOS (941-212-1972)
Listing Agent: Diann Thelen (941-920-0758)
2425 GULF OF MEXICO DR #4E, LONGBOAT KEY, FL 34228
$9,0001950 Days on yellowkey MLS ID: A4494373
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $7,171 (2021)Community: Sea Gate ClubCondo
Taxes:$7,171
Remarks: LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award- winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen. Master bedroom has two full size beds as well as one full size bed in the 2nd bedroom. A five minute walk to shopping & pharmacy. Short drive to St. Armand's or downtown Sarasota, for restaurants , theaters and boutique shopping. SARASOTA FL.BEACHFRONT,GULF OF MEXICO,RENTAL,SEASONAL,LUXURY. THIS PROPERTY HAS BEEN RENTED FROM 12/15/2026-3/31/2027.
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Teresa Ribaudo (941-376-4500)
360 GULF OF MEXICO DR #312, LONGBOAT KEY, FL 34228
$6,000113 Days on yellowkey MLS ID: A4687695
0 Days Off yellowkey (back on 6/19/2026)
REDUCED by $500 (7.7%) on 04/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2298 Built: 1992Community: Tangerine Bay ClubSpa: NoCondo
Remarks: WILL CONSIDER A 6 TO 12 MONTH LEASE AND WILL FURNISH FOR $7750 PER MONTH. Welcome to Tangerine Bay Club An Island Resort-style condo located at the premier location on Longboat Key. This professionally painted 2 bedroom, 2.5 bath with office/den features views of Sarasota Bay. It is in close proximity to New Pass and the pristine beaches of the Gulf of Mexico. Upgraded Ergon Fall White stone ceramic tile flooring is as beautiful as it is durable. The kitchen will satisfy your culinary desires an features; European cabinetry, lavish corian counters, Ge Profile Stainless steel appliances, Gas cooktop including an 18-bottle wine cooler and double oven. The chef's kitchen desk space will help you plan your extravagant meals. It is conveniently located near the breakfast nook and view of your courtyard. The open floor is illuminated by natural direct and indirect sunlight. Catch breathtaking sunrises over Sarasota Bay or relax by the gas fireplace during the winter. Hang out on the patio enjoying your favorite beverage and enjoy the lush exotic view. Mahogany doors through the residence give the condo a splendid feel. Stay cool all summer long with the brand- new Comfort Maker A/C unit that was just installed. Cleanses and refresh in your spa-like remodeled master bathroom with a new vanity, separate sinks, new toilet, new jacuzzi tub, tile quartz counters, and spacious neutral tile shower. Come enjoy the outrageous serenity of a LBK sunset. Maybe you will be lucky enough to witness a Flash of Green or Bioluminescence lights. Tangerine Bay offers resort-style amenities centered around one of the luxurious private pools on all of Longboat Key. The amenities include a cabana, fitness center, library, hot tub, and pool surrounded by tropical landscape. The resort also features tennis courts, pickleball courts, and a clubhouse. Organized social including group happy hours in the Cabana, scheduled group pickleball games, and planned excursions to local cultural happenings. Come hang out at Your Private Beach Access at Bay Isles Beach Club for only $250 per year. The privacy and island feel of Tangerine Bay is highlighted by its Bay front living enjoy the recently renovated boat dock which is a secret fishing spot or slip into your kayak and launch out for some peace and serene calm. Longboat key is one of the top destinations for enthusiasts of golf, tennis, fine dining, world-class fishing, and boating. In addition, Tangerine Bay Club is positioned at the southernmost point of the island , walking distance to Quick Point Nature Preserve located on the New Pass and Sarasota Bay. Come check out all the tropical birds and enjoy a stroll through the nature path. Bring your fishing pole or picnic lunch. Tangerine Bay is located across from the famous Longboat Key Club Golf Course . Come enjoy fine dining in downtown Sarasota, St Armands Cir, or many highly rated island restaurants. Just over the bridge is City Island, Mote Aquarium, Ken Thompson Park, and Sarasota Sailing Squadron marina. The St. Armand's Circle shopping district and Lido Key Beach are just a few minutes drive.
Listing is courtesy of: SUNREAL ESTATE INC (941-376-7653)
Listing Agent: Karl Helbig (941-376-7653)
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