Location: Longboat Key
Do Not Show Listings
1211 GULF OF MEXICO DR #405, LONGBOAT KEY, FL 34228
$14,000807 Days on yellowkey MLS ID: A4604126
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1598 Built: 1985Community: PromenadeCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the stylish seating, dining! The master suite offers wonderful Gulf views and access to the open patio, a king bed, flat screen TV, and walk-in closet. The master bath has dual sinks, soaking tub and an oversize shower. The guest bedroom offers two twin beds, flat screen TV, and views of the lushly landscaped grounds and views of the bay. In unit washer and dryer. This is one of the most sought-after buildings on Longboat Key, this well managed community was recently renovated with elegantly redecorated lobby and corridors, along with two social rooms, the Sunrise and Sunset rooms. There are Men's and Women's workout rooms, four Har-Tru tennis courts, two outdoor gazebos with gas grills and seating, a gorgeous gulf side heated resort style pool and spa, all surrounded by meticulously maintained grounds. Take the walkway to the sparkling sands of the private beach where there are plenty of chairs and chaises to relax and restore! The community offers 24/7 security and concierge services, and on-site management. Wake up, and fall asleep to, the sound of the waves gently lapping the shore. Welcome to Paradise! Booked January through April 2027.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)
Listing Agent: Stephanie Deshaies (941-780-3229)
4325 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$12,000769 Days on yellowkey MLS ID: A4608766
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1411 Built: 1975Community: Tiffany PlazaCondo
Remarks: Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel appliances. The dining area offers seating for four, there is a wet bar with beverage chiller for convenience. The living room offers comfortable seating, a flat screen TV and amazing water views! The primary bedroom has a king bed, amazing views, a flat screen TV, and a walk-in closet. The primary bath offers dual sinks and a walk-in shower. The guest bedroom has a King bed and Flat screen TV for streaming. You will love this wonderful location, with shopping and dining close by, and Historic St. Armands Circle is just a short drive away. Welcome to Paradise! (All rates are plus taxes and fees) (Booked May through the end of November, 2026 and booked January and February of 2027)
820 SPANISH DR S #., LONGBOAT KEY, FL 34228
$3,0003 Days on yellowkey MLS ID: A4695386
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1390 Built: 1971Community: Spanish Main Yacht Club CondoCondo
Remarks: Coastal Living at Its Finest in the Spanish Main Yacht Club! Discover your perfect Florida retreat in this beautifully maintained, free-standing 2-bedroom, 2-bathroom villa located on the highly coveted southern end of Longboat Key at 820 Spanish Dr S. Offering 1,390 square feet of bright, open living space, this single-story residence perfectly blends maintenance-free comfort with an active, coastal-resort lifestyle in a premier 55+ community.Step inside to find a spacious layout featuring a generous living area centered around a cozy fireplace, a classic split-bedroom design for optimal privacy, and a wonderful enclosed porch perfect for morning coffee or unwinding after a day in the sun. The property also features a durable concrete tile roof, central A/C, a dedicated utility space, and an open porch area to soak in the Gulf breezes. Please note this is a strictly no-smoking and no-pets property.Available in-season for $6,000 per month turnkey, and off-season for $3,000 per month turnkey. Situated in Manatee County’s renowned Spanish Main Yacht Club, an established and highly desirable waterfront community zoned LBK_R-3MX, residents enjoy unparalleled amenities including a private marina (with boat slips available for a nominal fee), a heated community pool overlooking the active harbor, a lively clubhouse, shuffleboard, and deeded private beach access just steps across the street to the pristine sands of Longboat Key. Located within easy reach of local island dining, area attractions, and the highly-rated Anna Maria Elementary school district, this waterfront gem offers the ultimate island lifestyle.
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
842 BAYPORT WAY, LONGBOAT KEY, FL 34228
$3,97551 Days on yellowkey MLS ID: A4689796
REDUCED by $825 (17.2%) on 05/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983Community: Bayport Bch & Ten Ph FCondo
Elementary School: Southside Elementary
Middle School: Booker Middle
Remarks: Available June through December. This first-floor corner condo means extra privacy, added natural light and the convenience of a walk-out patio. Nicely furnished and move-in ready for a comfortable stay. A spacious dining and living area opens out to a screened lanai and large west facing outdoor patio overlooking landscaped grounds. A patio gate allows easy access to a path out to the beach access road plus it makes dog walking a breeze. Yes, Bayport is small pet friendly- a rarity in island condo communities. The primary bedroom has a king bed, large walk-in closet, and an alcove with a desk overlooking the garden. The guest bedroom can be configured as a king or two twins. There is under building parking for one car, outside locked storage and plenty of guest parking. Bayport Beach and Tennis Club is a true Gulf to Bay community, with a fishing pier and kayak launch out to Sarasota Bay, and access to 1200 feet of private beach with beach chairs and umbrellas, just 2-3 minutes from your front door. Enjoy a swim in the Jr Olympic pool, tennis on 4 har-tru courts, a club house, a well equipped gym, and shelled walking paths along tropical landscaped grounds. Groceries, parks and conveniences are within 2 miles, with shopping and terrific dining dotted along the Key. Sarasota's entertainment and cultural attractions are a short drive away.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rosemarie Mckee (941-504-9396)
6980 POINSETTA, LONGBOAT KEY, FL 34228
$3,95049 Days on yellowkey MLS ID: A4687628
REDUCED by $300 (7.1%) on 06/01/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 700 Built: 1940Single Family
Remarks: Tucked away in a quiet fisherman’s village on Longboat Key, this elegant one-bedroom cottage blends classic island charm with modern luxury. The bright, open living space features soaring vaulted ceilings and a sleek, contemporary kitchen. Premium comforts include high-speed internet, in-unit laundry, a reverse osmosis water filtration system, and UV air purification. Perfect for couples seeking a tranquil seaside getaway, the property offers boat parking and convenient access to a nearby boat launch. Whitney Beach is just a short stroll away, making this an ideal private retreat with easy access to the Gulf of Mexico.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Christina Vescovo (314-743-7111)
640 BROADWAY ST, LONGBOAT KEY, FL 34228
$7,500189 Days on yellowkey MLS ID: A4673491
INCREASED by $2,000 (36.4%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1500 Built: 1940Community: Longbeach Rev Of R P Jordans SubSpa: NoSingle Family
Remarks: Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and elevated in 2025 to the highest modern standards after the 2024 storms, this turnkey coastal residence offers unmatched peace of mind and contemporary luxury. The light-filled, open-concept interior features vaulted ceilings, a gourmet kitchen with new stainless-steel appliances and quartz countertops, and two beautifully appointed spa bathrooms with premium fixtures and rainfall showers. The primary suite indulges with a king bed, wet bar, mini-fridge, and a windowed en-suite bath, while the second bedroom provides a comfortable queen bed. A dedicated home office is your third bedroom, with its full-size Murphy bed/desk. Available August 31, 2026. If needs are sooner, call for other cottages listed for same owner! The private tropical backyard serves as a tranquil oasis, complete with a serene lily-pad pond, fire pit, and mature landscaping. Delivered fully furnished with beautiful coastal décor and equipped with high-speed fiber internet, the home is ideal for immediate personal enjoyment, remote work, or proven vacation-rental income. Grandfathered Village zoning permits short-term rentals. Enjoy an unparalleled lifestyle just a short walk from Whitney Beach, historic fishing docks, bay kayak launches, and waterfront dining. Longboat Key Club, St. Armands Circle, and downtown Sarasota’s world-class amenities are only minutes away. Rarely available: authentic historic significance, a total top-to-bottom 2025 rebuild, and the quintessential Village address. Move-in ready
2020 HARBOURSIDE DR #446, LONGBOAT KEY, FL 34228
$5,9507 Days on yellowkey MLS ID: A4695127
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 fully remodeled 2-bedroom, 2-bath residence located in the Bay Isles community on Longboat Key. Situated within the highly desirable Bay Harbour community, this modern coastal retreat is ready for immediate occupancy with flexible lease terms available from 6 to 12 months. Step inside to discover a bright and open floor plan featuring upscale contemporary finishes, designer furnishings, updated flooring, a stunning modern kitchen with premium appliances, and elegantly renovated bathrooms. The spacious primary suite offers a relaxing retreat, while the second bedroom provides comfortable accommodations for guests or a home office setup. Expansive living spaces and a private balcony create the perfect atmosphere for enjoying the coastal lifestyle. Residents of Bay Harbour enjoy exceptional resort-style amenities including a waterfront heated pool and spa, fitness center, clubhouse with social room, kayak launch, secure under-building parking, beautifully maintained grounds, and marina access with stunning Sarasota Bay views. As part of Bay Isles, tenants also receive access to the exclusive Bay Isles Beach Club featuring private deeded beach access on the Gulf of Mexico, gated parking, picnic areas, grills, restrooms, and some of Longboat Key’s most pristine sand beaches. Perfectly located just minutes from St. Armands Circle, world-class dining, golf courses, marinas, shopping, and downtown Sarasota, this residence offers the ultimate combination of luxury, convenience, and island charm. Available for minimum 6-month lease up to 12 months. Fully furnished and move-in ready.
Listing is courtesy of: VIVE REALTY (941-600-8162)
Listing Agent: Jeffrey Swanson (248-938-1775)
450 GULF OF MEXICO DR #303, LONGBOAT KEY, FL 34228
$2,4005 Days on yellowkey MLS ID: A4695053
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1301 Built: 1970Community: Bay Harbour ApptsCondo
Remarks: Annual furnished rental: Discover the ultimate island lifestyle in this comfortably furnished 2-bedroom, 2 bath, unit located in the highly sought-after community of Bay Harbour on the southern end of Longboat Key. Just minutes from St. Armands Circle, downtown Sarasota, restaurants, shopping, county tennis and pickleball courts, walking trails, parks and of course – Longboat Key public beach accesses along Gulf of Mexico Drive. Doesn’t get much better than this! Entering the condo you immediately feel the spaciousness and inviting interior. Just bring your personal possessions for an easy move-in! The updated kitchen offers granite counter tops, stainless appliances and both an eat-in space to share a meal along with full-size laundry closet. The kitchen also overlooks the dining and living areas, which are great for entertaining friends and family. From most rooms you’ll have a lovely view of the pool and partial view of the Bay. This split-plan layout provides privacy for both you and your guests. Master suite features a large bedroom, plenty of closet space and generous size private bath. Guest bedroom offers a full and day bed for your guests and family with nice size closet. Second bath is conveniently located next to the guest bedroom. Perfect for unwinding after a day of sunbathing or beachcombing you can relax with your favorite beverage overlooking the pool and water views. If you’re actively inclined, step outside and immerse yourself in the beauty of Sarasota Bay, where you'll enjoy direct access to a kayak launch or a work out in the fitness area – or just lounge by the pool.Bay Harbour is a true gem which offers a wealth of amenities, including a heated waterfront pool, kayak storage, a floating kayak launch, a fitness center, assigned covered parking, and inside locked bike storage. Take advantage of excellent fishing on property, or simply relax and take in the views. Bay Harbour offers the perfect combination of location and lifestyle. Don’t miss your chance to call this home! Background Check required, along with First, last and Security deposit. Sorry, but no smoking nor pets are allowed.
Listing is courtesy of: GULF COAST RENTAL HOMES&CONDOS (941-212-1972)
Listing Agent: Diann Thelen (941-920-0758)
3240 GULF OF MEXICO DR #603, LONGBOAT KEY, FL 34228
$5,7001100 Days on yellowkey MLS ID: A4571215
INCREASED by $900 (18.8%) on 05/30/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1975Community: PortobelloCondo
Remarks: VACATION RENTAL!!! AVAILABLE JAN - MARCH 2027! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and warm and features an updated kitchen with granite counter tops and appliances. Stunning views await you from most rooms! This bright and airy unit provides views of Buttonwood Bayou and Sarasota Bay whether you're sitting inside or relaxing on your beautiful private balcony. The master bedroom features a king size bed and private bath and twin beds in the second bedroom. The deeded private beach access is right across the street! Community amenities feature heated community pool, club house, tennis court, boat dock and fishing pier...all yours to enjoy! The exclusive shops and restaurants at St Armands circle are a short drive away as well as the famous Lido Beach. Take a drive over the John Ringling bridge into downtown Sarasota and you'll find theater, art galleries as well as exquisite dining and shops. Don't wait...your home away from home is move-in ready! No pets or smoking.
840 BAYPORT WAY #840, LONGBOAT KEY, FL 34228
$4,20015 Days on yellowkey MLS ID: A4694333
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1640 Built: 1983Community: Bayport Bch & Ten Ph FCondo
Remarks: This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The beautiful upgrades to the kitchen and baths go hand in hand with the elegant decor of this property. Fully furnished and fully equipped and ready for your arrival, covered parking for one vehicle and guest parking is available as well. The clubhouse has a full kitchen facility and is large enough for meetings, private parties, and social functions, The exercise room is well equipped with machines and free weights. Classes in water Aerobics are held several times a week during the winter at a nominal cost, Available May to December at OFF Season rate of $4,200 per month plus 13% tourist tax. The property is a NO smoking/NO pet unit.
Listing is courtesy of: REALTY SERVICES INC (941-954-4443)
Listing Agent: Shirley Cuddy (941-321-1549)
501 CHANNEL LN, LONGBOAT KEY, FL 34228
$13,0002196 Days on yellowkey MLS ID: A4468386
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2349 Built: 2019 Tax: $10,296 (2021)Community: New Pass ShoresSpa: NoSingle Family
Taxes:$10,296
Tax Year: 2021
Remarks: Booked May-July, September, and November 2026. Looking for a 3 month rental for January-March 2027. Booked April-December 2027. This fabulous newly constructed 4 bedroom 3 bath pool home is located on the south end of Longboat Key. Spacious with an open floor plan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous countertops and wonderful warm beachy flooring, this home has it all. Sit outside on the upper deck with a view of the refreshing pool during breezy afternoons or the covered deck downstairs which offers shade while not sunning. Ping pong and bocce ball complete the picture for hours of fun. The dining table sits (6) with (4) breakfast bar seats nearby. Two bedrooms have (1) Queen and (1) twin each, one quest bedroom has a Queen and the master has a King bed, all with large screen televisions.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
531 BIRDIE LN, LONGBOAT KEY, FL 34228
$14,000450 Days on yellowkey MLS ID: A4643954
0 Days Off yellowkey (back on 5/28/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3268 Built: 2017Community: Country Club ShoresSpa: YesSingle Family
Remarks: Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home features four bedrooms, a spacious bonus room, and a dedicated office, providing plenty of space for both relaxation and productivity. The private heated pool and spa create a resort-style retreat in your own backyard, surrounded by lush, meticulously maintained landscaping. Inside, the gourmet kitchen boasts modern appliances, ample counter space, and an open layout ideal for entertaining. Sunlit living areas with high-end finishes enhance the home’s beauty and warmth. A boater’s paradise, this home includes an 11,000 lb boat lift for effortless access to Sarasota Bay and the Gulf of Mexico. Located just minutes from pristine beaches, championship golf courses, and the upscale shopping and dining of St. Armands Circle, this home offers the perfect blend of luxury and convenience. NO storm damage! Available for an annual rental. Contact us today to schedule a private showing! NO storm damage!
Listing is courtesy of: WAGNER REALTY (941-727-2800)
Listing Agent: Karie Gorgone (941-313-5469)
3330 GULF OF MEXICO DR #202D, LONGBOAT KEY, FL 34228
$2,795104 Days on yellowkey MLS ID: A4683216
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1106 Built: 1971Community: Longboat ArmsSpa: NoCondo
High School: Booker High
Remarks: BAYSIDE CONDO WITH FULL BAY VIEWS – AVAILABLE FOR ANNUAL RENTAL Experience the best of Longboat Key living in this beautifully furnished 2-bedroom, 2-bath second-floor condo (with elevator access) located in the desirable Longboat Arms community. This turnkey residence offers stunning, unobstructed bay views and a well-designed open floor plan. The kitchen flows seamlessly into the dining and living areas, creating a comfortable and inviting space for everyday living or entertaining. A full-length, spacious enclosed lanai overlooking the bay provides the perfect setting to enjoy peaceful mornings and spectacular evening sunsets. The primary bedroom features a king bed and breathtaking full bay views. The guest bedroom offers two twin beds, ideal for family or visiting guests. A washer and dryer are conveniently located in the adjacent laundry room. Longboat Arms is a charming bayside boating community offering exceptional amenities, including a heated pool, tennis court, clubhouse, bayside fishing docks, and a private boat launch. Covered carport parking and ample guest parking are available. Ideally situated mid-key, you’re just a short distance from Publix and directly across the street from deeded beach access with a private pathway to the Gulf. Enjoy tranquil waterfront living in one of Longboat Key’s most sought-after bayside communities. Don’t miss this rare opportunity at a competitive rate—call today to schedule your private showing.
Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)
Listing Agent: Heidi Thompson (941-807-2241)
5757 GULF OF MEXICO DR #305, LONGBOAT KEY, FL 34228
$5,50028 Days on yellowkey MLS ID: A4692913
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1561 Built: 1973Community: The ShoreCondo
Remarks: A little slice of Gulf-front heaven. Seasonal rental only, available July 15 through December 31, 2026! 60 Day Minimum Lease, not available Jan 1, 2027-March 31, 2027. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches are perfectly complemented by the beautifully redesigned interior and thoughtfully updated floor plan. The gathering room opens to the extended kitchen to create continuity in the main living area, perfect for entertaining. Custom imported cabinetry with frosted glass accents, pantry storage, complementary upper and lower cabinetry, solid surface countertops, and a waterfall-edge peninsula with seating for four elevate the space. Premium KitchenAid appliances include a French door refrigerator, dishwasher, double oven, and cooktop. A skylight fills the home with natural light alongside LED, recessed, and drop lighting throughout. Imported marble flooring, porcelain tile, and neutral Berber carpet complete the interior finishes. Both bathrooms have been beautifully modernized with Corinthian Fossil showers, frameless glass doors, floating vanities, and Quartz countertops. The primary en suite features a walk-in closet and sitting area. Multiple sets of sliding glass doors open to the covered balcony, creating the perfect place to enjoy our million dollar sunsets. Residents can unwind seaside along more than 500 feet of shoreline, stroll the lushly landscaped grounds and paver pathways, or enjoy the private community pool and spa. All lease terms shorter than 6 months are subject to 13% tourism tax.
Listing is courtesy of: TNG PROPERTY MANAGEMENT (941-773-9599)
Listing Agent: Scott Nold (941-773-9599)
500 SCHOONER LN, LONGBOAT KEY, FL 34228
$11,5501185 Days on yellowkey MLS ID: A4561269
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1657 Built: 1964Community: Country Club ShoresSingle Family
Remarks: Booked May-June 8th, October, and Dec 2026 through April 15th 2027, May 2027. There is 2 week minimum stay required. Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was thought out from kitchen to bathrooms. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for the gourmet chef in you all. Outdoor living could be your everyday enjoyment while sipping wine by your private heated pool and on cool nights curl up at the fire pit. Sit back and relax with many seating areas and full outdoor dining table in this cozy beach themed oasis in Country Club Shores. Quiet sought out neighborhood on south end of Longboat Key with beach access between LBK Club and Beach Place. It is fully equipped with everything you will need to feel at home while enjoying the sights and comforts that Longboat Key has to offer. 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.
2109 GULF OF MEXICO DR #1203, LONGBOAT KEY, FL 34228
$10,000962 Days on yellowkey MLS ID: A4584050
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1463 Built: 1984Community: Sunset BeachSpa: YesCondo
High School: Riverview High
Remarks: Booked Dec 1st 2026-March 31st 2027. Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill. You are welcome to beach chairs along the private beach. Under-building assigned parking directly across from security coded entry lobby with elevator and mailboxes. Plenty of guest parking inside the welcome security gates. Full time maintenance crew keeps the grounds immaculate. Wake up to beach and water views from Living room, both bedrooms and terrace. The apartment has an fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room furniture, decor and linens. Utility room with Maytag washer and dryer. Sunset Beach is currently replacing all lobby and hallway flooring. 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.
3390 BAYOU SOUND, LONGBOAT KEY, FL 34228
$11,000253 Days on yellowkey MLS ID: A4665246
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2772 Built: 1980Community: Bay IslesSingle Family
Remarks: **This is a 2 month minimum vacation rental** Booked January-March 2027 Welcome to 3390 Bayou Sound, located within the exclusive, gated community of Bay Isles on picturesque Longboat Key. This prime location offers access to world-renowned beaches, a marina, golf courses, biking trails, and tennis facilities. Nestled on an oversized, beautifully landscaped corner lot in the Bayou part of Bay Isles, this remodeled and meticulously maintained pool home boasts nearly 3,000 square feet of living space—including 2,021 square feet on the main level and an additional 942 square feet on the walk-out lower level. As you approach the property, you’ll notice the gentle slope of the lot from the street up to the main entrance, framed by lush palms, mature oaks, and banyan trees. The double-door entry opens to an inviting, open-concept great room that seamlessly connects to a spacious outdoor deck overlooking the backyard and pool area below. The updated, modern kitchen features custom cabinetry, stainless steel appliances, a built-in double oven, and a six-burner Viking gas cooktop—perfect for entertaining. Also on the main level are three bedrooms, including two guest rooms and a full guest bathroom. The expansive master suite offers a large walk-in closet and a well-appointed en-suite bathroom. The lower level, with its wall of sliding glass doors, opens directly to the screened pool deck and a 40-foot pool equipped with a new pump. This level also includes a full bathroom and laundry area. The two-car tuck-under garage offers ample storage space and a small workshop area. As a resident of Bay Isles, you’ll enjoy access to the Private Bay Isles Beach Club, located at 2111 Gulf of Mexico Drive, just across from the community. The club features a pristine stretch of beach, picnic tables, tiki huts, barbecue grills, an ice machine, and storage bins for beach gear. A key fob, included with the rental, is required for access. More information can be found on the Bay Isles website. The base rent for January through April is 11,000 and off months is 9,000
1050 LONGBOAT CLUB RD #502, LONGBOAT KEY, FL 34228
$5,0001154 Days on yellowkey MLS ID: A4566128
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1290 Built: 1974Community: Privateer NorthCondo
Remarks: Available 05/01/2026 through 12/30/2026 FOR $5000. LEASED SEASON JAN, 2026 THROUGH MARCH, 2027. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have private lanais, walk in closets. Double queen beds in one of the ensuites. open floor plan features large eat in area with granite counters neutral tile floors, and extra storage outside unit. Laundry is located right outside of your unit. Covered Carport and guest parking available. Building amenities WIFI, renovated social room and fitness center. Resort style living with heated Olympic size pool, tennis courts, biking trails, and outside showers. Enjoy the Publix Grocery just minutes away along with many restaurants for fine dining. This building is located the furthest South end of Longboat Key so you miss a lot of traffic. Just minutes to St. Armand's Circle for shopping, restaurants and entertaining. Enjoy Lido Beach also just minutes away.
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Marni Hayden (941-809-5044)
4420 EXETER DR #208, LONGBOAT KEY, FL 34228
$4,900268 Days on yellowkey MLS ID: O6342792
REDUCED by $100 (2.0%) on 05/26/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1168 Built: 1970Community: Longboat HarbourSpa: YesCondo
Remarks: Must read entirely. 2026 RENTAL- Not Available until Nov 2026. Talk about the perfect beach place. Intercoastal view and private easy access to the beach with a private beach house! Longboat Harbour Condominium Association has tennis courts, a fitness center, Kayak launching pads, docks, fishing areas, many pools, private access to the beach on the Gulf of Mexico. Marina slips MAY be available so you can bring your boat! The home was newly renovated with space and comfort in mind. The Master has a king size bed and a great view of the canal! The screened in porch overlooks the intercoastal with all its wildlife. Try out Sarasota and stay on the beach! St. Armand’s circle is nearby with world class shopping/dining and entertainment. Cleaning fee/resort taxes not included. HOA application with background and credit check required. NO PETS. NON SMOKING UNIT. Not available for less than 2 months. Available for 3 months or longer at a discount for $5,000/monthly. Vacation rental rates: December -April: $6,000; and May: $4,500. 2-month minimum stay during peak season (December through April).
Listing is courtesy of: AG REALTY SERVICES LLC (407-374-7295)
Listing Agent: Armando Gonzalez (407-346-6229)
LONGBOAT KEY, FL 34228
$6,0001099 Days on yellowkey MLS ID: A4572396
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1977Community: Seaplace IiiCondo
Remarks: SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the primary suite. Primary bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST ARMANDS CIRCLE of restaurants, shops and entertainment.
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Jane Hunter (941-896-0622)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.