Location: Longboat Key
Do Not Show Listings
501 CHANNEL LN, LONGBOAT KEY, FL 34228
$13,0002218 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,296
Elementary School: None
High School: None
Tax Year: 2021
Middle School: None
Remarks: Booked May-July, September, and November 2026. Looking for a 3 month rental for January-March 2027. Booked April-December 2027. Experience elevated island living in this stunning coastal retreat featuring 4 bedrooms, 3 bathrooms, a private pool, and exceptional indoor-outdoor entertaining spaces. Designed with comfort and style in mind, the bright open-concept living area features soaring ceilings, designer finishes, and large sliding glass doors that open to a spacious covered balcony overlooking the pool below. Whether you're enjoying morning coffee, afternoon cocktails, or evening conversations, the balcony provides the perfect setting to relax and unwind. The heart of the home is the beautifully appointed chef's kitchen, complete with premium stainless steel appliances, custom cabinetry, quartz countertops, a large center island with seating, and ample space for gathering with family and friends. The adjacent dining area comfortably accommodates group meals and celebrations. The luxurious primary suite offers a peaceful retreat with private balcony access, abundant natural light, and a spa-inspired en-suite bathroom featuring dual vanities, upscale finishes, and a large walk-in shower. Outside, you'll find your own private tropical oasis. Take a refreshing dip in the sparkling pool, lounge in the sun, or enjoy friendly competition with a game of ping pong in the covered entertainment area. The outdoor kitchen and grilling station make poolside dining effortless, while multiple seating areas provide plenty of space to gather, relax, and enjoy Florida's beautiful weather. Surrounded by lush tropical landscaping, this home offers privacy, comfort, and all the amenities needed for an unforgettable vacation. Whether you're seeking a relaxing escape or a place to entertain family and friends, this exceptional property delivers the perfect blend of luxury and coastal charm.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
3390 BAYOU SOUND, LONGBOAT KEY, FL 34228
$11,000275 Days on yellowkey MLS ID: A4665246
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2772 Built: 1980Community: Bay IslesSingle Family
Taxes:
Tax Year:
Remarks: **Two-Month Minimum Rental** Escape to paradise at this beautifully updated Bay Isles retreat on Longboat Key. Nestled among lush tropical landscaping and majestic oak trees, this private island getaway offers the perfect blend of luxury, comfort, and relaxation. Located within the exclusive gated community of Bay Isles, guests enjoy easy access to Longboat Key's world-renowned beaches, marinas, golf courses, tennis facilities, and scenic biking trails. Inside, the bright and airy open-concept living space features vaulted ceilings, contemporary coastal décor, and expansive sliding glass doors that open to a spacious elevated deck overlooking the pool and tropical gardens below. The chef's kitchen is designed for entertaining, featuring custom cabinetry, premium stainless-steel appliances, double wall ovens, a six-burner Viking gas cooktop, and generous seating for family and friends. The main level offers three comfortable bedrooms, including a spacious primary suite with a walk-in closet and private en-suite bath. Downstairs, a wall of sliding glass doors opens directly to the resort-style outdoor living area, where a sparkling 40-foot pool is surrounded by lush landscaping and peaceful island privacy. Whether you're enjoying morning coffee on the balcony, lounging poolside beneath the palms, or spending your days exploring Longboat Key's beaches and attractions, this exceptional home provides the perfect setting for an extended coastal escape. Booked January-March 2027 The base rent for January through April is 11,000 and off months is 9,000
6980 POINSETTA, LONGBOAT KEY, FL 34228
$4,50071 Days on yellowkey MLS ID: A4687628
INCREASED by $550 (13.9%) on 06/09/2026
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)
5801 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$19,975269 Days on yellowkey MLS ID: A4666928
Bed: 4 Bath: 4.0 Gar: 5 Liv Area Sq Ft: 4236 Built: 1997Community: H & M AssocSingle Family
Remarks: One or more photo(s) has been virtually staged. Beach Access & Gulf Views From This Incredible Luxury Home on Longboat Key. Welcome to your own Gulf-front retreat on Longboat Key! This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views. Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows that bring in natural light and frame the Gulf. The primary suite includes a private balcony, a walk-in closet, and a spa-style bath. The kitchen is stocked with modern stainless steel appliances and features gorgeous counters, a curved island, and extensive storage with full cabinetry all while enjoying the breath taking views. Step outside to enjoy a private pool surrounded by generous patio space, perfect for lounging or dining outdoors. From the backyard, you’ll have direct access to the beach, making it easy to watch the sunset or stroll along the shoreline every night. The home also includes a spacious 4-car attached garage. SMALL dogs are allowed; cats are NOT permitted.
Listing is courtesy of: KEYRENTER SARASOTA PROPERTY MANAGEMENT (561-889-2308)
Listing Agent: Kevin Hase (941-928-2666)
3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228
$4,20071 Days on yellowkey MLS ID: R4911069
REDUCED by $100 (2.3%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Community: Beach Harbor ClubSpa: NoCondo
Remarks: Looking next season (2026-2027) Lease or Lease/Option - Owner looking to lease up to 6 Months $4200 a Month of Longboat's Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seeds oats beside the azure blue Gulf of Mexico. The beach Harbor club offers 133 condo units, deeded beach access with showers, umbrellas and beach chairs. Amenities also include newly constructed boat slips, rooftop decks, outdoor cook areas, heated oversized swimming pool, community area for kayaks, clubhouse, and shuffle board. Longboat Beach Harbor is a friendly community with group events and many fun times to build relationships and enjoy sense of community living. Close to Bayfront Park with Tennis, Publix/CVS shopping. This renovated condo is situated on the 3rd floor not requiring flood insurance. Air conditioned indoor hall-way with electronic security entrance. Newly appointed high grade appliances, bathrooms, HVAC, luxury flooring and trim. Up-scale appointed fixtures and details throughout
Listing is courtesy of: LEN SCAVRON (908-304-5454)
Listing Agent: Len Scavron (908-304-5454)
3330 GULF OF MEXICO DR #202D, LONGBOAT KEY, FL 34228
$2,795126 Days on yellowkey MLS ID: A4683216
3 Days Off yellowkey (back on 6/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1106 Built: 1971Community: Longboat ArmsSpa: NoCondo
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
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)
842 BAYPORT WAY, LONGBOAT KEY, FL 34228
$3,98073 Days on yellowkey MLS ID: A4689796
INCREASED by $5 (0.1%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983Community: Bayport Bch & Ten Ph FCondo
Remarks: Peaceful and private corner condo with the convenience of a walk-out patio. Comfortably furnished and move-in ready with everything on hand for a carefree stay. A spacious dining and living area opens out to a screened lanai and large west facing outdoor patio overlooking landscaped grounds. 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, 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. Plus, Bayport is small pet friendly, and 842’s location makes dog walking a breeze. 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)
1511 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$25,500107 Days on yellowkey MLS ID: A4685769
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2940 Built: 1978Community: Tencon BeachCondo
Remarks: Offered at $25,500 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 Longboat Key this winter or spring. A great value at $25,500 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)
1591 GULF OF MEXICO DR #619, LONGBOAT KEY, FL 34228
$78,00023 Days on yellowkey MLS ID: A4695816
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5334 Built: 2024Community: St. RegisCondo
Remarks: 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 #405, LONGBOAT KEY, FL 34228
$14,000829 Days on yellowkey MLS ID: A4604126
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1598 Built: 1985Community: PromenadeCondo
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
$12,000791 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
$3,00025 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)
640 BROADWAY ST, LONGBOAT KEY, FL 34228
$7,500211 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
450 GULF OF MEXICO DR #303, LONGBOAT KEY, FL 34228
$2,40027 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
$5,7001122 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
$4,20037 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)
531 BIRDIE LN, LONGBOAT KEY, FL 34228
$14,000472 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)
5757 GULF OF MEXICO DR #305, LONGBOAT KEY, FL 34228
$5,50050 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)
1050 LONGBOAT CLUB RD #502, LONGBOAT KEY, FL 34228
$5,0001176 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
$4,900290 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)
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