Displaying: For Rent
Location: Longboat Key
Property Type(s): Condos
Do Not Show Listings
Longboat Key - 80 properties found
2425 GULF OF MEXICO DR #7C, LONGBOAT KEY, FL 34228
$12,0003003 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,896
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2021
Middle School: Booker Middle
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
$9,0001927 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
Elementary School: None
High School: None
Middle School: None
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
$6,00090 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
Taxes:
Tax Year:
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)
1050 LONGBOAT CLUB RD #506, LONGBOAT KEY, FL 34228
$4,75092 Days on yellowkey MLS ID: A4687317
REDUCED by $250 (5.0%) on 06/18/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1080 Built: 1974Community: Privateer NorthCondo
Remarks: Beachfront Longboat Key Luxury Living. Wake up every day to sweeping **Gulf views** from this beautifully renovated **5th-floor beachfront residence**. Designed for comfort, tranquility, and effortless coastal living, this 12-month annual rental places you steps from the sand and moments from the world-class dining and boutique shopping of **St. Armands Circle**. Property Highlights *Direct Gulf-front setting** with dramatic water and sunset views *Renovated interior** designed for relaxation and peace of mind *Primary suite** with a king-size adjustable bed *Guest bedroom** featuring a twin that converts to a king Resort-Style Amenities - Beachfront **pool & spa** with private beach access - Tennis courts**, fitness center, and sauna - Gated entry and secured building access - Library, grill area, and firepit for gathering and unwinding - Assigned **carport parking** plus guest spaces Experience the best of the **Florida coastal lifestyle**—sun, sand, and serenity wrapped in luxury.
Listing is courtesy of: WAGNER REALTY (941-756-7800)
Listing Agent: Donna Channey (941-527-6909)
730 SPANISH DR S #99, LONGBOAT KEY, FL 34228
$2,8007 Days on yellowkey MLS ID: A4697407
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1255 Built: 1969Community: Spanish Main Yacht Club CondoCondo
Remarks: Experience the pinnacle of coastal living in this beautifully updated, ground-floor condominium in the highly desirable Spanish Main Yacht Club on Longboat Key. This 2-bed, 2-bath residence offers 1,255 sq. ft. of bright, air-conditioned space featuring elegant engineered hardwood floors, modern stone kitchen countertops, and a welcoming living/dining room combination ideal for entertaining. The thoughtful layout includes built-ins, ceiling fans, and a serene primary suite with a spacious walk-in closet. Life at Spanish Main Yacht Club feels like a year-round vacation. This active 55+ community provides premium amenities including deeded beach access just steps away, a sparkling community pool, shuffleboard courts, and a clubhouse with a library and social rooms. Boating enthusiasts will appreciate the bay and harbor access along with an on-site marina. Practical conveniences include inside laundry, an attached carport, **a personal charging station for your electric car**, and maintenance-free living with grounds care and management included. One small pet (up to 35 lbs) is welcome. Ideally situated just minutes from the upscale dining and shopping of St. Armands Circle and a short drive to Anna Maria Island, this home is perfect for those seeking a tranquil waterfront lifestyle. Whether you're boating, fishing, or relaxing in the Florida room, this property offers a rare opportunity in one of the area’s most desirable locations. Available for annual lease this unfurnished coastal retreat invites you to embrace the best of Longboat Key living.
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
2020 HARBOURSIDE DR #446, LONGBOAT KEY, FL 34228
$5,49527 Days on yellowkey MLS ID: A4695127
REDUCED by $455 (7.6%) on 06/13/2026
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)
3240 GULF OF MEXICO DR #B303, LONGBOAT KEY, FL 34228
$7,2002781 Days on yellowkey MLS ID: A4418888
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1975 Tax: $4,086 (2021)Community: PortobelloCondo
Taxes:$4,086
Remarks: Absolutely beautiful turnkey furnished condo at the sought after Portobello on Longboat Key. The meticulously maintained, light and bright two bedroom, two bathroom unit has a combination living room/dining room, separate kitchen with stainless steel appliances, split bedrooms and a washer and dryer in the unit. Newly renovated bathrooms and kitchen with high end finishes round out this fabulous property. Enjoy your morning coffee while sitting on the screened lanai that looks out over the bay. Community amenities include private beach access, pool, tennis courts, clubhouse, kayak launch and BBQ area. Call today as this will not last long!!!
Listing Agent: C. Alison Hunter (941-587-5667)
1465 GULF OF MEXICO DR #504, LONGBOAT KEY, FL 34228
$15,000785 Days on yellowkey MLS ID: A4609098
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1710 Built: 1981Community: Players Club ICondo
Remarks: LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds and sparkling sandy beaches from the expansive terrace of this light and bright, corner unit, turnkey furnished condo. The property has three bedrooms, three bathrooms, living room/dining room combination with floor to ceiling sliding glass doors to enjoy the breathtaking waters of the Gulf of Mexico, brand new wood tile flooring and fresh paint throughout. The large kitchen has solid stone counters, wood cabinets, offers plenty of space for cooking/food preparing and a closet pantry. The primary bedroom has a king sized bed, amazing views of the Gulf of Mexico and walk out access to a private terrace, a walk in custom closet and an on suite bathroom with a garden tub, stall shower and double sinks. The first guest bedroom has a view of the Gulf of Mexico, a king sized bed, a custom walk in closet and on suite bathroom with a walk in shower. The second guest bedroom has two queen sized beds and a custom walk in closet. The guest bathroom has a stall shower. The condo has a laundry closet with full sized washer and dryer. Two parking spaces come with the rental of which one is covered and one is in the garage. The Player Club is abound with amenities which include 24 hour guard gated entry, private beach access with cabanas, putting green, heated salt water community pool and hydro therapy spa, BBQ grills, fire pits, 4 Har-Tru tennis courts, fitness center and a large clubhouse with a rooftop deck. No pets allowed. Three month minimum rentals due to the Association. CALL TODAY. This is not one to miss and will not last long!!
1485 GULF OF MEXICO DR #109, LONGBOAT KEY, FL 34228
$11,0001373 Days on yellowkey MLS ID: A4548403
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1839 Built: 1981Community: Players Club ISpa: NoCondo
Remarks: LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players Club. This light and bright turnkey furnished condo has two bedrooms, two and a half bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized washer and dryer. The primary bedroom has a king sized bed, on suite bathroom with double sinks and a stall shower, and walk in closet and a ocean view lanai with lounge chairs and table for enjoying the view. The guest bedroom has two twin beds and ocean views from two large windows. Guest bathroom has a stall shower. Front entry is set up as a sitting area with a queen sized murphy bed. The Player Club is abound with amenities. The amenities include a gated entry, beach access, putting green, heated community pool with spa, BBQ grills, tennis, clubhouse, fitness center and large meeting room. No pets allowed. Three month minimum rentals only due to the Association. CALL TODAY. This is not one to miss!!
1975 GULF OF MEXICO DR #G4-401, LONGBOAT KEY, FL 34228
$9,50010 Days on yellowkey MLS ID: A4697063
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; $9,500/mo May–Nov, $12,500/mo Dec–Apr; annual considered. Refundable deposit = 1 mo. Available for showings.
Listing is courtesy of: THE AGENCY SARASOTA (941-500-5150)
Listing Agent: Robert Hildreth (941-326-0278)
750 BAYPORT WAY #750, LONGBOAT KEY, FL 34228
$3,8001450 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 JUNE 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)
455 LONGBOAT CLUB RD #401, LONGBOAT KEY, FL 34228
$8,0002648 Days on yellowkey MLS ID: A4431350
REDUCED by $1,000 (11.1%) on 06/10/2026
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)
1211 GULF OF MEXICO DR #1005, LONGBOAT KEY, FL 34228
$15,000351 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)
2109 GULF OF MEXICO DR #1203, LONGBOAT KEY, FL 34228
$10,000982 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. **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.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228
$4,20069 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
$2,795124 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
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
$3,98071 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
$25,500105 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
$78,00021 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
$14,000827 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.
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.