Displaying: For Rent
Location: Longboat Key
Property Type(s): Condos
Living Area Square Feet: 1000 to 1499
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Longboat Key - 45 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)
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
Taxes:
Tax Year:
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)
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)
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)
4325 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$12,000789 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
$3,00023 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.
450 GULF OF MEXICO DR #303, LONGBOAT KEY, FL 34228
$2,40025 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.
3240 GULF OF MEXICO DR #603, LONGBOAT KEY, FL 34228
$5,7001120 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.
1050 LONGBOAT CLUB RD #502, LONGBOAT KEY, FL 34228
$5,0001174 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
$4,900288 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
$6,0001119 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 Agent: Jane Hunter (941-896-0622)
4825 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$7,800419 Days on yellowkey MLS ID: A4651021
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970Community: Westchester Condo Apts Un 3Condo
Remarks: SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite features King-sized bed, TV, & opens to a private balcony. The comfortable guest bedroom offers a Queen and 1 twin bed with ceiling fan, and guest bathroom with tub/shower. The Westchester community is located on 7-plus acres of beautifully landscaped grounds, meticulously maintained with tennis court, 2 heated pools, updated Clubhouse and 3 private Tiki-hut areas. Gulf beaches are what make Longboat Key unique and you can walk for miles on the beach from the condo. Longboat Key also has 10 miles of bicycle paths on either side of Gulf of Mexico Drive. Located just 6 miles from fashionable St. Armands Circle and only a short drive to downtown Sarasota with arts, theatre, restaurants and shopping. This is non-smoking unit. Sorry, this condo association does not allow pets. BOOKED JAN-MAR, 2027.
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