Displaying: For Rent
Location: Longboat Key
Property Type(s): Condos
Living Area Square Feet: 1000 to 1499
Do Not Show Listings
Longboat Key - 34 properties found
2301 GULF OF MEXICO DR #102N, LONGBOAT KEY, FL 34228
$9,0004 Days on yellowkey MLS ID: A4692071
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970Community: Islander Club Of LongboatSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Wake up to breathtaking Gulf of Mexico views from this beautifully remodeled 2-bedroom, 2-bath oceanfront residence at The Islander Club. Spanning approximately 1,233 sq ft, this turnkey condo offers sweeping panoramic views of the Gulf from the spacious living room and both bedrooms. Step inside to find a thoughtfully updated interior featuring modern finishes, a fully equipped kitchen with stainless steel appliances, and a bright, open living and dining area that flows seamlessly onto a private balcony—perfect for morning coffee while watching dolphins play or enjoying spectacular sunsets. The primary bedroom boasts an en-suite bath, while the guest bedroom provides comfort and privacy. Both bedrooms, along with the living room, deliver direct, unobstructed ocean views. This residence comes fully furnished and includes a washer and dryer in-unit for ultimate convenience. Additional features include impact-resistant windows and doors, covered parking, and access to The Islander Club’s exceptional amenities: a 24-hour fitness center with Har-Tru tennis courts, two swimming pools (one beachfront), billiards, a library, and a vibrant community atmosphere just steps from the sugar-sand beach. Located in the heart of Longboat Key on St. Armands Circle and downtown Sarasota, this property offers the perfect blend of coastal luxury and relaxed island living. Whether you're seeking a seasonal rental or a long-term retreat, this oceanfront gem is move-in ready and delivers the best of island living with direct beach access and unforgettable Gulf vistas.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Michele Conn (612-414-7052)
601 LONGBOAT CLUB RD #902S, LONGBOAT KEY, FL 34228
$9,000146 Days on yellowkey MLS ID: A4674604
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1458 Built: 1970Community: Longboat Key TowersSpa: YesCondo
Remarks: Your winter on the Gulf begins here. This is a rare opportunity to enjoy direct Gulf front living in a fully furnished seasonal residence, available January through March 2027. Tucked behind the private gates of Longboat Key, this premium condo blends the ease of coastal condo living with the comfort of generous, well-designed interiors. Mornings begin with soft sunrise views over the golf course from the bedrooms, while evenings wind down with glowing sunsets over the Gulf from the main living spaces. The primary suite offers walk-in closets and a peaceful retreat, and the open layout creates an effortless flow for entertaining or quiet nights at home. Residents enjoy resort-style amenities including a heated beachfront pool and spa, fitness center, sauna, steam room, and around the clock gated security. Water, cable, Wi Fi, and parking are included, making your stay truly effortless. Located within the Longboat Key Club community, Longboat Key Towers offers a serene beachfront escape while keeping you just minutes from the dining, culture, and lifestyle that make Sarasota so special.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Irma Scherer (305-490-8981)
4325 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$12,000739 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)
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)
Listing Agent: Stephanie Deshaies (941-780-3229)
3330 GULF OF MEXICO DR #104D, LONGBOAT KEY, FL 34228
$6,5008 Days on yellowkey MLS ID: A4690993
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1106 Built: 1971Community: Longboat ArmsCondo
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease. Groceries are carried in with ease, morning coffee is enjoyed on your lanai, and just beyond, a nearly private lawn stretches out like your own backyard retreat. Only sixty feet away, the tranquil waters of Cranes Bayou create a breathtaking backdrop along with the Sarasota Bay. From your windows and lanai, the view feels intimate and serene as dolphins surface in the distance, manatees glide through calm waters, and coastal birds fill the sky. Just outside, an eagle’s nest tucked within a Spanish pine offers a daily reminder that nature is not something you visit here; it’s something you live beside. The lifestyle extends beyond the view. A deeded private walkway leads you directly to the soft sands of the beach, inviting spontaneous sunset strolls, morning shell hunts, and afternoons spent with your toes in the sand. For boaters, a private slip just steps from your front door makes life on the water feel effortless, ready for quiet cruises or sunset rides along the coast. Recently refreshed with a 2025 community pool upgrade and lush landscaping, the setting feels nature-filled with peacefulness. Inside, the residence reflects a thoughtful balance of high-end furnishings, warm textures, and a blend of contemporary design and classic Old-Florida charm, creating a space that feels both elevated and inviting. Carefully curated lighting, including modern fixtures and Frank Lloyd Wright–inspired sconces, lets you shape the atmosphere, whether you're hosting friends, unwinding with a book, or enjoying a quiet evening at home. This is more than a seasonal escape; it’s a place where mornings feel slower, evenings feel softer, and everyday moments carry the calm of island living. For those looking for a coastal rental that blends privacy, tranquility, and a seamless connection to the water, this inviting retreat delivers an island lifestyle you’ll appreciate the moment you step inside. ANNUAL RATE $4,000 / month. SEASONAL RATE $6,500 / month.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: John Schafer, V (954-298-6229)
2109 GULF OF MEXICO DR #1203, LONGBOAT KEY, FL 34228
$10,000932 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: ***NEW VACATION RENTAL LISTING** * Booked Dec 1st 2026-March 31st 2027. Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill. You are welcome to beach chairs along the private beach. Under-building assigned parking directly across from security coded entry lobby with elevator and mailboxes. Plenty of guest parking inside the welcome security gates. Full time maintenance crew keeps the grounds immaculate. Wake up to beach and water views from Living room, both bedrooms and terrace. The apartment has an fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room furniture, decor and linens. Utility room with Maytag washer and dryer. Sunset Beach is currently replacing all lobby and hallway flooring. Just minutes to St Armand’s Circle or Lido Beach for shopping, fine dining or laying at the public beach with all your favorite people. Longboat is known for their waterfront golf, fine dining and luxury resorts. In fact, its 12 miles of white sand beaches have helped to make this a luxury Gulf Coast resort community. There are numerous Activities and Attractions in the Sarasota/Bradenton/Siesta area. -Just a few of the many treasures and cultural events are Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, fishing charters out of Marina Jack's, Florida's Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, and the Van Wezel.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
3806 GULF OF MEXICO DR #C108, LONGBOAT KEY, FL 34228
$5,500280 Days on yellowkey MLS ID: A4660366
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1401 Built: 1970Community: Beach Harbor ClubSpa: NoCondo
Remarks: Available for season 2027! Experience resort-style living in this spacious 2-bedroom, 2-bath condo located in Beach Harbor Club on Longboat Key. Nestled along Sarasota Bay, this community offers refreshing bay breezes and an array of waterfront amenities, including kayak storage and lift, a boating and fishing pier, and private beach access to the pristine sands of the Gulf of Mexico. Relax by the heated pool, gather at picnic areas and cabanas with grills, or explore the water with provided kayaks. Residents also enjoy a newly renovated clubhouse with library and card & game room and state-of-the-art fitness center. In addition to that, get crafty at the wood workshop (all tools included). This ground floor condo has room to sleep six with three queen size beds. The kitchen is fully equipped with everything you need to prepare meals. There is ample seating for dining and gathering space. In addition to our renowned beaches, Sarasota and Manatee county boasts a vibrant cultural scene, with live theater, concerts, ballet, opera, galleries, museums, and even a rich history with the circus arts! Escape the winter and come enjoy Florida living on Longboat Key.
Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)
Listing Agent: Maureen Plichta (941-812-5799)
3235 GULF OF MEXICO DR #A302, LONGBOAT KEY, FL 34228
$5,5003016 Days on yellowkey MLS ID: A4208788
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1975 Tax: $6,545 (2021)Community: PortobelloSpa: NoCondo
Taxes:$6,545
Tax Year: 2021
Remarks: Stunning Portobello Vacation 2/2 Condo on Longboat Key. Season rate is $8000 (Jan-Apr) and off season rate is $5500 (May-Dec). Minimum 2 month rental and full months only. This beautiful condo provides easy and relaxed living with gorgeous direct gulf views. Full length screened lanai to enjoy the view. This totally renovated condo features luxurious and relaxed beach style décor, new windows and sliding glass doors, new laminate flooring and carpet, new kitchen appliances, three flat screen TVs with HD boxes and HD Extreme channel lineup, king size Master bed and guest bedroom provides two double beds, in unit washer and dryer for convenience. One assigned parking space and guest parking available for second car. Wi-Fi and cable package are provided. Heated swimming pool, tennis court and boat dock located conveniently across the street on the bayside of the complex. Only 1/2 mile to Publix shopping and dining center and approximately 5 miles from fabulous St. Armand's Circle. Sorry no pets permitted (no exceptions). No smoking permitted. 13% sales and tourism taxes apply for any rental less than 6 months. Property is available Apr 2025-Dec 2026 and Apr 2027 and after.
Listing is courtesy of: LINDSAY LEASING LLC (941-404-8878)
Listing Agent: Terri Lindsay (941-404-8878)
741 BAYPORT WAY #741, LONGBOAT KEY, FL 34228
$6,000873 Days on yellowkey MLS ID: T3492089
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1426 Built: 1983Community: Bayport Bch & Ten Ph DCondo
Remarks: ABSOLUTELY GORGEOUS INSIDE! Bayport Beach & Tennis Club is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully FURNISHED rental is tastefully and brilliantly decorated. This residence offers a wonderful retreat as a Seasonal rental or a shorter Monthly respite. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to private beach on the Gulf of Mexico for morning beachcombing, surf casting or memorable sunsets. NOW AVAILABLE: July through December 2026 - OFF SEASON RATES NOW APPLY. Please contact Agent for availability.
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Antonietta Car (813-684-9500)
1000 LONGBOAT CLUB RD #406, LONGBOAT KEY, FL 34228
$4,00011 Days on yellowkey MLS ID: A4691368
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 1080 Built: 1972Community: Privateer SouthSpa: YesCondo
Remarks: Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for easy seasonal living, along with a private balcony overlooking the Gulf—perfect for enjoying morning coffee or taking in breathtaking sunset views. Whether you're starting your day or winding down after time on the beach, you'll appreciate the peaceful atmosphere and coastal charm throughout. The Privateer provides true resort-style living with private beach access, a heated beachfront pool and spa, tennis courts, a fitness center, clubhouse, grilling areas, covered parking, 24-hour gated security, and the added convenience of on-site guest suites available for visiting friends and family, creating the perfect setting for a stress-free and enjoyable stay. Ideally located just minutes from St. Armands Circle, you’ll have convenient access to some of the area’s best restaurants, boutique shopping, and entertainment, along with nearby local cafes and waterfront dining options that make Longboat Key such a desirable seasonal destination. This property is available beginning in December, with a high season rate of $4,000 per month and an off-season rate of $2,200 per month. The community is governed by a homeowners association, and all tenants must comply with HOA rules and regulations, including any application and approval requirements prior to occupancy.
Listing is courtesy of: RENT SARASOTA (941-328-8999)
Listing Agent: Cody Smith (404-991-0209)
1930 HARBOURSIDE DR #134, LONGBOAT KEY, FL 34228
$7,000437 Days on yellowkey MLS ID: A4641782
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982Community: Fairway BaySpa: YesCondo
Remarks: GORGEOUS BAY VIEWS plus Private Beach Club Access! You will love the views from this Bay Front, 2 bed, 2 bath third floor condo in the highly sought-after Bay Isles community. The spacious Kitchen had been updated along with the both baths, with Quartz counter-tops and new cabinetry, the Primary suite offers a King bed, views of the bay and the Primary bath has dual sinks, new vanity, new lighting, new shower and an updated large closet. The Guest bedroom has two twin beds that can be made into a King bed, and the guest bath has a new vanity, new mirror and lighting. Enjoy your morning coffee or a sunset cocktail on the Lanai overlooking the Bay and intercoastal waterway. This location has its own pool, and a larger community pool and spa with the clubhouse just a few steps away, you can take advantage of the newer fitness room and reserve a court for tennis or pickle ball. Pack up the car and spend the day at the BAY ISLES PRIVATE BEACH CLUB, located at 2111 Gulf of Mexico Drive. (Booked January through the end of April, 2027)
842 BAYPORT WAY #842, LONGBOAT KEY, FL 34228
$4,80021 Days on yellowkey MLS ID: A4689796
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983Community: Bayport Bch & Ten Ph FCondo
Remarks: Available June through December or as an 18-month rental. Nicely furnished and fully equipped for a comfortable stay, this first floor corner residence offers extra privacy and added natural light. A spacious dining and living area opens out to a screened lanai and large outdoor brick 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. A large kitchen is fully equipped for easy meal prep. There is under building parking for one car, outside locked storage and plenty of guest parking. Bayport Beach and Tennis Club is a true Gulf to Bay community, with a fishing pier and kayak launch out to Sarasota Bay, and access to 1200 feet of private beach with beach chairs and umbrellas, just 2-3 minutes from your front door. Enjoy a swim in the heated Jr olympic pool, tennis on 4 har-tru courts, a club house, fitness room, and shelled walking paths along tropical landscaped grounds. Groceries, parks and conveniences are within 2 miles, with shopping and terrific dining dotted along the Key. Sarasota's entertainment and cultural attractions are a short drive away. Condo may be rented long term.
Listing Agent: Rosemarie Mckee (941-504-9396)
618 BAYPORT WAY BAYPORT WAY #618, LONGBOAT KEY, FL 34228
$6,250211 Days on yellowkey MLS ID: A4667152
INCREASED by $200 (3.3%) on 04/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1980Community: BayportSpa: NoCondo
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Escape to paradise with a stay in this newly renovated 2-bedroom, 2-bath second floor condominium at Bayport Beach & Tennis Club on Longboat Key. Perfectly positioned for your dream beach getaway, this condo blends comfort, style and unbeatable amenities. Bright, modern, and welcoming, this condo has been thoughtfully updated with all the comforts of home, including a king-size bed in the primary bedroom. Enjoy access to Bayport's Junior Olympic-sized pool, clay court tennis, bocce ball court, and a private dock on Sarasota Bay with stunning sunrise views. Located mid-island, you have private access to our white sand beach with stunning Gulf Coast views. Chairs and umbrellas are provided--ideal for morning walks, sunbathing, or watching the sunset. The property offers a semi-private entrance, providing a more secluded and peaceful experience for your vacation. Whether you're looking to relax by the pool, play tennis, or simply enjoy the beach, Bayport Beach & Tennis Club is the perfect blend of relaxation and recreation--a true hidden gem. 30 Day minimum stay required. Call for availability. Rates vary by season: $4,750 to $9,250/month. CONTACT AGENT FOR A QUOTE BASED ON YOUR DATES.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Alzira Meierling (941-299-9229)
750 BAYPORT WAY #750, LONGBOAT KEY, FL 34228
$5,0001400 Days on yellowkey MLS ID: A4540609
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1983Community: Bayport Bch & Ten Ph DCondo
Remarks: AVAILABLE NOW DUE TO A CANCELLATION, OPEN FEBRUARY, MARCH, APRIL AND BEYOND!!!Seasonal 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 7 months subject to additional taxes and fees. Booked for March and April 2026.
3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228
$4,30019 Days on yellowkey MLS ID: R4911069
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Community: Beach Harbor ClubSpa: NoCondo
Remarks: Lease/Option - Owner looking to lease 6 Months $4300 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 security entrance. Newly appointed 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)
3806 GULF OF MEXICO DR #C212, LONGBOAT KEY, FL 34228
$2,500223 Days on yellowkey MLS ID: A4666147
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1062 Built: 1970Community: Beach Harbor ClubCondo
Remarks: LONGBOAT KEY...Lovely 2 bedroom 2 bath condo directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile. Split floor plan, master suite with a king size bed and the guest room has bunk beds with one single bed and one full size bed. Spacious, open, light and bright. Very well maintained GULF TO BAY complex with lush landscaping, large heated pool, clubhouse, marina, fishing pier, kayak and bike storage, fitness center, all for your enjoyment and covered parking. OWNER PREFERS AN ANNUAL RENTAL AT $2500 A MONTH. A SEASONAL WILL ALSO BE CONSIDERED AT $5000 A MONTH + TAX & FEES. PLEASE NOTE, UTILITIES ARE NOT INCLUDED IN AN ANNUAL RENTAL. SARASOTA, VACATION RENTALS, LUXURY, GULF OF MEXICO, LONGBOAT KEY VACATION, LONGBOAT KEY ANNUAL RENTAL.
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Teresa Ribaudo (941-376-4500)
914 SPANISH DR S #76, LONGBOAT KEY, FL 34228
$6,75032 Days on yellowkey MLS ID: A4687894
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1341 Built: 1968Community: Spanish Main Yacht Club CondoCondo
Remarks: Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the sought-after community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bath residence features all brand-new furnishings and is ideally situated just steps from the marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning bayfront sunrises, with Gulf-side sunsets just a short stroll away. Thoughtfully designed and tastefully furnished, the home offers high-end mattresses dressed in organic cotton linens and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. Residents enjoy access to a private marina with available boat docks and kayak storage, deeded beach access, a heated community pool, shuffleboard courts, and wonderful neighbors. Ideally located just minutes from the upscale dining and boutiques of St. Armands Circle and a short drive to Anna Maria Island, this property offers the perfect blend of tranquility and accessibility. Whether you're boating, fishing, or simply relaxing in the bright Florida room, this is a rare opportunity to experience the Longboat Key lifestyle at its finest. Seasonal rental rates are $6,750/ month in-season and $4,450/ month off-season. One tenant must be age 55 or older in accordance with community requirements. Apply now!
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
2109 GULF OF MEXICO DR #1402, LONGBOAT KEY, FL 34228
$8,0003177 Days on yellowkey MLS ID: A4194846
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1273 Built: 1984 Tax: $5,819 (2021)Community: Sunset BeachCondo
Taxes:$5,819
Remarks: LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with ease. Enjoy shopping on St. Armands Circle, downtown Sarasota or on the key. South end of Longboat Key makes for easy access anywhere you want to go. Plenty of restaurants to choose from, from the key to downtown Sarasota. This property is available for January & February 2027. VACATION, LUXURY, GULF OF MEXICO, SARASOTA FL. RENTALS.
Listing is courtesy of: Jennette Properties Inc (941-953-6000)
1000 LONGBOAT CLUB RD #1001, LONGBOAT KEY, FL 34228
$10,000221 Days on yellowkey MLS ID: A4666443
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972Community: Privateer SouthCondo
Remarks: Available for 2027 Season. Welcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coastal living with panoramic, unobstructed views of the Gulf of Mexico. From the moment you step inside, you are greeted by a light-filled interior that opens seamlessly to two private balconies, each offering a front-row seat to breathtaking sunsets, gentle sea breezes, and the soothing sound of waves meeting the shore. Offered fully furnished, this home is designed for both style and comfort, making it the perfect seasonal escape or extended retreat. The residence features a spacious and thoughtfully designed floor plan that emphasizes relaxation and entertaining. The living and dining spaces flow effortlessly toward the water, creating a serene atmosphere for hosting guests or enjoying quiet evenings by the Gulf. The well-equipped kitchen, comfortable bedrooms, and elegant furnishings reflect a refined coastal aesthetic, allowing you to settle in with ease from the very first day. Life at The Privateer is defined by its unparalleled amenities and direct beachfront setting. Residents enjoy a heated beachfront pool and jacuzzi overlooking the Gulf, a fully equipped fitness center, tennis courts, and beautifully maintained grounds. Outdoor grilling areas, shaded dining spaces, and gathering lounges provide endless opportunities for entertaining or enjoying the company of neighbors. For days spent on the sand, beach chairs and umbrellas are thoughtfully provided, ensuring every day feels like a private resort experience. Located on the southern end of Longboat Key, The Privateer combines the peace and privacy of a gated beachfront community with convenient access to world-class dining, shopping, and cultural attractions in nearby St. Armands Circle and downtown Sarasota. Available seasonally beginning October 15, 2025, with owners open to discussing longer lease terms, this residence is the perfect opportunity to experience the best of Longboat Key living—where luxury, comfort, and the beauty of the Gulf of Mexico meet. 3D walkthrough available!!
Listing Agent: Jenna Genovese (860-575-0088)
1050 LONGBOAT CLUB RD #506, LONGBOAT KEY, FL 34228
$5,00042 Days on yellowkey MLS ID: A4687317
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)
4325 GULF OF MEXICO DR #208, LONGBOAT KEY, FL 34228
$5,500988 Days on yellowkey MLS ID: A4580185
Remarks: Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk in closet and dual sinks and a spacious shower. The second bedroom has a Queen bed, and there is a lovely guest bath. This wonderful end-unit condo has all you need for your perfect vacation! This boutique community offers a sparkling heated pool and private beach, grill area, club room and sauna. All rates are plus taxes and fees. Rates vary by month, call for availability. Booked February through end of April 2026, and July 2026. Also 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.