Location: Longboat Key
Do Not Show Listings
817 BAYPORT WAY #817, LONGBOAT KEY, FL 34228
$6,000765 Days on yellowkey MLS ID: T3520822
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1601 Built: 1981Community: Bayport Bch & Ten Ph ECondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Southside Elementary
High School: Booker High
Tax Year:
Middle School: Booker Middle
Remarks: STUNNING BAY VIEWS! Enjoy picturesque sunrises from your private deck in this tastefully decorated 2 bedroom, 2 bathroom furnished condominium. This home has an open concept floor plan which features an expansive Living/Dining/Kitchen area. The generous size master bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a small alcove that accommodates a desk. Bayport Beach & Tennis Club is an amenity-rich community at sea's edge with 27 acres of lush mature tropical landscaping. This gulf to bay community offers 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 the private beach on the Gulf of Mexico for a morning of beachcombing, surf casting or memorable sunsets. Just minutes to St. Armand's Circle which is well known for its world class shopping and dining. Cross over the Ringling Bridge to Downtown Sarasota where you will find additional dining, theater, opera, ballet, symphony, art galleries, the Van Wezel Performing Arts Hall, Selby Gardens and of course the Ringling Museum. Please call for availability. OFF SEASON RENTAL ONLY - AVAILABLE : MAY - DECEMBER 2026. Please call 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
$4,00033 Days on yellowkey MLS ID: A4691368
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 1080 Built: 1972Community: Privateer SouthSpa: YesCondo
Elementary School: None
High School: None
Middle School: None
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)
1211 GULF OF MEXICO DR #1005, LONGBOAT KEY, FL 34228
$15,000323 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! Be the first to lease 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. Booked from November 1, 2026 to May 1, 2027.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)
Listing Agent: Stephanie Deshaies (941-780-3229)
1211 GULF OF MEXICO DR #405, LONGBOAT KEY, FL 34228
$14,000799 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!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)
1930 HARBOURSIDE DR #134, LONGBOAT KEY, FL 34228
$7,000459 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)
5621 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
$5,500890 Days on yellowkey MLS ID: A4593076
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1731 Built: 1985Community: Salty AcresCondo
Remarks: Call for rates and availability .Looking for a vacation in warm sunny Florida in a condo where you walk directly out onto the deck directly onto the beach? Stay in this 3 bedroom (2 king beds/1 queen), 2 bath condo in Salty Acres with 2 covered parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and recently remodeled. It must be a monthly rental. $5,500 a month April - October. $5,750 November, $5,500December, $7,000 January, $8,000 February, $9,000 March $12,000
Listing is courtesy of: WILLIAM GLADE LIC. REAL ESTATE BROKER (941-356-1054)
Listing Agent: William Glade (941-356-1054)
747 SAINT JUDES DR S #2, LONGBOAT KEY, FL 34228
$3,20099 Days on yellowkey MLS ID: A4682877
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 667 Built: 1967Community: Saint Judes AptsCondo
Remarks: GORGEOUS BAY VIEWS. Located in a quiet association of only eight units. Annual Unfurnished unit; open kitchen/living and dining area with master bedroom and tub/shower combo in en-suite bath. Canal views with private dock and boat lift (a boater and fisherman's dream). Drop a line outside your back door! Screened lanai with washer/dryer. Exterior parking immediately outside the unit with gas BBQ grill. From your kitchen window and exterior lanai enjoy panoramic views of Sarasota Bay with the distant Sarasota skyline and the untouched mangrove preserves of nearby Durante Park. Private deeded beach access with white sand beaches and turquoise waters of the Gulf of Mexico! Enjoy the best Longboat Key has to offer from this quiet residential retreat with fishing, boating, bicycling, hiking, canoeing/kayaking or just relaxing. Make this your next vacation destination. NO PETS. 1st, last and security due at move-in. Note that rates are subject to change without notice and reservations are not guaranteed until initial reservation deposit is received.
Listing is courtesy of: WAGNER REALTY (941-383-5577)
Listing Agent: Gregory Koss (941-383-5577)
1925 GULF OF MEXICO DR #309, LONGBOAT KEY, FL 34228
$10,0001153 Days on yellowkey MLS ID: A4565848
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2698 Built: 1978Community: Seaplace ViSpa: YesCondo
Remarks: LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Primary Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and just minutes to ST Armand's Circle and Downtown Sarasota. The SEAPLACE community features include half mile of beach front, two large swimming pools,two spas, three Har-Tru Tennis courts, clubhouse, fitness center, barbecue grills, and a one mile walking trail.
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Jane Hunter (941-896-0622)
1925 GULF OF MEXICO DR #G8-208, LONGBOAT KEY, FL 34228
$8,0004193 Days on yellowkey MLS ID: A4109016
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1604 Built: 1978 Tax: $9,651 (2021)Community: Seaplace ViSpa: YesCondo
Taxes:$9,651
Tax Year: 2021
Remarks: Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Primary Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis courts and a great expansive white sand beach on the Gulf of Mexico.
5757 GULF OF MEXICO DR #202, LONGBOAT KEY, FL 34228
$5,50041 Days on yellowkey MLS ID: A4690373
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1561 Built: 1973Community: The ShoreCondo
Remarks: Pristine Gulf Beachfront on Longboat Key Welcome to this beautifully updated 2-bedroom, 2-bathroom luxury beachside retreat located in The Shore on mid-Longboat Key. This inviting second-floor condo offers stunning Gulf views and is just steps from the powdery white sand and crystal-clear waters—an ideal setting for a relaxed island getaway. Highlights -Sweeping Gulf views from living room and master bedroom -Thoughtfully remodeled with an airy, open-concept layout and generous living spaces -Modern kitchen featuring granite countertops and a spacious island, perfect for dining and entertaining -Fully furnished and well-appointed for a turnkey, stress-free stay -Breathtaking Gulf views from the main living area, showcasing unforgettable sunrises and sunsets Configuration - Primary Bedroom: King bed - Walk-in closet - En-suite bathroom with double sinks and walk-in shower - Direct access to the patio for refreshing Gulf breezes - Second Bedroom - Two Queen-size beds Additional Conveniences & Amenities - In-unit washer and dryer - Watch dolphins, manatees, turtles, birds, and passing boats right from your retreat - Beachside heated pool and hot tub - Fitness center and sauna - Large social room with catering kitchen - 1 Covered parking spot, plus guest parking - Bicycle and kayak storage - Beautifully maintained grounds with lush tropical landscaping and mature trees - Weber grill on your private patio - perfect for cooking and dining while taking in breathtaking Gulf views Note: 60-Day Minimum Rental (January through April are not available) Please call or text listing agent for questions or showings 2nd Floor Unit - Elevator and/or stairs available Association Application Required No Pets
Listing is courtesy of: DARAK GROUP INCORPORATED (704-430-1670)
Listing Agent: Matt Darak (704-430-1670)
3806 GULF OF MEXICO DR #C212, LONGBOAT KEY, FL 34228
$2,500245 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 Agent: Teresa Ribaudo (941-376-4500)
1591 GULF OF MEXICO DR #410, LONGBOAT KEY, FL 34228
$40,000148 Days on yellowkey MLS ID: A4676510
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3130 Built: 2024Community: St. RegisSpa: YesCondo
High School: Sarasota High
Remarks: An exceptional opportunity to lease the largest two-bedroom residence at the prestigious St. Regis Longboat Key. This premier corner home offers sweeping panoramic views of the Gulf of Mexico, Sarasota Bay, lush resort grounds, and the tropical saltwater lagoon, all enjoyed from an expansive wraparound terrace. Bathed in natural light, the spacious living area is ideal for entertaining and relaxation, featuring a custom bar and beverage refrigerator. The chef’s kitchen is beautifully appointed with Poggenpohl cabinetry and top-of-the-line Wolf and Sub-Zero appliances, including double ovens, a gas cooktop, refrigerator, microwave, and dishwasher. An outdoor Wolf gas grill on the terrace allows for seamless indoor-outdoor dining. The owner’s suite serves as a private coastal retreat, highlighted by floor-to-ceiling glass with breathtaking Gulf views. A morning bar adds convenience, while a custom Closet Envy wardrobe provides generous storage. The spa-inspired bath features dual vanities, two private water closets, a walk-in shower, and a luxurious soaking tub with stone surround. The ensuite guest bedroom, complete with custom built-ins, opens directly to the terrace, offering effortless indoor-outdoor living for guests. Designer finishes throughout, curated by Marc Michaels Interior Design, deliver timeless elegance. Residents enjoy exclusive access to St. Regis Longboat Key’s world-class amenities, including a private clubhouse with fitness center, pool and spa, and the signature St. Regis Butler and Concierge services. Additional resort offerings include an oceanfront spa, beachfront cabanas, multiple dining venues, a lazy river, and a saltwater lagoon featuring tropical fish, stingrays, and resident tortoises. Set on 17 acres of pristine beachfront and just 3.5 miles from the renowned shopping and dining of St. Armands Circle, this residence offers a rare opportunity to experience the iconic St. Regis lifestyle—where luxury, comfort, and legendary service define every stay. Rental rates vary according to month, please call agent for details.
Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)
Listing Agent: Jaime Barcelo (941-275-3233)
1945 GULF OF MEXICO DR #M2-414, LONGBOAT KEY, FL 34228
$3,750670 Days on yellowkey MLS ID: A4618406
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 928 Built: 1978Community: Seaplace VCondo
Remarks: AVAILABLE IMMEDIATELY PENDING HOA APPROVAL! 2 MONTH MINIMUM! BOOKED FOR JAN-MARCH 2027 SEASON! LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the condo has to give with the natural light that floods through the large sliding glass doors. From the beautifully updated kitchen, you can see the dining room, living room, screened patio and the Gulf of Mexico! The kitchen also offers stone countertops, stainless steel appliances and plenty of cabinet and counter space. The condo sleeps four (1 king bed & 2 twin beds) and has walk-in showers in both updated bathrooms. All top-of-the-line upgrades throughout the condo including impact doors and windows, Washer/Dryer and all utilities provided with two TVs in the unit. The back patio is fully screened in and features beautiful views of the ocean! The private beach access is just off the clubhouse which is steps away. Seaplace is one of the largest, most highly sought after complexes on Longboat Key. This resort style community offers 2 heated pools, hot tub, kiddie pool, beachfront patio, 4 grills, 3 har-tru tennis courts, game room, work out room, library, sauna, 24-hour security, and monthly events for anyone to enjoy. Longboat Key Club golf course is approx. 2 miles away. Also enjoy strolling around St. Armand's Circle which offers top-rated dining and shopping. ** Rent includes electricity, water, cable, internet, sewage, pest control, extra storage and all the amazing community amenities! *No pets allowed *Application Fee: $100 per applicant *HOA Application Fee: $100 per applicant *250 cleaning fee *$50 booking fee *Security Deposit: $750 for short term *13% seasonal rent tax applies to 6 month and under rentals.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Brigette Marcus (941-315-9500)
615 DREAM ISLAND PL #201, LONGBOAT KEY, FL 34228
$10,500225 Days on yellowkey MLS ID: A4668491
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1514 Built: 1985Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Remarks: BRING YOUR BOAT, deeded private boat slip that accommodates up to a 60 ft boat INCLUDED! Picturesque Waterview of Sarasota Bay and easy access by boat to the Gulf. Recently renovated with high end appliances, finishes and designer furniture. The Harbor Villa Club Complex consists of 38 condos in a 3-story plus pool, spa, community boat ramp, kayak launch/storage, 3 tennis/pickle ball courts, covered parking and 400' of boat slips and bayfront. This unit features 2 assigned covered parking spaces, over 1500 sq ft of living space in this end unit, high ceilings, water views in all rooms, open floor plan, large, enclosed balcony off living/dining room plus separate balconies off each bedroom, washer/dryer and extra-large bathrooms. High Speed Wi-Fi, SMART TV's with cable and utilities included. Seasonal rental for select times of the year ONLY. 10-day notice required along with application for owner approval. Weekly rentals available with owner approval January 7-April 15
1581 GULF OF MEXICO DR #507, LONGBOAT KEY, FL 34228
$30,000449 Days on yellowkey MLS ID: A4642934
REDUCED by $2,000 (6.3%) on 04/01/2026
Bed: 1 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 1684 Built: 2024Community: St Regis Longboat KeyCondo
Remarks: Enter the unit from a private elevator which features a spacious, open-plan living area with large windows allowing natural light and incredible views of the surrounding landscape and Sarasota Bay. The lavish living space opens up onto a stunning balcony that overlooks Sarasota Bay and the St. Regis grounds and includes a gas grill. The stylish living area includes high-end furniture with a modern, chic design, featuring plush seating, rich textures, and sophisticated décor. The gourmet kitchen is fully equipped with top-of-the-line stone countertops, custom cabinetry, and state-of-the-art appliances. The elegant bedroom includes a king-sized bed with luxurious linens, soft lighting, and unique, custom-made furniture. 2 modern bathrooms- one half bathroom for guests and a full bathroom off of the master bedroom that includes high-end finishes, a freestanding soaking tub, a spacious walk-in shower, double vanities, and a calming color palette. The unit also offers a sound system, parking in the private garage and full laundry room. The Resort has plenty of amenities for everyone to enjoy. Enjoy first class dining, an underwater sea lagoon or a lazy river float after drinks at the Monkey Bar. The Resort also offers a spa, coffee shops, butler service, event planning, fitness center, private cabanas and much, much more.
Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)
Listing Agent: Larry Starr (941-914-6869)
2109 GULF OF MEXICO DR #1402, LONGBOAT KEY, FL 34228
$8,0003199 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
$10,000243 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 is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Jenna Genovese (860-575-0088)
1591 GULF OF MEXICO DR #313, LONGBOAT KEY, FL 34228
$18,000436 Days on yellowkey MLS ID: A4644494
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 2143 Built: 2024Community: St. Regis Longboat KeyCondo
Remarks: 2027 Season Rental Rate will be $24,000. The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet kitchen showcases Wolf and Sub-Zero appliances, a six-burner gas cooktop, double ovens, and a panel-ready side-by-side refrigerator/freezer. The owner's suite includes a spacious walk-in closet with custom cabinetry, a frameless walk-in shower, and a private water closet. A semi-private elevator with keyless entry provides direct access from the private garage. Residents enjoy access to The St. Regis Resort's legendary Butler and Concierge services, a private clubhouse, resident-only pool and spa, a state-of-the-art fitness center, and beachside cabanas. Just steps away, the resort offers a private Gulf-front beach, multiple pools with cabanas, a family-friendly waterway, an exclusive saltwater lagoon with Aldabra tortoises, and a world-class oceanfront spa. Experience the pinnacle of coastal elegance at The Residences at The St. Regis Longboat Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Melissa Gissinger (941-404-2722)
1050 LONGBOAT CLUB RD #506, LONGBOAT KEY, FL 34228
$5,00064 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
$5,5001010 Days on yellowkey MLS ID: A4580185
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1411 Built: 1975Community: Tiffany PlazaCondo
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.
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