Longboat Key Apartments for Rent - 102 rentals

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)

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)

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)

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)

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)

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)

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)

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)

Listing Agent: Stephanie Deshaies (941-780-3229)

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)

Remarks: A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian architecture and designed to dissolve the boundaries between indoors and out, this estate home unfolds through airy pavilions connected by elevated walkways. Towering palms and lush tropical landscaping envelop the home, while its 18-foot elevation ensures both peace of mind and panoramic, horizon-level vistas. Inside, the freshly reimagined kitchen serves as the gathering heart of the home, with sleek quartz countertops, modern cabinetry, and a spacious oversized island that effortlessly bridges culinary function and relaxed entertaining. Expansive sliding glass doors draw natural light into the living space and frame sweeping views of the sandbar and bay, perfect for sunset watching. The main residence includes four bedrooms and four-and-a-half baths, plus a separate guest suite offering an additional bedroom, kitchen, and full bath, ideal for hosting with comfort and privacy. The primary suite is where the pace of the island truly settles in. Wake up to wide-open bay views, linger with coffee in the sitting area, or enjoy a glass of wine as the sun sinks toward the horizon. The ensuite feels fresh and spa-like, with a soaking tub, walk-in shower, and water views. A series of screened porches and wraparound decks encourage slow living, morning yoga on the deck, afternoon reading in the shade, sunset grilling and cocktails overlooking the Gulf. Outdoors, a newly installed pool and spa with a sun shelf and expansive sundeck overlook the storied Jewfish Key Sandbar. A private dock with jet ski lift offers instant access to calm waters perfect for fishing, snorkeling, paddle boarding, or exploring neighboring Longboat Key and Anna Maria Island, both just minutes away by boat and beloved for dining, boutique shopping, and laid-back coastal culture. Equal parts island hideaway and refined coastal home, this one-of-a-kind property offers the rare combination of true privacy, effortless access, and natural beauty, set against a backdrop of turquoise water, powder soft sand, and endless sky. Here, relaxation, adventure, and natural beauty converge in a setting that feels almost like an escape, yet unmistakably home.

Listing is courtesy of: SIGHT REAL ESTATE, LLC (877-361-0878)

Listing Agent: Chase Moore (727-325-7272)

Remarks: Seldom available annual rental on the coveted north end of Longboat Key. This beautifully remodeled 2-bedroom, 2-bath condo boasts new appliances, cabinets, flooring, and modern fixtures throughout. Both bedrooms feature spacious walk-in closets, and a separate utility room includes washer and dryer hookups. Embrace the laid-back coastal lifestyle with quick access to beaches, restaurants, shopping, and area attractions—only 0.1 miles to public beach access on the breathtaking Gulf.

Listing is courtesy of: WAGNER REALTY (941-383-5577)

Listing Agent: Gregory Koss (941-383-5577)

Remarks: Remodeled Single-Family Home in Historic Longbeach Village Available for annual lease on the north end of Longboat Key, this beautifully updated 4-bedroom, 2-bath single-family home is located in the charming and historic Longbeach Village. The home features brand-new appliances, cabinetry, fixtures, and flooring throughout. Lawn maintenance is included in the monthly rent, and the utility room offers convenient washer and dryer hookups. Enjoy close proximity to pristine beaches, dining, shopping, and the premier lifestyle amenities of the Gulf Coast.

Listing is courtesy of: WAGNER REALTY (941-383-5577)

Listing Agent: Gregory Koss (941-383-5577)

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)

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)

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.

Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)

Listing Agent: Jane Hunter (941-896-0622)

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)

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)

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)

Remarks: Come and enjoy a little piece of Paradise! This beautiful canal front home is located in the idyllic and picturesque Longboat Key. A charming mid-century style cottage nestled in one of Longboat Key's most private and serene settings. This spacious 2 bedroom + Bonus room, 2.5 bathrooms with outdoor shower residence offers 1,755 square feet of luxurious living space perfect for those seeking a tranquil beach lifestyle. Recently impacted by Hurricane Helene, the home has undergone professional remediation and renovation including kitchen, bathrooms and pool. The living area boasts an open floor plan with a cozy corner wood-burning fireplace that adds a warm touch, creating the perfect setting for snug evenings during the cooler winter months. The kitchen has been completely remodeled and equipped with all new cabinets, quartz countertops and appliances, offering plenty of space for culinary adventures. The master suite includes a cedar walk-in closet, an extra linen closet, and direct access to the pool area. In addition to the 2 bedrooms, there is a bonus room that could be made into a bunk room perfect for the little ones or teenagers to make their own retreat. Lyons Lane is renowned for its tranquility and privacy, with lush mangroves lining the opposite side of the street, creating a natural, peaceful ambiance. This unique setting offers the best of both worlds: a serene retreat just moments away from the pristine beaches, boutique shopping, and fine dining that Longboat Key is famous for.

Listing is courtesy of: ROOST REALTY INC. (813-326-2569)

Listing Agent: Steve Barthelemy (813-943-2841)

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)

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

Listing is courtesy of: WILLIAM GLADE LIC. REAL ESTATE BROKER (941-356-1054)

Listing Agent: William Glade (941-356-1054)