Longboat Key Condos For Rent - 72 condos

Remarks: Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room. Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom, two-bath condominium boasts a stylishly designed interior that is sure to impress. Experience tranquility in the master bedroom, which offers exquisite bedding and a sitting area with a stunning view of the azure waters. The ensuite master bath provides the perfect sanctuary for relaxation. The gourmet kitchen with stainless steel appliances is perfect for entertaining and the light and bright living room features exquisite seating and state-of-the-art digital components, including a 75-inch TV and DVR. Stay connected with dedicated desk space, a washer and dryer, and Wi-Fi. Large-screen smart TVs are also available for your added enjoyment. Take advantage of resort-style amenities including a gulf-side heated pool, har-tru tennis court, updated social room, state-of-the-art fitness area, and storage for kayaks, paddleboards, and bikes. Conveniently located to shopping, dining, St. Armand’s Circle, downtown Sarasota, and the Arts, this vacation rental has everything you need for a truly unforgettable stay. Don't miss out on this opportunity to live the life you've always imagined! Minimum 4 months stay!

Listing is courtesy of: ANMARK REALTY LLC (941-363-1043)

Listing Agent: Andrey Markov (941-363-1043)

Remarks: 2 bed, 2 bath paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy the community’s private beach access complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community kayaks, socialize with neighbors in the expansive clubhouse, and get your daily work out in the fitness center! This turnkey, corner unit offers gulf views from the living room and primary bedroom. On-site community laundry and covered parking is available for your convenience. Ideally located in the middle of the key, with easy access to Publix, the chic St Armands Circle, Downtown Sarasota, and the charming Anna Maria Island. Your dream residence awaits! Off season price: $2,500 per month, Seasonal price: $5,000 per month.

Listing is courtesy of: FLORIDA GALLERY REAL ESTATE (941-315-6678)

Listing Agent: Dakota Cole (516-749-6958)

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: Janette Schafer (954-298-7791)

Remarks: Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next Florida escape. As you step inside, you're greeted by a light, bright, and cozy atmosphere, with large windows that frame the sparkling blue waters of the Gulf. The kitchen is a chef’s delight, featuring granite countertops, stainless steel appliances, and a breakfast bar with barstool seating—ideal for enjoying a quick bite or gathering with family and loved ones. The main living space is designed for comfort and relaxation, with two plush sofas, a flat-screen TV, and an adjacent dining table that seats four comfortably—all with sweeping ocean views. Step through the sliding doors to one of the condo’s two private balconies, where you can sip your morning coffee or unwind with a glass of wine as the ocean breeze rolls in. The primary bedroom is a peaceful retreat, complete with a king-size bed, a sitting area with chairs, a TV, and its own balcony overlooking the pool and Gulf. The attached bathroom boasts an updated vanity and a gorgeous walk-in shower with modern finishes. The second bedroom features a queen-size bed, TV, ample closet space for personal belongings, and its own private balcony with more stunning ocean views. The second bathroom includes an updated vanity and a shower/tub combo, perfect for relaxing after a day in the sun. ?? Community Amenities at Privateer: Beachfront heated pool & spa Direct private beach access Tennis courts Fitness center & sauna Social room & library Grilling area & firepit Gated entry with secured building access Assigned covered parking Lush tropical landscaping throughout Located just minutes from St. Armands Circle, golf courses, fine dining, and cultural attractions in Sarasota, this condo offers the perfect blend of relaxation and adventure. Whether you're seeking tranquil beach days or exploring the vibrant coastal lifestyle of Longboat Key, this condo at Privateer is your perfect home away from home. There is a communal washer and dryer facility that is on the same floor as the unit.  It is agreed that once the application for your vacation has been approved by the board, a check in the amount of $500.00 will be sent to Privateer North Condo Assn. The check will be held if any damage to common properties. Is done during the check in/check out once your stay is complete (in and out) the deposit will be refunded.  House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets.t

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Andy Moore (941-877-5588)

Remarks: VACATION RENTAL!!! AVAILABLE JAN - MARCH 2026! 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.

Listing is courtesy of: GULF COAST RENTAL HOMES&CONDOS (941-212-1972)

Listing Agent: Diann Thelen (941-920-0758)

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

Listing Agent: C. Alison Hunter (941-587-5667)

Remarks: Rented February and March 2026. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. BEACHPLACE is one of Longboat Key's most popular vacation rental resorts on the Island. The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. Relax on the lanai and take in the beautiful gulf views at sunset. The Large primary bedroom has a King bed and bathroom with a walk-in shower with his/her sinks and a separate seating area. A privacy door has been added from the Master bedroom to the en-suite bathroom. The unit comes with a large utility closet for ample storage and a stackable washer and dryer in the kitchen. Guest Bedroom has 2 twin beds and an adjoining bathroom. Amenities include a 24 hour manned guard gate, private beach access, Wi-Fi, lighted tennis courts, pickleball, heated pool and hot tub, two state of the art fitness centers, and BBQ gas grills by the pool. This condo comes with 2 parking spaces - one inside the building close to the elevator and the other outside. Minutes to St. Armand's Circle for first class shopping and dining. Off-season guests pay the monthly electric bill. Sorry, no pets or smoking permitted.

Listing is courtesy of: JENNETTE PROPERTIES, INC. (941-359-3435)

Listing Agent: Margaret Young (941-359-3435)

Remarks: Seasonal. Not available Jan - April 2025. Amazing sunsets from this fabulous 5th floor, direct Gulf beach front, 2 BD, 2 BA condo. Meticulously maintained, this condo has everything you need for a care-free beach vacation! Master suite features king size bed, private bath with Gulf view. Guest room offers twin sleeping arrangements with private entrance to bath. For your comfort, there's flat screen TV's, wireless internet and in-unit washer and dryer. Amenities abound at Beachplace including a junior-sized Olympic pool, kiddie pool, spa, tennis courts, grilling areas, clubhouse, and fitness center. Walkers or joggers will love the lush landscaping and extensive (1450 lineal feet) private beach. St. Armand's Circle's shops and restaurants is less than a 5 minute drive and downtown Sarasota with its arts and culture is less than a 15 minute drive. If you simply want to relax, beach umbrellas and chairs are laid out daily for your relaxation. Simply enjoy! No pets or smoking allowed.Booked Jan- Apr, 2026. Available June, August, September, October and December, 2026.

Listing is courtesy of: Gulf Coast Rental Homes&Condos (941-212-1972)

Listing Agent: Diann Thelen (941-920-0758)

Remarks: Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Welcome to Seaside Dream! Beautifully furnished and decorated, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. If you enjoy resort-style living, then the Beach Harbor Club is for you! Situated on Sarasota Bay, you will enjoy refreshing breezes which will entice you to utilize the available kayaks and kayak lift, boating, and fishing pier, and head out to enjoy the beach with private access to the sandy beaches of the Gulf of Mexico. In addition to the oversized heated pool, Beach Harbor Club has a new fitness center and a library/media room. Elevator accessible and assigned parking complement the amenity package. This second-floor unit is centrally located and minutes away from urban activities. The master bedroom features a queen bed, a TV, a walk-in closet, and an unsuited bathroom. The second bedroom features twin beds, a TV, and plenty of space for your personal belongings. The fully equipped kitchen is the perfect place to prepare all your favorite meals and treats. The spacious living and dining areas are ideal for relaxing and enjoying the beach breeze. When you are ready to explore, head out to the nearby white sandy beaches of Lido Key or Siesta Key -the choice is yours. The world-famous St. Armand’s Circle is located just a couple miles away and offers endless boutique shopping and dining experiences, or you can enjoy an array of artistic events in Downtown Sarasota, such as the Sarasota Opera, the Sarasota Orchestra, ballet, theatre, the infamous Ringling Art Museum, Maria Selby Botanical Gardens, and Marina Jacks for boat tours. If you love outdoor adventures, come get lost amid the labyrinth of mangrove tunnels and explore their unique ecosystem aboard a rented kayak or stand-up paddleboard in South Lido Beach Park, or hike the Northern Nature Trail. This area seamlessly combines the energy and vibe of Downtown Sarasota cosmopolitan life with a seaside paradise that you do not want to miss. One visit to this St. Armand’s retreat and you will not want to leave. Come, enjoy Florida living at its best! House Rule: No smoking. No burning candles inside of lodging. No parties. No pets, no exceptions, per HOA. **30 day processing for application with the HOA. **Taxes and fees not included.

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Andy Moore (941-877-5588)

Remarks: Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You are just across the street from the gorgeous Gulf Beaches, with private beach access. Upon entering this condo, you will see an ocean view from the third floor. As you enter, you will find the large kitchen, which has stainless steel appliances, six barstools, a giant kitchen island, a lounge area with a sofa, and plenty of space to prepare your family’s favorite treats. You will find lovely natural lighting throughout, due to this condo having windows on all four sides. Adjacent is the dining table, with gorgeous West Elm chairs that accommodate up to six. The spacious living room has a sizeable “L” shaped couch, an entertainment center, and beautiful natural lighting through the windows. There are views from the master bedroom and the reading nook in the kitchen area, where you will love to enjoy your morning coffee with the sunshine streaming in those windows. The primary bedroom has a king-size bed, a chair, a TV, and plenty of closet space for your personal belongings. Attached is the primary bathroom, which has a large vanity with a stunning walk-in shower that has exquisite masonry work, and a detachable showerhead. The second bedroom has a queen-size bed and plenty of closet space. The second bathroom has a large vanity with a shower/tub combo. There is community Kayaks with a lift for use by renters, there are two rooftop patios in the building which are shared. The one at the front is perfect for watching the sunset every evening. This condo is a short drive to St. Armands Circle and Downtown Sarasota where there are restaurants, boutiques, shopping, theater, opera, ballet, botanical gardens etc. we are close to many great restaurants. Come see why people come to Longboat Key year after year. There is a dedicated covered parking spot and additional guest parking. House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets. **Taxes and fees not included.

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Andy Moore (941-877-5588)

Remarks: Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. The brand new living room furniture features a sleeper sofa, perfect for the occasional guests. The condo comfortably sleeps 6. This beachfront community features a large, heated swimming pool, fitness rooms, bicycle racks, and a clubhouse with a catering kitchen perfect for get-togethers. Conveniently located across from the Centre Shops and just a short drive north to the famous Beer Can Island or drive south to St. Armand’s Circle and downtown Sarasota. The possibilities are endless! Perfect for an extended stay.

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Jaime Barcelo (941-275-3233)

Remarks: This magnificent Gulf front vacation retreat sits on the 6th floor of the beautiful Westchester of Longboat Key, boasting expansive full Gulf views. This is a stunning property situated on a 7-acre stretch of white, powdery beaches and meticulously manicured landscape. The amenities can’t be beat and include 2 heated pools, tennis court, Clubhouse, shuffleboard, private Tiki-huts, & covered parking. As you step into this beautiful 2 bedroom 2 bath turnkey furnished condo, you will find tiled floors throughout and a split floor plan. The large family room has beautiful views of the Gulf, from the sliding glass doors that open to your screened-in balcony. Cable & Wi-Fi Included. There is a gorgeous chandelier over the quaint dining table with 4 chairs, where everyone can gather for a wonderful meal. The kitchen boasts gorgeous granite counters and white cabinetry a ceiling fan, & recessed lighting. The Master has a King-sized bed, TV, & opens to the balcony.  The en-suite Master Bath offers double sinks, a shower stall and large walk-in closet.  The adorable guest bedroom boast 2 twin beds to share, a ceiling fan, and a guest bathroom with tub/shower. Ideally located near everything the area has to offer, including world-class dining & shopping of historical St. Armand’s. There are plenty of outdoor activities as well to keep you busy, such as kayak rentals, bicycle rentals, and take a quiet stroll through Bayfront Park. Your quaint & cozy retreat awaits you! Sorry, no furry friends thank you.

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Jaime Barcelo (941-275-3233)