Longboat Key Condos For Rent - 53 condos

Remarks: Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of the gulf. Gorgeous custom kitchen. Granite counters, beautiful muted gray plank flooring. Turnkey furnished with newer linens and a brand new hurricane door off kitchen and dining to master bedroom balcony. Just bring your toothbrush and clothes. Desired location and direct front penthouse sitting right on the Gulf of Mexico w Private beach and chairs and umbrellas for quit time on your beach. The two balconies bring the water to you so you can enjoy a breathtaking sunsets and the unobstructed views everyday. The enormous heated pool and spa, and tennis courts, clubhouse and fitness center. Onsite management from 9 to 4 Monday through Friday. Go over Longboat Key Bridge and take a turn at first stoplight into LONGBOAT KEY RESORT GOLF AND TENNIS CLUB, TELL GATE GAURD AND SAY SHOWING PRIVATEER NORTH AND GO DIRECT TO BUILDING. This complex PRIVATEER NORTH is located furthest South to St. Armand's S0 YOU ARE NOT IN A LOT OF TRAFFIC and minutes to St. Armand's and the mainland.

Listing is courtesy of: CHROME REALTY LLC (941-363-6300)

Listing Agent: Marni Hayden (941-809-5044)

Remarks: Available 07/15/2025 through 12/30/2025. LEASED SEASON JAN, 2026 THROUGH MARCH, 2026. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have private lanais, walk in closets. Double queen beds in one of the ensuites. open floor plan features large eat in area with granite counters neutral tile floors, and extra storage outside unit. Laundry is located right outside of your unit. Covered Carport and guest parking available. Building amenities WIFI, renovated social room and fitness center. Resort style living with heated Olympic size pool, tennis courts, biking trails, and outside showers. Enjoy the Publix Grocery just minutes away along with many restaurants for fine dining. This building is located the furthest South end of Longboat Key so you miss a lot of traffic. Just minutes to St. Armand's Circle for shopping, restaurants and entertaining. Enjoy Lido Beach also just minutes away.

Listing is courtesy of: CHROME REALTY LLC (941-363-6300)

Listing Agent: Marni Hayden (941-809-5044)

Remarks: AVAILABLE OFF SEASON RENTAL JULY 1, 2025 THROUGH NOVEMBER 30, 2025 AT $5000 A MONTH AND SEASONAL JANUARY 2026 THROUGH APRIL 30, 2026 through MAY 30, 2026 Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th floor residence. Views from all windows and from the outdoor patio a great view of of the Gulf. Split bedroom plan for privacy. Master bedroom with a king size bed, walk in closet and the all tile bathroom has a convenient walk in shower. 2nd bedroom has a queen comfortable pull out sofa and built in desk area and bathroom tub and shower combination. Large open living area completely tiled with dining table and enjoy all the best of the galley kitchen for easy entertaining. The amenities will complete your time in Paradise in Florida. New clubhouse room with full kitchen. Enormous heated swimming pool and spa, fitness center, sauna, tennis courts, bike storage, pickle ball and have dinner on the beach with outdoor grill area. Restaurants are everywhere along with only minutes to Famous ST. Armand's Circle for great shopping and more of top notch Restaurants. . Walk the 9 mile Beach or ride your bike on Special Longboat Key. Includes internet, electric and cable and more. Turn key furnished. Just pack your bags. Won't last long.

Listing is courtesy of: CHROME REALTY LLC (941-363-6300)

Listing Agent: Marni Hayden (941-809-5044)

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: DIRECTLY on the GULF. WITH PRIVATE BEACH .Be Prepared for style, relaxation and Longboat luxury. This stunning boutique condominium renovated in 2024 and located on Longboat Key's Gulf of Mexico Beach. Its newly designed layout emphasizes the magnificent ocean view throughout its open floor plan that is visible from the time you walk in the door, through the beautiful dining area, upscale kitchen, and tranquil living area. The primary King suite features an elegant walk-in shower and double vanity, along with a guest closet that will provide everything you need for a peaceful night’s sleep. A spacious queen guest bedroom next to the second bathroom, and a cozy third bedroom designed around a queen bed with a twin bunk perfect for additional guests. This unit in a hard to find 8-unit complex with breathtaking Gulf views, a private beach access located on the North end gives you the best of what the Key has to offer, privacy, amazing restaurants throughout Longboat, relaxing beach walks, unforgettable sunsets, a short stroll to many nearby restaurants and is centrally located; only 8 miles north from the renowned St. Armond’s Circle known for its outstanding restaurants and shopping scene, and 8 miles south of Anna Maria Island, known for its good eats, live music and fun atmosphere. Call for rates and availability.

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

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

Remarks: SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite features King-sized bed, TV, & opens to a private balcony. The comfortable guest bedroom offers a Queen and 1 twin bed with ceiling fan, and guest bathroom with tub/shower. The Westchester community is located on 7-plus acres of beautifully landscaped grounds, meticulously maintained with tennis court, 2 heated pools, updated Clubhouse and 3 private Tiki-hut areas. Gulf beaches are what make Longboat Key unique and you can walk for miles on the beach from the condo. Longboat Key also has 10 miles of bicycle paths on either side of Gulf of Mexico Drive. Located just 6 miles from fashionable St. Armands Circle and only a short drive to downtown Sarasota with arts, theatre, restaurants and shopping. This is non-smoking unit. Sorry, this condo association does not allow pets. BOOKED JAN-MAR, 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)