41 Properties

  • $5,250

    1085 Gulf of Mexico Drive

    1085 Gulf of Mexico Drive, Longboat Key, FL 34228

    2 Beds • 2 Bath

    2 Beds, 2 Baths

    $5,250

    1,500 Sqft

    1 Floor Plan

    Top Amenities

    • Washer & Dryer In Unit
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Cable Ready

    Pet Policy

    No Pets

      Longboat Key Condo for Rent

      Enjoy everything Longboat Key FL has to offer. The unit is in the Beachplace development. Beachplace is on the beach side of Gulf of Mexico Drive, and consists of 11 high rise buildings, clubhouse, gym, olympic size swimming pool, tennis courts and a long stretch of the white sand beach. The location is 3.3 mi from St. Armand's circle with shops and multiple restaurants, and 5.7 mi for the Sarasota Main Street with multiple food and shopping offerings. Publix on Longboat Key is within 2.1 mi away. The unit on the second floor of a high rise building. The balcony is facing a golf course, with 150 yards walk to the well groomed and maintained white sand beach.The unit has 2 bedrooms and 2 bathrooms and easily sleeps 4 adults. Condo is rented fully furnished and equipped for comfortable stay. Internet and basic cable included. Parking is included and guaranteed spot right outside the building. Rental rules 1.Minimum stay 30 days per Longboat Key town rules. 2. Rental requires HOA approval application $165, cleaning fee $160 3. Per night rental costs $175 for 12/1-12/31/23. 4. Payment of the local rental 6 % tax required.

      Condo for RentView All Details
      (844) 665-3449
    • $18,210

      500 Schooner Ln

      500 Schooner Ln, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $18,210

      1,657 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Neighborhood

      Country Club Shores

      Longboat Key House for Rent

      Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was thought out from kitchen to bathrooms. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for the gourmet chef in you all. Outdoor living could be your everyday enjoyment while sipping wine by your private heated pool and on cool nights curl up at the fire pit. Sit back and relax with many seating areas and full outdoor dining table in this cozy beach themed oasis in Country Club Shores. Quiet sought out neighborhood on south end of Longboat Key with beach access between LBK Club and Beach Place. It is fully equipped with everything you will need to feel at home while enjoying the sights and comforts that Longboat Key has to offer. Just minutes to St Armand's Circle or Lido Beach for shopping, fine dining or laying at the public beach with all your favorite people. Longboat is known for their waterfront golf, fine dining and luxury resorts. In fact, its 12 miles of white sand beaches have helped to make this a luxury Gulf Coast resort community. There are numerous Activities and Attractions in the Sarasota/Bradenton/Siesta area. -Just a few of the many treasures and cultural events are Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, fishing charters out of Marina Jack's, Florida's Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, and the Van Wezel.

      House for RentView All Details
      (941) 922-0792
    • $9,500

      1050 Longboat Club Rd #906

      1050 Longboat Club Rd #906, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $9,500

      1,409 Sqft

      1 Floor Plan

      Top Amenities

      • Air Conditioning
      • Deck
      • Dishwasher
      • Elevator

      Longboat Key Condo for Rent

      Stay right on the edge of the Gulf of Mexico and enjoy Direct Gulf views from multiple vantage points within this 9th floor Condo! Located in the serene community of Privateer North offering vast amenities such as a swimming pool/spa, fitness center with sauna, tennis courts and easy private beach access. Situated on Longboat Key with miles of magnificent beaches and turquoise waters and close to St. Armand's Circle where you will find plenty of convenient dining, entertainment and shopping. This exquisite short-term rental is beautifully fully furnished and features a newer kitchen, master suite beachfront balcony, additional balcony off Great Room, custom built ins and one covered parking space. Dazzling views, tranquil peace and amenities galore will have you never wanting to leave! Monthly rent is $9500. Electric included with a $125.00 cap, tenant is responsible for overage.! 3 Month Minimum leases with a $100 application fee to the association and a $60 application fee to RoseBay. Unfortunately, no pets are allowed.

      Condo for RentView All Details
      (941) 366-7673
    • $9,500

      1906 Harbourside Dr #301

      1906 Harbourside Dr #301, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $9,500

      2,097 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Townhome for Rent

      End unit beautifully turnkey furnished townhouse in Fairway Bay of Longboat Key. All new decorating in this light and spacious unit that has a view of the canal. Lots of windows and two stories with skylights giving the unit loads of light. Living room is two stories with a vaulted ceiling. All new decorating, two master suites with King and Queen sized beds, two dens with double fold out couches. One of the master suites is on the main living area. Private two car garage and boat dock. The unit has two stair master chairs from the garage to the first floor. Two month minimum per the Association rules.

      Townhome for RentView All Details
      (941) 953-6000
    • $4,900

      2012 Harbourside Dr #2102

      2012 Harbourside Dr #2102, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $4,900

      1,590 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      Step into serenity with this expansive 2-bedroom, 2.5-bath residence on the coveted Longboat Key. Perfect for those seeking a tranquil retreat, this unfurnished property is ready for you to personalize and make your own. Enjoy the abundance of amenities the community offers: dip into the refreshing pool at the clubhouse, indulge in some self-care at the adjacent spa, or rinse off after a relaxing swim with the convenient outdoor shower. Fitness enthusiasts will appreciate the state-of-the-art fitness center, while those seeking relaxation can unwind in the designated lounging area. Tennis buffs? Perfect your serve on the well-maintained courts. Beyond the immediate comforts of home, this community boasts an exclusive beach club, ensuring your days are filled with sun-soaked memories. Daily errands are a breeze, with a supermarket just 1.2 miles away and a gas station a mere 2.2 miles, making island living as convenient as it is luxurious. Experience the epitome of Longboat Key living - where there's truly no need to ever leave. Secure this slice of paradise today!

      Condo for RentView All Details
      (941) 803-7522
    • $11,000

      2109 Gulf of Mexico Dr #1203

      2109 Gulf of Mexico Dr #1203, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $11,000

      1,463 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher
      • Elevator

      Longboat Key Condo for Rent

      ***NEW VACATION RENTAL LISTING** Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill. You are welcome to beach chairs along the private beach. Under-building assigned parking directly across from security coded entry lobby with elevator and mailboxes. Plenty of guest parking inside the welcome security gates. Full time maintenance crew keeps the grounds immaculate. Wake up to beach and water views from Living room, both bedrooms and terrace. The apartment has an fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room furniture, decor and linens. Utility room with Maytag washer and dryer. Sunset Beach is currently replacing all lobby and hallway flooring. Just minutes to St Armand's Circle or Lido Beach for shopping, fine dining or laying at the public beach with all your favorite people. Longboat is known for their waterfront golf, fine dining and luxury resorts. In fact, its 12 miles of white sand beaches have helped to make this a luxury Gulf Coast resort community. There are numerous Activities and Attractions in the Sarasota/Bradenton/Siesta area. -Just a few of the many treasures and cultural events are Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, fishing charters out of Marina Jack's, Florida's Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, and the Van Wezel.

      Condo for RentView All Details
      (941) 922-0792
    • $8,000

      2109 Gulf of Mexico Dr #1402

      2109 Gulf of Mexico Dr #1402, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $8,000

      1,273 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      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. VACATION, LUXURY, GULF OF MEXICO, SARASOTA FL. RENTALS.

      Condo for RentView All Details
      (941) 953-6000
    • $8,000

      2425 Gulf of Mexico Dr #4E

      2425 Gulf of Mexico Dr #4E, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $8,000

      1,470 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award- winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen. A five minute walk to shopping & pharmacy. Short drive to St. Armand's or downtown Sarasota, for restaurants , theaters and boutique shopping. SARASOTA FL.BEACHFRONT,GULF OF MEXICO,RENTAL,SEASONAL,LUXURY

      Condo for RentView All Details
      (941) 953-6000
    • $6,700

      2936 Gulf of Mexico Dr #2936

      2936 Gulf of Mexico Dr #2936, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $6,700

      1,431 Sqft

      1 Floor Plan

      Top Amenities

      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      ***POPULAR UNIT ALERT!!! HIBISCUS UNIT*** CURRENTLY AVAILABLE: OCT, NOV, DEC 2023***MAY BE AVAILABLE FOR 2024 SEASON***RATES MAY VARY BY SEASON*** GREAT WAY TO SPEND TIME WITH FAMILY & FRIENDS***BRAND NEW***RENOVATED*** TURNKEY UNIT *** Private, Luxurious, Comfort & Beach Tranquility can all be yours all season long in this beautifully redone beach house unit. ***It is a very short, under 1 minute stroll across the street to the pristine beaches of the fabulous Gulf of Mexico via the public beach access.*** There's a one story walk up that leads you to your complete yet private wrap around deck that is perfect for your garden and pool views. The balcony is furnished with your own private outdoor seating which can also be accessed from your Living Room, Dining Room or Your Master Bedroom. If your not out enjoying all the fabulous eats of St. Armand's Circle or Ana Maria to the north, You will thoroughly enjoy cooking and entertaining in this fully stocked and first class kitchen. Beautiful glass door cabinets, stocked wine rack, all new stainless steel appliances, eat in kitchen with gorgeous island. You will enjoy this beach cottage paradise, a true home away from home as you simply have all the things you need to enjoy your relaxing stay. From large 75 inch televisions, internet/wifi, cable, comfy sectionals coupled with a cozy electric fireplace, King Size Bedding in the Master Bedroom with a nice sized en-suite, Double Full beds in the Guest Suite, comfortable sitting areas in both bedrooms, remote controlled blinds, beautiful lighting for all the various ambiance your heart desires, inside laundry room, linens, towels, hair dryers, beach chairs/umbrellas, printer and so much more!! We even have classic board games your sure to enjoy! Feel free to walk or bike ride 2 blocks to the town center where you will find Publix, CVS, banking, library, shopping and a lovely park on your way there. 2 Bicycles are included with your stay for you to enjoy along with 2 vehicle parking spaces for your convenience. The heated pool with night time lighting is for the enjoyment of this very quaint and intimate size complex of only 4 Treehouse units. The Pool is gated for safety and has a large deck with outdoor furniture as well as a shower head for rinsing off salt and sand if you are coming back from the beach. You will appreciate the outdoor storage unit where all the beach toys are stored for your use. The convenience of this location is not to be overlooked! Group rentals with multiple units can also be accommodated for special occasions. All the elements of a fulfilling island lifestyle getaway awaits your exploration! **** BE SURE TO WATCH THE WALK THRU VIDEO. **** https://hausimages.vids.io/videos/119dd9b51c1fe3ce98/2936-gulf-of-mexico-dr-longboat-key-fl-34228 ****

      Condo for RentView All Details
      (813) 463-4300
    • New Lower Price
      $6,900

      3240 Gulf of Mexico Dr #B303

      3240 Gulf of Mexico Dr #B303, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $6,900

      1,260 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      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. Available for June through November at $4,600 per month and wide open winter 2024. Call today as this will not last long!!!

      Condo for RentView All Details
      (941) 953-6000
    • $4,600

      3235 Gulf of Mexico Dr #A302

      3235 Gulf of Mexico Dr #A302, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $4,600

      1,260 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      Stunning Portobello Vacation 2/2 Condo on Longboat Key. OFF SEASON RENTAL ONLY. NOT AVAILABLE JAN-APR 2024 (ALREADY LEASED). AVAILABLE MAY-DEC with a 3-MONTH MINIMUM. 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 decor, 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. WiFi 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. Minimum one-month rental required. Sorry no pets permitted (no exceptions). Property has been rented Jan-2023 and is not available. No smoking permitted. Off Season ($4600). 13% sales and tourism taxes apply for any rental less than 6 months.

      Condo for RentView All Details
      (941) 404-8878
    • $4,000

      3810 Gulf of Mexico Dr #F205

      3810 Gulf of Mexico Dr #F205, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $4,000

      1,007 Sqft

      1 Floor Plan

      Top Amenities

      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      Turnkey Furnished Vacation is for a seasonal or longer-term rental. This beautiful second floor condo located in the private tropical oasis of the Beach Harbor Club between the bay and the beach with provided chairs and umbrella. Turnkey furnished 2 bedrooms, 2 baths, an updated kitchen with stainless steel appliances, granite countertops and lots of cabinets. The living room has two couches and is the perfect spot to relax after the beach. The master bedroom has a King-size bed, the second bedroom has two double beds. There are washer and dryer in the laundry room. Unit comes with an assigned covered parking space. Take a dip in the newly resurfaced pool or launch a kayak into the bay. Fish from the community pier or play a game of shuffleboard. There are several grills, poolside, bayside. Nearby are championship golf, tennis, basketball, fishing charters, water sports and the restaurants/shops of Longboat Key and Saint Armands Circle. Off season rate is $4000 + taxes and fees, per month, 90 days minimum, January through end of April rate is $5200, + taxes and fees. Welcome to paradise! Association requires 30 days for approval. AVAILABLE from September 1st, 2024.

      Condo for RentView All Details
      (941) 999-1179
    • $10,500

      511 Bayport Way #511

      511 Bayport Way #511, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $10,500

      1,601 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      SPECTACULAR VIEWS! This beautifully remodeled two bedroom, two bathroom condo has an open concept floor plan which features an expansive Living/Dining/Kitchen combo. In addition, it boasts a generous sized master bedroom with en suite bathroom, an alcove that accommodates a small desk and a private lanai leading off the bedroom. At the end of each day relax and enjoy natures' most beautiful canvas sunsets from your enclosed lanai from either the family room or the master suite. An additional outdoor deck can be enjoyed from the front of the condo as well. This gulf to bay community is full of lush, mature landscaping and offers private beach access across the street. The amenities feature a junior Olympic-sized heated pool, four Har-tru tennis courts, fitness center, fishing pier, kayak storage, clubhouse with active social calendar, and more. Just minutes away from shopping, dining, and entertainment in world famous St. Armand's Circle and downtown Sarasota. Please contact Agent for availability.

      Condo for RentView All Details
      (813) 684-9500
    • $9,000

      720 Bayport Way #720

      720 Bayport Way #720, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $9,000

      1,260 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      Bright and Spacious! This lovely 2 bedroom, 2 bathroom furnished condominium is nestled comfortably in a lush tropical setting with a spacious eat-in kitchen that is open to the living area. Elegantly furnished in a natural color pallet. The master suite is tastefully decorated, with a built in vanity, double sinks and his and her closets. It also features a small alcove with a desk with access to a private screened in patio with gulf view. Additionally there is a large private deck for sunbathing, relaxing or enjoying an outdoor BBQ! Bayport Beach and Tennis Club is directly across from the sandy beach of the Gulf of Mexico with 1200 feet of private beach. Amenities include (4) Har-tru tennis courts, one of the largest swimming pools on the island and a clubhouse with kitchen facilities for private parties and social functions, fitness center, a fishing pier on the bay, a kayak launch and nature paths all on 27 lushly landscaped acres.

      Condo for RentView All Details
      (813) 684-9500
    • $10,500

      739 Bayport Way #739

      739 Bayport Way #739, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $10,500

      1,601 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      This beautifully remodeled end unit condo, boasts two bedrooms, two bathrooms and has an open concept floor plan which features an expansive Living/Dining/Kitchen combo. In addition, it has a generous sized master bedroom with en suite bathroom, an alcove that accommodates a small desk and a private lanai leading off the bedroom. Begin each day by enjoying nature's' most beautiful the serene garden views from your enclosed lanai from either the family room or the master suite. An additional outdoor deck from the front of the condo allows for outdoor lounging,sunbathing or dining while being able to experience some of the most amazing sunset views. This gulf to bay community is full of lush, mature landscaping and offers private beach access across the street. The amenities feature a junior Olympic-sized heated pool, four Har-tru tennis courts, fitness center, fishing pier, kayak storage, clubhouse with active social calendar, and more. Just minutes away from shopping, dining, and entertainment in world famous St. Armand's Circle and downtown Sarasota.

      Condo for RentView All Details
      (813) 684-9500
    • $9,000

      517 Bayport Way #517

      517 Bayport Way #517, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $9,000

      1,260 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      Gorgeous Inside! Furnished Rental at the exceptional Bayport Beach and Tennis Club. Single story end unit with private entrance. Very Private screened lanai and patio area. Amenities abound at this beautifully landscaped Beach and Tennis Club. Four professional quality Hart-Tru Clay Courts with ball machine, Junior Olympic (heated) swimming pool, ping pong table, bocce ball court, fitness center and fishing pier on the bay. The grounds of this community resemble the botanical gardens. Just walk across the street to the Gulf of Mexico pristine Longboat Key Beach. Please contact Agent for availability.

      Condo for RentView All Details
      (813) 684-9500
    • $6,000

      605 Sutton Pl #404

      605 Sutton Pl #404, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $6,000

      1,132 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      This is a completely updated PENTHOUSE unit with incredible views of the bay at Sutton Place. Both bathrooms, kitchen, floors, windows and more are completely updated. The community has a pool that overlooks the bay and the grounds are very well kept. The community is very quiet and the views of the bay are stunning. If you are looking for an updated rental....this is your place. Everything has been updated. The kitchen has quartz counters, beautiful backsplash and stainless appliances, both bathrooms have been refinished and the living room, kitchen and patio overlooking Sarasota bay are all finished with new luxury laminate. There is one covered parking space but plenty of guest parking that can be used.

      Condo for RentView All Details
      (941) 232-4485
    • $10,000

      100 Sands Point Rd #211

      100 Sands Point Rd #211, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $10,000

      1,941 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      This gorgeous waterfront condo is the perfect place to call home! Located on Longboat Key with private beach access just steps away from your door! Offering this 2 bedroom 2 bathroom resort style condo furnished as a long term rental. Featuring full Gulf views from both bedrooms and living room, stone countertops, stainless steel appliances, crown molding, and an oversized walk-in closet in the master. With an open floor plan and almost 2,000 sq. ft this light and bright unit is island living at it's finest! Rent includes water, sewer, basic cable, and internet. Electric will be tenant's expense. Community amenities include a heated pool & spa, a grill, and other recreational facilities. Situated just 2.2 miles from the lovely St. Armand's Circle with tons of options for restaurants and shops. Also just 5 minutes from Mote Marine and 15 minutes from Anna Maria Island. AVAILABLE November 1, 2023. Owner is willing to consider 2 options, either a 6 month lease @ $12,500/month or a 1 year lease @ $10,000/month. Don't miss out on this opportunity to be on the water with beach access, call now to schedule your showing!

      Condo for RentView All Details
      (941) 955-7368
    • $13,000

      435 L Ambiance Dr #H402

      435 L Ambiance Dr #H402, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $13,000

      2,385 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck

      Longboat Key Condo for Rent

      LUXURY LIVING...behind the gates of LONGBOAT KEY CLUB. Spacious two bedroom, 3 bath condo with a FABULOUS VIEW OF THE GULF OF MEXICO and the SARASOTA BAY FRONT. A huge wrap around balcony to enjoy your morning coffee and beautiful sunsets every night. Conveniently located, a short distance from restaurants and shopping on St. Armand's Circle. A few minutes drive to downtown Sarasota with our expansive theatre district, casual and fine dining rows of shopping. King bed in the master and a queen bed in the guest room. If it's comfort and luxury your seeking for your vacation...you've just found it! GULF OF MEXICO, SARASOTA VACATION PROPERTY, SARASOTA BAYFRONT, LUXURY.

      Condo for RentView All Details
      (941) 953-6000
    • New Lower Price
      $9,000

      524 Yawl Ln

      524 Yawl Ln, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $9,000

      2,226 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Neighborhood

      Country Club Shores

      Longboat Key House for Rent

      Location, Location, Location! Longboat Key canal home freshly decorated for a seasonal rental. Situated on South Longboat Key with easy access to St. Armands Circle, Lido Key and downtown Sarasota. The light and bright single family home has two bedrooms, two bathrooms, living room/dining room combination, bonus Florida room with comfortable couches and a television. The kitchen has plenty of counter and cabinet space and a breakfast nook with table. The large master bedroom has a king sized bed and on suite bathroom. The guest bedroom has two twin beds. The expansive lanai has several sitting areas to enjoy the canal view and private pool. One car garage. No pets allowed. SEASONAL, SHORT TERM SINGLE FAMILY HOME, LONGBOAT KEY, FLORIDA

      House for RentView All Details
      (941) 953-6000
    • $7,500

      1485 Gulf of Mexico Dr #303

      1485 Gulf of Mexico Dr #303, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $7,500

      1,569 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      Live the ultimate beachfront lifestyle in this stunning two-bedroom, three and a half bath condo located on the beautiful shores of Longboat Key. With views of the Gulf of Mexico and access to a wide range of amenities, this elegant and spacious residence is the perfect getaway for those seeking serenity and luxury. Located just a short drive from downtown Sarasota and walking distance to St. Armands, you'll have access to the many shops, restaurants, and cultural attractions, making this waterfront condo the perfect base for exploring all that Longboat Key has to offer. Don't miss the opportunity to rent this spectacular condo and experience the beauty of Longboat Key living at its best.

      Condo for RentView All Details
      (813) 754-3586
    • Filter by Price

      Set a maximum price for your search.

      price
    • $6,500

      2045 Gulf of Mexico Dr #313

      2045 Gulf of Mexico Dr #313, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $6,500

      1,265 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher
      • Elevator

      Longboat Key Condo for Rent

      Live your Florida Dream in this 2 bed/2 bath condo on beautiful Longboat Key! Just steps away from the soft sandy beaches and sparkling waters of the Gulf of Mexico, this unit is one of the closest to the beach of all the Seaplace condos, directly across from the large resort style pool and the beach. Relax on the lanai, have a cocktail, and watch one of our spectacular Longboat Key sunsets! The open and spacious floor plan allows for gathering and entertaining, breakfast on the deck, or just hanging out. The serene master bedroom with peek-a-boo view of the Gulf is large enough to accommodate the built-in desk and work station, plus the king sized bed with plenty of room to move about and also features a large master bath with tons of closet space. The guest bedroom is cozy, has built-in closet and drawers and is conveniently located just across from the guest bath. Seaplace is a very desirable south Longboat destination; you'll be surrounded by the privacy and comfort of Longboat Key yet still be so close to shopping and dining on St. Armand's Circle, the culture and nightlife of downtown Sarasota, and everything else our beautiful area has to offer. Play tennis on the Har-Tru courts! Swim in your choice of two community pools! Walk our beautiful beaches! A covered assigned parking spot and storage closet are included. AVAILABLE NOW THROUGH NOVEMBER AT $3k PER MONTH. High season rate is $6500 per month.

      Condo for RentView All Details
      (941) 953-6000
    • Find Homes
      with AT&T Fiber® Internet

      AT&T Sphere
      AT&T Fiber
    • $9,737

      2105 Gulf of Mexico Dr #3403

      2105 Gulf of Mexico Dr #3403, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $9,737

      1,463 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      short stories"...Stunning direct Gulf front condo with magnificent views of the turquoise water. Every evening enjoy breathtaking sunsets on your private balcony. Start your day with a leisurely stroll on the soft sand beach. Take a refreshing dip in the pool. This condo is beautifully furnished and decorated. Both bedrooms have a view of the Gulf. Ride your bike along the Gulf of Mexico. Conveniently located close to restaurants and shopping. A short drive to St. Armand Circle with world class shopping and dining. Available February/March 2023.

      Condo for RentView All Details
      (941) 803-7522
    • Filter by Bathrooms

      How many bathrooms do you need?

      bathroom
    • $6,700

      2932 Gulf of Mexico Dr #2932

      2932 Gulf of Mexico Dr #2932, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $6,700

      1,445 Sqft

      1 Floor Plan

      Top Amenities

      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      HIGHLY SORT AFTER RENOVATED UNIT now available OCT, NOV & DEC 2023. JAN- APRIL 2024 Is also NOW AVAILABLE **** SUNFLOWER UNIT ***Private, Luxurious, Comfort & Beach Tranquility can all be yours all season long in this beautifully redone beach house unit. ***It is a very short, under 1 minute stroll across the street to the pristine beaches of the fabulous Gulf of Mexico via the public beach access.*** There's a one story walk up that leads you to your complete yet private wrap around deck that is perfect for A NICE PEEKAVIEW OF THE GULF, along with garden and pool views. The balcony is furnished with your own private outdoor seating which can also be accessed from your Living Room, Dining Room or Your Master Bedroom. If your not out enjoying all the fabulous eats and amenities in the area, You will thoroughly enjoy cooking and entertaining in this fully stocked and first class kitchen. Beautiful glass door cabinets, and all new stainless steel appliances. You will enjoy this beach cottage paradise, a true home away from home as you simply have all the things you need to enjoy your relaxing stay. From large 85 inch televisions, high speed internet/wifi, cable, wireless printer and work area, comfy sectionals coupled with a cozy electric fireplace, King Size Bedding in the Master Bedroom with a nice sized en-suite. Double Full beds in the Guest Suite, brand new bathroom with glass shower enclosure with all the bells and whistles! Comfortable sitting areas in both bedrooms, remote controlled blinds, beautiful lighting for all the various ambiance your heart desires. Lots of closet space, inside laundry room, linens, towels, hair dryers, beach cady, beach chairs, umbrellas and so much more all for your use! We even have classic board games your sure to enjoy! Feel free to walk or bike ride 2 blocks to the town center where you will find Publix, CVS, banking, library, shopping and a lovely park on your way there. 2 Bicycles are included with your stay for you to enjoy along with 2 vehicle parking spaces for your convenience. The heated pool with Cigar/BBQ Grill area along with night time lighting is for the enjoyment of this very quaint and intimate size complex of only 4 Treehouse units. The Pool is gated for safety and has a large deck with outdoor furniture as well as a shower head for rinsing off salt and sand if you are coming back from the beach. The convenience of this location is not to be overlooked! Group rentals with multiple units can also be accommodated for special occasions. All the elements of a fulfilling island lifestyle getaway awaits your exploration! ****

      Condo for RentView All Details
      (813) 463-4300
    • $7,999

      3420 Gulf of Mexico Dr #B307

      3420 Gulf of Mexico Dr #B307, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $7,999

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Elevator

      Longboat Key Condo for Rent

      VACATIONAL RENTAL. Relax and enjoy with family or friends this wonderful two bedrooms, two full baths apartment in front of the #1 beach in Florida, white quartz sands and dreamy sunsets, enjoy a warm winter here!

      Condo for RentView All Details
      (305) 924-5915
    • $8,000

      519 Bayport Way #519

      519 Bayport Way #519, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $8,000

      1,456 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      Seasonal rental in Bayport Beach and Tennis Club which is a beautiful, established, award-winning, amenity-rich community with immediate access to a peaceful private beach that continues in both directions for miles along the Gulf of Mexico shore. The complex includes a large pool surrounded by flowering trees, four immaculately maintained clay tennis courts, fitness center, a large clubhouse, bike trails, and a private fishing pier on the bay side surrounded by mangroves. Turnkey furnished on the upper level of a quiet end unit, including two full bedrooms - one with a king bed and the other with two twin beds. You can see the Gulf from the entrance and the guest bedroom. Each bedroom has its own bathroom; the guest bath has a shower and the master bath has double sinks and a bathtub. The kitchen has granite countertops and there is a separate tiled dining area with a glass table, that seats up to six. There is also seating in the kitchen at a granite counter. The living room has comfortable, large couch with an entertainment unit. The condo has a lanai overlooking lovely tropical gardens. In unit washer/dryer. Nearby is a convenient grocery store, great restaurants, museums, galleries, marinas and shops at St. Armand's Circle. One covered parking space is provided, with plenty of guest parking spaces.

      Condo for RentView All Details
      (813) 684-9500
    • $5,000

      706 Bayport Way #706

      706 Bayport Way #706, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $5,000

      1,601 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      This beautiful 2 bedroom/2 bath split and open floor plan condo is spacious and bright. The kitchen featuring a built-in desk and granite counters has been opened to the dining/living room area with views of the pond, fountain and lush tropical landscaping. A stackable washer/dryer in closet for your convenience. Lanai enclosed with tropical views. Bayport Beach and Tennis Club is bordered by the Gulf of Mexico to the West with 1200 feet of private beach and Sarasota Bay to the East. This resort community is situated in the heart of Longboat Key. A popular residential enclave of 136 quality-constructed homes on 27 picturesque acres. Residents enjoy a heated, Jr Olympic sized pool. fishing pier, steps to a private Gulf beach, kayak launch and storage, 4 Har-Tru tennis courts, golf practice net, bocce court, social room with full kitchen, library, piano, fitness center, shelled nature walking paths, tropical gardens and a number of social activities. Shopping, Restaurants and the Arts are located within minutes including St Armand's Circle, Downtown Sarasota & Anna Maria to name a few. Golf, Marina and Restaurants at the Longboat Key Club. A "PET" friendly community.

      Condo for RentView All Details
      (813) 684-9500
    • $9,000

      744 Bayport Way #744

      744 Bayport Way #744, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $9,000

      1,456 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      Delightfully appealing seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes fully furnished and equipped with flat screen TV's, cable and WiFi. This residence features a spacious screened lanai with garden views in addition to an outdoor sun deck with loungers for basking in the sun. Bayport sits on 27 lushly landscaped acres and has 1200 feet of pristine private beach for your exclusive use. Complimentary beach chairs and umbrellas are provided for guests. Enjoy an active lifestyle at Bayport as the Community includes a junior sized heated Olympic swimming pool, 4 har-tru tennis courts for the Tennis enthusiasts, a fitness center, fishing pier, kayak storage, nature trails and a clubhouse perfect for gathering. 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. NOW AVAILABLE JAN - MARCH 2024

      Condo for RentView All Details
      (813) 684-9500
    • $5,000

      522 Bayport Way #522

      522 Bayport Way #522, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $5,000

      1,260 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Dishwasher

      Longboat Key Condo for Rent

      GORGEOUS LONG TERM RENTAL!! 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 beautifully appointed. This residence offers a wonderful retreat as a annual. 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 the private beach on the Gulf of Mexico for a morning of beachcombing, surf casting or memorable sunsets. Please contact Agent for availability.

      Condo for RentView All Details
      (813) 684-9500
    • $9,000

      502 Bayport Way #502

      502 Bayport Way #502, Longboat Key, FL 34228

      2 Beds • 2 Bath

      2 Beds, 2 Baths

      $9,000

      1,456 Sqft

      1 Floor Plan

      Top Amenities

      • Washer & Dryer In Unit
      • Air Conditioning
      • Deck
      • Dishwasher

      Longboat Key Condo for Rent

      Beautifully appointed rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes turnkey furnished and equipped with flat screen TV's, cable and WiFi. This residence features a large outdoor patio with garden and ocean views. Bayport sits on 27 lushly landscaped acres and has 1200 feet of private beach. Complimentary beach chairs and umbrellas are provided for guests. Enjoy an active lifestyle at Bayport. Community features include a junior sized heated Olympic swimming pool, 4 har-tru tennis courts for the Tennis enthusiasts, a fitness center, fishing pier, kayak storage, nature trails and a clubhouse perfect for gathering. 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.

      Condo for RentView All Details
      (813) 684-9500