Vacation Rentals By Owner In Longboat Key, FL

$282.5

Gulf & Greenbelt Views, No-Expense-Spared Remodel, Seaplace Oasis

Longboat Key, Florida, United States

Escape to paradise in this completely remodeled, no-expense-spared 2nd floor end-unit condo with no unit above at the gated Seaplace beachfront community on Longboat Key. This oversized 1-bedroom, 1.5-bath gem (1,094 sq ft + 112 sq ft screened lanai) offers partial gulf views and greenbelt setting from the expansive lanai—perfect for sipping wine while watching spectacular sunsets. Just 178 yards from the pristine white-sand beach, the convenient second-floor location gives you quick access to the shore from the nearby elevator or stairs adjacent to the condo. Relax on your private screened-in lanai with high-quality Polywood furniture and a WiFi-enabled ceiling fan, all protected by custom 95% UV-blocking solar shades. The redesigned layout features a gourmet open-concept kitchen with soft-close cabinetry, Cambria Quartz counters, GE Café appliance suite (convection oven, warming drawer, induction cooktop), and a fully-stocked kitchen to make your extended stay feel like home. The coastal vibe interiors include porcelain plank driftwood tile floors, Cypress pecky wood and shiplap accent walls, smooth plastered ceilings and custom LED recessed lighting. Fully updated bathrooms with Carrara marble counters, elegant tile accents and double-vanity in the primary bath off the bedroom on the second level. There are smart flat screen TVs in the living room and bedroom to enjoy all of your favorite streaming and an LG stacked washer/dryer on the first level. Enjoy resort-style living across 42 manicured acres with two heated lap swimming pools, spas, a fitness center, three tennis courts, one mile of scenic trails, barbecue areas, and clubhouse with barbecue grills. Seaplace offers 24/7 guarded gate security and you're just one complex north of the iconic St. Regis. This turnkey coastal retreat delivers luxury, comfort, and unforgettable Gulf Coast memories. Book now for your slice of Longboat Key paradise! AVAILABLE NOV. & DEC. 2026 - BOTH MONTHS $7,500 PER MONTH. OR.. EITHER NOV. OR DEC. FOR THE MONTH: $8,000. ALSO AVAILABLE JAN. 2027-MAY 2027 WITH A 3-MONTH MINIMUM AT $7,000 PER MONTH. Please inquire with owner on preferred dates.

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1

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2

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$183.27

/ Nightly

Condo

Fairway Bay #155 by FVC

Longboat Key, Florida, United States

Fairway Bay Fifth-Floor Retreat: Unparalleled Sarasota Bay Views brOffered by Florida Vacation Connections brbrExperience the epitome of coastal living in this exquisite two-bedroom, two-bathroom residence, perfectly perched on the fifth floor of Fairway Bay, a sought-after, amenity-rich community on Longboat Key. Spanning 1,442+/- sq. ft., this recently renovated condo showcases breathtaking panoramic views of Sarasota Bay, manicured grounds, serene waterways with mangroves, and the vibrant city skyline beyond. A private elevator leads to this stunning retreat, where natural light and refined design details create an ambiance of luxury and tranquility. brbrLiving and Entertaining Spaces brUpon entering the foyer, you’ll be greeted by a bright, open-concept living space thoughtfully designed for comfort and elegance. New waterproof flooring flows seamlessly throughout, complementing coastal-inspired tones and furnishings. The spacious living room is furnished with all-new furniture, linens, and two smart TVs, ensuring relaxation and modern convenience. A computer desk, complete with an on-site HP wireless printer, caters to your work-from-home needs. brbrThe kitchen, open to the dining and living areas, is both stylish and functional. With ample cabinetry, a large pantry, and brand-new countertop appliances, cookware, and cutlery, it’s perfect for both casual meals and entertaining guests. brbrBedrooms and Guest Accommodations br- Primary Suite: The primary bedroom offers direct access to the oversized terrace, where you can wake up to the serene beauty of Sarasota Bay. Highlights include wood floors, a walk-in closet, a new ceiling fan, and a spa-inspired en-suite bathroom with dual vanities, a separate water closet, and a walk-in shower featuring a frameless glass door, safety grab bars, and a new showerhead. br- Guest Suite: The guest bedroom provides comfort and privacy, complete with twin beds, an oversized closet, a ceiling fan, and an en-suite bathroom with a tub/shower combination and new fixtures. brbrThis residence comfortably accommodates up to six guests, making it ideal for family vacations or extended stays. brbrOutdoor LivingbrThe expansive terrace is the true showstopper of this residence, offering a peaceful oasis for relaxing or entertaining against the stunning backdrop of tropical landscaping and Sarasota Bay. Furnished for comfort, it’s the perfect spot to savor morning coffee, sunset cocktails, or al fresco dining. brbrFairway Bay Amenities brFairway Bay residents enjoy a host of exclusive amenities, including: br- Private, gated beach access and beach club. br- 24-hour gated security for peace of mind. br- Scenic walking trails through lush landscapes. br- Resort-style pools, hot tubs, and exercise facilities. br- Tennis and pickleball courts for active recreation. brbrLocated just a short walk from the luxurious new St. Regis Resort and a quick drive to St. Armands Circle, this residence is ideally positioned for enjoying world-class dining, shopping, and entertainment. Optional memberships at the Longboat Key Golf & Tennis Country Club and access to deepwater slips are also available. brbrThis fifth-floor Fairway Bay residence is a rare find—move-in ready with all-new furnishings, just waiting for you to bring your suitcase. Don’t miss the chance to experience Longboat Key’s unparalleled charm and luxury. brbrOffered exclusively by Florida Vacation Connections.

2

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2

Bath

4

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$405.39

/ Nightly

Apartment

Sunset and beach view from your balcony Unit 501

Longboat Key, Florida, United States

Unit 501 is a stunning corner condo offering unobstructed views of the Gulf of Mexico and extra space thanks to its desirable corner layout. Enjoy sweeping, direct Gulf views along with additional natural light from the side window, creating a bright and airy coastal retreat.brbrThis one-bedroom, one-bath residence is located on the 5th floor and features an extra-large private balcony — the perfect place to relax, listen to the gentle sound of the waves, and watch some of the most breathtaking sunsets on Longboat Key. Located in the Tower and overlooking the Gulf, the condo is bright, spacious, and thoughtfully designed for comfort.brbrThe bedroom offers two queen beds, while the living room includes a convenient queen sofa bed, comfortably accommodating up to six guests. The generous living area provides plenty of room to unwind after a day on the beach.brbrPlease note: Cancellations are subject to a 4% credit card transaction charge.brbrThe condo also includes a fully equipped kitchen, dining area, cable TV, and Wi-Fi. Large sliding glass doors open to the balcony, allowing you to enjoy spectacular Gulf views from the comfort of the living space.brbrWith elevator access, you are just steps away from the heated pool, pristine beach, and community amenities. Our friendly on-site office staff is always available to assist and help make your stay enjoyable.brbrWhether you’re looking for peaceful beachside relaxation or easy access to nearby dining and nightlife, this is one of the best one-bedroom condos on Longboat Key — offering comfort, location, and excellent value.brTravel Insurance Recommendation:brWe strongly recommend purchasing travel insurance to protect against unexpected disruptions, including medical emergencies, flight cancellations, severe weather, and other unforeseen events. For a small daily cost, travel insurance offers peace of mind and financial security.

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4

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$286.55

/ Nightly

Private Vacation Home

Country Club Shores 4brm pool home by FVC

Longboat Key, Florida, United States

Soaring Spirits – A Newly Renovated Coastal Escape brProudly offered by FL Vacation Connection brbrStep inside this beautifully newly renovated, single-story coastal retreat, and you’ll instantly understand how it earned the name Soaring Spirits. Designed to be both calming and invigorating, the home’s coastal-chic décor features soothing hues that invite relaxation, while vibrant pops of color add a lively, uplifting energy. brbrIndulge in the ultimate indoor-outdoor lifestyle with an expansive covered patio, now enhanced with a motorized screen enclosure—allowing you to enjoy the fresh air with the touch of a button! Whether you're savoring an alfresco meal, gathering for a family game night, or unwinding with a good book, this inviting space is perfect for every occasion. brbrA Kitchen with a View brThe European-style kitchen is a dream for any home chef. With a smart, streamlined layout that makes meal prep a breeze and a window that frames stunning views of the sparkling pool and serene canal, cooking here is nothing short of a pleasure. brbrPoolside Perfection & Waterfront Bliss brThe sun-drenched pool beckons for a refreshing swim, while the surrounding deck offers plenty of lounge chairs for soaking up the Florida sunshine. Prefer the shade Retreat to the covered patio, where you can sip a chilled drink while embracing the gentle coastal breeze. brbrTake a leisurely stroll to the private dock, where you might catch a glimpse of a gentle Manatee swimming by. Feeling lucky Try your hand at fishing and see if you can reel in dinner! brbrRest & Recharge in Style brWhen the day winds down, retreat to one of the inviting bedrooms, each designed for comfort and tranquility. Sink into plush bedding, close your eyes, and drift into a restful sleep—tomorrow is another day to let your spirit soar! brbrImportant Notes:br- Renters do not have access to the boat, boat lift, or electrical box on the dock. br- No trailers or boat trailers of any kind are permitted on the premises. brbrTown of Longboat Key RRR.00188.2025

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3

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7

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$394.64

/ Nightly

Cottage

2 bedroom 2 bath. Peaceful, Sunsets, White sands !! On the Gulf

Longboat Key, Florida, United States

Located in Longboat Key, enjoy what this 2-bedroom cottage has to offer. The welcoming space features a king bed and a twin bed, plus a cozy living room with a sofa bed for extra guests. Sleeps 5-6 people . Two bathrooms include refreshing showers and handy hair dryers. Stay comfortable year-round with air conditioning and heating throughout the cottage. Whether you’re relaxing indoors or planning your day, this perfect spot invites you to unwind and recharge from the walking distance to the beach and your nightlife restaurants from the Shore and Whitney‘s. We think our place will help you experience everything Longboat Key has to offer. For short or long vacations snowbirds welcome. 5 minutes walking distance to the beach.

2

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2

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5

Sleeps

$423.75

/ Nightly

Condo

Renovated Beach Penthouse sleeps 10 - luxurious Longboat Key Beach Florida!

Longboat Key, Florida, United States

One week Penthouse on beach of Longboat sleeps up to 10! Jan 9th to the 23rd availibility! Veranda Longboat Key Beach Resort!Two story penthouse suite off the Gulf of Mexico, sleeps ten, 4 full baths and 4 bedrooms. Private entry from either floor. Includes amenities: pool, jacuzzi, sauna, sailboats, kayaks, cabanas, bikes, indoor racquetball, fitness center, tennis & basketball courts, outdoor grills, and staff to help you find what you need and security to keep you safe. Award-winning restaurants and beaches in Longboat Key, nearby St Armand’s Circle, and downtown Sarasota and Siesta Key. Close to Sarasota/Bradenton International Airport.

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$755.36

/ Nightly

Apartment

LaPlaya 205D January 2025 Discount!

Longboat Key, Florida, United States

Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. LaPlaya Condominiums provides a private beach, sheltered pool with sundeck, and beachfront grills so you won’t miss a minute of the sunset. The unit has a fully equipped kitchen plus washer and dryer. All linens and beach towels are provided. Welcome to our island-style living.brbrThis spacious unit is bright and breezy with new décor and totally renovated kitchen and baths featuring sparkling granite and tile. The open floor plan provides sweeping views of the beach and gulf from the kitchen to the living and dining area, and on to the private porch and steps leading to the beach. All bedrooms are carpeted. The master bedroom on the 2nd level has floor-to-ceiling windows, and sliders to a sundeck overlooking the beach.brbr Soft shades of aquamarine provide a quiet color scheme for relaxing while enjoying the spectacular views of the beach and Gulf. Listen to the waves, or enjoy exquisite sunsets from the spacious balcony off the third level master bedroom, or from the screened lanai off the living/dining area on the second level.

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$812

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Condo

Updated Beachfront Condo at Prestigious Long Boat Key Resort

Longboat Key, Florida, United States

Welcome to Suite Serenity, a beautiful beachfront King suite at the amazing Longboat Key Club resort. brbr Property Highlights:br✨ Heated resort-style poolbr✨ Elevatorbr✨ Beach chairs and umbrellabr✨ Beach and pool towelsbr✨ Private balconybr✨ Outdoor showerbr✨ Washer/dryer in unitbr✨ Free on-site parkingbr✨ Directly on the beachbrbrEnjoy a peaceful stay at one of the top resorts in the state of Florida. Take a dip in the resort style pool, and then walk to the beach and enjoy the warm waters of the Gulf of Mexico. In the evening, take in beautiful sunsets from your private balcony overlooking Lido Key. brbrThis spacious apartment is located on the second floor, beachfront in building 1. From the balcony you can see dolphins swim past and sunsets over the Gulf of Mexico. A dream vacation on a luxury getaway island that offers lazy beach days but also a large variety of golf courses and tennis courts, as well as top restaurants. brbrThe unit has wireless Internet access, a full-size kitchen, cable TV, complimentary parking, a large private balcony, and is located in a gated community and right at the beach. It is the perfect escape. brbr**PLEASE NOTE that use of the Golf/Tennis courts, hotel bars and restaurants, as well as other Country Club resort privileges are NOT included.** However, the use of the pool, whirlpool, and beach area is allowed. Guests are able to utilize beach chair, umbrella, and cabana rentals at their expense through the resort on the beach**brbrPAYMENT AND CANCELLATION TERMS WHEN BOOKING ON VRBObrbrAt the time of booking your credit card will be charged by Shore Thing Property Services LLC for your deposit payment. You will also see a separate charge by VRBO for their service fee.brbrWe require 25% deposit with the final payment due 60 days prior to your arrival date. Full payment will be due immediately if the arrival date is within 60 days.brbrAlthough the VRBO policy states no refunds, we will refund in the event that you need to cancel your reservation prior to 60 days before your arrival date. We will implement our Shore Thing Properties cancellation policy as indicated on the rental agreement. This allows for a refund of the deposit paid minus a $250 cancellation fee and the original management fee. Within 60 days of arrival there are no refunds.brbrADDITIONAL INFORMATION:brbrHouse keeping will provide you with a starter supply of toilet paper, soap, and garbage bags, but guests will likely need to replenish the supply during their stay.

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1

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4

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$321.88

/ Nightly

Condo

2 Bedroom Beachfront Condo by FVC

Longboat Key, Florida, United States

Welcome to Players Club 402, a beautifully renovated 2-bedroom, 2-bathroom beachfront condominium located on the pristine shores of Longboat Key. Offered by Florida Vacation Connection, this stunning residence combines modern comfort, coastal style, and breathtaking Gulf views for the perfect island retreat.brbrStep inside to find a freshly updated interior with new furnishings throughout, creating a bright and relaxing space designed for effortless coastal living. The open living and dining area is filled with natural light and flows seamlessly onto the large private balcony, where you can enjoy incredible views overlooking the resort-style pool and the sparkling waters of the Gulf of Mexico. It’s the perfect setting for morning coffee, sunset cocktails, or simply taking in the beauty of Longboat Key.brbrThe primary suite features a comfortable king-size bed, ample closet space, and a beautifully updated en-suite bathroom. The guest bedroom offers two full beds, making it ideal for family or visiting guests, with convenient access to the second fully renovated bathroom.brbrThe fully equipped kitchen provides everything needed to prepare meals at home, and for added convenience the condo also includes an in-unit washer and dryer, allowing you to enjoy a longer stay with all the comforts of home.brbrPlayers Club is one of Longboat Key’s premier beachfront communities, offering direct private beach access, a heated beachfront pool and spa, fitness center, clubhouse, tennis and pickleball courts and beautifully maintained tropical grounds.brbrWhether you're enjoying the expansive balcony views, walking miles of white sand beach, or relaxing by the pool, Players Club 402 offers the perfect luxury island escape.brbrExperience the beauty and tranquility of Longboat Key, where every stay truly feels like coming home.brbrProfessionally managed by Florida Vacation Connection.

2

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2

Bath

4

Sleeps

$350.93

/ Nightly

Condo

Waterfront, Spa/Pool, Private Paradise on Longboat Key!

Longboat Key, Florida, United States

Welcome to Paradise at the Harbour Villa Club #114! Enjoy the Captains Quarters end unit which boasts over 1500 sf of living space. A lovely 2/2 to nicely sleep 4 persons. All your living is conveniently on one floor, with open den next to kitchen. Spa and large pool just a short walk outside the lanai and just a few feet from the bay. 15 min walk to a private & gorgeous Beach! Spectacular bay views from every room. Enjoy onsite Tennis and grilling by the pool You will love it here!brbrStarter Supplies ProvidedbrbrTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrThe spacebrCome enjoy some peace & quiet in beautiful Longboat Key!brbrThis clean and comfortable 2 bedroom, 2 bathroom condo on Sarasota Bay is perfect for a relaxing getaway. You can have the perfect vacation without even leaving this condo complex!brbrWe hope you have the opportunity to enjoy some of the unique features of this beautiful unit:brbr• Carefree check-in, go straight to your unit no office visit required.br• Fully-loaded Kitchen including microwave, stove, dishwasher, fridge, and coffee maker and even a wet bar.br• Dining Room Table that’s seats six.br• Bright and cozy living room area w/ large flat screen TV.br• Washer and Dryer Conveniently located inside unit.br• Master bedroom with a king-sized bed, walk-in shower, and peaceful view of the garden area.br• Spacious guest bedroom with Queen bed and private walk-in shower.br• Large Patio overlooking the bay with outdoor seating and a table.brbrHarbor Villa Club amenitiesbr• Heated Poolbr• Hot Tubbr• Tennis Courtbr• Covered ParkingbrbrSurrounding AreabrThe Harbour Villa’s are just a 3-minute drive to the north end of the key home to the historic Longbeach Village, known in its earlier days as a transient fishing village. While taking a stroll through this neighborhood your likely to see peacocks on roofs or resting in someone’s yard. It is also a great place for dinner with a view, with options for waterfront restaurants such as the rustic Mar Vista or the more modern Shore. The north end of the key also holds a hidden gem known as Beer Can Island. Erosion has uprooted many of the Australian pines trees here giving it a deserted island feel, a great place worth exploring. 3 minutes in the other direction will put you at Harry’s your local corner store since 1979. Harry’s also has both a deli and an upscale restaurant behind the store, so you have options for whatever you’re in the mood for.brbrLooking to go for a hike Joan M. Durante Community Park is a 3-minute drive south and has excellent walking trails through the mangroves with portions that overlook the bay. There is a lot of wildlife to see here and a small park out front for children. Mote Marine Laboratory & Aquarium is also a great place to visit if you are interested in marine life. There are many actives to enjoy on the key as well such and Paddle boarding, Kayaking, and golf. Longboat Key charters offers sightseeing/ecotours, fishing, and sunset tours. The south end of longboat meets at St. Armand’s Circle which has a great mix of restaurants, bars, and unique shops. The north end of the island runs into Anna Maria Island which is a hub of entertainment as well.brbrOther things to notebr- Phenomenal Longboat Key location - Only minutes to Beaches, Restaurants and other local favoritesbr- HOA Application required-No Fee (Furnished after reservation made)br- This property has a minimum primary renter age requirement of 25.br- No Pets allowed per HOA. No exceptions.br- Upon booking, a signed rental agreement and government-issued photo identification are required prior to receiving an electronic access code to the property.br-Stays in excess of three weeks may incur an additional cleaning fee.

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$315.27

/ Nightly

Private Vacation Home

Peaceful Longboat Key Canal Home

Longboat Key, Florida, United States

Enjoy the complete island experience in this 2-story two bedroom, one and a half bath, canal front condo, with boat docking. We're located on a quiet street in close proximity to Sarasota Bay, with direct bay access, and next to Joan Durante Park with 32 acres of trails, boardwalks and preserve.brbrRelax on your waterfront patio, perfect for outside dining, barbecues and quiet evenings. Bike, Kayak and Paddleboard rentals are available nearby to explore the island and waters. Beach wagon, chairs and umbrella included for your easy 0.5 mile walk to the beach. brbr30 Night Minimum

2

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1

Bath

4

Sleeps

$332.41

/ Nightly

Condo

Breathtaking Beach Front Property Ground Floor Condo

Longboat Key, Florida, United States

Granite and stainless steel appliances in the kitchen. The living room’s sliding patio door provides first floor access (no stairs) to the beach, heated pool, and a courtyard with shuffle board and outdoor grills. brbrThis fully equipped condo comfortably accommodates six people with: master bedroom (king) & bathroom with a flat screen TV; 2nd bedroom with two twin beds (can slide together to form a king); second full bathroom; den with queen size pull out sofa bed, loveseat and flat screen SMART TV; dining room for 6 people, large patio adjacent to the pool; and a full kitchen that includes all items necessary for cooking. brbrAdditional amenities include free Netflix in the den and living room, a Blue Ray player, an in-unit washer and dryer, unlimited local and long distance calling. In unit full size wash machine and dryer, beach umbrellas and water toys. brbrCondo’s location provides an easy day-trip to Tampa Busch Gardens, Orlando & Disney Attractions

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$323.35

/ Nightly

Condo

2BR King & Queen Gulf-front Luxury at Private Whitney Beach Longboat Key

Longboat Key, Florida, United States

Book your dream vacation in unit 310 at the tranquil Whitney Beach Gulfside resort! On the second floor, this pet-free haven boasts a heated pool and an EV charging station. Enjoy direct access to the beautiful Gulf on a private beach at the peaceful northern end of Longboat Key. Stroll to nearby restaurants, a liquor store, Sips coffee and shops. Instacart and Uber are also available for your convenience.brbrGulf to bay resort property includes a gulf-facing heated, community pool, beachfront lounge chairs, two tennis courts, a fishing dock, kayak and bike racks. Just a heads up, smoking is not allowed inside, on the walkway, or around the pool.brbrStep through the covered entryway into your spacious 1470 square foot unit. It’s furnished with luxurious Stressless leather recliners and high-end coastal furniture. Open the floor-to-ceiling sliders to enjoy the soothing sounds of surf and birds overlooking the dunes. Sleeping with the doors open during cooler months is simply bliss!brbrWe’ve taken care of all your needs… indulge in a chef-inspired kitchen with granite countertops, a stunning sea-glass backsplash, Keurig, drip, and press coffee makers, an electric water kettle, a micro-convection oven, and top-notch cookware.brbrIn the living room and primary bedroom, you’ll find Samsung Frame TVs loaded with 220 Cable stations. The entertainment center is filled with a variety of games and puzzles.brbrThe Master bedroom (18’x13’) features a walk-in closet and a Tempurpedic adjustable split-King bed with a massage feature. The spa-like ensuite bathroom has a bidet, shower, and a lit medicine cabinet. The spacious second bedroom (15’x12’) has a queen adjustable bed, large closet, and is next to the hall bath with a walk-in shower and bidet. The adjoining laundry area has a fold-down table for folding laundry or setting up your computer. Two guests can be accommodated on the queen sleeper sofa in the living room. brbrWe’ve also included complimentary beach towels, tennis and pickleball racquets, beach chairs, two umbrellas, sand toys, paper products, dish, and laundry detergent, shampoo, conditioner and body wash. Just pack your essentials!brbrEnjoy flexible check-in and check-out dates. For any cancellation refunds, please refer to the rental agreement.

2

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2

Bath

6

Sleeps

$180.52

/ Nightly

Apartment

Landing | Modern 2BD, Gym, Pool

Longboat Key, Florida, United States

Feel like you're on vacation every day at Champions Walk in sunny Bradenton, FL. Our fully-furnished homes offer full kitchens, in-unit laundry, fast WiFi, and private patios or balconies, ideal for short visits, monthly stays, or longer getaways. Dive into a resort-style stay with a sparkling pool, tennis courts, and serene lakeside spots. Just minutes from IMG Academy, Coquina Beach, and major employers like Blake Medical Center and HCA Healthcare, you're perfectly positioned for work and play.br Guest ScreeningbrAll guests must complete CLEAR ID verification and a background check (no evictions, collections, or criminal records).brA passport is required for international guests.brbrStays of 30+ NightsbrThe primary guest must complete a soft credit check (minimum score of 550) and provide a valid SSN.brbrAfter BookingbrWe will request your email address to send a secure check-in link.brbrCredit Card RequirementbrA valid credit card is required to complete the check-in process and secure the reservation.brbrParking InformationbrParking availability, arrangements, and fees vary by property and are managed by third-party providers in some locations. Costs may apply. Please contact us prior to booking to receive specific details for your selected property.brbrPet PolicybrPet fee: $50 per pet, per stay (for stays under 30 nights); $150 per pet, per month (for stays of 30 nights or longer).brOur member service team will promptly reach out and share all details prior to your arrival.

2

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2

Bath

4

Sleeps

$226.0

/ Nightly

Condo

Longboat Key - Bayport Beach & Tennis Club Condo

Longboat Key, Florida, United States

Longboat Key - Bayport Beach & Tennis Club condo. This 1,623 SQFT, 2 bedroom, 2 bathroom gives you the space, tranquility, and privacy to truly relax and embrace the exclusive and peaceful lifestyle that LBK provides. Surrounded by lush landscape and the best tennis courts on the island, the community of Bayport provides you with private deeded beach access, community swimming pool & spa, fitness center, and tennis courts. While already being an over sized, large 2/2 condo unit, it also features a shaded terrace patio in the back to enjoy the outdoors.

2

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2

Bath

6

Sleeps

$196.59

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Condo

Newly renovated two bedroom/two bathroom condo in LBK

Longboat Key, Florida, United States

Gorgeous coastal renovation, waterfront location, deeded beach, pet friendly and more. Enjoy this new, fully renovated two-bedroom, two-bath furnished bayfront condominium in Longboat's Pelican Harbour & Beach Club. Association amenities include private beach, tennis and pickleball courts, heated resort-style pool, clubhouse, and kayak launch. This condominium features include hurricane windows and doors, new air conditioner, engineered hardwood flooring, custom cabinetry, quartz tops, stainless appliances, induction cooking, built-in ovens, bar area with beverage refrigerator and a large center island, all opening to the great room and dining areas. Spacious primary suite features private bath with custom walk-in shower, dual vanity, built-in closets and water views. The guest suite, split from the primary, offers friends and family alike private space with a king-size bed and adjoining bath with a custom walk-in shower, as well. There is plenty of closet space and storage throughout, and an in-unit laundry with matching front-load HE washer and dryer. You'll even find brand new linens, towels, dishware, etc. included. Pelican's private beach is near the unit and offers stunning sunset and Gulf views, and miles of turquoise waters and crystal sands. You'll also appreciate the convenient mid-island location close to Bayfront Park, restaurants, shopping, places of worship, and easy access to St Armands, Sarasota and Anna Maria. Gorgeous coastal renovation, brand new furnishing, fantastic mid-island location, pet-friendly and one of the best amenity packages on the island.

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$301.58

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Condo

Direct gulf view!!!!

Longboat Key, Florida, United States

2 bedroom, 2 bath condo located directly on the Gulf of Mexico on beautiful Longboat Key, Florida!! Both condos sleep 4. The condo is fully furnished and includes a washer and dryer, free wi-fi, DVD player, covered parking, beach chairs and a beach umbrella. Both of our available condos are located on the first floor and have an outdoor patio facing the gulf with a table and chairs and a lounge chair. It’s an ideal location for those who love the outdoors! You'll find tasteful luxury and quiet pleasures will welcome you to this very plush island location. Whether you enjoy water sports, rollerblading, fishing, biking, tennis or golf, you are sure to find the perfect outdoor activity. A ten mile bike path that winds along the beautiful and scenic Gulf of Mexico Drive is a must for bike riders or rollerbladers! Longboat Key boasts two championship golf courses and you'll find dozens more in nearby Sarasota or Bradenton. If you enjoy shopping, you will love visiting Sarasota and St. Armands Circle.brbrIn addition to the advertised rate there is a $150.00 condo association application fee plus a 12% tax, a $125 cleaning fee, and a $1,000.00 damage deposit. Please note the application does ask for some personal information and we just encourage you to fill out what you are comfortable with. And you are welcome to send the application directly to the condo association. If they deny your application we will refund you all monies paid in full. brbrSorry but we do not allow pets unless they are authorized service animal or emotional support animal per the Florida law. The association does require forms filled out by a health care professional attesting to this. brbrDuring high season (January thru March) we do have a full three month minimum rental period. br

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$189.12

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Condo

Spectacular Sarasota Bay Views from all rooms

Longboat Key, Florida, United States

Seasonal Rental. Spectacular views of Sarasota Bay and the Gulf of Mexico from this island penthouse condo. Enjoy the majestic sunrise and sunset from the comfort of this beach home. Watch the manatees play while having your morning coffee on the Lanai. Only steps to the beautiful sandy beaches of Longboat Key. Background check fee assessed by HOA. This vacation home is fully equipped with flat screen TVs, WiFi, modern appliances, washer/ dryer in the unit, and beautiful furnishings. The spacious master suite features a King size bed, ensuite bath and large walkin closet. The 2nd bedroom has a queen bed. Both have panoramic views of the Bay with access to the lanai. This 4th floor penthouse condo in Windward Bay is perfect for those seeking an active lifestyle. Free use of a single / tandem kayak to enjoy fishing on the bay or simply paddling around the bird filled mangroves. Association Amenities include two marinas with rentable slips, kayak storage, almost 2 miles of walking and bike trails within the community, tennis court, pickle ball court, fitness center, two heated pools, saunas, on-site management, views of Sarasota Bay and deeded beach access directly across Gulf of Mexico Drive. 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, theatre, opera, ballet, symphony, art galleries, the Van Wezel Performing Arts Hall, Selby Gardens and of course the Ringling Museum.

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Sleeps

$325.95

/ Nightly

Condo

Can't Get Closer to the Beach Without Getting Your Feet Wet!

Longboat Key, Florida, United States

**Luxury Gulf-View Condo on Florida’s Most Exclusive Beach – Longboat Key** brbrWelcome to your slice of paradise on Florida’s most exclusive beach. This beautifully appointed 2-bedroom, 2-bath condo on Longboat Key offers unobstructed views of the Gulf of Mexico and is just steps from the wide powdery white sand beach and turquoise waters.brbrRelax and unwind in a spacious, coastal-inspired retreat featuring a large enclosed lanai—perfect for enjoying breathtaking sunsets over the Gulf. Inside, you’ll find everything you need for a comfortable stay, including a 65-inch flat-screen HDTV and thoughtfully designed living spaces.brbr**Highlights:**brbr• Unobstructed Gulf of Mexico viewsbr• Only steps to the beachbr• Large enclosed lanai for sunset viewingbr• 2 bedrooms / 2 full bathroomsbr• 65” HDTV and fully equipped living spacebr• Access to community pool, tennis and pickle ball courtsbrbr**Location & Lifestyle:**brbrLongboat Key is known for its manicured beauty, sugar-white beaches, and tranquil atmosphere. From your condo, enjoy sweeping views of both Sarasota Bay and the Gulf. The surrounding waters are home to dolphins, manatees, and vibrant marine life, while pelicans and osprey soar overhead.brbrWhether you’re shelling along the shoreline, biking scenic island paths, golfing at nearby courses, or dining at upscale waterfront restaurants, the possibilities are endless.brbr**Nearby Attractions:**brbr• St. Armands Circle shopping & fine diningbr• Downtown Sarasota arts & culturebr• World-class golf coursesbr• Day trips to Orlando & Disney (approx. 115 miles)brbr**Why You’ll Love It:**brbrThis condo offers the perfect blend of location, comfort, and exclusivity—making it ideal for a relaxing vacation, seasonal escape, or extended stay on Longboat Key.brbrBook your stay today and experience the beauty, serenity, and luxury of **Florida’s most exclusive beach**.brbrbrKeywords: condo,beach,exclusie,pickle,white,sand,tennis,pool,boat,dock,hdtv,wifi,entertainment,internet,scenic,sunset,picturesque,kitchen,porch,lanai,water,gulf,turtles,birds

2

Bed

2

Bath

4

Sleeps

$191.13

/ Nightly

Condo

Bayfront Escape- Beach Harbor Club F202

Longboat Key, Florida, United States

Bayfront Escape at Beach Harbor Club with Rooftop Deck for Stunning Sunsets, Dolphin & Manatee WatchingbrbrExperience the beauty of bayfront living on Longboat Key at this beautifully appointed 2-bedroom, 2-bath condo in the highly desirable Beach Harbor Club. This Longboat Key vacation rental offers breathtaking water views, resort-style amenities, and a peaceful coastal setting—perfect for seasonal renters, snowbirds, and guests seeking an extended Florida Gulf Coast getaway.brbrWake up to sparkling Sarasota Bay views in a bright and welcoming living space designed for comfort and relaxation. The open living and dining area features large windows that fill the condo with natural light while showcasing beautiful waterfront scenery. The fully equipped kitchen makes preparing meals easy, whether you're enjoying a leisurely breakfast before heading to the beach or hosting friends for dinner after a day of exploring.brbrThe spacious primary suite includes a queen bed, ensuite bath, and tranquil bayfront views, while the guest bedroom also features a comfortable queen bed—ideal for visiting family or friends during your Longboat Key seasonal rental stay.brbrRooftop Deck – A True Highlight of This Longboat Key RentalbrbrOne of the most unique features of this property is the community rooftop deck, offering panoramic views of both the Gulf of Mexico and Sarasota Bay. This elevated vantage point is the perfect place to:brbr• Watch spectacular Longboat Key sunsets over the Gulfbr• Enjoy morning coffee with sweeping waterfront viewsbr• Spot dolphins and manatees swimming in the baybr• Relax and unwind in a peaceful coastal settingbrbrThis rooftop experience adds exceptional value for guests searching for a waterfront condo on Longboat Key with memorable outdoor amenities.brbrBeach Harbor Club is known for its resort-style amenities and prime location. Guests enjoy private beach access, a heated swimming pool, fitness center, shuffleboard, BBQ grills, and a waterfront dock for kayaking, boating, or fishing—making this an ideal choice for travelers seeking a Longboat Key condo rental with beach access.brbrAccommodations: Two-bedroom, two full-bathbrBedding: 2 QueensbrView: Bay ViewbrMinimum Stay: 90 daysbrLocation: 3810 Gulf of Mexico Dr. F202, Longboat Key, FLbrPets: No Pets AllowedbrElevator: YesbrAmenities: Community Kayaks (deposit required), Private Beach Access, Heated Pool, Fitness Center, BBQ Grills, Community Washer & Dryer, Rooftop Deck AccessbrbrConveniently located, you are just minutes from the world-class shopping and dining of St. Armands Circle and the cultural attractions of Sarasota. Whether you're planning a relaxing winter retreat or an extended coastal escape, this bayfront Longboat Key condo delivers the perfect combination of comfort, location, and unforgettable scenery.

2

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2

Bath

4

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