Vacation Rentals By Owner In Longboat Key, FL

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Wireless Internet access is available in the privacy of your individual unit, at the garden area or on the pool deck.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units.brbrbrbrUnit #254 Features: 1-bedroom, 1-bathroom unit in the Green Building with a direct pool view and a distant Gulf view from your private patio. brbrbrbrView: Pool/Gulf ViewbrbrbrbrBedding: 1 Queen, Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

1BR Beach Getaway – Silver Sands #254 by RVA

Longboat Key, Florida, United States

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Exceptional(77)

$509.84

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game on our putting green or relax on our beautiful beach with your favorite novel. Wireless Internet access is available in the privacy of your individual unit, at the garden area or on the pool deck.brbrLimited Membership Privileges: Guests of Silver Sands Gulf Beach Resort #250 will have temporary membership privileges at Cedars Tennis Resort located at 645 Cedars Court on Longboat Key. The limited temporary membership allows the guest access to fully-lit Har-Tru tennis and pickleball courts (after 1 p.m. daily and subject to availability), community bicycles and Jr. Olympic heated swimming pool. The guest will also have access to the community fitness center.brbrbrbrAccommodations: Silver Sands Gulf Beach Resort is a relaxing retreat located directly on the Gulf of Mexico on the northern-end of Longboat Key. Choose from our various unit styles including hotel rooms, one- and two-bedroom garden view units, and one- and two-bedroom beach front units. brbrbrbrUnit #250 Features: 1-bedroom, 1-bathroom unit in the Orange Building with direct Gulf Front views from your private patio.brbrbrbrView: Gulf Front ViewbrbrbrbrBedding: 1 King, Sleeper SofabrbrbrbrResort Features: On-Site Office, Wi-Fi Internet Access, Coin-Operated Washer/Dryer, Community Pool, Private Beach Access, Shuffleboard Courts, Putting Green, Private Lanai (certain units), Complimentary Parking, Designer Decorated Units, Fully-Equipped Kitchen or Kitchenette, BBQ Area

Gulf Views – Silver Sands #250, Longboat Key by RVA

Longboat Key, Florida, United States

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Sleeps

$343.49

Beautiful unit on the 3rd floor with pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit.brbrCome stay a month or more!brThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fi and Cable TVbr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.brbrYou are just moments from St Armand's Circle with all its top shopping and dining options. Easy access to the areas arts and cultural activities and moments from Sarasota Airport.

Partial Beach View 2 Bedroom Condo

Longboat Key, Florida, United States

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Exquisite beach and Gulf view unit on the 3rd floor of building 3. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. New owner has upgraded unit including tiling, furniture replacement, painting, new kitchen appliances, new linen, TV's and more. This condo also has new windows and doors. This is a new and bright condo ready for your beach adventure. Condo is located in the Gated Beachplace complex with pre-set chairs and umbrellas on the beach and a very amenity rich environment.brThis unit has two parking spaces. One covered and one outside, brbrCome stay a month or more!brThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fi and Cable TVbr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.brbrYou are just moments from St Armand's Circle with all its top shopping and dining options. Easy access to the areas arts and cultural activities and moments from Sarasota Airport.

Beachplace 3 - 302 by FGC

Longboat Key, Florida, United States

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Beautiful beachview unit on the 3rd floor with lake view and Gulf views. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit. This unit has large beds in both bedrooms. Great for 2 couples. Kitchen recently remodeled and all new windows and doors. brbrThe online system will only book 12 months out, so please call us directly if you wish to book further in advance.brbrOn the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Amenities include large community pool and exercise facility.brbrThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fibr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.brRental includes Cable tv, Wifi, parking, water and electric.br1 Month minimum requiredbrbrRRR-00583.2023

Beachplace 4 - 304 by FGC

Longboat Key, Florida, United States

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Rental located directly on a Canal with a boat lift available for use. This is a single family home that contains 2,192 sq ft and contains 3 bedrooms and 3 bathrooms and a private swimming pool. Dining room has views to the water. Canal connects directly to the Bay and the neighborhood is located on the southern end of Longboat Key, convenient to St Armand's Circle and Sarasota. Bring your boat as a lift is included. Come stay a month or more. Master bedroom has a King bed, second bedroom has 2 twin beds and third bedroom has a queen.brbrNo pool cagebrbrBring your boat - Boat dockage included. No trailer parking available. brbrDogs may be allowed but must be approved at the time of booking. brbrbrRRR-00602.2023

Private Vacation Home

581 Yardarm Lane by FGC

Longboat Key, Florida, United States

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$353.27

2 bedroom + Den and 3 bathrooms with views of the Beach of Longboat Key. Prestigious entrance to the Pierre through the lobby with a concierge doorman to great your guests as they arrive to visit. This unit offers 2 balconies to relax on and enjoy the view of the sunset or calm waters of the Gulf of Mexico. Beautifully appointed kitchen and living areas complement the modern features of the condo. You will feel right at home staying at the Pierre.

The Pierre 507 by FGC

Longboat Key, Florida, United States

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$180.12

This 2-bedroom, 2-bath condo offers stunning bayfront views and is located in the desirable Longboat Harbour community. Enjoy private beach access, a community pool, tennis and pickleball courts, and scenic walking paths along the canal. Close to top restaurants, shops, and St. Armands Circle, this is the perfect spot to experience the best of Sarasota.brExperience the epitome of coastal living in this beautifully appointed 2-bedroom, 2-bathroom condo, perfectly situated on the second floor in the highly sought-after Longboat Harbour community. This bayfront gem offers breathtaking views and private beach access just across Gulf of Mexico Drive, complete with a full beach pavilion for your convenience.brbrEnjoy seamless access to a range of amenities, including a community pool, tennis and pickleball courts, and scenic walking paths that meander along the canal—ideal for wildlife watching. Immerse yourself in the vibrant local scene with top-rated restaurants and boutique shops just moments away. Plus, you're only a short drive from the iconic St. Armands Circle and all the cultural delights Sarasota has to offer.brbrBook your stay with Florida Vacation Connection, the premier rental agent, and let us ensure you have an unforgettable experience in this stunning Longboat Harbour condo.brbrRRR - 00962.2024

Longboat Harbour Bay Front 2 BR / 2 BA by FVC

Longboat Key, Florida, United States

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$646.84

Welcome to Sanctuary B202 by FVC, your idyllic retreat nestled in the heart of Longboat Key. This stunning 3-bedroom, 3-bathroom residence offers a perfect blend of comfort and luxury, ideal for your next getaway. brbrStep inside to find a spacious, open-concept living area adorned with modern furnishings, perfect for unwinding after a day of exploration. The fully equipped kitchen features stainless steel appliances, granite countertops, and all the essentials you need to prepare delicious meals. brbrThe master bedroom boasts a plush king bed, an ensuite bathroom with a step-in shower, and a private balcony where you can savor breathtaking sunrises. Two additional guest bedrooms, each with a queen bed and ensuite bathrooms, provide ample space for family or friends. brbrEnjoy the convenience of a private entrance, free parking, and a private beach access with beach chairs and equipment storage. The property also features a communal heated pool, hot tub, and fitness center, ensuring you have everything you need for a relaxing stay.brbrLongboat Key offers a wealth of activities and attractions. Explore the pristine beaches, embark on a dolphin-watching cruise, or indulge in some retail therapy at the nearby shops and boutiques. Dining options abound, from casual cafes to fine dining restaurants, ensuring a delightful culinary experience.brbrWhether you're seeking adventure or relaxation, Sanctuary B202 by FVC promises an unforgettable stay. Book your perfect getaway today and create lasting memories in this beautiful coastal paradise.brbrLBK RRR-01198.2024

Luxury Beachside 3-BR Condo at The Sanctuary by FVC

Longboat Key, Florida, United States

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$158.9

FL Vacation Connection presents Salty Acres - a small, picturesque, beachfront community on Longboat Key. brbrThis unit has beautiful views of the Gulf of Mexico from the 2nd floor location. It has been recently updated with a new sectional sofa, fresh paint and new draperies. The kitchen features an open pass through breakfast bar, plus an eat-in area with a table and chairs. A comfortable dining room has seating for 4-6. Decorated in light colors and floral fabric, the living room features a matching sofa and loveseat, entertainment center with TV, DVD and VCR. For your convenience, wireless high speed internet is provided. Sliding glass doors lead to the lanai area. The spacious master suite has a King size bed plus a a new sleep sofa for an overflow of family. The guest bedroom has two twin beds. brbrPlease note that this is a second floor unit with one small flight of stairs and one regular flight of stairs.brbrTown of Longboat Key RRR.00189.2025

Beachfront 2BR / 2 BA at Salty Acres on LBK by FVC

Longboat Key, Florida, United States

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$160.73

Players Club is a beachfront property located at the south end of Longboat Key. It is well known as an active tennis community with 4 har tru courts. If tennis is not your thing, the community swimming pool awaits you. There is a fitness center as well. And, the beautiful beach is steps away.brbrEnjoy the updated eat-in kitchen with an open plan overlooking the dining room and living room, out to the turquoise waters of the Gulf of Mexico. Comfortably furnished throughout including 3 TVs; one in the living area and one in each bedroom. WiFi is included. brbrThe covered patio is a perfect spot to enjoy the sights and sounds of the Gulf and coastal nature. Enjoy relaxing outdoors or dining alfresco morning, noon or night. Come enjoy the Players Club on Longboat Key and be as active or relaxed as you please!brTown of Longboat Key RRR-00193.2023

Beachfront 2BR 2 BA at Players Club by FVC

Longboat Key, Florida, United States

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Wonderful location on Longboat Key. Located mid-Key, just a short distance north of Publix, right on the beach. Longboat Yacht and Tennis is a small complex with a nice swimming pool and views that can't be beat. brbrFL Vacation Connection is proud to present this beautifully remodeled property. The new kitchen has stainless steel appliances and granite counters. All new furnishings and wonderfully appointed; the decor is sure to please. Great floor plan; nearly all rooms have sliding glass doors leading to an open balcony and showcasing the beautiful view. brbrCome, relax and enjoy a piece of paradise.brbrTown of LBK RRR-001964.2023

Mark III Beachfront Condo by FVC

Longboat Key, Florida, United States

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$242.33

FL Vacation Connection welcomes you to Casa Blanca. From the moment you step inside you’ll know that this is the perfect place for a family vacation. Just off the entrance foyer are two Bedrooms, each with two twin beds and a shared Bath. A perfect kid zone!br brKeep walking and you’ll find yourself in the Great Room where comfortable sofas and a flat screen TV greet you. In this open-concept room you’ll enjoy spending time watching movies and playing games in the company of friends and family. br brThere are counter height barstools in the Kitchen so you can enjoy a good conversation while cooking your favorite meals. You want to barbecue You’ll find a gas grill in the screened in pool area. And when it’s dinnertime, you have your choice of eating in the indoor Dining Room or stepping outside and enjoying your meal in the covered Lanai. Just make sure everyone is out of the pool on time.br brIf you want to enjoy the canal, just step out back and walk down to the dock where you can swing your legs over the water and breathe in the air. Bring a fishing pole if you’d like to catch some dinner, or bring a chair if you’d like relax to the gently lapping water of the canal.br brEverything you need is right here, but if you’re feeling the need to spread your wings, the beautiful walking beach is less than a half a mile away.brbrNO TRAILERS/BOAT TRAILERS OF ANY TYPE ALLOWED ON PREMISES. PLEASE CALL THE OFFICE FOR A SOLUTION IF IT IS NECESSARY TO HAVE ONE DURING YOUR STAY!brbrTown of Longboat Key RRR.00197.2023

Private Vacation Home

Waterfront Pool Home by FVC

Longboat Key, Florida, United States

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Penthouse Paradise on Longboat Key – Beachfront Luxury Steps from the St. RegisbrbrExperience unparalleled coastal elegance in this stunning penthouse-level retreat on the pristine shores of Longboat Key. This exquisite three-bedroom, two-bath beachfront condo offers breathtaking, unobstructed views of the Gulf of Mexico from every room, ensuring a luxurious escape where the beauty of the ocean is always within sight. Professionally managed by Florida Vacation Connection, this exclusive residence promises a seamless and stress-free stay.brbrFrom the moment you enter, you’ll be captivated by the soaring ceilings, abundant natural light, and sophisticated coastal design. Recent upgrades include custom built-ins, updated flooring, elegant crown molding, designer lighting, and beautifully renovated bathrooms. The chef-inspired kitchen is a masterpiece, boasting stainless steel appliances, granite countertops, a spacious breakfast bar, and a built-in wine rack with a cooler, perfect for entertaining.brbrStep onto the screen-enclosed lanai and soak in the gentle Gulf breezes and breathtaking sunsets as you overlook the beach and resort-style community of Seaplace. Whether you’re sipping your morning coffee or toasting to another perfect day in paradise, this is the ideal spot to relax and unwind.brbrThis beachfront haven also comes with a rare covered parking space that accommodates up to four vehicles, making it effortless to come and go as you please. However, you may find little reason to drive—this prime location is just steps from the brand-new, ultra-luxurious St. Regis Resort, where you can indulge in world-class dining, spa treatments, and upscale amenities.brbrAs part of the vibrant Seaplace community, guests will enjoy access to an impressive array of resort-style amenities, including:brbrA manned guard gate for security and peace of mindbrA clubhouse with a game room, library, and social spacesbrA state-of-the-art fitness center with a saunabrTennis courts, walking trails, and a playgroundbrTwo heated swimming pools and a spa for endless relaxationbrA beachfront deck with barbecue stations and sitting areas, perfect for gathering with friends and familybrWith the soft, sugar-white sands of Longboat Key right at your doorstep, and St. Armands Circle just minutes away, this penthouse offers the perfect balance of tranquility and excitement. Whether you’re spending your days lounging by the beach, exploring local boutiques, or dining at some of Florida’s finest restaurants, this is the ultimate getaway for relaxation, adventure, and effortless coastal luxury.brbrBook your stay in this spectacular beachfront retreat today!brTown of Longboat Key RRR-00146.2023

SeaPlace M2 512 by FVC

Longboat Key, Florida, United States

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$330.2

Summary:brExperience refined coastal living in this beautifully renovated ground-floor 1-bedroom condo on Longboat Key. Enjoy direct beach access, panoramic Gulf views, and upscale interiors with a king suite, modern kitchen, and queen sleeper sofa. Relax on your private patio, unwind at the heated pool, and explore nearby fine dining and luxury activities. Perfect for seasonal guests seeking elegance, comfort, and convenience. Minimum 1-month rental. $125 application fee and association approval required.brRRR-00359.2023brbrGuest Access:brPrivate entrance. Keyless lock system. Open off street parking.brbrThe Neighborhood:brLocated on the northern region of Longboat Key, Whitney Beach III is located beachfront and offers low rise 2 story buildings. Off-street parking, tennis court, beachfront pool all enhance the island lifestyle.

Gulffront Elegance | Renovated 1BR Condo w/ Direct Beach Access & Sunset Views

Longboat Key, Florida, United States

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$259.23

Beautiful beachfront unit on the 5th floor with lake view and partial Gulf. Beautifully appointed 3 bedroom, 2 bath unit with a real feel of home. King Bed in Master, Queen Bed in 2nd Bedroom and 2 twins in 3rd bedroom.brbrRRR-00586.2023brbrCome stay a month or more!brThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fi and Cable TVbr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.brbrYou are just moments from St Armand's Circle with all its top shopping and dining options. Easy access to the areas arts and cultural activities and moments from Sarasota Airport.

Beachplace 4 - 505 (3BR) by FGC

Longboat Key, Florida, United States

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$369.97

Beautiful beachfront unit on the 5th floor with pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades.brbrThe well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fibr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.brbrNew windows/doors installed in condo ( not yet in pictures).brbrThis rental is managed by FGC - Florida Gulf Coast Vacation Rentals

Beachplace 3 - 503 by FGC

Longboat Key, Florida, United States

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Sleeps

$319.12

**brbrWelcome to our beachfront Longboat Key condo!brbrIf you’re looking for a special two-bedroom, two-bathroom retreat with beautiful waterfront gulf and sunset views, white sandy beach, palm trees and resort style community pool, this may be the place for you! We invite you to look at our photos of Beachplace 8-204 and see for yourself.brbrBy the way, the unit is located on thirty-one beautifully landscaped acres on the second floor of Building 8 at Beachplace. The condo’s second floor location feels intimate to the gulf and beach. And the pool and lush grounds provide added attractions. Two parking spaces (one covered and one outside) are also available for use.brbr.The well-maintained and gorgeous grounds include the following amenities:br • 24 hour manned guard gate.br • Private beach access with chairs and umbrellas includedbr • Wi-Fibr • Lighted tennis courtsbr • Heated pool and hot tubbr • Two state of the art fitness centersbr • Air conditioned clubhousebr • BBQ gas grills by the pool.

Full Beach View 2 Bedroom Condo

Longboat Key, Florida, United States

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Bath

Sleeps

$227.98