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Condos and Beach Rentals in Longboat Key, FL

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    Travelers to Longboat Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 7
    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 14
    4 of 5 stars (6) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 7
    5 of 5 stars (9) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 11
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Longboat Key Bargain on the beach. Our cozy get away on the beach is a favorite of many guests who enjoy the quiet beachfront. Just a simple beach hideaway for your next quiet stay at the beach It's neat studio apartment with patio and sandy beach at your door. The full size galley kitchen... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed March 12, 2016
    The place was wonderful - right on the beach - walk out the door with no need for the car! The unit was very clean and modern, and the owners even provided many of the accessories...
    5 of 5 stars Reviewed April 18, 2015
    This is just such a quite and relaxing place to stay. The beds are wonderful and you are provided with lots of fresh and soft towels. No elevators to deal with or noisy...
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    1 / 6
    4.5 of 5 stars (3) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 1 week ago
    Our first time to Longboat Key & it won't be our last!! The gulf is beautiful & coming from NC & trips to the Atlantic we are sold on the gulf coast beaches. Couldn't say enough...
    5 of 5 stars Reviewed April 24, 2015
    Lovely, well appointed, spotlessly clean beach house with tasteful decor and everything to make our stay comfortable and relaxed. Everything tastefully and thoughtfully done...
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    1 / 23
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    THE BEACH ON LONGBOAT KEY - One Bedroom Gulf Front Condo **Ocean Front Special**460/4 nts , $390/3 nts ** 9/13 - 10/7 . This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. A heated... View all property information
    Location Information
    Longboat Key, Florida 34231
    5 of 5 stars Reviewed April 12, 2016
    The unit is kind of small, but the private balcony made it! Wonderful view, private beach, and the fact that the complex is only 14 units made for a very intimate experience...
    5 of 5 stars Reviewed December 29, 2015
    We thoroughly enjoyed our time in your beautiful condo on Longboat Key. The weather was perfect and the condo was absolutely lovely. You’ve done a beautiful job decorating – we...
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    1 / 23
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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    About this property
    !!!!END OF SUMMER SPECIAL!!!! AUGUST 13 TILL SEPTEMBER 30, 2016 - ONLY 800 USD/WEEK OR 1,400 USD FOR 2 WEEKS Feel at home in this spacious waterfront condominium on Longboat Key with luxurious amenities, including heated pool and hot tub with views of the Sarasota Bay, tropical gardens, private... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 9, 2015
    All 'first" for us. First time on Longboat Key, first time at spring training and first time using Tripadvisor/Flipkey. And the property - first rate : ). The location was great...
    5 of 5 stars Reviewed October 15, 2014
    The condo was spotless and well equipped with all of our vacation needs. The rooms are spacious and the view is stunning. We will never stay anywhere else when we go to Florida...
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    1 / 17
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This beautifully appointed spacious 1 BR/1BA is recently renovated and with new furniture, tile flooring, and kitchen upgrades. Enjoy the 180 degree view of the horizon over the beach and the Gulf of Mexico with incredible sunsets. SeaHorse Beach Resort consistently ranks at the top of the... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed June 1, 2016
    We enjoyed our stay at the Seahorse Beach Resort and this unit was very nice. Everything is as pictured and laid out nicely. There were only 2 drawbacks. 1) The balconies are...
    4 of 5 stars Reviewed February 17, 2016
    We enjoyed this unit with the great views of the Gulf and sandy beaches!! There is a heated pool and the grounds and rooms are immaculate. New towels arrive each day and you...
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    1 / 18
    4.5 of 5 stars (2) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    ** OCEAN FRONT SPECIAL** $350/4 nts , $290/3 nts , $198/2 nts ** Sep 5-9 , Sep 12-15 , Sep 18-23 . This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo,... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed March 18, 2016
    We stayed at this unit for two weeks and found it an ideal place to stay overlooking the Gulf of Mexico on Longboat Key. The studio unit is cozy, but did not feel cramped with two...
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    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Private Indoor Pool
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    About this property
    Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' This beachfront resort is set on beautiful white sand beaches that meet the beautiful turquoise waters of the Gulf of Mexico. Resort with golf courses, 6 restaurants, tennis courts, spa, and deep water marina. Rate... View all property information
    Location Information
    Longboat Key, Florida 34228
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    1 / 18
    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Outrigger Resort is a quaint 10 unit complex. This unit is equipted with very comfortable furniture and all your needed appliances and accessories. Included in the kitchen is stove, refrigerator, toaster, coffee pot, etc., including all necessary utensils. The unit is designed with front... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed May 9, 2016
    We needed three rooms with three bathrooms. There was one couple with a toddler, one couple and one adult. The unit was clean and spacious. The kitchen could have been better...
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
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    About this property
    $$$ last minute rate $175 for a 5 nights stay between August 20 and September 2, 2016 $$$ Groundfloor Beachfront! From large living and dining area with open kitchen just step outside to your private patio and walk right out to the BEACH (25 seconds!) Magnificent condo 1100 sqft with open floor... View all property information
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    Longboat Key, Florida 34228
    1 / 18
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short walk (200 meters) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing golden sunsets. Located in the prestigious yet... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed August 10, 2015
    What a Villa, one of the best I have had the pleasure of staying in during my 15th visit to Florida. Many mod cons, some a little too modern for me, so that's where your teenage...
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    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Spacious, bright Bayside PET-FRIENDLY town home with partial Bay view and lush tropical landscaping. Unit has Full Kitchen, 2 LARGE BEDROOMS and 2 1/2 BATHS. Enjoy the fishing pier, large pool, tiki bar/restaurant. Come enjoy our Tropical Paradise! First level is extended parking garage. Second... View all property information
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    Longboat Key, Florida 34228
    1 / 9
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • x
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    About this property
    Beautiful 2 bedroom condo for rent by owner on Sand Cay beach. Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you need to have an amazing vacation. Please read our reviews, you won't be dissapointed! The condo is unit 208 at the... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed June 29, 2015
    I had to go to a work-related meeting in nearby Parrish, FL so I decided to rent a beach condo for a few days in order to mix work with leisure. I was traveling with my spouse...
    5 of 5 stars Reviewed May 2, 2014
    We three enjoyed four days in late April. Kitchen has every spatula know to mankind, among other tools. Balcony table nicely shaded in the afternoon with sun lounger out in the...
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    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Yard
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    About this property
    The cutest most afforable 3 BR Cottage Available 640 Broadway "The Cottage" Beautiful Longbeach Village! Gulf is 4 blocks and Bay is 2 blocks Bring your dog and invite your grandkids to stay over for the holidays. Extra grandkids coming to stay no problem? Three bedroom cottage available... View all property information
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    Longboat Key, Florida 34228
    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Comfortable Turn-Key Tropical Home is just a two-minute walk to the private sandy white beaches and dazzling blue waters of North Longboat Key. There is ten miles of sidewalks for your enjoyment to bike, jog, or walk as well as direct access from your backyard to Durante Park, a gorgeous Nature... View all property information
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    Longboat Key, Florida 34228
    1 / 43
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Directly across the street from this community is the beautiful gulf beach with white sand. Grocery shopping is less than a mile away; St. Armand's Circle with its many shops and restaurants is a 10 minute ride. A 15 minute ride will bring you to the cultural center of Florida, Sarasota, where... View all property information
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    Longboat Key, Florida 34228
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Beautiful, spacious 2/2 condo on Longboat Key available for 2016 season! Newly remodeled with designer kitchen, high-end appliances, and modern furnishings. Completely turnkey stocked with all essentials. Condo offers canal and bay views. Washer/dryer in unit. Community features three pools,... View all property information
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    Longboat Key, Florida 34228
    1 / 52
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Nestled among majestic palms and tropical landscaping, this Country Club Shores home is situated on a deep sailboat water with 113 feet of waterfront, and offers outstanding boating opportunities - all just two houses away from Sarasota Bay! Southern exposure on the canal side provides year-round... View all property information
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    Longboat Key, Florida 34228
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    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Pet friendly, Unique Bungalow Canal Home on the North End of Longboat Key. Unique Bungalow Canal Home on the North End of Longboat Key. QUICK WALK TO THE BEACH ! If you have been putting off writing the next great American novel due to the lack of a peaceful setting then this quaint canal home... View all property information
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    Longboat Key, Florida 34228
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Holiday paradise on the stunning Florida west coast on the island of Longboat Key. Stunning, elegant and luxurious complex. For selfcatering there is the kitchen with all necessities and modern devices. Of course, there is a washing machine and dryer avialable. First-class furnishing. Safe and... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    We are in the process of expensive renovation. Be first to rent it. Unit photo coming soon. Our 2 bedroom, 2 bath 1235 Sq.Ft unit is elevated to the 7th floor level, with an elongated terrace that provides partial bay views. Enjoy a partial view of the gulf from the master suite with a large... View all property information
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    Longboat Key, Florida 34228
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Beautifully furnished 1 bedroom/1 bath condo overlooking the Gulf of Mexico. Stroll for miles on the white sandy beaches of Beautiful Longboat Key or just relax and enjoy the sunsets View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Florida's SeaHorse Beach Resort on Longboat Key is located on the white sand beaches of the Gulf of Mexico. From the moment you arrive, the friendly and professional staff will welcome you to this Premier property where you can experience a panoramic view of the Gulf from your suite, or while... View all property information
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    Longboat Key, Florida 34228
    1 / 43
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    At our beautiful low-rise resort, located directly on the beach, our two-bedroom condominium is fifty paces from the pool and a private beach of soft white sand. 15F in popular Casa del Mar provides a spacious living room/home theatre (46 inch plasma TV & BlueRay Player), vaulted ceilings, and a... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed March 19, 2015
    Casa Del Mar is located in a beautiful part of Long Boat Key. The beach is beautiful and F15 condo was only steps away from the beach. There were plenty of lounge chairs on the...
    5 of 5 stars Reviewed July 4, 2014
    This is the first time we stayed at this property, and it was amazing !!! It was everything we were told it would be. Our unit had updated appliances, a TV in every room, a brand...
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Unit 2F is a corner unit on the 2nd fl overlooking Pool,Beach,Gulf and beautiful Sunsets. 1750 sq ft W/2bd,2ba,W/Murphy beds and sofa bed. Fully furnish,W/3TV,50" is in the Family rm., W/D,Cable,Computer,WiFi,Telephone,Tennis ct,Exercise rm and Library. Across st. from Publix grocery store.... View all property information
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    Longboat Key, Florida 34228
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    LOCATION, LOCATION, LOCATION! Beautiful view of Sarasota Bay with private beach access just across the street. Newly renovated open kitchen and breakfast bar with seating for three, upgraded stainless appliances, and quartz countertops. Entire unit is freshly painted and immaculate with new tile... View all property information
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    Longboat Key, Florida 34228
    1 / 24
    5 of 5 stars (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    About this property
    We offer 2 beautiful, completely renovated in October 2015 1 Bedroom / 1 Bath apartments in the Beachcomber condo. Unit 303 and 401 The guest will pay directly to condo management, this will be the most secure way of payment. See our condo website:AwayToParadise. com Welcome to the Longboat... View all property information
    Location Information
    Longboat Key, Florida 10312
    5 of 5 stars Reviewed September 22, 2014
    If you think that Florida off-season cannot be enjoyable, think again! We have just spent 2 weeks in September, stayed in #303 and had a fabulous vacation. Below are some...
    5 of 5 stars Reviewed August 20, 2014
    It was the best vacation in last 20 years! Property location was great, just a few steps away from the beach and nice swimming pool. Unit was very clean, newly renovated...
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    1 / 14
    5 of 5 stars (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Balcony
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    • x
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    About this property
    NATURAL BEAUTY of Longboat Key RIGHT ON THE BEACH PANORAMIC 2ND FLOOR BALCONY VIEWS Our Studio condo is right on the beach with magnificent panoramic views from its second floor balcony position. ENJOY THE BEACH FROM YOUR BED, LIVING, DINING AND KITCHEN! Our studio sleeps 3 with new in 2016... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed January 20, 2016
    My husband and I stayed 2 nights at this mid-key studio condo. It has everything you need and the beach front location is amazing. The property is a former motel that has been...
    5 of 5 stars Reviewed December 24, 2015
    Great place to stay, right on the ocean. Everything was clean and well maintained. The kitchen is modern and provides plenty of pots and pans to use. It feels private and cozy...
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    1 / 41
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Available for 3 MONTH MINIMUM rental with approval from condo association. Beautiful beach front condo located just 1.5 miles from St. Armand's Circle. Very upscale and beach feels very private. Pool, spa, and deck newly renovated. We have 24 hour, 7 days a week, guard gated community and... View all property information
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    Longboat Key, Florida 34228
    1 / 10
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    == Up to 25% discount on the regular resort rate == Special rates and discounts are available depending on time and length of stay. Beautiful 3rd floor 2BR/2BR unit #309, overlooking pool, in Sand Cay Beach Resort on the exclusive island of Longboat Key. South facing balcony. Striking views... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed July 14, 2015
    This was my first stay at Sand Cay Beach Resort and I can't say enough positive things about my experience. I have been to Longboat Key on several occasions and was excited to be...
    5 of 5 stars Reviewed June 22, 2015
    My wife and I stayed at the resort for one week in June 2015. I so wish we'd booked for 2 weeks. The apartment was lovely. No faults from us on the apartment, the pool area or the...
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Perfect holiday apartment that is continually renovated. Building was completely renewed in 2008. With 103 sq. m. and balcony, accommodation for up to 5. With all imaginable furnishing, e.g. full HD TV, free Pay TV in a great quality in every room, CD stereo system, Blu Ray DVD, High Speed... View all property information
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    Longboat Key, Florida
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The perfect island getaway, located on the southern tip of Longboat Key with a beautiful beach and pool area. This deluxe unit features approximately 1700 square feet with a 52' long, open beachfront lanai. The views cannot be beat! The beach is great and the pool and hot tub inviting too! The... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    SEA PINES This rarely available premier oceanfront location has one of the best views on Longboat Key looking out over the low dunes to the Gulf of Mexico where you can see the dolphins play, and the most amazing sunsets you’ll see anywhere. Quiet and serene with magnificent views, yet only a ten... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Million dollar view! Beautiful waterfront bay penthouse condo. Gorgeous panoramic views of Sarasota Bay and downtown Sarasota in this Windward Bay award winning condo complex! This condo has a bay view from every room, makes you feel like you are on a cruise. Starting April 2016 this condo is... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Welcoming, distinctive, fully furnished 2 bedroom, 2 bathroom condo in a verdant, tropical environment.<BR>• Very private and quiet first floor, 1600 ft. unit with lush garden views.<BR>• Master suite with office niche, king size bed, walk-in closet and double sinks in bathroom.<BR>• Guest... View all property information
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    Longboat Key, Florida 34228
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Lovely completely new fully equipped 3 bedroom beach cottage beautifully decorated with lush landscaping and outdoor lanai for dining and relaxing. Master bedroom, 2 other bedrooms, and 2 full baths plus lanai dining area. Quiet upscale residential neighborhood. Two minute walk to a quiet clean... View all property information
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    Longboat Key, Florida 34228
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Ground floor Condo with two steps that lead out the back lanai to the white sands of Longboat Key. You can't get any closer to the beach than in this unit. The private beaches out the back door offer miles of shell collecting, sandcastle making, snorkleing, and dolphin sightings. Silver Sands... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ONE MONTH MINIMUM RENTALS ONLY. NO WEEKLY RENTALS. ONE OF LONGBOAT KEY'S BEST KEPT SECRETS! Longbeach is located at the north end of the island, right on the Gulf of Mexico. This quiet community offers a pool and two tennis courts. This charming 2nd floor walk-up has been lovingly furnished... View all property information
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    Longboat Key, Florida 34228
    1 / 44
    4 of 5 stars (1) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    This spacious 5 bedroom villa is situated directly on the beautiful white sand beaches of Longboat Key. Offering a large outdoor private heated swimming pool and glorious views of the Gulf of Mexico from almost every corner, fully-equipped gourmet kitchen, fireplace, BBQ, and much more - it is your... View all property information
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    Longboat Key, Florida 34228
    4 of 5 stars Reviewed April 27, 2015
    I have had my eye on this house for 2 years now. Boy am I glad that I finally pulled the trigger and decided to stay here. Traveled with my wife, two children ages 2&4 and...
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Located near the historic town of Longboat at the north end of Longboat Key, this Key West-style home is located less than 150 yards from Whitney Beach and the Gulf of Mexico. One of 16 unique homes built by famed architect Frank Folsom Smith, on property formerly owned by the long-time resident,... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beach Castle Resort BC9 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. Offering a beautiful view of the gulf, but more economical than the other Gulffront condominiums at the Beach Castle Resort, the owners have spared no expense in renovating this condo.BEautifully... View all property information
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    Longboat Key, Florida
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    * CONDE NAST VOTED LONGBOAT KEY THE SECOND BEST ISLAND DESTINATION IN NORTH AMERICA * Located on fabulous Longboat Key approximately 3 miles south of Anna Maria island, 6 miles north of Armand's Circle at Windward Bay.This 27 acre condominium complex situated between the Gulf Of Mexico and the... View all property information
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    Longboat Key, Florida 34228
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    A special address on the Gulf of Mexico beach at the very north end of Longboat Key overlooking a bird sanctuary with views of the sea, sky and our extraordinary sunsets. One of nine contemporary townhomes designed by noted architect Tim Seibert (Sarasota School of Design), this stunning home is... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Set on a 30 acre private island a few hundred yards off North Longboat Key, this new water front home (completed in 2012) will provide an island vacation experience for you and your family like no other. The house has 2 bedrooms, an outside sleeping porch/bunk bed, along with 2 1/2 bathrooms and an... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Welcome to Longboat Key! This 2 bedroom one bath ground floor condo offers a full kitchen, with open living and dining area. There is a enclosed patio opening to the community pool. Covert Condominiums are located on the northern part of Long Boat Key on Sarasota Bay. There is deeded beach access... View all property information
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    Longboat Key, Florida 34228
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    6 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    Looking for tropical seclusion on a private island? Gorgeous sunsets with blue, blue waters? If so, then look no further. Nestled among the lush vegetation, your private Island Polynesian beach house awaits your arrival! Accessible only by boat,this getaway assures you complete privacy and... View all property information
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    Longboat Key, Florida 34228
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' This beachfront resort is set on beautiful white sand beaches that meet the sparkling, turquoise waters of the Gulf of Mexico. This is the perfect location for catching the warm Florida sun, swimming, or walking the... View all property information
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    Longboat Key, Florida 34228
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This exclusive beach house is located on the waters edge, directly on the Gulf of Mexico on prestigious Longboat Key. When you open the back door, walk out onto the pristine private beach and into the warm waters of the Gulf. This modern luxury property is newly renovated and has all the amenities,... View all property information
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    Longboat Key, Florida 34228
    Beachfront condos and bayside villas – your vacation rental on Longboat Key

    Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.

    Longboat Key - the upscale coastal vacation destination

    This gorgeous Florida key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. The aristocratic heritage of the St. Armand and Ringling families resonates through quiet gardens and plush Palm Beach-style shopping. Umbrella-draped cafes and handsome restaurants offer exceptional European fare and inventive coastal specialties. Work off that decadent dessert with a stroll around the circle for leather, jewelry, resort wear and art gallery browsing.

    Cultural treasures along Sarasota Bay

    Venture just across the bridge over Sarasota Bay for unrivalled cultural treats. The Ringling circus family bequeathed an elegant legacy of art and architecture. The estate includes the acclaimed John and Mable Ringling Museum of Art, the family’s winter Ca’ d’Zan mansion – a Venetian Gothic masterpiece - the Circus Museum and historic Asolo Repertory Theater. With elegant gardens and terraces spread over 20 bayside acres, the complex provides hours of enjoyment.

    Waterfront dining

    Beyond the eclectic mix of St. Armand Circle restaurants, you’ll want to sample excellent bay front restaurants. The Dry Dock is a favorite of locals and visitors alike, with waterside dining under coconut palms or indoor seating with the same exceptional views. Boasting ultra fresh grouper sandwiches, char-grilled burgers and a host of pasta and chicken selections, the Dry Dock grill is a casual dining treat. Diners arrive by car or boat to enjoy Mar Vista Dockside Restaurant and Pub in the historic village at the North end of the key. With quaint indoor or outdoor dining and spectacular views, try steamer pots of fresh seafood or exotic scallop and crab dishes that wash down quite well with islander mojitos, margaritas and other such flavorful concoctions. Land lovers can choose from the number of chicken, steak and pork dishes.

    Visitor reviews aid vacation rental selection

    You’ll have no trouble knowing what to expect, as you search for the just-right villa or condo rental. Our unbiased visitor reviews offer clear descriptions and candid evaluations, so you can feel confident in your choice.