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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
    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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    1 / 6
    4.5 of 5 stars (2) Very good
    Studio, 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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    About this property
    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 in a residential area. One block to the grocery and the trolley stops right in front to take you to St Armands... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 22, 2016
    How much we enjoyed our stay at Starfish #3. A nice place and great location. We really enjoyed "Harry and Izzy" as well as having that wonderful beach at our back door. It was...
    5 of 5 stars Reviewed January 3, 2016
    It's a nice place for a couple -- very comfortable and relaxing. The back door opens up directly onto the beach. Each morning we had breakfast out on the patio. During the...
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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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    !!!!SUMMER SPECIAL!!!! JULY & AUGUST 2016 - ONLY 1,000 USD/WEEK OR 1,750 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 boat dock and four... View all property information
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    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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    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
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    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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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Recently upgraded, second floor, Gulf front condo. Open concept kitchen, dining, living and family room with spectacular views of the Gulf. King size bed in Master bedroom with walk-in shower. Amenities include: flat screen televisions in den and both bedrooms, VCR/DVD and free high speed wireless... View all property information
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    Longboat Key, Florida 34228
    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 / 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*** $295/3 nights , $350/4 nights Monday to Friday July - September . 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 / 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 / 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 # 225 ** Ocean Front Special *** July 5 - 7 $195 for 2 nts , July 24 - 31 30% disc . This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual beach... 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 / 9
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    Location Information
    Longboat Key, Florida
    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 / 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
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    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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    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
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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 plan. 2 bedrooms, 2 full bathrooms, ceiling fans, full kitchen with stainless steel... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    This newly built waterfront home will take you to another place and time. Tucked away in native tropical vegetation perched on the Bays edge looking out to Longboat Pass, this home is the perfect retreat for a couple or small group. Modern, open floorpan with a Scandinavian feel boasts hardwood... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
    Location Information
    Longboat Key, Florida 34228
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Porch
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    ***Minimum 30 Day Rental*** Longboat key offers uncrowded beaches, great food and serene accommodations. Bayport Beach and Tennis Club is a beach to bay complex made up of 2 story buildings that offer privacy in a very serene and relaxing environment. This condo is a 2 bedroom 2 bath condo that is... 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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    About this property
    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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    637 Norton - Private canal home 4 Bedroom/ 3.5 Bath with private pool, maximum occupancy of 8 people. Live the Florida lifestyle in this beautiful, comfortable 4 bedroom, 3 bath private home located in the Sleepy Lagoon on the quaint end of Longboat key. This home sleeps 8 - 10 people. Offering... View all property information
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    Longboat Key, Florida
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Yard
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    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 / 24
    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
    1 / 70
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    ***ONLY ONE RENTAL PER MONTH, SO BOOK FAST TO SECURE YOUR SPOT!*** Known for tasteful luxury and manicured surroundings, Longboat Key is rich in gorgeous beaches, wildlife and upscale amenities. High-end boutiques and five-star restaurants make it an ideal destination for vacationers who like... View all property information
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    Longboat Key, Florida 34228
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Paradise is not lost. Beachplace is a private gated Gulf front community with 24 hour security located on the famous Longboat Key. Being steps away from the longest stretch of private beach on Longboat Key and 30 acres of manicured grounds makes Beachplace one of the island’s most beautiful Gulf... View all property information
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    Longboat Key, Florida
    1 / 24
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beach Castle Resort BC6 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. Beautiful Gulf View unit, all updated. Screened in lanai overlooking the gulf - wake up, take your coffee/tea and gaze out over the pristine waters of the gulf. Awaken each morning to the view from... View all property information
    Location Information
    Longboat Key, Florida
    3 of 5 stars Reviewed May 9, 2016
    Stayed in unit 6 of at Beach Castle Resort the week of 4th of July. It was a last minute vacation opportunity and this was one of a very few units available on Longboat Key. We...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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
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    Longboat Key, Florida 34228
    1 / 28
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    One bedroom one bath cottage all new beds, Linens, towels etc. Cottage available weekly or monthly in the Lovely North Longboat Key Village where resident peacocks visit daily. Sit out on your porch in the evening and relax or dine out at many of the water front restaurants. <BR><BR>Offered FULLY... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed January 26, 2016
    We really enjoyed our stay at this wonderful cottage. It is extremely well equipped and features everything you need for a great beach holiday, It is in a very quiet and nice...
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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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    1bed 1Bath Cottages Available Now For Summer Fun. Refurbished, new linens. Old Florida at it's best. Stroll or ride bike in one of the most quaint villages on the gulf coast of Florida. Keep an eye out for the Peacocks. One bedroom one bath cottage all new beds, Linens, towels etc. Cottage... View all property information
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    Longboat Key, Florida 34228
    4 of 5 stars Reviewed August 4, 2015
    We rented both the Luxury Log Cabin and the Tree House next door. Only complaints were in the Log Cabin - they need to put up drape/curtain in loft bedroom for those guests as...
    3 of 5 stars Reviewed June 30, 2015
    Cons: 1. In the picture of the kitchen, it shows a crock pot and salt/pepper shakers. Neither were provided, so don’t plan on a crock pot meal like I did! And bring your own...
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    All amenities including laundry. Grocery delivery available. Walking distance to private Longboat Key Beach, Durante Park (playground, nature trails, and mangroves) and fine dining and corner store. Condo is on the Sarasota Bay access canal, which leads to Gulf of Mexico. Ideal for boating,... 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
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 43
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    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 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Light, nicely decorated and well appointed condo in a small friendly two floor / 12 unit building located on bay side of Island and mere steps from private beach. Everything is provided for your stay. Located mid-island - a walk to nearby shops and terrific restaurants. Heated pool, fishing dock, &... 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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    **ONE WEEK MINIMUM RENTAL HOME** This casual beach home is just the right place to enjoy a laid-back, toes-in-the-sand vacation! Nestled on the shores of the Gulf of Mexico at the north end of Longboat Key, it's the perfect spot for relaxing days on the beach, followed by fabulous sunsets 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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    * 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 / 14
    5 of 5 stars (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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
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    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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    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
    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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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 26
    5 of 5 stars (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Beautifully decorated one bedroom condo directly on the beach. New kitchen with granite counter tops, and a 47in flat screen TV. Watch the sunset from your living room or porch, the sand is only 20 feet from your front door. Contact owner before booking View all property information
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    Longboat Key, Florida 33312
    5 of 5 stars Reviewed April 16, 2016
    We were so excited to have such a beautiful, clean and well equipped suite. Kim has done such a great job. The gorgeous quiet beach was fantastic and the view was fabulous. We...
    4 of 5 stars Reviewed May 6, 2014
    Stayed there for a week and found it close to perfect. Waking up in the morning and being blessed with dolphins swimming about 10 yards from the beach is bril! If you are...
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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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Roomy one story villa with views of Bayou , pool and steps to private beach. Private beach conservancy offers tennis, shuffleboard, bocci ball, cabanas, grills and private beach chairs. Large master suite with roomy walk in closet. Bonus small bedroom with twin bed and dresser and hall bath.... 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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    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
    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.