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Cheap Longboat Key Holiday Homes

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    Travellers to Longboat Key are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    25 Matching Rentals in Longboat KeyView all 102 rentals
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    LONGBOAT KEY - Beautiful Gulf to Bay. Bayport Beach and Tennis Club is a rare find. This award winning, amenity-rich community at sea’s edge is situated in the middle of Longboat Key. A popular residential enclave of 136 homes on 27 acres of picturesque gardens. Bayport is bordered by the Gulf of...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Balcony
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    Pet friendly
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    Smoking allowed
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    SUMMER- FURNISHED- 2 bedroom/ 1.5 bathroom unit is ready to go! Completely turn key, with bicycles,kayak and beach chairs! Amazing pool right on the Sarasota Bay! Great Kayaking right on the property! Private beach access on the Gulf of Mexico drive. The house has been totally remodeled with...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Pet Friendly on Longboat Key1 / 25
    (27)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Washer
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    Pet friendly
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    Reviewed 23 July 2018
    Really enjoyed our stay at Longboat. Great beach and great location. Really liked the condo, updated and clean, kids loved it. Will be back!
    Reviewed 22 July 2018
    The condo offered many extras including a blender and a food processor. Even though we did not use it, but it was nice to have for someone staying more than a week. We enjoyed...
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    About this property
    ****Please go to longboatbeachcom .**** for more information. I will email you a quote from my booking program. Condo was updated July 2016, so pictures are current. Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit. Best...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Why stay with us? Sleeps 2 and small children. 1 bed, 1 Bath Cottages. One bedroom and 3 chairs. Dining table for 4 and outside patio for 4. We just update our cottage with New Queen bed, Linens, towels etc. We offer a full form mattress for children. Cottage available weekly or monthly in the...
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    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beachfront Unit 4, Cozy Getaway for two1 / 11
    (10)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    Pet friendly
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    Reviewed 1 July 2018
    The location couldn’t be more perfect. Quiet and secluded beach. Your next door neighbors are locally owned beach houses so you won’t find the high rise hotels. The details of...
    Reviewed 1 May 2018
    Wonderful vacation. Everything was as good or better than expected. The beach was beautiful.I would recommend this place to anyone.
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Village of Longboat Key, 1 BR & 1 BA Comfortable Cottage Very Clean1 / 15
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed 4 August 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...
    Reviewed 1 July 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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    About this property
    Orchard is a Private Cottage. The garage is shared area, washer and dryer, beach chairs and 3 bikes for you to use. You have outside fire pit and lounge chairs. Housekeeping is off-site. Lawn service arrives in the am on Friday's The very quiet area in the North Village of Longboat Key, Fla. Enjoy...
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    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Smoking allowed
    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,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    ** OCEAN FRONT DLX STUDIO - SPECIAL FROM $99/NIGHT **1 / 27
    (4)Very good
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 April 2018
    Location and proximity to the beach was great. The minuses were that the pool was often dirty with dead bugs. Also would be nice if unit had a screen door. Other units did...
    Reviewed 19 March 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...
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    About this property
    ** OCEAN FRONT DLX STUDIO - SPECIAL FROM $99/NIGHT ** **SPECIAL MARCH 3-10 FOR $995 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    Whitney Beach 1451 / 28
    (1)Terrible
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Terrace
    • Balcony
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
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    Whitney Beach 145 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 4 people. Community pool. Distance to the Beach: 500 ft. Enjoy a relaxing holiday in this lovely two bedroom, two bath ground floor unit at popular Whitney Beach, nestled at the north end of Longboat Key. Located...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beachfront Longboat Key Studio #11 / 6
    (7)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Ocean Views
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    Pet friendly
    Kid friendly
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    Reviewed 11 July 2018
    Studio #1 was very clean. It was perfect for my wife & I. We loved walking out the door & on being on the beach. It was just a few steps to the ocean. The beach was...
    Reviewed 11 April 2017
    Our second visit, stayed at this place again and will continue to do so. Everything you need is there. Always clean, right at beach and close to great places to eat. If you want...
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Little Gull is the perfect resort for complete relaxation in this lovely cottage on Longboat Key. We are offering week 37 of this timeshare. (Sept 14-21) Unit 10 is on the Bayside is fully equipped; has a four poster beds and wood burning fireplace. You won't find another resort quite like this...
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    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    About this property
    House Has 4 Bedrooms sleeps up to 8 people Fully stocked Kitchen with updated appliances across street from Beach and shopping and dining lots of water activities available Also has a bbq and a room in one bedroom that is private 2 tvs and cable are at house also in the summer time you can see...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sand Cay Resort is centrally located on beautiful Longboat Key next to the new Zota hotel, with it's beautiful restaurants and bars. There are other restaurants and shopping close by. The resort has a heated pool, shuffleboard, basket ball and full tennis court, in addition to an immaculate...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LUXURIOUS 1 BEDROOM ON THE BEACH , $150.00 PER NIGHT FOR DECEMBER AND JANUARY1 / 24
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2018
    We absolutely loved Kim’s condo. The location was outstanding and the condo was beautiful. We loved everything about being here. Nothing like waking up and sitting on balcony...
    Reviewed 12 May 2018
    Booked this resort because of all the great reviews it gets,and the reviews were right!A very relaxing atmosphere,our 1 bedroom condo was clean,well equipped and spacious on the...
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    About this property
    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
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    Longboat Key, Florida 33312
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Children's Pool
    • DVD Player
    • Sauna
    • Cable/satellite TV
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    • Washer
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your family vacation in the two beds,two baths 1,503 sf spacious condo,fully turn key equipped waiting for you to move-in. All utilities are free including hi speed internet, Wi-Fi, three flat TV's, landline phone, in-unit washer and dryer. Condo unit 203 located on the 2nd floor,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    1400 sq ft free standing villa Our villa has 2 bedrooms, 2 bathrooms, living/ dining room, full kitchen and two bonus rooms. It is located on the bay which comes into the center of the community and features a marina - manatees and dolphins have been known to stop by! .Our unit is close to the...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Longboat Key Retreat1 / 8
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 September 2016
    Located on it's own in very quiet area we did not feel safe as no other people about. House was not as clean as it should have been lots of bugs etc. well equipped, not as near...
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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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Tranquility and rejuvenation is what you will find renting this apartment. This is an apartment, located on Longboat Key, between the bay and white sand beaches. With 1 bedroom, 1 bathroom, equipped kitchen and TV equipped living room, it can perfectly accommodate a couple. You do not need to leave...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf of Mexico Paradise1 / 13
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Porch
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    About this property
    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Las Hermanas/Starfish #2 Beachfront Longboat Key1 / 7
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 3 May 2017
    My husband and I had the best vacation ever !!! We feel like we spent three weeks in paradise . Our unit was perfectly equipped for our vacation with everything we needed to...
    Reviewed 4 February 2016
    This was an exceptional find for us. The unit was very clean, and every attempt was made to make sure we were comfortable. We enjoyed our "home away from home" and...
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    About this property
    Peaceful and quiet spot on the beach. Your one bedroom vacation home has a private beachfront patio and direct gulf views from the patio, lanai, and bedroom. A full kitchen so you can enjoy meals at sunset instead of fighting the crowd at restaurants. Las Hermanas is just one block from our...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Las Hermanas/Starfish #3 Beach front Longboat Key1 / 7
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Grill
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    • Ocean Views
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2018
    If you like to avoid the high-rise condos, this is your place. Close enough to "the circle" , Sarasota, and Siesta Key beach. But not so far as Bradenton Beach, where...
    Reviewed 25 July 2017
    We visited Las Hermanas again after three years. It was as beautiful as ever. This condo. is right on the beach and has every amenity you can think of. I have two teenage...
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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