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Longboat Key Vacation Rentals

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    All 96 Rentals in Longboat Key
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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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    Beachfront Condo on the Beautiful Gulf of Mexico1 / 37
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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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    Beachfront Longboat Key Studio #11 / 6
    (7)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 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 April 10, 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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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located directly on the healing waters of Sarasota Bay, this home starts each day with glorious sunrises and ends with joyful dolphins swimming right up to the sea wall. Located at the end of a quiet street on Longboat Key’s exclusive Country Club Shores, this grand home was fully renovated only a...
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    Longboat Key, Florida 34228
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Charming Beach House in Longboat Key/ pool/pet/dock1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Washer
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 13, 2018
    We enjoyed our stay so much at this cute, cozy house. The house has all the amenities needed and was comfortable and very clean. The neighborhood was very quiet and has private...
    Reviewed October 25, 2017
    This house is a great place for vacation. We enjoyed all amenities provided. The house is fully equiped with everthing you need. Thank you very much.
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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...
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    Longboat Key, Florida 34228
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Longboat Key Gulf-front 2 BR/2 BA, amazing views1 / 12
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 17, 2017
    Our family really enjoyed our stay. The beach is at your doorstep and the view just amazing. The condo as you can see from the pictures is well equipped and very conformable. We...
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Ocean Views
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 2, 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 February 3, 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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    ** DIRECT OCEAN FRONT SPECIAL MONDAY TO FRIDAY **1 / 27
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Patio
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2018
    The view from the second floor balcony was wonderful. We were close to a Publix and not far from St Armand’s Circle. Good restaurants nearby. My friend had his birthday dinner...
    Reviewed September 23, 2017
    My husband and I had an enjoyable 3 night stay at this wonderful cozy conbo. We frequent Longboat Key to get our "beach fix" and have found a new favorite place. The...
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    About this property
    THE BEACH ON LONGBOAT KEY - One Bedroom Gulf Front Condo OCEAN FRONT SPECIAL 20% OFF WEEKDAYS ~ 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 pool overlooks the Ocean....
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    Longboat Key, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Steps to the Sand! Longboat Key 2 Bed 2 & 1/2 Bath Gulf Front Condo with Den.1 / 28
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Sauna
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 15, 2018
    Really clean, comfortable place for our family of 5...two king beds with own bathroom and a comfy pull out sofa for a young child. All matresses were temperpedic and nice...
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    About this property
    Newly Renovated in November 2016 our unit features direct gulf views from the living room, kitchen and master bedroom. Brand new appliances and fixtures throughout including in unit washer and dryer. Each bedroom has a flat screen TV, king size bed and an on-suite bathroom. The den has a queen...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Terrace
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ' Captivating Luxury Canal Home on secluded upscale cove on Longboat Key with short walk to the beach!' 761 Penfield - Private canal home 3 Bedroom/ 2 Bath , maximum occupancy of 6 people. Your Home Away from Home! Completely renovated canal home tucked away on a lush cove in the heart of...
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    Longboat Key, Florida 34228
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spacious Gulf Front beach condo on Longboat Key1 / 17
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Ocean Views
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 7, 2017
    We really enjoyed our stay! What an incredible location! Great view, perfect pool, and close to a grocery store. Will definitely come here again!
    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...
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Grill
    • Parking
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Multi-level 4 bed/3 bath home w/elevator just a short walk to the beach NOW AVAILABLE DUE TO CANCELLATION! If you are looking for a spacious home that provides a sense of being in an exclusive gated community, is very quiet and tranquil and has access to one of the most beautiful beaches in...
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    Longboat Key, Florida 34228
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Outrigger Resort unit #31 / 18
    (2)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 2, 2018
    This 3 bedroom, 3-1/2 bathroom, 2 floor condo exudes lovely old Florida charm. Completely remodeled and very spacious, the condo is very quiet as are the beach and pool. Close...
    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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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Patio
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is our newest addition and being updated from floor to ceiling literally as I type this ask for PDF to see the amazing new look . In addition see below to get a feel for our brand and where we are taking this property . It is part of the Zilli Collection each with the Zilli touch of...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, 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
    • Wi-Fi
    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 9, 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Peaceful Cottage - Houses for Rent in Longboat Key, Florida, United States1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 23, 2018
    Thank you for everything, we enjoyed your cottage. We plan to do this again next holiday. Perfect location, plenty of room for everyone. Nice to have beach chairs, and bikes...
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    About this property
    Fully equipped cottage reflecting its own unique style of a beach getaway in paradise, full of character, and quaint as can be! Very clean, and well maintained. This cottage is on a private lot with a separate entrance and parking. Laundry room with washer and dryer in garage. The residence has...
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    Longboat Key, Florida 34228
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious end unit is a bright and breezy townhouse with new décor and totally renovated kitchen and baths featuring sparkling granite and tile. Comfortable new furniture in the living area. Third floor master bedroom with sliders to the sundeck offers a spectacular view of the Gulf. Private...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Paradise Cottage at Longboat Key1 / 28
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 9, 2016
    My husband and I, along with two other couples, just spent the most relaxing five days at Paradise Cottage. The name suits the house well. It was great. The house is very clean...
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    About this property
    Located between the nearby sandy white beaches and Sarasota Bay, enjoy plentiful water sports, fishing and relaxation. Paradise Cottage is a lovely vacation home located on Longboat Key between Sarasota and Anna Maria Island. The wonderful unit is just a 5min walk from the stunning white beaches...
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    Longboat Key, Florida 34228
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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
    • DVD Player
    • Washer
    • Porch
    • Grill
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    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    637 Norton1 / 70
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
    • Internet Access
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 2, 2018
    We loved our month in longboat key. The house was perfect. Large, sunny, and very comfortable. Four large bedrooms with king size beds that were so comfortable. The kitchen was...
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    About this property
    637 Norton - Private canal home 4 Bedroom/ 3.5 Bath with private pool, maximum occupancy of 8 people. Distance to the Beach: 1 block 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...
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    Longboat Key, Florida 34228
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 14, 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 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...
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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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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Yard
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded 2-bedroom private home with open floor plan including living room, dining area and well-equipped kitchen. Screened in lanai facing canal, gardens and active wildlife. One king bedded room and one queen bedded room with abundant closet space. Two newly renovated baths, washer/dryer,...
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    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Washer
    • DVD Player
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    • Hot Tub
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Longboat Key, Florida 34228
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 20
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Housekeeping Included
    • Waterfront
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    • Hot Tub
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful two story condo with views of the Gulf of Mexico. This condo includes a dining room, full kitchen, deck overlooking the Gulf of Mexico, housekeeping, free breakfast every Monday morning. The feeling of a private beach home with the benefits of a condo, including full access to a pool, hot...
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    Longboat Key, Florida 34228
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Sauna
    • Washer
    • DVD Player
    • Hot Tub
    • Patio
    • Ocean Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing totally furnished 5 Star beech front time share rental Property with PARTIAL ocean view. 2-bedrooms and 2-baths. Sleeps six comfortably: king size bed, two twin beds, and queen size sleep sofa. Wonderful free amenities. Check things out on line by looking up the Veranda Beach Club for...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit is a two bedroom condo available for rent during April 13-20, 2019 (Saturday...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Welcome to Paradise! View! View! View! A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit 403. Whether you want a relaxing visit enjoying the relaxation of all of the comforts of home with stunning views of...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Find your tropical oasis in sought after LONGBOAT KEY. Wake to sunrises over your dock overlooking Sarasota Bay and catch the sunset sinking into the Gulf of Mexico-. Enjoy Serenity in this lovely home, or By Bike or Car Minutes to St. Armands' Circle or jump into your Boat; down the Deep Water...
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    Longboat Key, Florida 34228
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    ZILLI VILLA1 / 25
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed January 23, 2018
    My husband & I stayed here last May. The home is absolutely beautiful. Very comfortable & it is definitely high end. Wow. You will not find a home to rent like this one...
    Reviewed January 8, 2018
    We are a well-traveled family of 5 (kids ranging from 1 to 8 yrs old) 2017 was our second stay at the villa, two years in a row - you can say that we love the villa! We're...
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    About this property
    Enjoy a relaxing getaway in our exclusive Zilli Villa. This tranquil two bedroom gem is perfect for a romantic honeymoon, family vacation or a restful week long retreat. It is a fabulous home one of a kind. There is nothing like Long Boat on the Gulf other than Naples. Spread the Word Zilli...
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    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    Beach Castle Resort 61 / 28
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    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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    About this property
    Beach Castle Resort BC6 - Condo 2 Bedroom/ 2 Bath on Longboat Key beach side , 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Quiet, end-unit is just steps to the beach or pool from your palm-shaded lanai. This one-level, ground-floor condo has all the comforts of home. Granite kitchen and updated bath with granite, tumbled marbled flooring & subway tile. Master includes walk-in closet. Tiled living areas and hardwood...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    About this property
    Leave your worries behind as you enter this condo with all the comforts of home plus a spectacular view. Beautifully appointed with exceptional attention to detail. This end unit offers privacy plus balmy Gulf breezes on the screened lanai. Sink into the comfortable sofa or lean back in the...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Spacious 2 Bedroom (King in MBR and Queen in Guest BR) and 2 bath unit with Gulf View (North side) - watch sunset go down over the Gulf. Well decorated and furnished with a screened in lanai. Walk out to pool, hot tub, Har-Tru tennis and Gulf. 2 month minimum rental. Gym on site. 1 mile walking...
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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
    Welcomes you to a unique eight unit condominium. Nestled on Longboat Keys finest beach. Gulf Front offers an intimate villa ambience by combining privacy with luxuries of condminium living. Relax in this totally renovated 2 bedroom 2 Bath condo.Wake up and enjoy your breakfast on your screened...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    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
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beach front condo in Longboat Key1 / 13
    (1)Average
    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    About this property
    Designer's hidden home: walk to Florida's best secluded beaches. Longboat Key is a tropical paradise. Just bring your yacht, golf clubs, tennis rackets and relax. Wi-Fi & TV Our Venetian Villa is nestled on the placid Longboat Key. With a short drive from the airport, Ringling Museum, St....
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    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    ~ DIRECT BEACH - OCEAN FRONT ~ SPECIAL ~ Please inquire about special rates ~ . This small complex is - AAA Approved and Superior Small Lodging Award Recipient for 2016. For your privacy, our unit is located on the second floor. Our one bedroom (4 Persons Max) condo is tastefully furnished,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Breezes, Soft Sand! Your Place on the beach!1 / 51
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
    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...
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    About this property
    Remodeling is complete! Our beautiful low-rise resort is located directly on the beach, and 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/dining area with 46 inch plasma TV & BlueRay Player,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    WestChester 304A- Condo 2 Bedroom/ 2 Bath gulf front , maximum occupancy of 6 people. Welcome to Paradise! This 2 bedroom 2 bath conod is on the 3rd floor with 2 private balconies where you can enjoy the sound of the rolling waves and some of the most spectacular sunsets in Longboat Key. There is...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Away to Paradise! Unit 301 with 180 degrees unobstructed Mexican Gulf View. Beachfront condos on Florida's gulf coast. This is a corner condo so you have a more space and side window view. A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    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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    Longboat Key Bayfront condo in Bay Isles1 / 24
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed April 30, 2017
    Enjoyed our stay in Bay Isles. The condo was very comfortable & the view of Sarasota day & night was awesome!! We would stay there again.
    Reviewed November 30, 2016
    We enjoyed our stay in the condo . a beautiful condo . wonderful location . recommend this condo when staying at Longboat Key.
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    About this property
    Beautifully updated 2 bedroom, 2 bath Fairway Bay condo in double gated Bay Isles on South Longboat Key. Sweeping views of Sarasota Bay with downtown Sarasota in the distance from this 3rd floor unit with elevator. Fairway Bay has two heated pools, gym, tennis courts and access to the private,...
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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 5 Quick View
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    About this property
    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...
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    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    About this property
    This is a spacious house, located in Halyard Lane on Longboat Key, close to St. Armands Circle (3 miles) and private beach (0.5 miles). With 3 bedrooms, 2 bathrooms, equipped kitchen and TV equipped living room, it can perfectly accommodate a family or group of friends of 6 guests. The house is...
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    Longboat Key, Florida 34228
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    This apartment is ideal for a vacation rental or bed and breakfast as it is literally 100 yards from the Ocean with panoramic views of the Caribbean from the lounge and bedrooms. Recently completely renovated with polished granite floors and upgrades to the kitchen, bathroom and bedrooms, the...
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    Longboat Key, Florida 18470044
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    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.

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