svg-sleeps svg-bedrooms svg-bathrooms svg-stay pets
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      $130 avg/night
      2 Bedrooms+, Sleeps 4
      31
    •  
      $371 avg/night
      4 Bedrooms, Sleeps 10
      12
    •  
      $710 avg/night
      4 Bedrooms, Sleeps 10
      30
    •  
      $81 avg/night
      1 Bedroom, Sleeps 3
      6
    •  
      $154 avg/night
      2 Bedrooms, Sleeps 6
      2
    •  
      $170 avg/night
      2 Bedrooms, Sleeps 4
      8
    •  
      $643 avg/night
      5 Bedrooms, Sleeps 10
      5
    •  
      $152 avg/night
      3 Bedrooms, Sleeps 7
      9
    •  
      $117 avg/night
      2 Bedrooms, Sleeps 5
      3
    •  
      $143 avg/night
      2 Bedrooms, Sleeps 4
      77
    •  
      $214 avg/night
      2 Bedrooms, Sleeps 6
      9
    •  
      $104 avg/night
      1 Bedroom, Sleeps 4
      26
    •  
      $357 avg/night
      4 Bedrooms, Sleeps 8
      51
    •  
      $238 avg/night
      3 Bedrooms, Sleeps 6
      23
    •  
      $139 avg/night
      1 Bedroom+, Sleeps 4
      66
    •  
      $386 avg/night
      3 Bedrooms, Sleeps 6
      9
    •  
      $140 avg/night
      2 Bedrooms, Sleeps 4
      10
    •  
      $117 avg/night
      2 Bedrooms, Sleeps 4
      2
    •  
      $100 avg/night
      1 Bedroom, Sleeps 4
      30
    •  
      $357 avg/night
      3 Bedrooms, Sleeps 8
      19
    •  
      $129 avg/night
      2 Bedrooms, Sleeps 6
    •  
      $266 avg/night
      4 Bedrooms, Sleeps 10
      1
    •  
      $350 avg/night
      3 Bedrooms, Sleeps 6
      4
    •  
      $69 avg/night
      2 Bedrooms, Sleeps 4
      3
    •  
      $463 avg/night
      5 Bedrooms, Sleeps 12
      1
    •  
      $236 avg/night
      2 Bedrooms, Sleeps 6
      28
    •  
      $140 avg/night
      2 Bedrooms, Sleeps 4
      24
    •  
      $174 avg/night
      3 Bedrooms+, Sleeps 7
      35
    •  
      $67 avg/night
      2 Bedrooms, Sleeps 6
      19
    •  
      $114 avg/night
      3 Bedrooms, Sleeps 4
      1
    •  
      $823 avg/night
      6 Bedrooms, Sleeps 12
      7
    •  
      $316 avg/night
      5 Bedrooms, Sleeps 12
      8
    •  
      $152 avg/night
      2 Bedrooms, Sleeps 4
    •  
      $213 avg/night
      2 Bedrooms+, Sleeps 5
      16
    •  
      $171 avg/night
      2 Bedrooms, Sleeps 6
      120
    •  
      $206 avg/night
      2 Bedrooms, Sleeps 6
      17
    •  
      $175 avg/night
      2 Bedrooms+, Sleeps 6
      22
    •  
      $227 avg/night
      3 Bedrooms+, Sleeps 8
      44
    •  
      $100 avg/night
      2 Bedrooms, Sleeps 2
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      View listing for price
      3 Bedrooms, Sleeps 7
    •  
      $199 avg/night
      2 Bedrooms, Sleeps 4
      15
    •  
      $108 avg/night
      2 Bedrooms, Sleeps 5
      8
    •  
      $118 avg/night
      2 Bedrooms, Sleeps 6
    •  
      $304 avg/night
      5 Bedrooms, Sleeps 10
      1
    •  
      $74 avg/night
      2 Bedrooms, Sleeps 4
      1
    •  
      $78 avg/night
      2 Bedrooms, Sleeps 4
    •  
      $110 avg/night
      2 Bedrooms, Sleeps 4
      5
    •  
      $124 avg/night
      3 Bedrooms+, Sleeps 6
      21
    •  
      $107 avg/night
      2 Bedrooms+, Sleeps 6
      2
    •  
      $110 avg/night
      3 Bedrooms, Sleeps 6
      5
Other areas nearby to Longboat Key:

Recent Longboat Key reviews

  • Loved it. Great sunsets from the balcony

    Paula A.

    "Beautiful place. We loved every minute of it. Can't wait to go again, but it looks like it is booked up for along time. Call me when you have openings. Please!"
    • Stayed January 2017
    • Submitted February 15, 2017
    • Source HomeAway Family
    View this listing
  • First class Villa. Lovely setting on the beach

    Mags

    "Our family stayed at the villa for 10 nights in April 2016. Four adults - a couple in their late 70's, a couple in their 40's and a 9 year old boy. We had a fabulous time The villa had everything we needed and is furnished to a high standard. The view from the huge window in the master bedroom is stunning as you overlook the beach and sea. The beach is tranquil and not busy and just down the path from the villa so couldn't be any closer if you wanted it to be. The selection of sunbeds to use around the pool and beach was great and helped you relax and soak up the sun. The pool table, table football and bikes were all enjoyed and made good use of as was the kayak on calm sea days. The pool was especially enjoyed by Finlay and the ducks who visited on a daily basis. We loved to watch the dolphins swim by most days and enjoyed seeing the birds take their dives for dinner! The walk, which is accessible for any age, along the beach is relaxing and interesting while you look for shells. If we were not on the beach or around the pool the lovely relaxing outdoor area with optional covered verandah was ideal. The whole set up of the villa was perfect and had everything we needed to have a brilliant holiday."
    • Stayed April 2016
    • Submitted April 24, 2016
    • Source HomeAway Family
    View this listing
  • Pleasantly Surprised

    New Yorkers

    "Every year we plan our vacation in December. Usually someplace warm and relaxing with an ocean nearby. I find myself not looking forward to these excursions for many reasons. The thought of spending a lot of money to stay at another beat up hotel room, sleep in another uncomfortable bed at a major resort is not all that exciting to me. When we do go on vacation my wife usually ends up planning enough outside excursions to keep us from thinking about the mediocre room which would make most folks look forward to returning home to their own beds. We are both 50 years old and nothing has surprised us in decades. If we left a hotel or resort review in the past it was usually as a warning to others. This December I got an amazing present that we haven't felt on a vacation in years. The Pineapple Cottage. It felt more like our home only nicer. Picture your dear friends the interior decorators have invited you to house sit, they leave you a long list of recommended places for you to eat, things to do and even people to clean the place. The hardest part of our trip was going home. This place is a breath of fresh air. The beds, sheets, pillows and covers feel brand new, the theme of the cottage from the furniture, to the brass lighting fixtures inside and out, mosaic tiling, granite kitchen counter tops and even the painted mural that adorns the pool area where all a very nice reminders that this was the vacation from home that we were looking for. We hardly used the beautiful kitchen during our stay except for the coffee maker and the refrigerator. We did use a handy list of restaurants suggested by the cottage management. They really spent their time recommending places and people from cleaning ladies, fishing boats charters, golf courses and beaches that would make our stay a better experience. Straying off go this list proved to be second best. I would highly recommend the Pineapple Cottage to anyone who is tired of vacation disappointments, except of course in the month of December, because thats our time to enjoy it."
    • Stayed December 2016
    • Submitted January 5, 2017
    • Source VRBO
    View this listing
  • Terrific Location

    Nancy D.

    "The location on the beach was wonderful and there were some really marvelous restaurants nearby. The condo itself was very clean and the appliances were new. While not plush, it was a terrific spot for a vacation stay. The layout was a little strange, with the front door leading right into the bedroom and the adjoining bedroom of the two bedroom suite also right in the master bedroom but it worked out fine and gave us a beautiful view of the beach and great sunsets. Unfortunately, the lock on the outside door of the adjoining room did not work properly and we got locked out on New Year's eve. It took some time, but the emergency number was answered and they helped us gain access to the room. Also, there was hardly any silverware in the drawer; but, again, the accommodating staff provided what we needed. The fitness center was about a block away but was well appointed, clean and available 24 hours a day, which we enjoyed."
    • Stayed December 2016
    • Submitted January 8, 2017
    • Source VRBO
    View this listing