Windward Bay 10 rentals
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      $143 avg/night
      2 Bedrooms, Sleeps 4
    •  
      $90 avg/night
      2 Bedrooms, Sleeps 4
    •  
      $194 avg/night
      2 Bedrooms, Sleeps 6
    •  
      $217 avg/night
      2 Bedrooms, Sleeps 4
    •  
      $103 avg/night
      2 Bedrooms, Sleeps 6
      1
    •  
      $150 avg/night
      2 Bedrooms, Sleeps 4
    •  
      $138 avg/night
      3 Bedrooms, Sleeps 8
    •  
      $126 avg/night
      Studio, Sleeps 6
      1
    •  
      $344 avg/night
      3 Bedrooms, Sleeps 6
    •  
      View listing for price
      2 Bedrooms, Sleeps 4

Recent Longboat Key reviews

  • An UNFORGETTABLE Vacation in a Tree House on an Island

    Christina B.

    "Our family spent a week on Jewfish Island and this will likely not soon be forgotten. On our way home we asked of all the amazing vacations we have taken around the world where would this rank and both our kids placed it first or second. We lived in the area previously prior to moving to the Carolina's. We knew a secluded island house, with limited television, intermittent wifi (only via your own connection) would be exactly what our family needed. Unplugging from the world around you to take in the beautiful Sarasota Bay, the Island life, nature and the simpler things was such a blessing. Dolphins, manatees, and an array of fish frolicked by the dock daily. We had use of a kayak and canoe which added to our adventure. We also rented a boat so we could cruise to dinner or lunch on occasion. Just outside this little tree house gem is an amazing dock which you must spend time on. The other side of the island boasts fun in the sun on the sandbar where boats like to hang out so you can enjoy people watching, floating, and it is a great place to find shells and sea life. Afterwards, you can walk back over to your nice secluded side and say ahh. Jordan the property manager is an absolutely top notch host. He goes out of his way when you arrive to help with your luggage and directions. Likewise, Patricia the homeowner is fantastic. Both ensure your stay will be unbelievable and you are happy while there. What I do recommend for future renters... I highly recommend renting a boat. The home does have 3 levels of a gorgeous floating staircase. So mommies that have young children keep this in mind. All bedrooms are open to enjoy the incredible views of the Sarasota Bay from the tree tops. Room dividers are available in the closets for privacy. We did not use them as it was AMAZING open. The home is in the TREES on a gorgeous ISLAND in FL! This is a positive. This also means there are some bugs. So make sure you bring your protection and if you open a slider or door sometimes one or two my fly in. It is to be expected. Wear shoes to your private beaches. Make sure to catch a sunrise and a sunset. You will never forget either. Be certain to enjoy the dock at night as well. Incredible what you will see in the water. The home is stocked with everything you will need. We will definitely be back if possible. We can't give enough praise. Jordan, Pat and Seashell Island Retreat (which we call the Island Treehouse) is in our hearts forever."
    • Stayed July 2016
    • Submitted July 12, 2016
    • Source VRBO
    View this listing
  • Glorious!~

    Anonymous

    "We had a wonderful stay at our Longboat Key location! The size of the overall property was quaint and quiet just the way we like it. The unit location next to the pool and just steps from the beach was perfect for the kids. Everything we needed was right the, the owners and staff at the unit were lovely and kind. Fabulous shopping and dining just minutes away from this beach-side retreat made it a perfect location! I would definitely go back!"
    • Stayed April 2016
    • Submitted April 12, 2016
    • Source HomeAway Family
    View this listing
  • Taylor

    Taylor

    "I've vacationed at the Outrigger Resort ,on and off , for 35 years. I first came here with my parents when I was 10 and now, vacation here with my adult children and grandchildren . What a joy it has been to have us all in one place to share the beach , our famous seafood pot boils, the pool and a generously sized Condo if you simply want to steel away for a nap. I love how convenient parking is for each room, it makes bringing in your luggage and groceries simple. Its very peaceful here and between the beach and the pool , you are assured some fantastic family memories here on Longboat Key ! Enjoy !"
    • Stayed October 2015
    • Submitted June 19, 2016
    • Source VRBO
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  • Had a wonderful time!

    Audrey D.

    "We really enjoyed this beautiful home. It had everything we needed and is very well taking care of. We appreciated not having to buy paper goods and soaps. The walk to the beach is few minutes and we felt like we were on a gorgeous deserted island! very quiet and pristine. Saw some dolphins and all sorts of wild life. There is construction next door but you could barely hear anything and the builders were very courteous. The manager Jessica responds super quickly to any questions and is wonderful to deal with. We really had a good time and came back home very relaxed! Thank you again Jessica for making our stay very comfortable. Audrey & William"
    • Stayed November 2015
    • Submitted November 19, 2015
    • Source VRBO
    View this listing