Search Vacation Homes in Windermere Island

"This home was absolutely amazing! Easiest check in and so beautifully appointed! "

"Excellent property. Great staff. Great food. Great pool & beach. Yes the road is a bit rough, but no difficulty driving it in a humble Kia rental car"

"House was great. Had everything we needed. My daughter loved the pool after being in the ocean all day and when boredom hit she would take a dip. We enjoyed our stay! "

" Cupid's Cay was an incredibly beautiful home and made our family vacation one of the best ever. The home was comfortable, provided everything we needed, and the views are unbeatable. Watching the sunset from your private deck, snorkeling with turtles in your private back yard ocean and starting each day by cliff jumping into the ocean are just a few of the highlights. The kayaks provided hours of fun as we could kayak all along the coast with a unique view of the caves and underwater scenery. The house is close to numerous restaurants, grocery stores and more beautiful beaches than we had time to explore.I would highly recommend this home and I know we will be back!!!"

"We have stayed in Winding Bay several times many years ago. This is a relatively new home that includes a 4 bedroom guest house so a great amount of space for all ages. Kitchen was well equipped, bedrooms were spacious and comfortable, and all the living areas perfect for those late afternoons before dinner. Outside space is incredible with a huge deck, picnic tables, lounges, chairs, covered area, kayaks, paddle boards, water trampoline, and water toys. There is a large bar/grill area with outdoor tv as well. We rented the large Suburban which the owner had left for us at the airport and was perfect for 7 of us and all our luggage. Winding Bay is the perfect spot if you want to spear lobster and/or fish as it is on the ocean side but protected from the Atlantic. We had lobster ever. single. night. Please note the season opens there on August 1st. This home was just great for our family with ages 6 - 75. The host, Chris, is outstanding and will communicate immediately if asked a question or have a concern. We would do a repeat visit to this compound. As our six year old said, "let's go home for two days and then come back." I agree. Thank you, Chris. It was a terrific vacation."

"we loved everything, the house was great!"

"bonefish barbie is an incredible house by the beach. "

"We had a great time, everything was nearby. Beach access right across the street. Resteraunts nearby and in the center of the island. Jethro is amazing and so helpful, we would come back in a heartbeat!Make sure to use the pool and enjoy the stars."

"Exceptional service. Very welcoming and friendly manager Sanom went above and beyond - even sent help for us when our rental car broke down on way to hotel. Also Daniella our bartender was very friendly and helpful. "