Windley Key, FL Guest Houses from ￥15,544

A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

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Our top choices for Windley Key guest houses

1. Ragged Edge Resort & Marina

Islamorada

Marianne

￥15,544 total

includes taxes & fees

Sep 20 - Sep 21

2. Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Matecumbe

￥186,437 total

includes taxes & fees

Sep 17 - Sep 18

3. Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Matecumbe

￥368,947 total

includes taxes & fees

Sep 16 - Sep 17

4. Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Matecumbe

￥388,168 total

includes taxes & fees

Sep 16 - Sep 17

5. Charming Suite @Islamorada With Pool Access - Twilight Suite

Matecumbe

￥388,513 total

includes taxes & fees

Sep 16 - Sep 17

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Top Windley Key Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent

"I had a wonderful solo stay at the resort. I felt safe at all times during my stay. The resort’s amenities were excellent and had an amazing variety of onsite things to do! I look forward to returning in the near future"

The Pelican Key Largo Cottages

10/10 Excellent

"This is my new go-to place to stay in Key Largo! It's clean, quaint & a good location. The view at the dock at Sunset was stunning. We had two queens & a bathroom. Our room was right behind the check in building so it was convenient to us. There also seems to be a table & chairs outside each room, I didn't know that when I booked but I was able to have my morning tea outside. Another nice feature was the in-room fridge (which was super cold), the coffee maker & the microwave. This microwave was nice! It had a USB & 3-prong plug on the front of it & when it stops running it's locked & you have to push the unlock button. If you are traveling with kids, this is a wonderful safety feature! We walked down to the docks twice on our overnight stay. There are chairs on the beach & on the dock. There were plenty of local places to eat, but I recommend C&Cs Wood Fired Pizza for their happy hour from 4-6 pm. A pizza (6 slices) & a pitcher for $10! At the Cottages, the staff were super nice. Irina & the other lady at check in were so helpful. I even asked a grounds person a question & he was helpful too. I don't care about super fancy. I care about CLEAN, a great view & beautiful surrounding. It's all of this & more!"