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

Windley Key, Islamorada hotel rooms at the Hersha Hospitality

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Check prices for these dates

Tonight
Sep 27 - Sep 28
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Sep 28 - Sep 29
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Oct 2 - Oct 4
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Oct 9 - Oct 11
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Top Windley Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Loved the kayak, and breakfast and the view! Everything!"
Sebastian 1-night trip
Posted 9 hours ago
Chesapeake Beach Resort
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Location was great!"
Desiree 2-night trip
Posted 10 hours ago
Bayside Inn Key Largo
Sunset Cove Beach Resort

Sunset Cove Beach Resort

10/10 Excellent
"Great getaway for weekend and bring the dog"
Brian 4-night trip
Posted 10 hours ago
Sunset Cove Beach Resort
Rock Reef Resort

Rock Reef Resort

8/10 Good
"Great location on the beach. Cottage with porch- kitchen a bit dated but comfortable beds and new bathroom. Close to lots of restaurants"
David 1-night trip
Posted 16 hours ago
Rock Reef Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"The resort was nice but a bit run down. It looks like the staff tries to work with what they have but some tlc is needed in certain areas. We went in September so the place was a bit quiet and not a lot to do but my husband and I enjoyed ourselves."
Caridad 1-night trip
Posted 16 hours ago
Reefhouse Resort & Marina
Cheeca Lodge & Spa

Cheeca Lodge & Spa

8/10 Good
"Overall, it was a wonderful and beautiful place to stay. The main downside was that our elevator was not working the entire 6 days we were here and having to pay $73/day in resort fees makes me think they should have fixed it promptly. We had to climb 4 flights of stairs every time we left our room. Also be warned that they put a $200 hold per night on your credit card which I was not aware of. So $1000 was immediately taken from my bank account which I had intended to use for spending money. The staff were great. Thanks"
Angela 5-night trip
Posted 17 hours ago
Cheeca Lodge & Spa
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

8/10 Good
"Was clean a little sparse & in need of updating. The staff was extremely helpful. The private beach was very nice."
Angela 1-night trip
Posted 1 day ago
The Pelican Key Largo Cottages
Drop Anchor

Drop Anchor

10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
Payman 3-night trip
Posted 3 days ago
Drop Anchor
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Excellent stay! Love this place and will definitely be back!"
Hailey Ritch and Patrick 3-night trip
Posted 9 days ago
Coconut Cove Resort and Marina

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