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

Windley Key hotel guide. Hersha Hospitality hotel in Windley Key, Islamorada

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
25 Sept - 26 Sept
Tomorrow
26 Sept - 27 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct
Save an average of 15% on thousands of hotels when you're signed in

Top Windley Key Hotel Reviews

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 3 hours ago
The Pelican Key Largo Cottages
Sunset Cove Beach Resort

Sunset Cove Beach Resort

10/10 Excellent
"This is my second time staying at this property. I loved it both times. The rooms are clean and spacious"
Alexis 4-night trip
Posted 3 hours ago
Sunset Cove Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

8/10 Good
"Comfortable bed, clean . It’s off the busy road and close to restaurants"
Maureen 3-night trip
Posted 7 hours ago
Waterside Suites & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"I liked the breakfast. One pool was being worked on and the pool workers helped themselves to the free breakfast. Some of them stood in the coffee and drink area and ate their free breakfast. The tree trimmers took up some of relaxing areas and they were noisy. The cleaning staff and the front desk staff were very good. The breakfast cook was friendly. The spa was hot but no jet action. We probably won’t be coming back. Thanks"
William 3-night trip
Posted 8 hours ago
Chesapeake Beach Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"There are some nice food and beverage options. Water sports 8n the property."
John 3-night trip
Posted 11 hours ago
Reefhouse Resort & Marina
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Very lovely stay, everyone who worked there was super friendly!"
Angela 2-night trip
Posted 13 hours ago
Lime Tree Bay Resort
Drop Anchor

Drop Anchor

10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
Payman 3-night trip
Posted 1 day ago
Drop Anchor
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Great location !!"
Jenny 2-night trip
Posted 2 days ago
Bayside Inn Key Largo
Rock Reef Resort

Rock Reef Resort

10/10 Excellent
"We love this beautiful little hotel on the water! The sunsets here are epic! The rooms are clean and comfortable. The staff is friendly and their communication is great! We’ve been here a couple of times. During our most recent visit, the staff was in constant communication before, during, and after our visit to ensure everything was comfortable. We loved our stay and will be back again, and again, and again! Close to attractions and great restaurants! There are even complimentary kayaks on site for guests to use. The true Key Largo experience!"
Monica 2-night trip
Posted 2 days ago
Rock Reef Resort

Explore a world of travel with Expedia