Windley Key Guest Houses

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

A beach with rows of sun loungers and palm trees.

1. Ragged Edge Resort & Marina

Islamorada

Nathalie

HK$1,117 total

includes taxes & fees

27 Sept - 28 Sept

A deck with a white railing, a lounge chair, a blue towel, and a large umbrella.

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

Matecumbe

HK$9,897 total

includes taxes & fees

26 Oct - 27 Oct

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

Matecumbe

HK$18,872 total

includes taxes & fees

2 Oct - 3 Oct

An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Matecumbe

HK$19,754 total

includes taxes & fees

26 Oct - 27 Oct

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

Matecumbe

HK$19,873 total

includes taxes & fees

2 Oct - 3 Oct

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Top Windley Key Hotel Reviews

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent

"Amando este lugar muchas gracias Yoli por toda la atención volveremos pronto"

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!"

Fisher Inn Resort & Marina

10/10 Excellent

"This place was the best place to stay I've ever been ever it is wonderful there's nothing not to like about this place the ocean the pool the people the place everybody's so nice and accommodating they will do anything they can to make sure you're happy it's paradise in paradise I would suggest to stay at this place anytime it would be a mistake not to"

Find out more about Windley Key