Cheap Hotels in Windley Key
Islamorada
Florida
United States of America
Cheap Hotels
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A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Find Cheap Hotels in Windley Key, FL

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Our top choices for Windley Key cheap hotels

A beach with palm trees and lounge chairs.

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

A beachfront hotel with multiple overwater bungalows, a swimming pool, and palm trees.

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

1. Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 star property

Matecumbe

9.4 out of 10, Exceptional, (1,823 reviews)

9.4/10

Exceptional

(1,823 reviews)

"Location is amazing make sure to book a balcony with a view"

Olga Vasiliy

The price is NT$4,966

NT$4,966

NT$7,436 total

includes taxes & fees

Nov 18 - Nov 19

Chesapeake Beach Resort

A swimming pool with lounge chairs and palm trees.

A beachfront area with palm trees, a sandy beach, and a marina with boats.

A multi-story hotel with balconies, palm trees, and a view of the water.

A marina with boats docked, surrounded by palm trees.

2. Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2.0 star property

Key Largo

8.6 out of 10, Excellent, (1,852 reviews)

8.6/10

Excellent

(1,852 reviews)

"Great place enjoyed the stay"

Dawn

The price is NT$4,241

NT$4,241

NT$5,696 total

includes taxes & fees

Nov 15 - Nov 16

Marina Del Mar Resort and Marina

A waterfront patio with outdoor seating, a yellow umbrella, and a view of the water.

A wooden dock extending over calm turquoise water, lined with white railings and palm trees.

A hallway with a tiled floor, a painting on the wall, a lamp, and a view of a pool area.

3. Creekside Inn

Creekside Inn

2.5 star property

Tavernier

7.8 out of 10, Good, (1,023 reviews)

7.8/10

Good

(1,023 reviews)

"Quite and relaxing place"

MARIO

The price is NT$4,328

NT$4,328

NT$4,869 total

includes taxes & fees

Dec 10 - Dec 11

Creekside Inn

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Windley Key Hotel Reviews

Chesapeake Beach Resort

Matecumbe

10/10 Excellent

Great staff friendly as hell. Had a great time relaxed and the place is A1 highly recommend it. I’ll probably be going next week again.

Paco

Reviewed July 17, 2025Reviewed July 17, 2025

Chesapeake Beach Resort

Marina Del Mar Resort and Marina

Key Largo

10/10 Excellent

We continue to come back to this not so secret “keysie” waterfront oasis. Letitcia and the hotel staff are there to serve. Coming back again.

STEVEN

Reviewed February 17, 2025Reviewed February 17, 2025

Marina Del Mar Resort and Marina

Creekside Inn

Tavernier

10/10 Excellent

This was an amazing stay. I loved the low key vibe, the canal and views. Well stay again 100%

Daniel

Reviewed April 26, 2025Reviewed April 26, 2025

Creekside Inn

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Find Cheap Hotels in Windley Key, FL

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windley Key cheap hotels

1. Chesapeake Beach Resort

2. Marina Del Mar Resort and Marina

3. Creekside Inn

Top Windley Key Hotel Reviews

Chesapeake Beach Resort

10/10 Excellent

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