Hotel>Florida>Monroe>Chesapeake Beach Resort

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General Info

Reviews

Location

Accommodation Rules

About

Resort

Chesapeake Beach Resort

Monroe, Florida

The Fun Awaits

Perfect for nature loversOnly 2.5 km to Windley Key Fossil Reef Geological State Park

Reviews

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4.7/5

FantasticFrom 100 reviews

5.0/526 Jun 2026

Ricky Ray • Couple Trip

Room was clean and the air conditioning was great. The breakfast was a bonus with personal omelets made to order. Plenty of lounge chairs throughout the property. Restaurants next door were also a plus. Tiki bar available and friendly staff. Bikes, paddle boards and kayaks were there just had to sign a waiver.

5.0/525 Jun 2026

Marsha • Solo Trip

I thoroughly enjoyed my stay here! The room was immaculately clean! The staff was very attentive. I will definitely stay here again.

5.0/523 Jun 2026

Kandi • Couple Trip

Everything here was amazing! It was my first time in the keys and I’ll never forget it!

5.0/522 Jun 2026

Juliana • Family Trip

Wonderful location, we stayed there years ago and came back for a night again this past weekend and it was excellent! Staff were great the hotel looks fantastic ! We will definitely book again soon! Juliana S

5.0/522 Jun 2026

Eric • Couple Trip

Just stayed for a night but definitely would be back soon. Room with ocean view was great and spacious. Staff was friendly and welcoming.

5.0/521 Jun 2026

Jacob

Incredible spot !! Views. Unreal. My usual place was not available. This is my new spot !!

5.0/520 Jun 2026

Brenda • Family Trip

We had a fabulous stay, would stay again!!

5.0/520 Jun 2026

Blake • Couple Trip

Great place

5.0/520 Jun 2026

Cynthia

We were pleasantly surprised at this property as it was a quick stop on our route to Key West. The staff was accommodating and friendly, our room was very nice, its walkable to restaurants & the marina and the complimentary breakfast was really good. Unfortunately the beach was lined with sargassum, but we were still able to enjoy the water beyond it. Highly recommend.

5.0/520 Jun 2026

Amy • Couple Trip

Clean rooms , beautiful view , great breakfast

5.0/519 Jun 2026

Christie

Great resort with friendly staff. Very clean!

5.0/518 Jun 2026

Sandra • Couple Trip

Beautiful resort with great amenities! We were even welcomed with a glass of champagne!

5.0/518 Jun 2026

Brian • Family Trip

Great place. Clean and convenient location. Helpful staff. It was a win for us… Will be going back.

5.0/518 Jun 2026

Davina • Couple Trip

This place was really nice and peaceful, I would book this place again! Also breakfast was really nice!

5.0/517 Jun 2026

Jerald • Couple Trip

My girlfriend and I really enjoyed our time at Chesapeake. The room was immaculate and the view from our balcony was amazing. The staff was extremely friendly and helpful. I was able to use fishing gear from the front office to fish the beachfront and harbor in the evenings and they have kayaks available for use as well. While I went on a fishing charter my girlfriend made use of the pool and enjoyed her day getting sun in one of the many chaise lounges along the beach. I will definitely choose the Chesapeake the next time we visit Islamorada.

5.0/516 Jun 2026

Daylis • Family Trip

Great hotel on Islamorada close to everything; lots of restaurants, near to Publix, property is nice and the staff extra nice/ Shut out to Kathy on the breakfast lounge she was extra helpful. Only bad thing was the beach area was full of sargasso and we couldn't use it but that's nature's fault. you can literally walk to some restaurants and there a lot of things to do in the Key.

5.0/515 Jun 2026

Sara

Staff was very helpful and friendly. 2 pools are great as is free kayaks and paddle boards. Breakfast cooked to order and delicious. 6&4 yr old grandkids had a ball. This is our 2nd time staying here.

5.0/513 Jun 2026

Linda • Couple Trip

Everyone was friendly and room was nice.

5.0/512 Jun 2026

Jeremy • Family Trip

This place was great! Very private, great amenities, staff, location, and accessible! Has everything you need for intimate location Oceanview is stellar, you can walk right into the ocean and relax with provided chairs, umbrellas, and towels. They have breakfast included with all breakfast types from made to order omelette, French toasts, pancakes, waffles, bagels, etc.y only complaint is the smell of grease inside the breakfast location that stays with you as soon as you walk in and you have to change your clothes right after. Also, wish they had a restaurant on property to order food.

5.0/511 Jun 2026

Rob • Solo Trip

I liked that I could fish in peace with very good resuts.I also enjoyed the free omlette.

Popular Facilities

Swimming Pool

WiFi

24-hour Front Desk

Sea View

Accessible Facilities

Free Parking

Sports & Recreation

On Private Beach

Outdoor Pool

Fishing

Public Facilities

Parking (Free)

Hotel Services

Multilingual Staff

Concierge Services

24-hour Front Desk

Food & Drinks

Continental Breakfast

Accesibility

Wheelchair Accessible

Hotel Policy

Smoke-free Property

Connectivity

Free WiFi

Location

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83409 Overseas Hwy, Islamorada, Florida, US

Nearby Destinations

All distances are measured in straight lines. The actual travel distance may be different.

Accommodation Rules

Announcement

You must show a valid photo ID and credit card upon check-in. Please note that all special requests cannot be guaranteed and are subject to availability upon check-in. Additional charges may apply.If you expect to arrive outside check in hours, please inform the property in advance. Guests are required to show a photo identification and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.

Check-in Procedure

Check-in4:00 PM-3:00 AM

Check-out11:00

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

Front desk staff will greet guests on arrival at the property. Information provided by the property may be translated using automated translation tools.

Want to check in early? Fill out the Special Requests form on the booking page.

More Policies

Pool access available from 8:00 AM to 6:00 PM.
Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.
Construction is underway at a neighboring building and there may be noise disturbance from the construction work.
Guests can arrange to bring pets by contacting the property directly, using the contact information on the booking confirmation (surcharges apply and can be found in the Fees section).
Contactless check-in and contactless check-out are available.

About Chesapeake Beach Resort

Chesapeake Beach Resort Location
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park. This beach hotel is 1.2 mi (2 km) from Islamorada Brewery & Distillery and 1.7 mi (2.7 km) from Lorelei Restaurant & Cabana Bar.

Chesapeake Beach Resort Facility and Service
Spend the day on the private beach or dip into one of the 2 outdoor pools. This hotel also features complimentary wireless internet access and concierge services.

Chesapeake Beach Resort Rooms
Make yourself at home in one of the 60 air-conditioned rooms featuring microwaves and flat-screen televisions. Your room comes with a pillowtop bed. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, designer toiletries, and hair dryers.

Restaurant and Cafe
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.

Room Type and Price

Sun, 27 Sep 2026 - Mon, 28 Sep 2026 (1 night)

1 Room, 1 Adult, 0 Children