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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

5.0/522 Jul 2026

Joseph

We stayed in the ocean front villa and we loved every bit of it. Rooms serviced each morning. Clean rooms. Staff were friendly and great. Fresh hot breakfast each morning. The bar is a great addition and the live music. Private beach, clear kayaks for personal use. Bicycles to ride around Islamorada. They even have fishing poles for guests. I love Chesapeake resort for our family. Lots of restaurants walking distance from resort.

5.0/521 Jul 2026

Samantha

2nd time staying. Nice friendly staff. I appreciate how they move the sargassum so we can still get into the water and use paddleboards.

5.0/520 Jul 2026

Suennia • Couple Trip

Good stay

5.0/516 Jul 2026

Mejreme • Family Trip

Beautiful place enjoyed every moment of it, breakfast was not good that's th3 only issue otherwise

5.0/516 Jul 2026

Gregory • Family Trip

5.0/516 Jul 2026

Leah • Family Trip

Traveled with my husband and three children and our stay was amazing! Room was clean and spacious. Big balcony. Housekeeping daily. More than enough towels. Big bathroom, but only one sink for the entire room. Property was quiet. Cook to order breakfast was good (omelets, French toast pancakes, fresh fruit, cereal, begals, toast, muffins, etc). Complimentary 2 hour rental per day includes kayak, paddle boarding, fishing poles, bikes. It's a smaller property, so even when fully booked we never had trouble finding a spot under an umbrella at the beach or the pool. Nice little beach and great snorkeling right on property. We got up close with tropical fish, stingrays, and crabs. We hardly even left the property and ended up extending our stay. Recommended to others traveling that way. We will definitely stay again.

5.0/516 Jul 2026

Eva • Family Trip

It’s always a great stay here! We were able to bring our dog who enjoyed his time in Islamorada. The included breakfast was a nice surprise.

5.0/515 Jul 2026

Ilene • Family Trip

My check-in was simple. The room was beautiful and my day was wonderful.

5.0/515 Jul 2026

Marie Edith • Family Trip

au top du top! Recommandation absolue

5.0/514 Jul 2026

Luis v • Family Trip

Buenisimo todo d buena calidad

5.0/514 Jul 2026

Meghan

It was perfect for what we needed

5.0/513 Jul 2026

Deborah • Family Trip

The room was clean and we had plenty of towels and bathroom supplies. The made to order omelets were delicious and there were plenty of other options to choose from, however the staff doing the cooking was a bit on the slow side.

5.0/512 Jul 2026

Hunter • Couple Trip

The property is great. You can walk out from the beach and snorkel.

5.0/512 Jul 2026

Christeen • Family Trip

Awesome staff. Great location. Nice property.

5.0/511 Jul 2026

Deanna • Trip with Friends

Wonderful place for family and friends. Breakfast is phenomenal. So many activities on site. Quiet location. No crowds. One of my favorites in the Keys!

5.0/511 Jul 2026

Kim • Family Trip

Excellent staff. Property was beautiful and well maintained. Room was beautiful.

5.0/510 Jul 2026

Elizabeth • Trip with Friends

Love the place very clean and peaceful

5.0/510 Jul 2026

Warren Scott • Couple Trip

We chose this property for location, price and water views. We were impressed and would stay again. Check in was quick with complimentary prosecco. The room was well appointed with robes and slippers, full length mirror, coffee maker, microwave and small fridge. Bathroom had a walk in shower , single sink, barn door that provided privacy. Lots of parking available. A very well stocked section in the reception building offered items for purchase such as snacks, drinks, toiletries you may have forgotten to pack. The complimentary breakfast was excellent. The beach bar is a nice addition. We stayed mid week and it closed at 7pm. We didn’t use the pools but they looked clean and well maintained. The views are beautiful. Plenty of loungers. The staff we interacted with were very pleasant.

5.0/510 Jul 2026

Jennifer • Family Trip

Perfect place to stay to explore Islamorada on land and by water.

5.0/59 Jul 2026

mary agnes • Family Trip

The place was lovely. Great staff and breakfast! The pools on the beach were fantastic!

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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View on maps

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

Fri, 23 Oct 2026 - Sat, 24 Oct 2026 (1 night)

1 Room, 1 Adult, 0 Children