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Others 1, Chesapeake Beach Resort, Monroe
Exterior & Views 2, Chesapeake Beach Resort, Monroe
Public Area 3, Chesapeake Beach Resort, Monroe
Bedroom 4, Chesapeake Beach Resort, Monroe
Exterior & Views 5, Chesapeake Beach Resort, Monroe
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Resort

Chesapeake Beach Resort

Monroe, Florida

The Fun Awaits

Perfect for nature lovers
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
5.0/520 May 2026
Jon • Couple Trip
Beautiful renovated property. Nice free breakfast with eggs, pancakes and French toast. Paddle boards and kayaks available for use, 2 pools and a nice beach area on the ocean.
5.0/518 May 2026
Cecilia • Couple Trip
Check in was so professional and friendly. Room was very clean. Staff very helpful! Great stay!
5.0/517 May 2026
Ramona • Couple Trip
Kayak, pools and breakfast were awesome
5.0/517 May 2026
Michael • Trip with Friends
Just show up and lay low. Forget all the noise you left behind...
5.0/517 May 2026
Frankie • Trip with Friends
What a low key place...it was a well maintained and serviced place. The front desk and other property associates were willing to bend over backwards to help.
5.0/517 May 2026
Dan • Couple Trip
The breakfast was wonderful!
5.0/517 May 2026
Alexander • Couple Trip
Sehr aufmerksames freundliches Personal. Bei Ankunft gab es erstmal einen Willkommensgetränk. Personal beim Frühstück super nett und zuvorkommend. Zimmer sauber, Anlage ein Traum! Bestes Hotel auf Islamorada!
5.0/516 May 2026
Maria
Our stay at Chesapeake Beach Resort was absolutely amazing from start to finish! The check-in process was quick and easy, and every staff member made us feel so welcomed and accommodated throughout our stay. The complimentary breakfast each morning was fresh and delicious. I had a made-to-order omelet with spinach, tomato, and feta cheese that was SO good! A huge thank you to Jose, Kathy, and Dilcia for going above and beyond — they were incredibly kind, attentive, and even brought our food directly to the table with a smile. Their hospitality truly made the experience special. Later, we had lunch and drinks at the bar with Jose Y, and he was fantastic! He made amazing drinks and provided outstanding service the entire time. Everything about this resort exceeded expectations, and we can’t wait to come back!
5.0/515 May 2026
David
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5.0/514 May 2026
Bryce Griffin • Couple Trip
Great, will recommend
5.0/514 May 2026
Bruna • Family Trip
Hotel excelente com diversas atividades café da manhã delicioso.
5.0/514 May 2026
Jesse • Family Trip
Breakfast was one of the best in the world…
5.0/513 May 2026
Joni • Family Trip
Free, breakfast free, bike rentals great beach, great rooms nice and cool. Honestly, it was a great place.
5.0/512 May 2026
Heibar • Family Trip
The Villas are great! Nice and clean/ modern We had an amazing time with my elderly parents and my litte kids.
5.0/512 May 2026
Ramsey • Couple Trip
This was a beautiful calm serene resort! Bed and pillows were amazing. Loved our stay!
5.0/512 May 2026
Peggy • Couple Trip
Breakfast was great
5.0/511 May 2026
Gregor • Couple Trip
Amazing breakfast! Location very good. Attentive staff, plenty of wild life such as iguanas, sharks (we spotted a baby shark and a bigger one!), fish, birds etc. The nice thing is that you can use 2 hours per day a sub, kajak, fishing rod, bicycle and more for free!
5.0/511 May 2026
doris • Couple Trip
the place is great for R&R
5.0/511 May 2026
Yolvert • Family Trip
Breakfast the best ! Staff wonderful!
5.0/510 May 2026
Cheryl • Family Trip
The breakfast was beyond our expectations. The staff went back and mopped the floors after we mentioned they were dirty. The rooms are super clean and spacious. Bathroom is larger than anticipated. Lovely upgrades. The queen beds so much better option then double beds! Quick walk to the water. Back deck was cozy for early morning coffee and night caps. Re booked to go back at the end of the week❣️

Location

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83409 Overseas Hwy, Islamorada, Florida, US
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.
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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.

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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, 21 Aug 2026 - Sat, 22 Aug 2026 (1 night)
1 Room, 1 Adult, 0 Children