Description
Spend the day on the private beach or dip into one of the 2 outdoor swimming pools. This hotel also features complimentary wireless internet access and concierge services.. Featured amenities include a computer station, a 24-hour front desk, and multilingual staff..
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 (2.8 km) from Keys History & Discovery Center.. Distances are displayed to the nearest 0.1 mile and kilometer. History of Diving Museum - 0.9 km / 0.6 mi Windley Key Fossil Reef Geological State Park - 1.8 km / 1.1 mi Islamorada Brewery & Distillery - 2 km / 1.2 mi Keys History & Discovery Center - 2.7 km / 1.7 mi Matecumbe United Methodist Church - 3.1 km / 1.9 mi Florida Keys Brewing Co. - 3.4 km / 2.1 mi MoradaWay Arts & Cultural District - 3.5 km / 2.2 mi Hurricane Monument - 3.6 km / 2.3 mi Indian Key Historic State Park - 4.9 km / 3.1 mi Rain Barrel Village - 5.1 km / 3.2 mi Founders Park - 5.2 km / 3.2 mi Islamorada County Park - 5.3 km / 3.3 mi Bud n' Mary's Dive Center - 6.2 km / 3.8 mi Old Road Gallery - 8.6 km / 5.4 mi San Pedro Underwater Archaeological Preserve State Park - 10.1 km / 6.3 mi The preferred airport for Chesapeake Beach Resort is Miami Intl. Airport (MIA) - 124.8 km / 77.5 mi . In Islamorada (Matecumbe).
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..
- Other
- Air conditioning
- Heating (free of charge)
- Additional services
- Laundry
- Laundry Service
- Lift
- Maid
- Reception
- 24-hour reception
- Concierge service
- Multilingual staff
- Entertainment
- Computer room
- Parking
- Nearby parking
- Parking
- Pets
- Pets allowed
- Smoking
- Smoking not allowed
- Wi-Fi
- Complimentary Wi-Fi
- Services
- Balcony
- Bike rental
- Café
- Courtyard
- Fan
- Garden
- Hair dryer
- Heated pool
- Iron
- Luggage storage
- Microwave
- Private check-in / check-out
- Public bathroom
- Room service
- Safe
- Serviced office
- Stores
- Supermarket in hotel
- Terrace
- Towel service
- Children
- Game area
- Kids' TV channels
- Kids' board games
- Kids' playground
- Bars
- Coffee/tea in public areas
- Vending machines
- Restaurants
- Barbecue / grill
- Breakfast buffet
- High chairs
- Swimming pools
- Children’s pool
- Outdoor pool
- Poolside parasols
- Poolside sun loungers
- Gym and SPA
- Jacuzzi
- Spa
- Accessibility
- Facilities for people with disabilities
- Wheelchair access
- Check-in/Check-out
- Deposit:
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- General
- Number of people: #{numberOfPersons}
- Floor: #{floorNumber}
- Tourism register number:
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- Our rentals include:
- Utilities
- Cleaning
- Admin fees and taxes
Good to know
About the deposit
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Some accommodation providers may require a deposit, which is not included in the price. This deposit will be payable upon arrival and refunded in full upon departure, provided that no damage has been caused.
Additional information
Key pick-up
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Taxes included in the final price
Any local tourist tax/resort fee has to be paid on spot directly by clients, if applicable Yes No
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Very good
Based on 322 reviews
Location
Quiet in the room
Rooms
Service
Value for money
Cleanliness
This accommodation stands out for being in the heart of Islamorada
Showing 5 featured reviews out of 322 TripAdvisor reviews
B
BJ c
Vancouver wa
11/05/2026
“Excellent resort”
Amazing resort can’t wait to come back awesome staff & Chef Jose & Dilcia made the best omelettes ever you guys Rock
A
aussiewanderers
Sydney, Australia
10/05/2026
“Luxurious resort with wide beach frontage but some minor room shortfalls”
We stayed here for almost a week and enjoyed the resort very much. It is about an hour's drive from mainland Florida and 2hrs from Key West. The resort pools are very nice and the beach looks inviting but in reality is difficult to swim in because the sand is littered with coral debris. An Oceanfro… more
J
Jazzy88
Oviedo, Florida
03/05/2026
“Great place to stay”
I'm so glad I found this little resort. It was such a nice place at prices lower than most other nearby places. Beautiful location, super friendly and helpful staff, and the included breakfast was so good. I cannot wait to come back here
G
Getaway55893863402
26/04/2026
“I'd go back in a heartbeat!”
I highly recommend Chesapeake Beach Resort in Islamorada! My husband and I visited to celebrate our wedding anniversary and they left us a nice note and bottle of champagne in our room at check in. We booked an ocean view room and what an amazing ocean view it was! The pictures on the website do no… more
R
Richard A
Milton Keynes, United Kingdom
08/05/2026
“Would recommend this place to and friend and would stay here again.”
Beautiful resort, location perfect for a stay in the keys as it is central with other keys accessible. Islamorada has a nice vibe as does the resort. Accommodation was clean and modern with a nice breakfast and friendly helpful staff.
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