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
- 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' board games
- Kids' playground
- Bars
- Coffee/tea in public areas
- 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
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- 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 314 reviews
Location
Quiet in the room
Rooms
Service
Value for money
Cleanliness
This accommodation stands out for being in the heart of Islamorada
Showing 4 featured reviews out of 314 TripAdvisor reviews
S
SidD665
Venice, Florida
11/04/2026
“Delightful resort!”
Probably my 5th stay there over many years...always for bonefishing down keys from there. Chesapeake just keeps getting better and better, and it started out quite highly rated. More and really nicely redone rooms, nice amenities, the freshly cooked breakfasts are a delicious morning treat! And … more
C
Cindy G
28/03/2026
“Great experience”
Perfect location in Islamorada with nice views of the water. The pools were lovely and water warm and the tiki bar and lounge chairs facing the ocean made relaxing easy. Service was good and the rooms and grounds very clean. The free breakfast with made to order omelets saved us driving to restaur… more
G
Guide07796627164
24/03/2026
“Great spot”
Honestly doesn't show great from.the road. Simple check in with a complimentary glass of champagne. We rounded the corner and saw a beautiful setting. Our room was spacious and clean with beautiful views of the ocean. The salt water pool was very nice. Plenty of chairs on the beach. A breakfast wa… more
S
summertime120
Saint Paul, Minnesota
19/03/2026
“Great spring break stay!”
We were here for a quick spring break getaway. We loved the low key vibe of the hotel. We stayed in a villa, which was nice for our family of four. I did not realize when I booked it that it was two double beds and a pullout sofa. That made for a few nights of uncomfortable sleep for my husband and… more
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