Online exclusive! Beat the clock -- stay at Chesapeake Resort in Islamorada for our lowest rate ever. Reserve online now for $225 - $400.00
Location. The Chesapeake Beach Resort is located in Islamorada, Fla., in the Florida Keys. Seafood restaurants, fine dining, casual restaurants and bars are available nearby on the Overseas Highway, starting one-half mile from the resort. America's only living-coral barrier reef, which runs the length of the Florida Keys, begins about five miles offshore. Teeming with colorful tropical fish, underwater gardens and shipwrecks, the Florida Keys is world famous for fishing, diving and snorkeling.
Features. This family-friendly resort is set amidst towering palms, flowering hibiscus and vibrant bougainvillea on six-and-one-half acres of tropical landscaping. Winding pathways, a lagoon and waterfalls add to the tranquil atmosphere. Many species of birds and butterflies are frequent visitors. The resort features a private, 700-foot white-sand beach and a private lagoon with a small harbor and boat docks. Continental breakfasts are served each morning on the beach. The resort offers two heated swimming pools and spa tub, a tennis court, and a fitness center. Bicycles, fishing gear and watercraft rentals are available at the water sports facility. The Danica Anne charter boat, located at the Chesapeake Beach Resort, offers deep-sea fishing charters for marlin, sailfish and tuna. A children's sandy play area offers a jungle gym, swings and slides.
Guestrooms. The Chesapeake Beach Resort offers guestrooms and suites with separate living and sleeping areas. Guestrooms, located in a two-story building without elevators, offer coffeemakers and mini fridges. Oceanfront suites feature kitchenettes. Select suites offer jetted tubs and dining tables with chairs. Rooms also have 37-inch HDTVs, clock radios with CD players and MP3 docking stations, and wireless Internet access. Private balconies or terraces boast ocean or garden views. Complimentary designer toiletries are provided, along with compact refrigerators, microwaves, and coffee/tea makers. All guestrooms are smoke-free.
Features. This family-friendly resort is set amidst towering palms, flowering hibiscus and vibrant bougainvillea on six-and-one-half acres of tropical landscaping. Winding pathways, a lagoon and waterfalls add to the tranquil atmosphere. Many species of birds and butterflies are frequent visitors. The resort features a private, 700-foot white-sand beach and a private lagoon with a small harbor and boat docks. Continental breakfasts are served each morning on the beach. The resort offers two heated swimming pools and spa tub, a tennis court, and a fitness center. Bicycles, fishing gear and watercraft rentals are available at the water sports facility. The Danica Anne charter boat, located at the Chesapeake Beach Resort, offers deep-sea fishing charters for marlin, sailfish and tuna. A children's sandy play area offers a jungle gym, swings and slides.
Guestrooms. The Chesapeake Beach Resort offers guestrooms and suites with separate living and sleeping areas. Guestrooms, located in a two-story building without elevators, offer coffeemakers and mini fridges. Oceanfront suites feature kitchenettes. Select suites offer jetted tubs and dining tables with chairs. Rooms also have 37-inch HDTVs, clock radios with CD players and MP3 docking stations, and wireless Internet access. Private balconies or terraces boast ocean or garden views. Complimentary designer toiletries are provided, along with compact refrigerators, microwaves, and coffee/tea makers. All guestrooms are smoke-free.
Check Rates: Chesapeake Resort
For the best prices at Chesapeake Resort, enter your dates:
Prices are in US dollars. If you have any questions or would rather book by phone, please call (800) 370-9416.
Not what you were expecting? Check rates at other hotels in Islamorada.
Not what you were expecting? Check rates at other hotels in Islamorada.
Guest Reviews: Chesapeake Resort
Provided by TripAdvisor
- Traveler Reviews brought to you by

- Chesapeake Beach Resort
- 83409 Overseas Highway, P.O. Box 909 | Islamorada, FL 33036
- TripAdvisor Traveler Rating:
-
Based on 84 traveler reviews
- Most Recent Traveler Reviews:
-
-
- Mar 4, 2010 hotelsnobMadison_WI, Madison,WI
- I booked this "resort" after viewing the web site. What a dissapointment. The location is pretty but the place is an old motel. Our room had some new furniture and... more »
-
- Mar 3, 2010 Keystravlers, Colorado
- We spent the weekend there and loved it. Great views and right next door to great charter fishing. The rooms have been updated and done very well. They are beautiful.... more »
-
- Feb 28, 2010 DentalDan, Cape Canaveral Florida
- I have been going to the Chesapeake for several years now, and I have to say that this place is all about being "the dude". Very laid back experience...yes, the... more »
-
- Jul 29, 2009 quiverranch, Oklahoma
- We really liked staying here. We stayed in a villa and had plenty of room for 5 kids, three adults. The kitchen had every thing we needed. We enjoyed our... more »
-
- Jul 28, 2009 MiamiKel, miami
- This hotel saved our vacation! We were booked for another hotel, but due to its unacceptable appearance/condition we did not even check in - it was a scary place! The... more »
-
These reviews are the subjective opinions of individual travelers and not of TripAdvisor LLC nor of its partners.
© 2010 TripAdvisor LLC
Map & Directions: Chesapeake Resort
GPS Coordinates: 24.94540 -80.60340
Address: 83409 Overseas Highway, Islamorada, FL 33036See other hotels near Chesapeake Resort.
Islamorada/Oceanfront
Nearest Airport
Points of Interest
Key West International Airport [EYW]
77mi
Points of Interest
Theater of the Sea on Islamorada
0.20mi
Downtown Islamorada
1.20mi
History of Diving Museum
1.45mi
Hurricane Monument
3.13mi
Bud n Marys Dive Center
4.72mi
Dolphins Plus - Key Largo
13.86mi
Downtown Key Largo
14.39mi
Long Key State Park
16.40mi
Dolphin Research Center
24.74mi
Curry Hammock State Park
27.67mi
General Directions
83409 Overseas Highway, Islamorada, Fla.
From Miami International Airport:
Take 836 West to the Florida Turnpike South.
Remain on the Turnpike until it ends at Florida City.
Continue South on Overseas Highway to mile marker 83-5.
Chesapeake Resort is on the left.
83409 Overseas Highway, Islamorada, Fla.
From Miami International Airport:
Take 836 West to the Florida Turnpike South.
Remain on the Turnpike until it ends at Florida City.
Continue South on Overseas Highway to mile marker 83-5.
Chesapeake Resort is on the left.
Amenities: Chesapeake Resort
Hotel Services
Kitchen
24-Hour Security
Laundry Facilities
Kitchen
24-Hour Security
Laundry Facilities
Recreational Services
Fitness Facility
Fitness Facility
Q&A: Chesapeake Resort
There are no current discussions to read in the forum - be the first to ask a question!
Not what you're looking for? View other hotels in Islamorada























“Save your money”
“One of the best places in Islamorada!”
“I love being a salty dog.”