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All 20 Islamorada hotels

Chesapeake Beach Resort

2.5 of 5 Resort   |   83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
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Ranked #14 of 20 hotels in Islamorada
A recent review
5 of 5 stars reviewed 3 days ago
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357 people have reviewed this hotel

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Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    4 of 5 stars
  • Rooms
    3.5 of 5 stars
  • Service
    4 of 5 stars
  • Value
    3.5 of 5 stars
  • Cleanliness
    4 of 5 stars
Traveler tips help you choose the right room.   Room tips (99)
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English first
Senior Reviewer
10 reviews 10 reviews
3 hotel reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed 3 days ago NEW

Once again, the Chesapeake Beach resort has made us ridiculously satisfied. If you're looking for a high-end hotel, keep going. It's a throwback-type motel that you would expect in the 50's or 60's but it really doesn't disappoint. It's quaint and the location is great. Unlike other resorts we've found throughout the Keys, they don't mind you bringing a cooler... More

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Fort Lauderdale, Florida
Senior Contributor
27 reviews 27 reviews
18 hotel reviews
32 helpful votes 32 helpful votes
4 of 5 stars Reviewed 1 week ago

My boyfriend and I chose this hotel because we have a 23ft Yamaha and wanted to launch and dock our boat at the hotel where we were staying. Upon arrival, James at the front desk checked us in quickly and our room was ready at 12:00 PM. Upon walking into our garden view room, I was overwhelmed by the smell... More

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Clinton, South Carolina
Senior Reviewer
10 reviews 10 reviews
4 hotel reviews
8 helpful votes 8 helpful votes
2 of 5 stars Reviewed 3 weeks ago

This place has so much going for it. The location is incredible. The sunrise is awesome and the grounds and offerings are nice. However they have let the place go. The ocean there smells horrible so I do not recommend swimming in it but the kayaks, paddle boats and other sports shack items are included in your stay. I did... More

Was this review helpful? Yes 2
DeBary, Fl
Senior Reviewer
9 reviews 9 reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 3 weeks ago

Once again stayed here.. Brought family with us.. We had three seperate reservations.. We had the time of our lives.. You can be as busy or as relaxed as you want. Staff were amazing friendly and attentive. Breakfast was always well stocked. The location is perfect with things to do and restaurants closeby. Rooms were well appointed and if we... More

Was this review helpful? Yes 1
jupiter, fl
Senior Reviewer
9 reviews 9 reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 3 weeks ago

We usually stay at The Islander but decided to try Chesapeake Beach Resort and we really enjoyed it. Breakfast wasn't just continental. They had eggs/bacon/sausage/waffles etc and it was included in the price as well as their outdoor sports. Kayaks, bikes, paddle boats are all included. At The Islander, you pay $40 to use a Kayak all day and they... More

Was this review helpful? Yes 1
Hialeah, Florida
Senior Contributor
25 reviews 25 reviews
6 hotel reviews
18 helpful votes 18 helpful votes
1 of 5 stars Reviewed 4 weeks ago

We have stayed there many times before, the last time was last weekend. My husband left his watch (a $3000 Bulova watch) in the top drawer of the dresser. He went fishing, came back went to dinner, came back went to sleep. The next day he packed his cloths and left When he got home he noticed his watch was... More

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Jupiter, Florida
1 review
5 of 5 stars Reviewed 4 weeks ago

This hotel was as nice as the big name resorts for a $100+ less. Clean, quiet, comfy beds, directly on the beach, balconies in all rooms, great restaurant with ocean views next door. I highly recommend & will stay again.

Was this review helpful? Yes 1
Savannah, Georgia
4 reviews 4 reviews
3 hotel reviews
8 helpful votes 8 helpful votes
1 of 5 stars Reviewed July 21, 2014

Only because the front desk people there are so rude, I rated this place Terrible! The views are wonderful and the housekeepers are okay but the front desk people hurry to check you in and get you out of the office quick and do not seem to care about the guests! When I checked in they gave me a map... More

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Townsend, MA
Top Contributor
87 reviews 87 reviews
20 hotel reviews
70 helpful votes 70 helpful votes
4 of 5 stars Reviewed July 20, 2014

Stayed in a deluxe oceanfront and the room was typical older resort room. Could definitely use an upgrade. Nice view, small waterfront. Good under building parking. Terrible breakfast - bacon sliced so thin you could see through it with no flavor. Horrible wifi. Got kicked off regularly.

Was this review helpful? Yes 1
Atlanta, Georgia
2 reviews
2 helpful votes 2 helpful votes
4 of 5 stars Reviewed July 7, 2014

A very friendly staff on a busy holiday weekend and a great experience throughout our stay. Overall, a good value and experience. Stayed in a Deluxe Ocean-view room. The room was clean each day on our return and the view from the room was as advertised. The bath counter and sink were updated as well as the room itself but... More

Was this review helpful? Yes 2
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Additional Information about Chesapeake Beach Resort

Address: 83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Phone Number:
Location: United States > Florida > Florida Keys > Islamorada
Price Range (Based on Average Rates): $$
Hotel Class:2.5 star — Chesapeake Beach Resort 2.5*
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Also Known As:
Chesapeake Beach Hotel Islamorada

249 photos of this hotel

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Pool/beach area (38)
Hotel & grounds (52)
View from room (18)
Room/suite (33)
Bathroom (7)
Dining (1)
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Beach Fitness Center with Gym / Workout Room Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Kitchenette Room Service Suites Swimming Pool Wheelchair access
Hotel Style
#4 Top resorts Hotel in Islamorada #9 On the Beach Hotel in Islamorada
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Official Description (provided by the hotel)
Islamorada’s famous beach and fishing destination, Chesapeake Beach Resort, rests on 6.5 acres of oceanfront sands and gardens halfway between Miami and Key West, in the Florida Keys. Our property is now exquisitely remodeled to deliver state-of-the-art amenities and luxurious accommodations to our guests. We are proud to offer 37” HDTV, Stereo radio/CD/alarm with MP3 docking capabilities and wireless internet connection, along with new carpeting, furniture and remodeled bathrooms and kitchens including granite countertops and vanities; all to make your stay more enjoyable and relaxing. ... more   less 
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  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

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