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“Tranquil and serene.....” 4 of 5 stars
Review of Chesapeake Beach Resort

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Chesapeake Beach Resort
2.5 of 5 Resort   |   83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036   |  
Hotel website
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Hotel amenities
Special Price
15% off room rate
Ranked #13 of 19 hotels in Islamorada
Phoenix, Arizona
Top Contributor
108 reviews 108 reviews
27 hotel reviews
Reviews in 58 cities Reviews in 58 cities
67 helpful votes 67 helpful votes
“Tranquil and serene.....”
4 of 5 stars Reviewed November 17, 2012

If you are looking for a relaxing time overlooking the ocean and surrounded by beautiful grounds, this is your place. It's not fancy and the rooms are a bit outdated but it's really a lovely place. Make sure you get the ocean front rooms, though! I don't think we would have enjoyed it nearly as much had we not had the balcony with the view. Breakfast is included and it was nice to grab a bit and sit outside near the water. There's a pool and jacuzzi on property and they were never crowded when we were there. It is walking distance to a couple of great restaurants...one of which provides "room service" through an agreement with the hotel.

Room Tip: Ocean front all the way!
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  • Stayed November 2012, traveled with friends
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
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317 people have reviewed this hotel

Traveler rating
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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 (78)
Date | Rating
  • English first
  • French first
  • German first
  • Spanish first
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English first
Plainfield, Connecticut
Top Contributor
102 reviews 102 reviews
14 hotel reviews
Reviews in 27 cities Reviews in 27 cities
42 helpful votes 42 helpful votes
4 of 5 stars Reviewed November 12, 2012

a good way to describe this place is like a " beach compound." its snuggled nicely within its property boundaries and even though your near the road and the neighbors on the sides, you wouldn't know it. pretty large beach area with large tiki hut where you can use the kayaks and paddleboats, also a small marina where you can stroll and watch the boats and talk to the captains and see the catch of the day. beautiful view of the sunrise and plenty of lounge chairs to sit by the water and relax or enjoy a cold beverage. also a nice pool, hot tub and respectable breakfast spread in the morning. eggs, bacon, toast, muffins, coffee, juice, fresh fruit and friendly staff. rooms were clean and room service comes from the restaurant next door called "wahoo's" and was fast and although not cheap, was very good food. no complaints!

  • Stayed November 2012, traveled with family
    • 3 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Columbia City, Indiana
Contributor
14 reviews 14 reviews
4 hotel reviews
Reviews in 6 cities Reviews in 6 cities
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed November 6, 2012

My wife and recently stayed at the Chesapeake Beach Resort on Islamorada for 3 days following a business conference in Miami. It's an older, smaller hotel with a bit of wear and tear, but overall a great value. The rooms were clean, breakfast was good, and the staff very friendly and helpful. The beds in our room were a bit on the hard side, but I slept well. The setting on the Atlantic side was beautiful, uncrowded, quiet and relaxing. I spent the better part of one afternoon reading and snoozing in a hammock about 30 feet from the shore. Just what we needed after being in Miami for several days. Plenty of good, close restaurants, including several with beautiful sunset views. Key West was approx. 1.5 - 2 hour drive away. We would definately go back.

  • Stayed November 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 3 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 5 of 5 stars Service
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Toronto, Canada
Reviewer
5 reviews 5 reviews
3 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed November 3, 2012

I am from Toronto, Canada and here at the Chesapeake Beach Resort for two weeks “working”. My room is overlooking the lagoon, there are hammocks between the palm trees, and the views are spectacular. I come every year to recharge my batteries. I love to swim in the lagoon; I have seen manatees and dolphins. I spend many leisurely hours on the point taking pictures, enjoying the sunrise and getting inspiration for my writings. The room is clean; the staff is so friendly and helpful. This is a wonderful place. A # 10 for me. it is a piece of Paradise.

  • Stayed November 2012, traveled solo
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
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Andover, New Jersey
Senior Reviewer
9 reviews 9 reviews
4 hotel reviews
Reviews in 6 cities Reviews in 6 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed November 2, 2012

I can't think of anything but excellent to say about this resort! The staff was friendly, rooms wer'e spotless and very comfortable. My husband and I make a trip to the keys several times a year for the last eight years wev'e stayed at alot of places. This is now are favorite place to stay! Book a room here and you won't regret it !!!! FANTASTIC.

Room Tip: We had a suite it was waterfront view excellent.
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  • Stayed August 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
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Milwaukee, Wisconsin
1 review
4 of 5 stars Reviewed October 30, 2012

We enjoyed our stay at this sleepy resort with beautiful ocean view. The rooms are slightly outdated, but very clean. The pools were nice, one with view of the ocean since in the Keys no places have very nice beaches. Enjoyed using the kayaks that were included in the resort fee. I'm not sure what some people expect reading some of these other reviews, but we very much enjoyed our stay. Walkable to restaurants and short car ride to charter fishing and snorkeling fun.

Most importantly, we left our iPad in the safe and the staff made sure it was returned to us!!!

Will stay here again..
Will definately come back again. Go for the ocean view rooms.

Room Tip: Choose ocean view
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  • Stayed October 2012, traveled as a couple
    • 2 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 3 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 5 of 5 stars Service
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Palm City, Florida, United States
1 review
3 helpful votes 3 helpful votes
1 of 5 stars Reviewed October 10, 2012

We stayed in the two bedroom villa with kitchen. There was mold in cabinets and rat poop under the sink. I had three young kids and they didn't even have a bath tub. The kitchen had only four plates and we were a family of five. The place when we walked in smelled like mildew. The only thing good about the place was the view. My son got so sick the last night we were there we had to bring him to the emergency room. We still are not sure why he got sick. We complained about the mold and told them where it was they said they would clean it and never did. I would never go back.

  • Stayed August 2012, traveled with family
    • 1 of 5 stars Value
    • 3 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 1 of 5 stars Rooms
    • 1 of 5 stars Cleanliness
    • 1 of 5 stars Service
Was this review helpful? Yes 3
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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Additional Information about Chesapeake Beach Resort

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