We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chesapeake Beach Resort

2.5 of 5 83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Hotel website
Best prices for your stay
Enter dates for best prices
Check In Check Out
Show Prices
Compare best prices from top travel sites
and 7 more sites!
Chesapeake Beach Resort
Professional photos View all
Browse nearby
Chesapeake Beach Resort
Chesapeake Beach Resort
Chesapeake Beach Resort
Write a Review

390 reviews from our community

Traveler rating
    120
    153
    57
    31
    29
See reviews for
111
157
13
4
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 (112)
Date | Rating
  • English first
  • French first
  • German first
  • Italian first
  • Spanish first
  • Any
English first
  • All months
    (390)
  • Mar-May only
    (129)
  • Jun-Aug only
    (102)
  • Sep-Nov only
    (81)
  • Dec-Feb only
    (78)
All months
Buntingford, United Kingdom
Senior Reviewer
10 reviews 10 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 1 week ago

Have stayed at Chesapeake Beach resort on numerous occasions and keep coming back because ,to me , it is the best value for money in the Keys. My room has always been very clean, well appointed and comfortable. The grounds are clean and pleasant and the staff very helpful. When staying with friends we have rented one of the villas... More 

Was this review helpful? Yes
Reviewer
4 reviews 4 reviews
1 of 5 stars Reviewed 1 week ago via mobile

FALSE ADVERTISEMENT. This is my first time to Islamorada and I will never stay at this "resort" again. This is NOT a resort but rather a outdated motel on gravel land with a man made fake beach. The room smelt like must and urine upon arrival and we were informed of an $18 daily fee to utilize old beach equipment.... More 

Was this review helpful? Yes
Cutchogue, New York
Senior Reviewer
9 reviews 9 reviews
3 hotel reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 2 weeks ago

excellent resort -like with clean, comfortable rooms and outside balconies are a great feature. Great little start to the day with breakfast in the Islamorada room. 2 pools and a jacuzzi right on the water with kayaks and bikes for all to use. The best feature… the friendly staff!!! Thank you guys for a great stay!!!

Was this review helpful? Yes 2
jericho, vt
Senior Contributor
36 reviews 36 reviews
5 hotel reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed 3 weeks ago

We rented a bungalow for 3 nights and could not have been happier. The accommodations were clean, comfortable and spacious. The entire resort staff was friendly and helpful. We took advantage of many of the amenities: kayaking, bicycles, swimming were all enjoyable. The shuffleboard area was the only disappointment. I had stayed in this resort several years ago and was... More 

Was this review helpful? Yes 1
Fort Lauderdale, Florida
Reviewer
3 reviews 3 reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed 3 weeks ago

I coordinated a large group of friends to celebrate my husband's 30th birthday in the keys. We stayed at Chesapeake Beach Resort and it was wonderful. It was close to restaurants. The pool was fabulous and the grounds and rooms are clean and well kept. We did bring a boat into the dock to go out to the sandbar. It... More 

Was this review helpful? Yes 1
Baltimore, Maryland
2 reviews
2 helpful votes 2 helpful votes
1 of 5 stars Reviewed 3 weeks ago

Hot tub was out of order, adjoining pool was out of order, construction work in the unit next to ours - hammering started at 7:30AM, toilet clogged, raw sewage backed up into our shower, required to move to a different unit twice without any compensation for our inconvenience. Will not return here!

Was this review helpful? Yes 2
Houston, Texas
Contributor
16 reviews 16 reviews
6 hotel reviews
10 helpful votes 10 helpful votes
4 of 5 stars Reviewed 4 weeks ago

Just spent three nights at Chesapeake and it was great. First off, this is not The Ritz or a W hotel. If that's your expectation, there are several options in Islamorada. Chesapeake is showing its age a little, but overall the resort is clean, the staff is friendly, and the cost is in line with other Keys resorts. Do pay... More 

Was this review helpful? Yes 3
Madison
2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 4 weeks ago

The Chesapeake Resort is the finest resort I have ever stayed at. The rooms were clean and smelled fresh. The tropical landscaping and the property are immaculately maintained. It has an excellent free breakfast buffet with an excellent selection. The staff is courteous and friendly. It is close to many fine restaurants and attractions and a trip to Key West... More 

Was this review helpful? Yes 2
2 reviews
2 helpful votes 2 helpful votes
1 of 5 stars Reviewed November 7, 2014 via mobile

First off our door didn't close all the way. There were bugs that were coming in with the door closed. We had the doors closed all day and somehow had ants that made their way in and were crawling on the dressers. To top it off there was absolutely the loudest festival that was going on in the lot next... More 

Was this review helpful? Yes 2
White Oak, Georgia
Senior Contributor
35 reviews 35 reviews
6 hotel reviews
18 helpful votes 18 helpful votes
4 of 5 stars Reviewed November 6, 2014

We've been vacationing the Florida Keys for 16 years so we've stayed in pretty much all the island and different hotels/ resorts but so far Cheasapeake Beach Resort has the BEST LOCATION. We didn't need to go somewhere else the beach and ocean for swimming were right there. I really loved the atmosphere, the hammock around the property, beach and... More 

Was this review helpful? Yes 5
Questions? Get answers from hotel staff and past guests. Ask a question
Owners: What's your side of the story?
Register now for free — and start getting automatic notification of new reviews, responding to traveler feedback, adding new photos to your listing and much more.
Manage your listing

Been to Chesapeake Beach Resort? Share your experiences!

Write a Review Add Photos & Videos

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*
Number of rooms: 65
Reservation Options:
TripAdvisor is proud to partner with Booking.com, TravelClick, Expedia, Hotels.com, Orbitz, Priceline, Travelocity, Odigeo, TripOnline SA and Tingo so you can book your Chesapeake Beach Resort reservations with confidence. We help millions of travelers each month to find the perfect hotel for both vacation and business trips, always with the best discounts and special offers.
Also Known As:
Chesapeake Beach Hotel Islamorada
Hotel Style:
#4 Top resorts Hotel in Islamorada
#9 On the Beach Hotel in Islamorada

514 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All traveler photos (241)
Viewed
Hotel & grounds (56)
Viewed
View from room (21)
Viewed
Pool/beach area (39)
Viewed
Room/suite (36)
Viewed
Bathroom (9)
Viewed
Dining (1)
Viewed
1:58
Videos (1)
Viewed
Other (78)

Expert photos: Taken by TripAdvisor travel experts

Viewed
All expert photos (252)
Viewed
Amenities (23)
Viewed
Beach (13)
Viewed
Efficiency Villa (30)
Viewed
Ocean View Queen (29)
Viewed
Pool (22)
Viewed
Premium Ocean Front Suite (47)
Viewed
Restaurants and Bars (9)
Viewed
The Hotel (16)
Viewed
Two Bedroom Villa (41)
Viewed
Two Doubles Garden View (22)

Management photos: Courtesy of the property manager

Viewed
All management photos (22)
Viewed
Pool/beach area (10)
Viewed
View from room (3)
Viewed
Room/suite (5)
Viewed
Other (4)
Hotels you might also like...
Check In Check Out
Price Your Stay