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.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

“Great value, beautiful setting.”

Best prices for -
Check In dd/mm/yyyy Check Out dd/mm/yyyy
Prices are for 1 room, 2 adults
Show Prices
Compare best prices from top travel sites
and 12 more sites!
Chesapeake Beach Resort
Ranked #13 of 19 Hotels in Islamorada
Columbia City, Indiana
Level Contributor
25 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
“Great value, beautiful setting.”
Reviewed 6 November 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, travelled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank Kevin R
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Write a Review

694 reviews from our community

Traveller rating
    200
    273
    124
    48
    49
See reviews for
212
303
21
10
Rating summary
  • Location
  • Sleep Quality
  • Rooms
  • Service
  • Value
  • Cleanliness
Traveller tips help you choose the right room.   Room tips (204)
Date | Rating
  • Danish first
  • English first
  • French first
  • German first
  • Italian first
  • Norwegian first
  • Portuguese first
  • Russian first
  • Spanish first
  • Any
English first
Toronto, Canada
Level Contributor
12 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
Reviewed 3 November 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, travelled solo
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
2 Thank birgittemelnick
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Andover, New Jersey
Level Contributor
15 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
Reviewed 2 November 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.
See more room tips
  • Stayed August 2012, travelled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
1 Thank Suzette W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Milwaukee, Wisconsin
1 review
Reviewed 30 October 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
See more room tips
  • Stayed October 2012, travelled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank Kirstin_S_Milw
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Palm City, Florida, United States
1 review
common_n_hotel_reviews_1bd8 4 helpful votes
Reviewed 10 October 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, travelled with family
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
4 Thank Rebecca C
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Jacksonville Beach, Florida
Level Contributor
108 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 24 helpful votes
Reviewed 26 September 2012 via mobile

Just canceled a reservation I made over 9 months ago. They have held my 1 nights deposit [~$200] for that time and now are popping me $25 cancellation fee even though the confirmation says it is 30 days before arrival. I even have a replacement guest waiting to take this room. BEWARE their hidden charges!

Stayed September 2012
Helpful?
5 Thank Doug H
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Bloomington, Illinois
Level Contributor
7 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 13 helpful votes
Reviewed 19 September 2012

The Resort is Awesome. Fish and snorkle right in front of the Resort. There are
no real beaches in the Keys. It's mostly rock. We like laid back relaxing places.
And that's what you get at the Chesapeake. The views are so beautiful. There
are hammocks and lounges everywhere. Great places to eat within walking
distance. Or get in the car and drive in either direction 5 minutes. 2 wonderful
pools. The people who are giving this place bad reviews are rich snobs who
need to stay elsewhere anyway. Great little resort in the Keys!!!

Room Tip: The garden view rooms are smaller because it's the older part. The ocean front rooms and villa...
See more room tips
  • Stayed July 2012, travelled with family
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
1 Thank beachlovers3
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Hotels you might also like...
Travellers also viewed these Islamorada hotels
3.6 mi away
Amara Cay Resort
Amara Cay Resort
#6 of 19 in Islamorada
4.0 of 5 bubbles 1,295 reviews
0.6 mi away
Postcard Inn Beach Resort & Marina
0.8 mi away
Pelican Cove
Pelican Cove
#5 of 19 in Islamorada
4.5 of 5 bubbles 647 reviews
Show Prices
Show Prices
Show Prices
1.5 mi away
Islander Resort, a Guy Harvey Outpost
1.9 mi away
Cheeca Lodge & Spa
Cheeca Lodge & Spa
#7 of 19 in Islamorada
4.0 of 5 bubbles 3,260 reviews
3.3 mi away
La Siesta Resort & Marina
La Siesta Resort & Marina
#11 of 19 in Islamorada
3.5 of 5 bubbles 558 reviews
Show Prices
Show Prices
Show Prices

Been to Chesapeake Beach Resort? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Chesapeake Beach Resort

Property: Chesapeake Beach Resort
Address: 83409 Overseas Hwy, P.O. Box 909, Islamorada, FL 33036-3526
Region: United States > Florida > Florida Keys > Islamorada
Amenities:
Beach Business Centre with Internet Access Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Kitchenette Room Service Suites Swimming Pool Wheelchair access
Hotel Style:
#6 Top resorts Hotel in Islamorada
#11 On the Beach Hotel in Islamorada
Price Range (Based on Average Rates): £££
Hotel Class:2.5 star — Chesapeake Beach Resort 2.5*
Number of rooms: 65
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 delivers state-of-the-art amenities and luxurious accommodations to our guests. We are proud to offer HDTV, Stereo radio/CD/alarm and wireless internet connection, along with carpeting, furniture, bathrooms and kitchens including granite countertops and vanities; all to make your stay more enjoyable and relaxing. ... more   less 
Reservation Options:
TripAdvisor is proud to partner with Travel Republic (UK), Expedia, Priceline, TravelUp, Booking.com, Hotels.com, TripOnline SA, Traveltool, S.L.U., Cancelon, Evoline ltd, getaroom.com and HotelQuickly so you can book your Chesapeake Beach Resort reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
Also Known As:
Chesapeake Beach Hotel Islamorada
Chesapeake Beach Resort Islamorada, Florida - Florida Keys

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing