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

Hotel website
83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Best prices for your stay
Enter dates for best prices
Check In Check Out
Check Availability
Book on
or compare prices from up to 200 sites including:
Professional photos
Chesapeake Beach Resort
Chesapeake Beach Resort
Panoramas (12)
View Map
Add Photo Write a Review

540 Reviews from our TripAdvisor Community

Traveler rating
Traveler type
Time of year
Language
  • More
Turin, Italy
Level Contributor
32 reviews
23 hotel reviews
common_n_hotel_reviews_1bd8 29 helpful votes
4 of 5 stars Reviewed 3 days ago NEW via mobile

It started bad because they didn't have our reservation made by booking.com But the manager gave us an upgrade to ocean view room which was lovely. Rooms are spacious clean with big bathroom and the balcone. View is stunning . WiFi working ok. Big tv, water daily housekeeping daily. Resort is lovely there are 2 swimming pools with heated water... More 

Helpful?
1 Thank sniegula
new york
Level Contributor
133 reviews
30 hotel reviews
common_n_hotel_reviews_1bd8 91 helpful votes
4 of 5 stars Reviewed 1 week ago

We had never been to the Florida Keys and were invited to a 'destination wedding' in Islamorada. We were looking for a moderately priced place to stay and found this Resort. We opted for a garden-view Villa. Nothing fancy, but quite adequate for our needs. 2 double beds, a full kitchen, table and 2 chairs, couch, sofa bed and flat-screen... More 

Helpful?
1 Thank NewYorkelena
Nottingham, UK
Level Contributor
17 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
4 of 5 stars Reviewed 1 week ago via mobile

We stayed here for two nights after leaving Miami and heading down to key west. It's was a great little stop off with the rooms being very comfy. It's a quiet resort with ample pool and beach areas. The breakfast was great in terms of choice and layout of items. Staff were always helpful too. We found a great free... More 

Helpful?
2 Thank HollieV
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
3 of 5 stars Reviewed 1 week ago via mobile

We stayed for our 25th wedding anniversary. So disappointing. Smelly room, dirty carpets, dated, no real sand just gritty cement. Disgusting breakfast served in a filthy room in black polystyrene bowls, plastic cutlery. No pool bar. The only good thing was the restaurant next door!

Helpful?
1 Thank Shelser
woodbridge, va
Level Contributor
11 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
4 of 5 stars Reviewed 1 week ago

They use the term "resort" very loosely and to charge $20 a day is ridiculous. The property has gorgeous views but no restaurant or bar on "resort" and rooms are adequate, not resort like at all. The breakfast is ok for one or two mornings and is more than you get at other hotels down there, but we went out... More 

Helpful?
1 Thank cant25
Miami, Florida
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

Chesapeake resort has breathtaking views. I really enjoyed my stay. I stayed in the garden view room with two double beds. It had a full kitchen, sofa bed, and a screened porch. The property is gorgeous and has a lot of areas where you can kick back and relax. I highly recommend this to someone who wants a nice view... More 

Helpful?
1 Thank Yvette H
Cranston, Rhode Island
Level Contributor
8 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
4 of 5 stars Reviewed 2 weeks ago

We brought our daughters - ages 10 and 12 - and all of us really liked this place. It was chilly (for south Florida) during our stay, so we enjoyed spending time in the hot tub and the warmer pool. (The other was too cold for the adults to enjoy, but the kids liked it.) The free breakfast wasn't fancy,... More 

Helpful?
2 Thank Joe G
2 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
3 of 5 stars Reviewed 4 weeks ago

The room was clean, but very old. I'm not hard to please so this was fine, but they charge you $20/day, on top of an expensive nightly rate. This extra charge is not included in the nightly rate. Why? Almost false advertisement, I think. The "free" breakfast, that you actually pay for is bad to say the least. One of... More 

Helpful?
Thank Maxkyl
Seaford, New York
Level Contributor
21 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 7 helpful votes
3 of 5 stars Reviewed January 4, 2016

We have been to this property multiple times. Great location for fishing. It has gotten rather pricey from when we first started going way back when. We like to stay in the cottages that have a kitchen.

Helpful?
Thank carafid1
2 reviews
5 of 5 stars Reviewed January 3, 2016 via mobile

Super helpful and friendly staff. Room was exactly what we expected and it was perfect for our stay. The housekeeping staff did a great job as well. The amenities were very nice, so many included items with the stay. Many things that the kids enjoyed trying. Would come back anytime.

Helpful?
Thank Amy L
Questions? Get answers from hotel staff and past guests. Ask a question

601 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All Traveler Photos (327)
Viewed
Pool/Beach Area (49)
Viewed
Hotel & Grounds (65)
Viewed
View from Room (26)
Viewed
Room/Suite (41)
Viewed
Bathroom (10)
Viewed
Dining (1)
Viewed
1:58
Videos (1)
Viewed
Other (134)

TripAdvisor Photos: Professional photos exclusively commissioned by TripAdvisor

Viewed
All TripAdvisor 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
Room/Suite (5)
Viewed
View from Room (3)
Viewed
Other (4)
Check In Check Out
Show Prices
Hotels you might also like...
Also consider these accommodations in or near Islamorada
3.6 mi away
Amara Cay Resort
Amara Cay Resort
#7 of 19 in Islamorada
4.0 of 5 stars 914 reviews
17.8 mi away
Hampton Inn Key Largo
Hampton Inn Key Largo
#4 of 17 in Key Largo
4.5 of 5 stars 2,584 reviews
0.6 mi away
Postcard Inn Beach Resort & Marina at Holiday Isle
Show Prices
Show Prices
Show Prices
1.9 mi away
Cheeca Lodge & Spa
Cheeca Lodge & Spa
#9 of 19 in Islamorada
4.0 of 5 stars 2,435 reviews
0.8 mi away
Pelican Cove
Pelican Cove
#8 of 19 in Islamorada
4.0 of 5 stars 318 reviews
2.4 mi away
Islander Resort, a Guy Harvey Outpost
Show Prices
Show Prices
Show Prices
Questions? Get answers from hotel staff and past guests. Ask a question

Amenities

Enter dates for best prices
Check In Check Out
Price Your Stay