Chesapeake Beach Resort

Top rated by guests
Beach
Bathroom
Beach
Beach
Hot Tub, Swimming pool
review stars
8.5Excellent
(739 Ratings)
"The staff was extremely helpful and friendly throughout our stay. The complimentary breakfast was excellent, and the location was perfect. We especially enjoyed the amenities, including the kayaks, bi..."
Verified guest
Don't miss out! Price and availability may change
8.5 / 10
Excellent(739 Ratings)

Resort in Upper Matecumbe Key, FL

3-Star Resort

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this resort

Guests at this Islamorada oceanfront resort can enjoy free WiFi access. Windley Key Fossil Reef Geological State Park is 2 miles away.

Amenities

Concierge services
Free WiFi/internet
Free Parking
Air conditioning
Pool
Non-smoking
Pets allowed
Gym
Heating
Wheelchair accessible
WiFi/Internet
Private beach access
Beach access
Accessible Parking
Beach front
Toilet with grab rails
Accessible by lift
Key card access
Housekeeping available
Fire alarm
Fire extinguisher
Cleaning products

Map of Upper Matecumbe Key, FL

city location on map

Available Rooms

Ratings and reviews

8.5 / 10
Excellent(739 Ratings)
100% verified reviews
10 / 10Outstanding·Sep 2026
The staff was extremely helpful and friendly throughout our stay. The complimentary breakfast was excellent, and the location was perfect. We especially enjoyed the amenities, including the kayaks, bikes, pool, and beach. The views were absolutely stunning and made our stay even more memorable.
8 / 10Excellent·Sep 2026
The pool, the jacuzzi, the room with ocean view, breakfast area with ocean view, and breakfast was great.
The beach. Too much algae to go swimming.
10 / 10Outstanding·Sep 2026
This resort is on an absolute beautiful piece of property with stunning views of the Atlantic. The sunrises couldn’t be more picturesque. The facilities are so clean & the rooms are spread out enough where you don’t feel on top of each other
The drinks & the food at their bar were very pricey.
5 / 10·Oct 2026
Confortable
Title: A Huge Disappointment – Terrible Customer Service This was the hotel we were most excited about during our entire trip. We carefully chose this property for our stay in Key West, expecting a wonderful and memorable experience. Unfortunately, our excitement turned into frustration from the moment we arrived. We arrived around 2:00 PM and were greeted by a staff member named Jasmine, who was extremely rude, unfriendly, and dismissive. She insisted that check-in was only possible at 4:00 PM. We completely understand that hotels have check-in policies, but the property appeared nearly empty at the time. Despite our polite request, Jasmine showed absolutely no willingness to help or even treat us with basic courtesy. To make matters worse, we had specifically booked an oceanfront accommodation, but we were assigned a room with a side ocean view instead. When we questioned this, Jasmine simply claimed that the hotel was fully booked, which was very difficult to believe given how empty the property appeared. What disappointed us most was not simply the check-in time or the room assignment, but Jasmine’s attitude and complete lack of hospitality. For a hotel of this category, such unprofessional and disrespectful service is unacceptable. We had such high expectations for this stay, and unfortunately, one employee’s behavior completely overshadowed what should have been a beautiful experience. A beautiful property means very little when guests are treated with such a lack of respect and consideration.

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FAQs

Is parking included with this resort?

Parking is not specified as an available amenity at Chesapeake Beach Resort. For more information, we encourage you to contact the property about where to park.

Is there a pool at this resort?

Yes, a swimming pool is available for use at Chesapeake Beach Resort. Enjoy the water!

Is Chesapeake Beach Resort pet friendly?

Yes! This resort is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Chesapeake Beach Resort?

We found 22 amenities for this rental. This includes concierge services, free wifi/internet, free parking, air conditioning, and pool.


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