Chesapeake Beach Resort

4.0

Good(873 Reviews)

Resort in Upper Matecumbe Key, FL

3-Star Resort

Reasons to book

Free cancellationFull refund if you change your mind

Great for petsBring all your friends and family, even the furry ones

High-end valuePrice for this property is higher than average in the 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

Pool

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Parking

Balcony or Patio

Dishwasher

Hot tub or spa

Wheelchair accessible

Beachfront or waterfront

Map of Upper Matecumbe Key, FL

Nearby attractions

Everglades National Park

30.1 mi

Everglades Alligator Farm

32.3 mi

Florida Keys Aquarium Encounters

29.8 mi

Theater of the Sea

0.8 mi

Available Rooms

1 King • 344 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

2 Double • 344 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

1 King • 365 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

2 Double • 365 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

1 Sofa • 1 Queen • 592 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

$$$$

Chesapeake Beach Resort

$$$$

4.0

Good(873 Reviews)

Resort in Upper Matecumbe Key, FL

3-Star Resort

Reasons to book

Free cancellationFull refund if you change your mind

Great for petsBring all your friends and family, even the furry ones

High-end valuePrice for this property is higher than average in the 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

Pool

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Parking

Balcony or Patio

Dishwasher

Hot tub or spa

Wheelchair accessible

Beachfront or waterfront

Map of Upper Matecumbe Key, FL

Nearby attractions

Everglades National Park

30.1 mi

Everglades Alligator Farm

32.3 mi

Florida Keys Aquarium Encounters

29.8 mi

Theater of the Sea

0.8 mi

Available Rooms

1 King • 344 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

2 Double • 344 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

1 King • 365 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

2 Double • 365 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

1 Sofa • 1 Queen • 592 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

Reviews

4.0

Good(873 Reviews)

100% verified reviews

0.5

Apr 2024

Inaffidabili

Nulla.

Siete poco onesti, vendere una camera a € 715 quando al massimo costa €400 è vergognoso. Oltre al pessimo servizio siete un server che non userò più.

1.0

Oct 2023

Poor value for money, poor service, lack of facilites. Would NOT recommend this hotel.

We booked this hotel because of its location right on the beach. The balcony of our room was east-facing, so we had a view of the sunrise. The king sized bed was very comfortable. The room and bathroom were modern with tiled floors. There we plenty of good quality towels, shower gel, shampoo and conditioner. We could park the car in the covered parking right under the room.

On top of the expensive cost of the room, the hotel charged a “ Resort Fee” of $40 per night. This seems like a poor attempt to get more money out of their customers. The two female staff who checked us in and out were impolite and unfriendly. The atmosphere was not at all welcoming. We arrived early, but there were no facilities in the public area where we could have changed to go to the pool and no restrooms. The option to use the pool before check in was not offered to us anyway. There was no bar or lobby in the reception area. The only “bar” in the whole hotel was a cart on the terrace in the sun. There was no place to sit under a sunshade. The room was not well cleaned at all. On floor of the balcony, there was a plastic glass from the previous guest. The table was not wiped clean nor was the floor. In the room, there was dirt in the corners and the floor has not been properly cleaned. Both the smaller windows were filthy (they looked as if they hadn’t been cleaned for weeks) and the balcony door was only cleaned as far up as the (probably smaller) person could reach without using something to stand on. There were no glasses for our beverages. “Breakfast”, if you could call it that, was included in the price of the room. The “buffet” which was very sparce, was set out in a what looked like a utility room on the beach on folding picnic tables. The atmosphere was that of a cheap little cafe, but without the service, tables and chairs. We had to sit outside at cheap picnic tables in the sun, as there were no sun shades. In a hotel that costs this much, we would have expected a proper “continental breakfast” as advertised, with proper tables and chairs and a proper proper service not a just few things laid out on picknick tables in a utility room! All in all, this hotel is very poor value for money. It appears to us that the owners are trying to profit by skimping on services. We would not recommend this hotel to anyone.

4.0

Oct 2023

AC in main bedroom area not working properly maintenance person unable to figure out only offered a resort fee taken off

Property was nice waited long time to have are room ready after sending them messages we were looking for early check in waited 4 hours from arrival time to room was available on Anniversary not a great start !

The water sports equipment old and beat up need to be upgraded the Iquana’s are all around pool areas very invasive and poop near pool not a good look some of concrete on balconies cracked as a building inspector that’s concerning had cones and tape in certain areas safety code violations!

3.5

Aug 2023

Amazingly beautiful with a lots of potential, maybe just going through some growing pains.

Beautiful views and newly renovated. There was an obvious effort to beautify the facilities and grounds and we really appreciated that aspect. Pictures are accurate! It is that pretty!

Not sure if it was short staffed or just mismanaged. While I understand that full daily cleaning services are are not the standard anymore and I appreciate their choice of checking in each day via text with what you need… they didn’t follow though and actually provide those needs not once in four days. We never had trash picked up, not once. So we would have to hunt the trash bins that moved around the property to dump trash. We had to ask several times each day to get fresh towels, soap and toilet paper. Toilet paper, one roll at a time! Perhaps they should keep some supplies at the front desk to help out, we always had to wait on someone to bring it.

4.0

Aug 2023

Beautiful beach

Very nice beach

Low water pressure in the shower but no big deal-I have seen worse.

4.5

Jul 2023

Adorable stay! Loved every minute.

There is a private beach at the resort that is absolutely beautiful. You can swim at the ocean, there is a clear space from the seaweeds, it's so beautiful. You can have 2 hours / day to use the kayaks and the stand up paddle, which is pretty convenient. If you take the ocean view room, the view is amazing. The room is also very comfortable. Parking is super easy. They don't have a restaurant at the property, but walking less than 2 minutes there is an amazing all you can eat seafood restaurant. You can also take the car and 2-3 minutes away you'll find amazing restaurants. The lady who was in the front desk welcoming the guests was adorable, very polite and kind.

The complimentary breakfast could be a little better - there is a boxed breakfast with few options to pick, we had it for the first day but from the second day we preferred to go to Publix and buy some breakfast items. This is not something related to the property, but some guests are not polite at all. Throwing garbage at the beach, leaving their things behind on the beach chairs, not good at all.

5.0

Jul 2023

Fantastic location, comfortable accommodation, gorgeous dining.

Fantastic location, right at the beach, very comfortable room with the terrace. Gorgeous restaurant with ocean view nearby. Good breakfast. Forthcoming staff. Excellent place, highly recommend.

Nothing.

5.0

Jul 2023

Exceptional

Location, facilities, cleanliness, parking, room design, everything. 😁☀️

Nothing

4.0

May 2023

great stay will return

location, property layout, staff

beach could have been cleaner, new beach chairs necessary, rental fees on the kayaks?

3.5

May 2023

Nice hotel, great location, weren't ready to leave the keys.

The beach area was absolutely beautiful and location was great!

Our air conditioner was not consistent and we didn't sleep well due to being hot. Also, the shower door did not close all the way.

5.0

May 2023

Exceptional

clean, location beautiful

chairs in the rooms

5.0

May 2023

Exceptional

rooms are big

3.5

May 2023

Good

good location clean

The breakfast is not breakfast muffin milk is not a breakfast

5.0

May 2023

great stay, enjoyed this resort

beautiful views, great location

beach chairs were not very comfortable

3.0

Apr 2023

Overrated location

The room was super comfortable, the bathroom was new and the pool was very clean

The beach is a no go. Impossible to get a swim due to seaweed. Breakfast was poor and pre-packaged. No care for sustainability.

3.0

Apr 2023

pricey bungalow with lots of construction ongoing

The bungalows are really nice on the inside but next to highway and the property is undergoing major construction for 3-6 more months.

The hotel is under construction which they do not mention until check in, and have no issue inconveniencing you at any point during your stay to work on things in or around your room.

4.5

Apr 2023

Great hotel in a good location!

Great coffee in the am and liked the to go breakfast. Very nice and great location!

Really noting it was great

4.5

Mar 2023

loved this resort ! Amazing staff, location, rooms were gorgeous and clean ! I will be back for sure , so glad I found t

The staff was amazing! Gorgeous Property right on the beach ! love how the whole parking lot is sand even in the parking lot. Complimentary champagne at check in, Loved this resort , will be back!

The breakfast is not continental like started at booking ..more like a boxed breakfast it was nice to have when you wake up though !

4.0

Mar 2023

We will certainly return when we travel the Keys again.

WYSIWYG! And a little bit more. Clean and comfortable rooms. Fantastic little beach areas. Pools also great for a swim and to stick around. Fast and friendly service if you ever need anything.

1.0

Feb 2023

Very poor

We checked in and immediately checked out. The air conditioner was dripping and the room had rodent droppings on the floor. We expressed our concerns and we’re told it was the last room available. We were basically told take it or leave it. We left it!

5.0

Feb 2023

awesome and can’t wait to see you guys again

location, how comfy the room was, how great the outdoors was how friend the staff was. shaniqua welcomed us with a. beautiful smile when we checked in and text me if I needed anything

breakfast was minimal.

4.0

Feb 2023

Very good

Nice place, not too crowded.

Cheaper rooms were close to the road, the trafic noise was annoying, especially in the night.

4.5

Jan 2023

Superb

The view from our room was spectacular. Pool and hot tub was great. Close to excellent restaurants and shops. We have stayed here twice and will be back again.

Need better pillows on bed

2.5

Jan 2023

Pretty place

Redone and fresh

Walls are paper thin could hear literally entire conversations

3.5

Jan 2023

Beautiful property in a great location

everything was new, clean and well organized

breakfast options were not great, we just decided to go to a restaurant I had some issues with the payment, whoever helped us with the check in messed that up. I have to say that they fixed the problem at the checkout though

FAQs

How much does this resort cost compared to others in Upper Matecumbe Key?

The average price for a rental in Upper Matecumbe Key is $531 per night. This rental is $301 less expensive than the average.

Is parking included with this resort?

Yes, parking is listed as an 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 12 amenities for this rental. This includes pool, air conditioner, pets allowed, kitchen or kitchenette, and internet / wifi.

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4.3

Excellent(892 Reviews)

Sunset Inn

Chesapeake Beach Resort

Resort in Upper Matecumbe Key, FL

Reasons to book

About this resort

Amenities

Map of Upper Matecumbe Key, FL

Nearby attractions

Available Rooms

Chesapeake Beach Resort

Resort in Upper Matecumbe Key, FL

Reasons to book

About this resort

Amenities

Map of Upper Matecumbe Key, FL

Nearby attractions

Available Rooms

Reviews

FAQs

How much does this resort cost compared to others in Upper Matecumbe Key?

Is parking included with this resort?

Is there a pool at this resort?

Is Chesapeake Beach Resort pet friendly?

What amenities are available at Chesapeake Beach Resort?

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