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Chesapeake Beach Resort

3.5 star property
Travelers relax on sun-kissed beaches or take refreshing swims in outdoor pools at this peaceful Florida Keys resort with private waterfront access

Choose dates to view prices

Chesapeake Beach Resort offers a quiet escape in Matecumbe. Start your day with a leisurely breakfast, then head to the private beach with sun loungers and kayaking. Enjoy two outdoor pools, while multilingual staff and concierge services help plan the perfect stay.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Breakfast included
  • Free Wi-Fi
The current price is £193
includes taxes & fees
8 Jun - 9 Jun

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Policies

Check-in

Check-in start time: 4:00 PM; check-in end time: 3:00 AM

Contactless check-in and check-out are available

Late check-in subject to availability

Minimum check-in age - 18

Check-out

Check-out before 11 AM

Contactless check-out

A late check-out fee will be charged

Special check-in instructions

Front desk staff will greet guests on arrival at the property

Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets are allowed for an extra charge of USD 50.00, per accommodation, per night, plus a deposit of USD 50.00 per night

Service animals are welcome, and are exempt from fees

2 total (up to 23 kg per pet)

Restrictions apply; for more information contact the property on the number on the booking confirmation

Children and extra beds

Children are welcome

Rollaway/extra beds are not available.

Payment types at the property

Important information

Optional extras

  • Pet deposit: USD 50.00 per night
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • A late check-out fee will be charged

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

We should mention

This property does not have any lifts
Pool access available from 8:00 AM to 6:00 PM
Some facilities may have restricted access; guests can contact the property for details using the contact information on the booking confirmation
Construction is underway at a neighbouring building and there may be noise disturbance from the construction work
Children under 16 years old are not allowed in the swimming pool without adult supervision

Frequently asked questions

Does Chesapeake Beach Resort have a pool?

Yes, this property has 2 outdoor pools. Pool access is from 8:00 AM to 6:00 PM.

How much does it cost to stay at Chesapeake Beach Resort?

As of 22 May 2026, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 8 Jun 2026 start from £193, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Chesapeake Beach Resort pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 23 kg per pet. There's a deposit of USD 50.00 per night and a fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; check-in end time: 3:00 AM. Late check-in is available during limited hours.

What time is check-out at Chesapeake Beach Resort?

Checkout is at 11 AM. Late checkout is available for a fee.

Where is Chesapeake Beach Resort located?

Nestled on the beach, this Matecumbe hotel is within 1 mi (2 km) of History of Diving Museum and Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Keys History & Discovery Center are also within 2 miles (3 km).

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on selected room rates because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Reviews

9.2

Wonderful

9.4

Cleanliness

9.2

Amenities

9.4

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 1281 out of 1725 reviews
Rating 8 - Good. 276 out of 1725 reviews
Rating 6 - Okay. 95 out of 1725 reviews
Rating 4 - Poor. 42 out of 1725 reviews
Rating 2 - Terrible. 31 out of 1725 reviews

Reviews

Verified

10/10 Excellent

Nathan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Perfect place to stay and a super friendly and helpful staff...definitely staying here again
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

NIDAL

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast is very good Staff is amazing Private beach with a walk to sandbar is Beautiful
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Brittany

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean, amazing breakfast, lovely staff.
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Jerrod

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and beautiful beach
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Matthew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was great!
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Patrick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome beachfront clean rooms walk to restaurants
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Monica

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful facility. Great breakfast
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Paul

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely loved it here. It was clean, beautiful and the made to order eggs/pancakes/french toast every morning was a huge plus. Our room had an amazing ocean view. Will definitely be staying here again when we go back to the keys
Stayed 4 nights in Mar 2026
Verified

8/10 Good

Rick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We enjoyed our stay. Amenities were goo
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Jerry

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice breakfast served - omelets, pancakes, French toast and many other items. Outdoor pool was nice as was the ocean beach. Friendly staff.
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Wasim

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, access to the water front. Very nice and quiet atmosphere. Excellent made to order breakfast and other options.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Steven

Liked: Cleanliness, amenities, property conditions & facilities
Great modern resort, very clean, very friendly.
Stayed 2 nights in Feb 2026
Verified

8/10 Good

Mariola

warm pool, beautiful view at the beach, pleasant front desk and breakfast staff
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Jordan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location. Beautiful grounds felt very private.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Lyle

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The people were helpful & friendly. Accommodations were superb. The free breakfast selections were more than you get at most hotel chains. The area was very picturesque with the turquoise waters, cool breezes, and multiple swimming pools for a relaxed, calm days.
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

Isabel

Liked: Cleanliness, amenities, property conditions & facilities
This place was perfect for my family. The continental breakfast saved us a lot of money on food, the staff was friendly and the resort was clean. Will 100% be back here.
Stayed 5 nights in Apr 2026
Verified

8/10 Good

Beth

Liked: Cleanliness, staff & service, amenities
Nice grounds beautiful view
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Roger

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful ocean view from our room staff was very helpful very clean room
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Emil

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was very helpful!
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

dian

Liked: Cleanliness, staff & service, amenities
Great room, wonderful staff and good location
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Keely

Liked: Cleanliness, staff & service, amenities
Clean rooms, beautiful scenery, gorgeous sunrise, delicious breakfast. Loved this place.
Stayed 4 nights in Feb 2026
Verified

10/10 Excellent

Douglas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful property! Every staff member was friendly, the room was clean and spacious, breakfast was cooked to order as we ate outside overlooking the water. We had a small dog and she was welcome everywhere. I would definitely stay here again!
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Alice

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The ocean was visible from our room and the balcony was wonderful!
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Melissa

Liked: Cleanliness, amenities, property conditions & facilities
The view and location were great.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Sara

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything about our stay here was fantastic! The staff were all very friendly and accommodating. Fresh-made omelets with friendly smiles to start every day! Everything was very clean. We will be back!
Stayed 5 nights in Mar 2026