Verified
10/10 Excellent
Nathan
2026/4/22
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nathan
Stayed 1 night in Apr 2026
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
Photo gallery for Chesapeake Beach Resort
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
9.29.2 out of 10
Wonderful
Popular amenities
- Free WiFi
The current price is NT$6,287
NT$6,287
NT$8,854 total
includes taxes & fees
May 11 - May 12
Room options
Check availability for these dates
Available filters for rooms
Showing 20 of 20 rooms
View all photos for Ocean View Queens
Ocean View Queens
9.69.6 out of 10
Exceptional
51 reviews
(51 reviews)
- Ocean view
- 366 sq ft
- 1 bedroom
- Sleeps 4
- 2 Queen Beds
- Free WiFi
View all photos for Ocean View King
Ocean View King
9.69.6 out of 10
Exceptional
99 reviews
(99 reviews)
- Ocean view
- 364 sq ft
- 1 bedroom
- Sleeps 3
- 1 King Bed
- Free WiFi
View all photos for ADA Ocean View King Suite
ADA Ocean View King Suite
8.68.6 out of 10
Excellent
8 reviews
(8 reviews)
- Ocean view
- 540 sq ft
- 1 bedroom
- Sleeps 4
- 1 King Bed
- Free WiFi
View all photos for ADA Ocean View King
ADA Ocean View King
8.88.8 out of 10
Excellent
20 reviews
(20 reviews)
- Ocean view
- 364 sq ft
- 1 bedroom
- Sleeps 3
- 1 King Bed
- Free WiFi
View all photos for ADA Ocean View Queens
ADA Ocean View Queens
9.09.0 out of 10
Wonderful
7 reviews
(7 reviews)
- Ocean view
- 366 sq ft
- Sleeps 4
- 2 Queen Beds
- Free WiFi
View all photos for Hearing Impaired Ocean View Queens
Hearing Impaired Ocean View Queens
10.010.0 out of 10
Exceptional
3 reviews
(3 reviews)
- Ocean view
- 366 sq ft
- 1 bedroom
- Sleeps 4
- 2 Queen Beds
- Free WiFi
View all photos for Hearing Impaired Ocean View King Suite
Hearing Impaired Ocean View King Suite
8.88.8 out of 10
Excellent
5 reviews
(5 reviews)
- Ocean view
- 540 sq ft
- 1 bedroom
- Sleeps 4
- 1 King Bed and 1 Queen Sofa Bed
- Free WiFi
View all photos for Standard Queens
Standard Queens
9.49.4 out of 10
Exceptional
65 reviews
(65 reviews)
- 307 sq ft
- 1 bedroom
- Sleeps 4
- 2 Queen Beds
- Free WiFi
View all photos for Standard Doubles
Standard Doubles
9.29.2 out of 10
Wonderful
102 reviews
(102 reviews)
- 272 sq ft
- 1 bedroom
- Sleeps 4
- 2 Double Beds
- Free WiFi
View all photos for Standard King with Sleeper Sofa
Standard King with Sleeper Sofa
9.29.2 out of 10
Wonderful
25 reviews
(25 reviews)
- 307 sq ft
- 1 bedroom
- Sleeps 4
- 1 King Bed and 1 Double Sofa Bed
- Free WiFi
View all photos for Standard King
Standard King
9.49.4 out of 10
Exceptional
40 reviews
(40 reviews)
- 272 sq ft
- 1 bedroom
- Sleeps 3
- 1 King Bed
- Free WiFi
View all photos for Ocean View King Suite
Ocean View King Suite
9.29.2 out of 10
Wonderful
19 reviews
(19 reviews)
- Ocean view
- 527 sq ft
- 1 bedroom
- Sleeps 4
- 1 King Bed and 1 Queen Sofa Bed
- Free WiFi
View all photos for Deluxe Ocean View Two Queen Suite
Deluxe Ocean View Two Queen Suite
9.09.0 out of 10
Wonderful
11 reviews
(11 reviews)
- Ocean view
- 650 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds
- Free WiFi
View all photos for 2-Bedroom Villa
2-Bedroom Villa
10.010.0 out of 10
Exceptional
1 review
(1 review)
- Resort view
- 646 sq ft
- 2 bedrooms
- Sleeps 6
- 1 King Bed, 1 Double Bed and 1 Double Sofa Bed
- Free WiFi
View all photos for Standard King Villa
Standard King Villa
- Resort view
- 323 sq ft
- 1 bedroom
- Sleeps 3
- 1 King Bed
- Free WiFi
View all photos for King Efficiency Villa
King Efficiency Villa
9.69.6 out of 10
Exceptional
4 reviews
(4 reviews)
- Resort view
- 517 sq ft
- 1 bedroom
- Sleeps 4
- 1 King Bed and 1 Double Sofa Bed
- Free WiFi
View all photos for ADA King Efficiency Villa
ADA King Efficiency Villa
10.010.0 out of 10
Exceptional
1 review
(1 review)
- Resort view
- 517 sq ft
- 1 bedroom
- Sleeps 3
- 1 King Bed
- Free WiFi
View all photos for Premium 1-Bedroom Ocean View Villa
Premium 1-Bedroom Ocean View Villa
8.08.0 out of 10
Very good
1 review
(1 review)
- Ocean view
- 700 sq ft
- 1 bedroom
- Sleeps 6
- 2 Double Beds and 1 Double Sofa Bed
- Free WiFi
View all photos for Premium Ocean View King Villa
Premium Ocean View King Villa
- Ocean view
- 829 sq ft
- 1 bedroom
- Sleeps 4
- 1 King Bed and 1 Double Sofa Bed
- Free WiFi
View all photos for Ocean View King Efficiency Villa
Ocean View King Efficiency Villa
10.010.0 out of 10
Exceptional
1 review
(1 review)
- Ocean view
- 517 sq ft
- 1 bedroom
- Sleeps 4
- 1 King Bed and 1 Double Sofa Bed
- Free WiFi
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About the neighborhood
Located on a private beach, Chesapeake Beach Resort is in Matecumbe, a neighborhood in Islamorada. Hurricane Monument and Indian Key Historic State Park are local landmarks, and some of the area's activities can be experienced at Islamorada Brewery & Distillery and Florida Keys Brewing Co.. With jet skiing and snorkeling nearby, you'll find plenty of adventures in the water. Visit our Islamorada travel guide
83409 Overseas Hwy, Islamorada, FL, 33036
What's nearby
History of Diving Museum12 min walk - 1.1 km
Windley Key Fossil Reef Geological State Park2 min drive - 2.0 km
Theater of the Sea2 min drive - 2.4 km- Islamorada Brewery & Distillery2 min drive - 2.4 km
- beach near Islamorada2 min drive - 2.7 km
Getting around
- Miami Intl. Airport (MIA)91 min drive
Restaurants
- Lorelei Restaurant & Cabana Bar3 min drive
- Wahoo's Bar & Grill2 min walk
- Hog Heaven3 min drive
- Tiki Bar13 min walk
- Wendy's2 min drive
About this property
Chesapeake Beach Resort
Hotel located in Matecumbe
Free continental breakfast, a marina, and a bar are just a few of the amenities provided at Chesapeake Beach Resort. With a private beach, sun loungers, and fishing, this hotel is the perfect place to soak up some sun. Enjoy onsite activities like kayaking and boat tours. Stay connected with free in-room WiFi.
You'll also enjoy the following perks during your stay:
- 2 outdoor pools along with sun loungers
- Free bicycle rentals, smoke-free premises, and beach towels
- Concierge services, a 24-hour front desk, and coffee/tea in the lobby
- Multilingual staff and a computer station
- Guest reviews give top marks for the breakfast, beach locale, and pool
Room features
All 60 rooms offer comforts such as laptop-friendly workspaces and air conditioning, in addition to perks like free WiFi. Guest reviews speak positively of the clean, spacious rooms at the property.
More amenities include:
- Hypo-allergenic bedding and pillowtop mattresses
- Designer toiletries, showers, and hair dryers
- 43-inch HDTVs with cable channels
- Wardrobes/closets, microwaves, and coffee/tea makers
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Property amenities
Internet
- Available in all rooms: Free WiFi
- In-room WiFi speed: 100+ Mbps (good for 1–2 people or up to 6 devices)
- Available in some public areas: Free WiFi
Parking and transportation
- Wheelchair-accessible parking available
- Onsite parking includes off-street options
Food and drink
- Free continental breakfast available daily 6:00 AM to 10:00 AM
- A bar/lounge
- Coffee and tea in common areas
Restaurants on site
- Tiki Bar
Things to do
- 2 outdoor pools
- Boat tours
- Fishing
- Free bicycle rentals
- Kayaking
Family friendly
- 2 outdoor pools
- Fenced pool
- In-room microwave
- Pool gate
Conveniences
- 24-hour front desk
Guest services
- Concierge services
- Housekeeping (daily)
- Multilingual staff
Business services
- Computer station
Outdoors
- Beach loungers
- Beach towels
- Marina
- On a private beach
- Pool loungers
Accessibility
- If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
- Assistive listening devices
- Braille/raised signage
- Handrails in hallways
- Handrails in stairways
- Lever door handles
- Pool hoist on site
- Upper floors accessible by stairs only
- Visual alarms in hallways
- Well-lit path to entrance
- Wheelchair accessible (may have limitations)
- Wheelchair-accessible parking
- Wheelchair-accessible pool
- Wheelchair-accessible public washroom
More
- 2 floors
- 9 buildings
- Built in 2020
- Smoking not allowed
- Traditional architecture
Room amenities
Bedroom
- Bedsheets provided
- Blackout drapes
- Hypo-allergenic bedding
- Pillowtop mattress
Bathroom
- Designer toiletries
- Hair dryer
- Shampoo
- Shower
- Soap
- Toilet paper
- Towels provided
Entertainment
- 43-inch flat-screen TV with cable channels
Food and drink
- Coffee/tea maker
- Microwave
More
- Access via exterior corridors
- Air conditioning
- Ceiling fan
- Free local calls
- Iron/ironing board
- Laptop workspace
- Phone
Policies
Check-in
Check-in start time: 4:00 PM; Check-in end time: 3:00 AM
Contactless check-in available
Late check-in subject to availability
Minimum check-in age: 18
Check-out
Check-out before 11 AM
Contactless check-out available
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 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 50 lbs per pet)
Restrictions apply; for more information contact the property at the number on the booking confirmation
Children and extra beds
Children are welcome
Rollaway/extra beds are not available
Property payment types
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
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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
We should mention
This property does not have elevators
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 neighboring 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
Property is also known as
Chesapeake Beach Islamorada
Chesapeake Beach Resort
Chesapeake Beach Resort Islamorada
Chesapeake Resort
Chesapeake Beach Hotel Islamorada
Chesapeake Beach Resort Hotel
Chesapeake Beach Resort Islamorada
Chesapeake Beach Resort Hotel Islamorada
Frequently asked questions
Does Chesapeake Beach Resort have a pool?
Yes, this property has 2 outdoor pools. Pool access is from 8:00 AM–6:00 PM.
How much does it cost to stay at Chesapeake Beach Resort?
As of 2026/5/3, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 2026/5/11 start from NT$6,287, excluding 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 50 lbs 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?
Check-out is at 11 AM. Late check-out 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 mi (3 km).
Can I cancel my reservation for free and receive a full refund?
Yes, this property offers free cancellation on select 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
Chesapeake Beach Resort Reviews
9.2
Wonderful
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.More informationOpens in a new window
9.4
Cleanliness
9.0
Amenities
9.2
Staff & service
9.2
Property conditions & facilities
Rating 10 - Excellent. 1264 out of 1709 reviews
10 - Excellent
1,264
Rating 8 - Good. 274 out of 1709 reviews
8 - Good
274
Rating 6 - Okay. 97 out of 1709 reviews
6 - Okay
97
Rating 4 - Poor. 42 out of 1709 reviews
4 - Poor
42
Rating 2 - Terrible. 32 out of 1709 reviews
2 - Terrible
32
Reviews
Verified
10/10 Excellent
NIDAL
2026/4/20
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast is very good
Staff is amazing
Private beach with a walk to sandbar is Beautiful
NIDAL
Stayed 2 nights in Apr 2026
Verified
10/10 Excellent
Brittany
2026/4/7
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean, amazing breakfast, lovely staff.
Brittany
Stayed 4 nights in Mar 2026
Verified
10/10 Excellent
Jerrod
2026/3/25
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and beautiful beach
Jerrod
Stayed 2 nights in Mar 2026
Verified
10/10 Excellent
Monica
2026/4/22
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful facility.
Great breakfast
Monica
Stayed 3 nights in Apr 2026
Verified
10/10 Excellent
Matthew
2026/4/3
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was great!
Matthew
Stayed 3 nights in Mar 2026
Verified
10/10 Excellent
Paul
2026/4/23
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
Paul
Stayed 4 nights in Mar 2026
Verified
10/10 Excellent
Patrick
2026/3/17
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome beachfront clean rooms walk to restaurants
Patrick
Stayed 1 night in Mar 2026
Verified
8/10 Good
Rick
2026/4/6
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We enjoyed our stay. Amenities were goo
Rick
Stayed 2 nights in Apr 2026
Verified
10/10 Excellent
Jerry
2026/4/23
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.
Jerry
Stayed 2 nights in Apr 2026
Verified
10/10 Excellent
Wasim
2026/4/12
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.
Wasim
Stayed 2 nights in Jan 2026
Verified
10/10 Excellent
Steven
2026/2/26
Liked: Cleanliness, amenities, property conditions & facilities
Great modern resort, very clean, very friendly.
Steven
Stayed 2 nights in Feb 2026
Verified
10/10 Excellent
Lyle
2026/4/20
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.
Lyle
Stayed 4 nights in Apr 2026
Verified
10/10 Excellent
Jordan
2026/3/18
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location. Beautiful grounds felt very private.
Jordan
Stayed 2 nights in Mar 2026
Verified
8/10 Good
Mariola
2026/2/28
warm pool, beautiful view at the beach, pleasant front desk and breakfast staff
Mariola
Stayed 1 night in Feb 2026
Verified
10/10 Excellent
Isabel
2026/4/11
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.
Isabel
Stayed 5 nights in Apr 2026
Verified
8/10 Good
Beth
2026/3/21
Liked: Cleanliness, staff & service, amenities
Nice grounds beautiful view
Beth
Stayed 3 nights in Mar 2026
Verified
10/10 Excellent
Roger
2026/3/4
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful ocean view from our room staff was very helpful very clean room
Roger
Stayed 1 night in Feb 2026
Verified
10/10 Excellent
Emil
2026/3/28
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was very helpful!
Emil
Stayed 2 nights in Mar 2026
Verified
10/10 Excellent
dian
2026/1/26
Liked: Cleanliness, staff & service, amenities
Great room, wonderful staff and good location
dian
Stayed 2 nights in Jan 2026
Verified
10/10 Excellent
Douglas
2026/3/27
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!
Douglas
Stayed 3 nights in Mar 2026
Verified
10/10 Excellent
Alice
2026/3/11
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The ocean was visible from our room and the balcony was wonderful!
Alice
Stayed 3 nights in Mar 2026
Verified
6/10 Okay
Lori
2026/4/15
The free breakfast was excellent. We upgraded to an ocean view room. The room was dated and not cleaned daily. The location was nice right on the beach with two pools.
Lori
Stayed 4 nights in Apr 2026
Verified
10/10 Excellent
Sara
2026/4/2
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!
Sara
Stayed 5 nights in Mar 2026
Verified
8/10 Good
ann
2026/3/11
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was always available and helpful. The breakfast and chefs were outstanding. Our ocean view room could not have been better!
ann
Stayed 6 nights in Feb 2026