On the beach.With a stay at this Matecumbe hotel, you'll be within half a mile (1 km) of History of Diving Museum and 2 miles (3 km) of Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Keys History & Discovery Center are also within 2 miles (3 km).
What's nearby
History of Diving Museum - 12 min walk - 0.7 miles
Windley Key Fossil Reef Geological State Park - 2 min drive - 1.3 miles
Theater of the Sea - 2 min drive - 1.5 miles
Florida Keys Brewing Co. - 4 min drive - 2.5 miles
Islamorada County Park - 7 min drive - 4.8 miles
Getting around
Miami Intl. Airport (MIA) - 91 min drive
Restaurants
Lorelei Restaurant & Cabana Bar - 3 min drive
Hog Heaven - 3 min drive
Wahoo's Bar & Grill - 2 min walk
Florida Keys Brewing Co. - 3 min drive
Whale Harbor Restaurant Marina - 2 min walk
About this property
Chesapeake Beach Resort
3.5-star beachfront hotel with 2 outdoor pools
Simply walk outside to smell the salt air and watch the ocean waves from the white sand beach. Cool off in one of the 2 outdoor swimming pools at Chesapeake Beach Resort, and enjoy amenities like a marina and complimentary bicycles.
Free breakfast is available daily. You can enjoy a drink at the bar/lounge. A computer station is on site and WiFi is free in public spaces. A complete renovation of Chesapeake Beach Resort was completed in January 2020.
This 3.5-star Islamorada hotel is smoke free.
60 guestrooms or units
2 levels
9 buildings
Built in 2020
Continental breakfast (free)
Beach lounge chairs
Towels for the beach
Poolside lounge chairs
Coffee in lobby
Front desk (24 hours)
Staff is multilingual
Concierge
Computer for guest use
No smoking on site
Bar or lounge
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include showers, complimentary toiletries, and hair dryers.
This Islamorada hotel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Business-friendly amenities include phones along with free local calls (restrictions may apply). Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.
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
Things to do
2 outdoor pools
Boat tours
Fishing
Free bicycle rentals
Kayaking
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
Room amenities
Entertainment
43-inch flat-screen TV with cable channels
Bedroom
Bedsheets provided
Blackout drapes
Hypo-allergenic bedding
Pillowtop mattress
Bathroom
Designer toiletries
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
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
Access methods
Staffed front desk
Pets
Pets: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
Maximum 2 (weight limit: 50 lbs per pet)
Restrictions apply
For more information, you can reach out to the property at the number on the booking confirmation
Service animals are exempt from fees
Children and extra beds
Children are welcome.
Rollaway/extra beds are not available.
Property payment types
Important information
Optional extras
The fees and deposits listed below will be charged at the time of service, check-in, or check-out.
Pet deposit: USD 50.00 per stay
Pet fee: USD 50.00 per accommodation, per night
Service animals are exempt from fees
A late check-out fee will be charged
This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.
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
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
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. This property accepts Visa, Mastercard, American Express, and Discover. Cash is not accepted.
We should mention
Pool access available from 7:00 AM to 10:30 PM.
Certain facilities might have restricted access. For details, you can contact the property at the number on the booking confirmation.
Guests may experience noise disturbance due to nearby construction work.
To make arrangements to bring your pet, contact the property directly at the number on your booking confirmation (please see the Fees section for related charges).
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
How close is Chesapeake Beach Resort to the airport?
Chesapeake Beach Resort is 77.5 mi (91-min drive) away from the Miami Intl. Airport (MIA) airport, the closest popular airport to the property.
How much does it cost to stay at Chesapeake Beach Resort?
As of Jul 12, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Aug 3, 2025 start from $169.15, 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.
Does Chesapeake Beach Resort have an airport shuttle?
Airport shuttle services are not available at Chesapeake Beach Resort.
How close is Chesapeake Beach Resort to the beach?
This hotel is on a private beach. Don't forget your sunscreen!
Does Chesapeake Beach Resort offer free breakfast?
Chesapeake Beach Resort offers free continental breakfast every day from 6:00 AM to 10:00 AM.
Is there a casino at Chesapeake Beach Resort?
No, there is no casino at this hotel.
What time is check-in at Chesapeake Beach Resort?
Check-in start time: 4:00 PM; Check-in end time: 3:00 AM.
Is there free parking at Chesapeake Beach Resort?
Free parking is not available at this hotel.
Does Chesapeake Beach Resort have a pool?
Chesapeake Beach Resort features 2 outdoor pools. Guests can enjoy pool access from 7:00 AM to 10:30 PM.
Does Chesapeake Beach Resort have a spa?
There are no spa services available at this hotel.
How close is Chesapeake Beach Resort to downtown Islamorada?
Chesapeake Beach Resort is 1.2 mi away from Islamorada.
Chesapeake Beach Resort Reviews
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.
Great views, easy beach and pool access. 2 hours of included daily use of kayaks and paddle boards. Quiet, relaxing, friendly staff. Great location between Miami and Key West.
The chef at the breakfast was so rude and hostile
When I complained to the front desk (Venessa she did not care even I told her he yelled at me in front of other guests. Venessa and that breakfast chef are very unprofessional hence I will never go there again
On the other hand, another person at the reception was very kind and professional and her name is Adriana
We enjoyed our stay at the Chesapeake very much. The ocean view suite was well maintained and spacious for our family. The location is fabulous within 1-2 miles of fabulous dining and adventurous activities. We chose not to have daily service in our room, but staff texted each day to see what we needed. Would highly recommend!
The view from my room was awesome. The public areas (to beach, pools, breakfast) were extremely convenient to get to.
The only negative comment I have concerns the room amenities. There should be a dresser for more drawer space and a few more hooks or racks in bathroom for towels. Other than that it was a fantastic resort that I would highly recommend