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US FL Monroe County Islamorada Hotels

Chesapeake Beach Resort

Updated on Jul 20, 2026

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Chesapeake Beach Resort

Hotels.com logo Lowest Price $241.51 Get Booking Details

Map image for 83409 Overseas Hwy ISLAMORADA, FL
Located in: ISLAMORADA, FL
At Chesapeake Beach Resort, you can relax at one of the 2 outdoor swimming pools, play on the private white sand beach, or spend the day at a marina.
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.


A private beach, a marina, and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.

Children under 16 years old are not allowed in the swimming pool without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

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.. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven. With jet skiing and snorkeling nearby, you'll find plenty of adventures in the water.
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Popular amenities
  • ac
  • bar
  • breakfast included
  • business services
  • frontdesk 24 hour
  • housekeeping
  • internet
  • microwave
  • no smoking
  • pool
  • tv
Property amenities
Food and Drink
  • 1 bar
  • Coffee/tea in common area(s)
  • Free continental breakfast available daily 6:00 AM–10:00 AM
Internet
  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi
  • In-room WiFi speed: 100+ Mbps (good for 1–2 people or up to 6 devices)
Parking
  • Onsite parking includes off-street options
  • Wheelchair-accessible parking available
Things to do
  • 2 outdoor pools
  • Boat tours
  • Fishing
  • Free bicycle rentals
  • Kayaking
Family Friendly
  • 2 outdoor pools
  • Fence around the pool
  • Microwave
  • Pool gate
Guest Services
  • 24-hour front desk
  • Concierge services
  • Daily housekeeping
  • Multilingual staff
Business Services
  • Computer station
Outdoor
  • Beach loungers
  • Marina onsite
  • Pool sun loungers
  • Private beachfront location
Language Spoken
  • English
  • Spanish
Accessibility
  • Assistive listening devices available
  • Braille signage
  • Handrails in hallways
  • Handrails in stairways
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Lever door handles
  • Pool hoist on site
  • This property does not have elevators
  • 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
Activities Nearby
  • Jet skiing
  • Snorkeling
More
  • Beach towels
  • Smoke-free property
Room amenities
Bedroom
  • Air conditioning
  • Bed sheets
  • Blackout drapes/curtains
  • Ceiling fan
  • Hypo-allergenic bedding
  • Pillow-top mattress
Bathroom
  • Designer toiletries
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels
Entertainment
  • Cable channels
  • 43-inch flat-screen TV
Food and Drink
  • Coffee/tea maker
  • Microwave
More
  • Access via exterior corridors
  • Free local calls
  • Iron/ironing board
  • Laptop-friendly 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
  • A late check-out fee will be charged
  • Check-out before 11 AM
  • Contactless check-out available
Pets
  • 2 total (up to 50 lbs per pet)
  • Pets allowed for an extra charge of USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per night
  • Restrictions apply; for more information contact the property at the number on the booking confirmation
  • Service animals are welcome, and are exempt from fees
Special check-in instructions
  • 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
  • Safety features at this property include a fire extinguisher
  • 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
Property payment types
  • American Express
  • Discover
  • Mastercard
  • Visa
Important Information
Optional extras
  • Pet deposit: USD 50.00 per nightPet fee: USD 50.00 per accommodation, per nightService animals are exempt from feesA 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
  • Safety features at this property include a fire extinguisher
  • 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
We should mention
  • Children under 16 years old are not allowed in the swimming pool without adult supervision
  • Construction is underway at a neighboring building and there may be noise disturbance from the construction work
  • 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
  • This property does not have elevators
 

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