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Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, FL 33036

+1 305 664 4662

per night


based on 371 reviews

About Chesapeake Beach Resort, Islamorada

Value for money

Located in Islamorada, Chesapeake Beach Resort is within a 40-minute drive of Florida Keys Marathon Airport and offers a Jacuzzi, an outdoor pool and a private beach. It also features free bicycle rental, a sun deck and outdoor tennis courts. Chesapeake Beach Resort Islamorada has recently been refurbished and offers a 24-hour reception, a BBQ/picnic area and a 24-hour business centre. In addition, the multilingual staff are available to offer local information. The resort has 65 rooms that are filled with all the essentials to ensure an enjoyable stay. Chesapeake Beach Resort has easy access to Hurricane Monument. Overseas Highway, John Pennekamp Coral Reef State Park and MarineLab Undersea Laboratory are a brief car trip from the property.

Chesapeake Beach Resort photos

Chesapeake Beach Resort room price & deals

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Deluxe Rooms - Park view


$383 totalSnaptravel
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Standard Rooms - Mountain view


$172 totalSnaptravel
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Double Rooms - Panoramic view


$197 totalFINDHOTEL
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King Rooms - Park view


$511 totalAgoda.com
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Queen Rooms - Harbor view


$320 totalTravelCLICK
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Other Rooms - Sea view


$590 totalmomondo
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Resort Amenities & Facilities

  • Private beach
  • Outdoor pool
  • Room service
  • Bicycle rental
  • Tennis
  • Free Wi-Fi
  • Coffee machine
  • Wi-Fi available in all areas
  • Flat-screen TV
  • TV


  • Free Wi-Fi
  • Wi-Fi available in all areas
  • Internet
  • Linens
  • Fan
  • Towels
  • Fire extinguisher
  • Shampoo
  • Free toiletries
  • Smoke alarms
  • Heating
  • Body soap
  • Air-conditioned
  • Trash cans
  • Conditioner

Accessibility and suitability

  • Entire unit wheelchair accessible
  • Pets allowed on request. Charges may apply.
  • Roll-in shower
  • Increased accessibility
  • Elevator
  • Multi-lingual staff
  • Accessible by elevator
  • No smoking
  • Lowered sink
  • Toilet with grab rails
  • Upper floors accessible by elevator
  • Private entrance

Health and safety

  • Face masks for guests available
  • Physical distancing rules
  • First-aid kit
  • Hand sanitizer in guest accommodation and key areas
  • Screens or physical barriers placed between staff and guests in appropriate areas
  • Use of cleaning chemicals that are effective against coronavirus
  • Guest accommodation is disinfected between stays
  • Thermometers for guests provided by property
  • Safe
  • Staff follow all safety protocols as directed by local authorities


  • Window
  • Sea view
  • Seating area
  • Interconnected room(s) available
  • Sofa
  • Telephone
  • Tile/marble floor
  • Pool view


  • Shower
  • Spa bath
  • Hairdryer
  • Toilet
  • Toilet paper
  • Private bathroom
  • Walk-in shower

Pool and spa

  • Heated pool
  • Spa
  • Hot tub
  • Outdoor pool
  • Pool towels
  • Pool with a view


  • Terrace/Patio
  • Beach towels
  • Balcony
  • Private beach
  • Garden

Services and conveniences

  • Room service
  • Key access
  • Key card access
  • Private check-in/check-out
  • 24hr front desk


  • Microwave
  • Refrigerator
  • Coffee machine
  • Kitchenette

Media and entertainment

  • Flat-screen TV
  • Cable or satellite TV
  • TV
  • Smartphone dock


  • Sofa bed
  • Alarm clock
  • Wardrobe or closet

Parking and transportation

  • Parking
  • Private parking


  • Laundry facilities
  • Iron and ironing board

Family friendly

  • Children's television networks
  • Complimentary breakfast


  • Computer use available


  • Vending machine (drinks)

Things to do

  • Bicycle rental


  • Tennis

Places of interest near Chesapeake Beach Resort

Attractions in Islamorada, Florida curated by momondo

Chesapeake Beach Resort location: 83409 Overseas Highway, Islamorada, FL 33036

Restaurants and Cafés

Whale Harbor Buffet0.1 mi
Wahoo's Bar & Grill0.1 mi
The Sand Bar0.1 mi
Ziggie & Mad Dog's0.5 mi

Chesapeake Beach Resort Reviews

GoodBased on 371 verified guest reviews

Pros +
  • Staff was very attentive and gracious. (in 38 reviews)
  • The location was perfect. (in 35 reviews)
  • The room was super nice! (in 26 reviews)
Cons -
  • Our room was dusty & dirty. (in 33 reviews)
  • The beach was dirty. (in 22 reviews)
  • The property was under construction. (in 21 reviews)

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Chesapeake Beach Resort room booking info

Check in/Check out

Check in anytime after 4:00 PM, check out anytime before 11:00 AM


Cancellation/prepayment policies vary by room type and provider.

Frequently asked questions

  • Chesapeake Beach Resort is typically below the average price of 3 star hotels in Islamorada. On average, you can expect to pay $359 per night in Islamorada. Chesapeake Beach Resort typically costs $238 per night, which is $121 cheaper than the Islamorada average.

  • Drive distance from Miami to Chesapeake Beach Resort and vice versa is 62.8 mi and the overall drive time is about 3h 8min. Driving time can vary based on the time of day and traffic.

  • A very popular option for travelers staying at Chesapeake Beach Resort would be to take a taxi or ridesharing service from Miami directly to the hotel.

  • Yes, you’re free to bring your dog with you while staying at Chesapeake Beach Resort.

  • If you are staying at Chesapeake Beach Resort, you are more than welcome to order food through the hotel’s room service menu.

  • Chesapeake Beach Resort does have a pool on site that hotel guests may use. Be advised that hotels typically have rules associated with pool usage. momondo would advise you to check with the front desk before taking a swim.

  • 1.2 mi separate the front steps of Chesapeake Beach Resort and the city center of Islamorada where you can keep busy with restaurants, shopping and of course Theater of the Sea, a very popular landmark in Islamorada.

  • For assistance from an employee at Chesapeake Beach Resort please call +1 305 664 4662.

  • Yes, Chesapeake Beach Resort has Wi-Fi available to hotel guests.

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