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Chesapeake Beach Resort, Islamorada

2.5-star2.5 stars
83409 Overseas HwyIslamoradaFL33036United States of America
Florida Keys getaway with 2 oceanfront pools
  • Free buffet breakfast, free WiFi, and free parking
Great pool
Beautiful beach
More comfort would be nice
Vibe is not too good
186See all 186 reviews
From 723 reviewsTripAdvisor Traveller Rating

Chesapeake Beach Resort, Islamorada

from $143
  • Standard Room, 2 Double Beds, Balcony, Garden View
  • Premium Room, 1 King Bed, Ocean View
  • Premium Suite, 1 King Bed with Sofa bed, Ocean View
  • Large Two Bedroom Villa
  • Villa, 1 Queen Bed, Kitchenette, Garden View
  • Villa, 1 Bedroom
  • Villa, 1 King Bed, Kitchenette
  • Premium Large One Bedroom Villa
  • Efficiency Villa 2 Doubles
  • Premium Villa, 1 Bedroom
  • Villa, 2 Bedrooms, Ocean View
  • Villa, 2 Bedrooms
  • Upper Villa
  • Premium Double Room, 2 Double Beds, Ocean View
  • Deluxe Double Room, 2 Double Beds
  • Deluxe Room, 1 King Bed

At a glance

Key facts

Hotel size

  • This hotel has 65 rooms
  • This hotel is arranged over 2 floors


  • Check-in time 3 PM-11 PM
  • Check-out time is 11 AM
The front desk is open daily from 7 AM - 11 PM

Required at check in

  • Credit card deposit required

  • Government-issued photo ID required

  • Minimum guest age is 21
  • Minimum check-in age is 21
  • Minimum Spring Break check-in age is 21

Travelling with others


  • Children (12 years old and younger) stay free when occupying the parent or guardian's room, using existing bedding


  • Pets not allowed

Extra people

  • Roll-away beds available, charges may apply*


  • Free WiFi in public areas

  • Free WiFi in rooms



  • Free self parking

Other information

  • Smoke-free property
  • Resort fee included
* See small print for additional details or extra charges

In the hotel

Food and drink
  • Free buffet breakfast daily
  • Room service (during limited hours)
  • Coffee/tea in a common area
  • Barbecue grills
Things to do
  • On private beach
  • Beach towels
  • Number of outdoor pools - 2
  • Pool sun loungers
  • Fitness facilities
  • Outdoor tennis court
  • Full-service spa
  • Spa treatment room(s)
  • Marina on site
  • Tennis on site
  • Spa tub
Working away
  • Computer station
  • Front desk (limited hours)
  • Laundry facilities
  • Free newspapers in lobby
  • Multilingual staff
  • Number of buildings/towers - 15
  • Garden
  • Picnic area
  • Library
  • Accessible bathroom

In the room

Home comforts
  • In-room climate control (air conditioning)
  • Air conditioning
  • Ceiling fan
  • Coffee/tea maker
  • Iron/ironing board
Sleep well
  • Pillowtop mattress
Things to enjoy
  • Balcony
Freshen up
  • Private bathroom
  • Shower only
  • Free toiletries
  • Hair dryer
Be entertained
  • 37-inch flat-screen TV
  • Satellite TV channels
Stay connected
  • Desk
  • Free WiFi
  • Phone
Food and drink
  • Refrigerator
  • Daily housekeeping
  • In-room safe
  • Connecting/adjoining rooms available

Special features


Chesapeake Beaches Spa has massage/treatment rooms and couples treatment room(s). Services include deep-tissue massages, hot stone massages, massages, and facials. A variety of treatment therapies are provided, including aromatherapy and hydrotherapy.


On Site

  • Fitness facilities
  • Marina on site
  • Outdoor tennis court
  • Spa tub
  • Tennis on site
  • Bicycle rentals on site
  • Free bicycles on site
  • Fishing on site
  • Kayaking on site
  • Playground on site
  • Rowing or canoeing on site
  • Sailing on site


  • Ecotours nearby
  • Parasailing nearby
  • Scuba diving nearby
  • Snorkeling nearby

Chesapeake Beach Resort, Islamorada’s small print

Also known as

  • Chesapeake Beach Islamorada
  • Chesapeake Beach Resort
  • Chesapeake Beach Resort Islamorada
  • Chesapeake Resort
  • Chesapeake Beach Hotel Islamorada


The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation.

Mandatory fees

The charges below are included in the total price displayed:

  • Resort fee

Resort fee inclusions:

  • Breakfast
  • Internet access (may be limited)

Inclusions may be listed elsewhere on the page as free or for a surcharge.

We have included all charges provided to us by this hotel. However, charges can vary, for example, based on length of stay or the room you book.

What’s around Chesapeake Beach Resort, Islamorada


  • History of Diving Museum (11-minute walk)
  • Theater of the Sea (21-minute walk)
  • Windley Key Fossil Reef Geological State Park (28-minute walk)
  • Hurricane Monument (43-minute walk)
  • Founders Park (3.3 mi / 5.4 km)
  • Bud n' Mary's Dive Center (3.8 mi / 6.2 km)
  • Lignumvitae Key Botanical State Park (6.5 mi / 10.4 km)
  • Anne's Beach (10.1 mi / 16.2 km)

Getting around

  • Miami, FL (MIA-Miami Intl.) 87-min drive
  • Free self parking

Chesapeake Beach Resort, Islamorada

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