Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, United States - Nearby coral reefs
4.0/5
· 88 reviews

The 3-star Chesapeake Beach Resort Islamorada enjoys an oceanfront location merely a 5-minute stroll from Whale Harbor Marina and offers 45 rooms with views of the courtyard. Boasting 2 outdoor swimming pools, this Islamorada resort is nestled 1.4 miles from natural attractions like Windley Key Fossil Reef Geological State Park.

Location

The hotel places you about 10 minutes by car from Hurricane Monument and a short way from Island Community Church. Rain Barrel Village in Islamorada is 3.1 miles from the traditional Chesapeake Beach Resort. Guests will also appreciate the vicinity of Windley Harbor, located approximately a -minute walk away. The nearby shopping sights include Lobster Trap Art Gift Shop and Gallery, which is 1.5 miles away.

Rooms

The rooms at Chesapeake Beach Resort include an air conditioner, as well as media facilities like a flat-screen TV with satellite channels. The rooms are complete with elegant furniture. Featuring a walk-in shower and a separate toilet, the bathrooms also come with a hairdryer and shower caps.

Food & Drinks

A free breakfast is served in the dining place. Guests can enjoy time in the lounge bar. While staying at the Chesapeake Beach Resort Islamorada, guests can choose from dining options nearby, such as Wahoo's Bar and Grill, located around a 5-minute drive away, or Shuck N Dive at a 5-minute walking distance.

Leisure & Activities

A tennis court and a playground can be enjoyed for a surcharge, and you can also go fishing. The property has a white sand beach area with free Wi-Fi access and lounge chairs. There is also kayaking and fishing for active guests.

Why choose Chesapeake Beach Resort Islamorada

Select room
  • Oceanfront venue for events

  • Private beach access available

  • All rooms with private balconies

  • Outdoor pool with ocean views

Main amenities

  • Wi-Fi

  • Free parking

  • 24-hour services

  • Swimming Pool

  • Private beach

  • Sports activities

  • Wheelchair access

  • Air conditioning

  • Pets

General
  • Wi-Fi
  • Free parking
  • 24-hour services
  • Swimming Pool
  • Private beach
  • Sports activities
  • Wheelchair access
  • Air conditioning
  • Pets
1/17

Internet

  • Wi-Fi

Parking options

  • Free parking

Activities

  • Yoga class
  • Fishing

Property services

  • 24-hour reception
  • VIP check-in/ -out
  • Security
  • Luggage storage
  • Housekeeping
  • Shops/Commercial services
  • Welcome drink

Dining options

  • Snack bar

In the kitchen

  • Cookware/ Kitchen utensils

For kids

  • Board games

Recreation

  • Private beach
  • Heated swimming pool
  • Outdoor swimming pool
  • Beach access
  • Sun loungers
  • Live entertainment
  • Pool with view
  • Shallow end

For disabled guests

  • Rooms/ Facilities for disabled
  • Wheelchair access
  • Toilet for disabled
  • Bathroom for disabled

In the rooms

  • Air conditioning
  • Heating
  • Sitting area
  • Garden furniture
  • Dining table

In the bathroom

  • Free toiletries
  • Sink

Devices

  • Flat-screen TV
  • AM/FM alarm clock

General facilities

  • No smoking on site
  • Allergy-free rooms
  • Lift
  • Smoke detectors
  • Fire extinguishers
  • Key card access

Pets

  • Pets allowed

Important information

Check-in:
from 16:00 until 23:00
Check-out:
from 07:00 until 11:00
  • Children and extra beds
  • There are no extra beds provided in a room.
  • There are no cribs provided in a room.

Enter dates to see availability

From USD 149 per night
Check-in 5 Jun 2026
Check-out 6 Jun 2026
Guests 2 guests

Adults:

2

Children:

0
All rates verified
How we verified prices Our team regularly checks prices to make sure you see the lowest available rates. We compare them with hotel prices and other providers. If discounts or promotions appear, prices on our site are updated accordingly.

Rooms

Photos of Chesapeake Beach Resort Islamorada

Location of Chesapeake Beach Resort Islamorada

83409 Overseas Highway, Islamorada, United States

 -  Nearby coral reefs
Attractions
Great restaurants
Transportation

Places nearby

    Guest reviews of Chesapeake Beach Resort Islamorada

    8.6 Fabulous
    764 reviews

    Write a review

    When did you travel?

    Your rating point

    Very bad
    Excellent

    Your details

    Where are you from?
    Thank you! Thank you for taking the time to share your experience. Your review will be published shortly.

    Review has not been sent.

    Please try again.

    Popular hotels in Kissimmee

    Find your perfect hotel stay today

    Popular hotels all over the world

    Find your perfect hotel stay today

    Currency
    • USD U.S. dollar
    • EUR Euro
    • GBP Pound sterling
    • AUD Australian dollar
    • CAD Canadian dollar
    • BRL Brazilian real
    • CNY Chinese yuan
    • CZK Czech koruna
    • DKK Danish krone
    • HKD Hong Kong dollar
    • ILS Israeli new sheqel
    • JPY Japanese yen
    • MYR Malaysian ringgit
    • NZD New Zealand dollar
    • NOK Norwegian krone
    • PLN Polish zloty
    • RON Romanian leu
    • RUB Russian ruble
    • SAR Saudi riyal
    • SGD Singapore dollar
    • ZAR South African rand
    • KRW South Korean won
    • SEK Swedish krona
    • CHF Swiss franc
    • TRY Turkish lira
    • UAH Ukrainian hryvnia
    • THB Thai baht
    • ARS Argentina, Peso
    Select language
    100% Verified Reviews
    Enter dates to see availability
    From USD 149 per night
    Check-in 5 Jun 2026
    Check-out 6 Jun 2026
    Guests 2 guests

    Adults:

    2

    Children:

    0
    All rates verified
    How we verified prices Our team regularly checks prices to make sure you see the lowest available rates. We compare them with hotel prices and other providers. If discounts or promotions appear, prices on our site are updated accordingly.
    Check-in & out
    5 Jun 2026
    6 Jun 2026
    Guests
    2 guests
    We're here to help
    Hi there! Have a question? Message us—our team is happy to assist.
    Your details:
    Subject:
    Message:
    Thank you for your message. We’ll get back to you shortly!
    Your message was not delivered
    Important information
    Chesapeake Beach Resort
    Check-in:
    from 16:00 until 23:00
    Check-out:
    from 07:00 until 11:00
    • Children and extra beds
    • There are no extra beds provided in a room.
    • There are no cribs provided in a room.