Chesapeake Beach Resort Islamorada Beach photoChesapeake Beach Resort Islamorada Exterior photoChesapeake Beach Resort Islamorada Exterior photo

CHESAPEAKE BEACH RESORT, Islamorada

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Check rooms and rates
From$149 /night
Check-in
11Jul
Check-out
12Jul
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

83409 Overseas Highway, Islamorada, 33036
-
Close to the History of Diving Museum
Great
8.6
9.1
/10
3.9
4.2
/5

Rooms, Suites & Villas

Chesapeake Beach Resort, situated between Everglades National Park and the Florida Strait in Islamorada, offers rooms, suites, and villas. Newly renovated rooms include plush bedding and rainfall showers. Ocean-view rooms feature king or queen beds and loveseat sleeper sofas. One-bedroom suites have king beds, ocean views, balconies, sitting rooms with dining tables for four, and queen-size sleeper sofas. Two-bedroom suites add larger dining tables. Villas provide kitchens with full-size refrigerators/freezers, stovetops, dishwashers, and dining areas. Premium Ocean View Villas come with king beds and sleeper sofas. Some villas are nestled among foliage near the water.

Onsite Dining

Chesapeake Beach Resort provides various dining options, including fresh seafood, landlubber favorites, and ethnic dishes. Guests can enjoy tiki-covered bars, dockside fish houses, beachfront cafes, and island bistros. Options include pasta, salads, garlic bread, spaghetti, and pizza.

Leisure and Entertainment

Chesapeake Beach Resort is known for live entertainment, including musicians, stilt walkers, acrobats, and fire-eaters. Every full moon, the beach near Pierre's Restaurant and Morada Bay hosts a large party with bonfires and live music. The resort offers outdoor pools with ocean views, a private beach, water sports rentals (kayaks, paddleboards, fishing rods), and beach games. A 2-night stay includes Champagne welcomes, sunset tiki cruises, beachfront yoga, and clear kayak paddles. A 3-night stay adds dolphin encounters and sandbar adventures. A 5+ night stay also features snorkeling reefs.

Location and Activities

Located in Islamorada, Chesapeake Beach Resort provides proximity to various attractions and activities. Theater of the Sea, 0.9 miles away, offers opportunities to swim with dolphins and sea life. The resort is near Alligator Reef (5.8 miles) and Hen and Chickens Reef for snorkeling and diving. Anne's Beach, 10 miles away, features a boardwalk and shallow waters. The Islamorada Sandbar is less than a mile offshore. The resort is close to seafood restaurants, bars, taverns, and pubs.

Services & Amenities

Chesapeake Beach Resort provides services such as cooked-to-order omelets, continental breakfast items, welcome drinks, in-room robes and slippers, high-speed internet, pool/beach towels, pool/beach lounge chairs, water sports rentals (two hours per room per night), seasonal resort activities, beach games, fish cleaning stations, 24-hour coffee and tea in the lobby, self-parking, and local calls. The resort offers group rates, wedding services, and room blocks for events. Pet-friendly accommodations are available.

Must-do experiences

  • Snorkel at John Pennekamp Coral Reef State Park for stunning marine life.
  • Savor the catch of the day at the famous Marker 88's waterfront dining.
  • Visit the History of Diving Museum for unique underwater artifacts.
  • Take a sunset cruise aboard the Islander Watersports boat tours.
  • Discover the hidden gems at the Islamorada Farmers Market on Saturdays.

Choose your room type

Chesapeake Beach Resort — double rooms, family rooms, and suites. Breakfast options and free cancellation available on selected rates
  • Ocean View Two Queens
    2 persons
    32 sq. feet
    2 Double beds
    Air conditioning
    Balcony
  • Ocean View King
    2 persons
    32 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
  • Deluxe King Suite
    2 persons
    55 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
Show all rooms

Hotel Price Calendar

Check availability and prices for your dates
July 2026 - July 2027
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Check-in/ Check-out

Facilities

What's included at Chesapeake Beach Resort — facilities and services available during your stay
Facilities: Great
8.6/10Review score

General

  • No smoking on site
  • Wi-Fi
  • Parking
  • 24-hour reception
  • VIP check-in/ -out
  • Pets allowed
  • Rooms/ Facilities for disabled
  • Wheelchair access
  • Security
  • Luggage storage
  • Private beach
  • Allergy-free rooms
  • Lift
  • Smoke detectors
  • Fire extinguishers
  • Key card access

Sports & Fitness

  • Yoga class
  • Fishing

Guest Parking

  • Cookware/ Kitchen utensils

Services

  • Housekeeping
  • Shops/Commercial services
  • Welcome drink

Dining

  • Snack bar

Children

  • Board games

Facilities for people with disabilities

  • Toilet for disabled
  • Bathroom for disabled

Spa & Leisure

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

Room features

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

Bathroom

  • Free toiletries
  • Sink

Self-catering

  • Cookware/ Kitchen utensils

Media

  • Flat-screen TV
  • AM/FM alarm clock
Show more

Chesapeake Beach Resort Location

83409 Overseas Highway, Islamorada, 33036
Explore Islamorada
Explore Islamorada
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
History of Diving Museum
History of Diving Museum
12 minutes' walk
Museum showcasing the history of diving with exhibits and artifacts. Interactive displays enhance the experience for all ages.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
25 minutes' walk
Center with exhibits on the cultural history and ecology of the Florida Keys, great for families and history buffs.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
4 minutes' drive
Geological park featuring fossilized coral reefs and nature trails. Ideal for hiking enthusiasts and eco-lovers.
Lobster Trap Art Gift Shop and Gallery
Lobster Trap Art Gift Shop and Gallery
4 minutes' drive
Local art gallery featuring unique works by local artisans. Perfect for picking up a special souvenir.
Water Sports Rentals
3 minutes' walk
Equipment rentals for kayaking, paddleboarding, and snorkeling right by the hotel. Exciting for solo adventurers and families.
Relaxing Spa Services
10 minutes' drive
Spa offering a range of treatments, from massages to facials, perfect for unwinding after a busy day.
Wahoo's Bar and Grill
3 minutes' walk
Casual dining spot with fresh seafood and tropical cocktails. Great atmosphere with live music on weekends.
Whale Harbor Seafood Buffet
3 minutes' walk
Buffet featuring a variety of seafood and local dishes. Family-friendly with a vibrant atmosphere.
Casa Mar Seafood
7 minutes' walk
Charming seafood restaurant known for its fresh catches and lovely outdoor seating. Reservations recommended.
Islamorada Beer Company
10 minutes' drive
Craft brewery with tastings, tours, and live music events. A relaxed spot perfect for enjoying a local brew.
The Islander Watersports
5 minutes' drive
Family-friendly watersport venue offering sunset cruises and dolphin tours. Fun for all ages, with memorable experiences.
Getting around
  • City Centre
    Islamorada 24 min  ·  1.2 mi
  • Bus
    Bus stop 8 min  ·  3.3 mi
Book early and pay less
See available rates for your dates
Check Rates
Property information and rules
Check-in
from 16:00-23:00
Check-out
from 07:00-11:00
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in the entire hotel for free.
Breakfast
A full breakfast is served at the price of US$0.10 per person per day.
Children & extra beds
There are no extra beds provided in a room.  There are no cots provided in a room. 
Pets
Pets are allowed on request.
Year renovated:
2008
Number of rooms:
45

Guest Reviews and Ratings

What guests said after staying at Chesapeake Beach Resort
Review score
Based on 993 verified reviews
8.9 /10
Great
89 %
Recommend
Cleanliness
9.0/10
Comfort
8.9/10
Facilities
8.6/10
Free WiFi
8.5/10
Location
9.0/10
Staff
8.6/10
Value for money
7.8/10
Pros
Helpful staff
Clean rooms
Daily breakfast
Sandy beach
Free parking
Cons
Rundown hotel
Guest reviews
based on 88 reviews
4/5
based on 740 reviews
8.6/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
Open reviews
FAQs
About Chesapeake Beach Resort
What time is check-in and check-out at Chesapeake Beach Resort?
Check-in is at 16:00 and check-out is by 11:00.
Is parking available at Chesapeake Beach Resort?
Free private parking is available on-site, with prior reservation needed.
What nearby attractions can be visited from Chesapeake Beach Resort?
Nearby attractions include the History of Diving Museum (0.5 km) and Theater of the Sea (6 km).
What outdoor amenities are featured at Chesapeake Beach Resort?
The resort offers a private beach, an outdoor heated pool, and sun loungers.
What kind of dining options are available at Chesapeake Beach Resort?
An on-site restaurant is available along with nearby options like Whale Harbor Seafood Buffet, Wahoo's Bar and Grill, and Shuck N Dive, all within 0.5 km.
What are the room features at Chesapeake Beach Resort?
Rooms include free Wi-Fi, air conditioning, a flat-screen TV, and a refrigerator.
Are there recreational activities offered at Chesapeake Beach Resort?
Guests can enjoy beach access, fishing, and free kayak and paddleboard rentals.
Does Chesapeake Beach Resort provide business services?
The resort offers a 24-hour reception and luggage storage services.
What facilities help to ensure accessibility at Chesapeake Beach Resort?
The resort features wheelchair access throughout the property.
What special features does Chesapeake Beach Resort offer for guests?
Guests enjoy personalized breakfast delivery service and complimentary water sports equipment rentals.
What languages do the staff at Chesapeake Beach Resort speak?
The staff speaks English to assist guests.

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