"The room was lovely, super clean, very modern style with an ocean view."
Ernesto from United States
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"Breakfast on the sea is a plus."
Masal9 from Italy
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"Freshly cooked omelettes in the morning were great!"
Christine from Australia
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"Perfect location in Islamorada with nice views of the water."
Cindy G from United States
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"Free use of kayaks if weather permits."
Esta K from United States
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Oceanfront Resort in Islamorada with Private Beach, Heated Pools, and Complimentary Kayaks
Beachfront Amenities
Chesapeake Beach Resort offers a private beach area exclusive to guests, with sun loungers and beach chairs. Two heated outdoor pools with ocean views sit on the beachfront, and the resort includes a shallow end for children. Guests receive complimentary kayaks, paddleboards, and bicycles, all included in the resort fee.
Rooms & Villas
Each room at Chesapeake Beach Resort includes a 37-inch flat-screen cable TV and a small refrigerator. Select rooms and suites have a balcony, and ocean-view rooms and suites are available. Spacious two-bedroom and premium villas provide additional space for families and longer stays.
Dining
Daily breakfast in the Sunrise Room includes made-to-order omelets, waffles, pancakes, fresh fruit, and yogurt. The on-site snack bar and minimarket supply drinks, snacks, and essentials. Guests can walk to Wahoo's restaurant, Lorelei, and Papa Joe's for additional dining options.
Location
The History of Diving Museum is a 3-minute walk from the resort. Theater of the Sea is a 4-minute drive away. Windley Key Fossil Reef Geological State Park is 2 miles from the property.
Guest Services & Pet-Friendly
The hotel provides personalized breakfast delivery service and regular guest check-ins via text. AAA and CAA member benefits are available on the property, and pet-friendly accommodations allow guests to bring dogs. Facilities for disabled guests include wheelchair access and braille signage; board games, puzzles, and live music performances are available on-site.
Highlights
Private Beach: Guest-only oceanfront area with loungers
Water Sports: Free kayaks, paddleboards, and bicycles
Rooms: Two-bedroom and premium villas
Dining: Made-to-order breakfast in the Sunrise Room
Location: 3-minute walk to History of Diving Museum
Pet-Friendly: Dogs allowed on property
Benefits: AAA and CAA member benefits
Must-do experiences
Snorkel at the John Pennekamp Coral Reef State Park for stunning views.
Savor the conch fritters at Mike's Kitchen, a local favorite.
Visit the Florida Keys History and Discovery Center for culture.
Take a sunset cruise with Islander Watersports for breathtaking sights.
Explore the hidden treasures at the Islander Watersports market.
Select your room type
Chesapeake Beach Resort offers a range of rooms across the Sunshine State — from double rooms to family suites — complete with breakfast, flexible cancellations, and seasonal deals for your Florida stay
Ocean View Two Queens
2 persons
345 sq. feet
2 Double beds
Air conditioning
Balcony
room details
Ocean View King
2 persons
345 sq. feet
1 King-size bed
Air conditioning
Balcony
room details
Deluxe King Suite
2 persons
595 sq. feet
1 King-size bed
Air conditioning
Balcony
room details
Show all rooms
Price and Room Availability Calendar
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Amenities
Chesapeake Beach Resort offers amenities for your Florida getaway, from theme park days to coastal escapes
Facilities: Great
8.5/10Review 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
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,
Map view
City landmarks
Museum
History of Diving Museum
3200 ft
Landmark
Windley Key Fossil Reef Geological State Park
1.4 mi
Gallery
Lobster Trap Art Gift Shop and Gallery
1.4 mi
Museum
Florida Keys History and Discovery Center
1.4 mi
Island
Upper Matecumbe Key
1.8 mi
Island
Windley Key
1.5 mi
Monument
Hurricane Monument
1.9 mi
Gallery
Michelle Nicole Lowe Art Gallery
1.7 mi
Landmark
Keys History & Discovery Center
1.5 mi
Landmark
In the Doghouse Art Studio
1.8 mi
Gallery
Pasta Pantaleo Signature Gallery
2.1 mi
Gallery
Gallery Morada
2.1 mi
Landmark
Carysfort Reef
1.8 mi
Island
Plantation Key
1.8 mi
Island
Raccoon Key
1.8 mi
Church
Matecumbe United Methodist Church
1.9 mi
Gallery
Elena Madden Studio Gallery
2.0 mi
Gallery
Portside Studio & Gallery
2.1 mi
Landmark
Cheeca Rocks
2.2 mi
Landmark
Indian Key State Historic Site
2.6 mi
Landmark
Lignumvitae Key Botanical State Park
2.6 mi
Landmark
Rain Barrel Village
3.1 mi
Landmark
FNX Club by Islamorada Fitness
2.7 mi
Landmark
Rain Barrel Sculpture Gallery
3.1 mi
Landmark
Crossland Gallery
2.8 mi
Nearby
Marina
Whale Harbor Marina
700 ft
Restaurants
Wahoo's Bar and Grill
700 ft
83413 Overseas Hwy
Whale Harbor Seafood Buffet
700 ft
83413 Overseas Hwy
The Sand Bar
700 ft
83413 Overseas Hwy
Shuck N Dive
700 ft
83413 Overseas Hwy
Casa Mar Seafood
1900 ft
97001 Oversea Hwy Islamorada
Ziggie & Mad Dog's
3000 ft
83000 Overseas Hwy
Explore Islamorada
Explore the Flavors and Fun
Top Attractions
Activities
Dining
Entertainment
History of Diving Museum
12 minutes' walk
Museum showcasing the history of diving and underwater exploration. Unique exhibits and informative tours offer rich insights.
Lobster Trap Art Gift Shop and Gallery
4 minutes' drive
Gallery featuring local artists' work and unique crafts. A great spot to find souvenirs and enjoy the artistic vibe of the Keys.
Florida Keys History and Discovery Center
5 minutes' drive
Interactive exhibits on the history and ecology of the Florida Keys. Educational programs and workshops enhance the experience.
Snorkeling at Carysfort Reef
5 minutes' drive
Thrilling snorkeling adventure to see vibrant coral reefs and diverse marine life. Rentals available nearby; guided tours recommended.
Yoga at FNX Club
10 minutes' drive
Relaxing yoga sessions offered with beautiful ocean views. Classes suitable for all levels; check for schedule and pricing.
Wahoo's Bar and Grill
3 minutes' walk
Casual eatery with fresh seafood and tropical drinks. Enjoy outdoor seating and the famous fish tacos in a laid-back atmosphere.
Whale Harbor Seafood Buffet
3 minutes' walk
Seafood buffet featuring local catches and diverse dishes. Family-friendly atmosphere with ample options for every palate.
Islander Watersports
3 minutes' walk
Live music and entertainment at a vibrant waterfront venue. Regularly hosts events, including open mic nights and local bands.
Getting around Florida
City Centre
Islamorada 24 min · 1.2 mi
Bus
Bus stop 8 min · 3.3 mi
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Property information and rules
Check-in
from 16:00-23:00
Check-out
from 07:00-11:00
Internet
Wireless internet is available in the entire hotel for free.
Breakfast
A full breakfast is served at the price of USD 0.1 per person.
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
Reviews and Ratings
Feedback about Chesapeake Beach Resort from previous guests about their experience.
Cleanliness
8.9/10
Comfort
8.7/10
Facilities
8.5/10
Free Wi-Fi
9.3/10
Location
9.0/10
Staff
8.5/10
Value for money
7.7/10
Pros
Friendly staff
Clean rooms
Good breakfast
Cons
Expensive fees
Guest reviews
based on 88 reviews
4/5
based on 723 reviews
8.5/10
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.
Guest reviews
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