"This resort served the best included breakfast we have had."
tmwyss from United States
read full review
"The layout and I like that's acomplete boutique hotel unique great staff and absolutely great planned villas n rooms"
Ventura from United States
read full review
"Resort is beautiful. Views, location. The beach was awesom3"
Adele from United States
read full review
"The resort provides kayaks, SUP, and fishing gear for any interested guest."
Becki W from United States
read full review
"Great location for being close to fishing charters and restaurants - nice new rooms with a relaxed energy and on site breakfast"
Cynthia R from United States
read full review
Private beach resort in Islamorada with complimentary watersports and daily breakfast
Beach & Waterfront
The hotel has a private beach area with loungers exclusive to guests. Complimentary kayaking, paddleboarding, and fishing poles are available for daily use. Two outdoor heated swimming pools overlook the ocean and are open all year.
Rooms & Suites
Spacious two-bedroom villas and premium villas are offered. Select suites include a balcony, a 37-inch flat-screen television, and a small refrigerator. The resort provides accessible parking and pet-friendly accommodations.
Dining & Evening Entertainment
A complimentary breakfast with made-to-order omelets, waffles, and fresh fruit is served each morning. The on-site restaurant overlooks the water, and the bar serves frozen shrimp for fishing. The hotel offers live entertainment events on-site and a tiki boat tour to the sandbar.
Activities & Guest Services
Yoga classes are held outdoors on the beach. Giant chess, checkers, and cornhole boards are available in the beach area for guest use. A personalized breakfast delivery service and regular guest check-ins via text are provided.
Location & Nearby Attractions
The resort is situated on the ocean side of Islamorada. The History of Diving Museum is a 3-minute walk away, and Theater of the Sea is a 4-minute drive from the hotel. Windley Key Fossil Reef Geological State Park is 2 miles from the property.
Highlights
Beach: Private beach area exclusive to guests
Water sports: Complimentary kayaks, paddleboards, and fishing poles
Breakfast: Fresh, cooked-to-order omelets and waffles included
Rooms: Two-bedroom villas and premium suites with balconies
Attractions: 3-minute walk to History of Diving Museum
Services: 24-hour front desk and guest check-ins via text
Pets: Pet-friendly rooms on offer
Must-do experiences
Visit the History of Diving Museum for a unique underwater journey.
Savor a stone crab sandwich at the iconic Hungry Tarpon restaurant.
Explore the serene Anne's Beach for stunning views and relaxation.
Take a sunset cruise with Islander Watersports for breathtaking sights.
Discover local art at the Green Turtle Inn's gallery space.
Select your room type
Chesapeake Beach Resort provides a range of room types, including doubles, family rooms, and suites, along with breakfast, free cancellation, and special offers.
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
Room Availability and Pricing Calendar
See today's rates and availability for your selected dates!
Facilities
Chesapeake Beach Resort offers amenities for a comfortable stay and memorable Florida Keys experiences
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
Islamorada Activities and Dining
Top Attractions
Activities
Dining
Entertainment
History of Diving Museum
12 minutes' walk
Diving history exhibits showcase artifacts and stories. Family-friendly with interactive displays.
Florida Keys History and Discovery Center
25 minutes' walk
Regional history and culture highlighted in interactive exhibits. Great for learning about the area's heritage.
Windley Key Fossil Reef Geological State Park
25 minutes' walk
Unique geological features with trails showcasing fossilized coral reefs. Ideal for nature walks.
Snorkeling Tours
3 minutes' drive
Exciting snorkeling trips to vibrant coral reefs. Equipment rental often included, seasonal availability.
Yoga on the Beach
5 minutes' drive
Relaxing beach yoga sessions. Perfect for unwinding with calming ocean views.
Wahoo's Bar and Grill
3 minutes' walk
Casual dining with a tropical vibe. Known for seafood dishes and outdoor seating.
Whale Harbor Seafood Buffet
3 minutes' walk
Buffet featuring fresh local catches. Family-friendly atmosphere with extensive options.
Mango's Bar & Grill
7 minutes' drive
Vibrant nightlife spot with live music events. Ideal for casual dining and drinks.
Islamorada Brewery & Distillery
7 minutes' drive
Local brews and spirits with tastings. Family-friendly with outdoor seating and food trucks.
Local transportation
City Centre
Islamorada 24 min · 1.2 mi
Bus
Bus stop 8 min · 3.3 mi
Want to see Exclusive Early Booking Rates for the Florida Keys?
Get exclusive Florida Keys rates now!
Check Rates
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
Ratings & Reviews
Read what previous guests have shared about their experience at Chesapeake Beach Resort.
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
Malfunctioning hot tub
Guest reviews
based on 88 reviews
4/5
based on 725 reviews
8.4/10
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
Bungalows Key Largo (Adults Only)
Bayside Villas By Islander Resort
Bayside Inn Key Largo
Islander Resort
Sunshine Key Rv Resort & Marina
Gilbert'S Resort & Marina
Seafarer Key Largo Resort And Beach
Ambrosia Key West
Caloosa Cove Resort By Coolvacay
Westwinds Inn
Blackfin Resort And Marina
Sea Dell Motel - Marathon