83409 Overseas Highway,
Islamorada,
Florida,
United States,
33036,
Florida
-
Steps from Whale Harbor Marina
Great
8.5
9.1
/10
3.1
4.2
/5
Loved by Chesapeake Beach Resort guests
Ocean views
Helpful staff
Adequate breakfast
Beach area
Modern rooms
"There is a private beach at the resort that is absolutely beautiful."
Paula from United States
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"The resort provides kayaks, SUP, and fishing gear for any interested guest."
Becki W from United States
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"This property has it's own little beach you can walk in the sand & swim in the ocean."
Amanda
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Chesapeake Beach Resort offers a family-friendly experience with oceanfront access and a private beach. This 3-star Islamorada hotel features outdoor pools, water sports rentals, and modern accommodations rated 8.5/10 on Booking.com.
Rooms & Amenities
Each newly renovated room at Chesapeake Beach Resort includes a private balcony and comfortable bedding. Options include ocean-view rooms, suites, and villas equipped with kitchenettes.
Dining & Nearby Options
Dining options include nearby seafood restaurants where guests can enjoy fresh local cuisine. Various eateries, like Whale Harbor Seafood Buffet and Wahoo's Bar and Grill, are within 0.3 miles.
Leisure Activities
Leisure activities at Chesapeake Beach Resort range from swimming in the outdoor pools to water sports like kayaking and paddleboarding. Guests can also explore the stunning coral reefs at nearby diving spots.
Nearby Attractions
Chesapeake Beach Resort is conveniently located near several attractions such as the History of Diving Museum and Plantation Key, both within 2 miles. The area provides ample opportunities for fishing and exploring the unique marine life.
Must-do experiences
Kayak through the mangroves at Florida Keys Kayak Tours.
Dine on fresh conch fritters at Morada Bay Beach Cafe.
Visit the History of Diving Museum for fascinating exhibits.
Catch a sunset at Anne's Beach for stunning views.
Shop for local crafts at the Islamorada Farmers Market on Sundays.
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Select your room type
The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Ocean View King
2 persons
345 sq. feet
1 King-size bed
Shower
Coffee machine
room details
Deluxe King Suite
2 persons
595 sq. feet
1 King-size bed
Shower
Coffee machine
room details
Standard Queen Room
2 persons
315 sq. feet
2 King Size Beds
Shower
Coffee machine
room details
Hearing impaired Ocean view Two Queen Beds
2 persons
370 sq. feet
2 King Size Beds
Shower
Coffee machine
room details
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Facilities
The hotel offers amenities for your comfortable stay and unforgettable experiences
General
No smoking on site
Free 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
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Location
83409 Overseas Highway,
Islamorada,
Florida,
United States,
33036,
Florida
Map view
83409 Overseas Highway,
Islamorada,
Florida,
United States,
33036,
Florida
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
Local Experiences
Top Attractions
Activities
Dining
Entertainment
History of Diving Museum
12 minutes' walk
Museum showcasing diving history with artifacts and exhibits. Offers guided tours and educational programs.
Windley Key Fossil Reef Geological State Park
4-minute drive
Natural park featuring fossilized coral reefs and scenic trails. Great for geology enthusiasts and hikers.
Florida Keys History and Discovery Center
5-minute drive
Center dedicated to the history and culture of the Florida Keys, with interactive exhibits and local artifacts.
Lobster Trap Art Gift Shop and Gallery
4-minute drive
Art gallery and gift shop with unique artworks. Known for its local crafts and marine-themed pieces.
Snorkeling at Carysfort Reef
5-minute drive
Thrilling snorkeling adventures in vibrant coral reefs. Rentals available, best enjoyed year-round.
Yoga Classes at FNX Club
10-minute drive
Relaxing yoga sessions in a serene environment. Check schedules online for classes or private sessions.
Wahoo's Bar and Grill
3 minutes' walk
Casual dining with local seafood. Signature dish includes fresh catch tacos. Reservations recommended.
Whale Harbor Seafood Buffet
3 minutes' walk
Buffet-style seafood restaurant with a variety of dishes. Kid-friendly and offers vegetarian options.
The Sand Bar
3 minutes' walk
Laid-back atmosphere with tropical drinks and live music on weekends. Signature cocktails and bar bites available.
Islamorada Brewery and Distillery
5-minute drive
Craft brewery with unique beers and artisan spirits. Offers tours and tastings, live music most weekends.
Theater of the Sea
10-minute drive
Marine park with animal shows and interaction experiences. Fun for families with all-ages shows available.
Getting around
City Centre
Islamorada24 min
·
1.2
mi
Bus
Bus stop8 min
·
3.3
mi
Reviews and Ratings
Feedback from previous guests about their experience.
Guest reviews
5.0/10
based on 5 reviews
4/5
based on 88 reviews
8.5
8.5/10 based on 818 reviews
#16 of 21 hotels in Islamorada based on Tripadvisor
Elaine
United Kingdom,
January
2025
5.8/10
The hotel has a beautiful beach area that's perfect for relaxation, and the views from the rooms are truly stunning. However, my experience was marred by several inconveniences, such as maintenance issues and a problematic dining experience. The property is undergoing significant renovations which might improve things in the future, but currently, there are quite a few areas that need attention.
Rooms
5.0
The first room had several issues, including a malfunctioning TV and noisy air conditioning. The second room was better but still lacked thorough cleaning in corners.
Service
6.0
Service was a mixed bag; while some staff members were helpful, I encountered issues with my reservation not being found initially which caused stress during check-in.
Location
7.0
The hotel is conveniently located near various dining options and attractions, making it easy to explore the area, but the property itself feels slightly neglected.
Dining
5.0
The breakfast options were quite limited and not very appealing, falling short of expectations compared to other resorts.
Facilities
5.0
While the beach area is beautiful, the overall facilities need major renovations and upkeep, which significantly detracted from the experience.
Amelia
United Kingdom,
December
2024
7.8/10
My stay had its ups and downs. The resort's beautiful layout and exceptional beach views were absolutely stunning, but I faced some frustrations with the food quality and issues with room amenities. Despite that, there were some great service moments that did help offset the inconveniences.
Rooms
7.0
The room was clean but had some odd furniture placements that made it feel a bit cluttered. Overall, it was spacious and had a lovely view.
Service
8.0
The service was responsive, especially when I had a situation with the room amenities. They helped promptly, but I did feel some hiccups in communication during check-in.
Location
9.0
I loved the location, with access to beautiful beaches and nearby dining options. It truly felt like a getaway.
Dining
5.0
Dining was a letdown; breakfast options were limited and not very tasty. I would suggest looking for local spots instead.
Facilities
7.0
The facilities were well-maintained, with clean pools that I enjoyed during my downtime, but I wish more activities were available.
Stunning beach views
Poor dining quality
Eva
United Kingdom,
December
2024
7.0/10
The resort offers a lovely beach front along with spacious rooms and friendly service. However, it was disappointing to find that key amenities, such as the hot tub and some beach areas, were closed due to hurricane damages. The value for money was mixed, especially with some lingering issues from the hurricane aftermath that were not disclosed prior to booking.
Rooms
7.0
Our room was spacious with a nice screened-in porch that overlooked the ocean, making it enjoyable to relax outside. Unfortunately, it could have used a bit more thorough cleaning.
Service
8.0
The staff was accommodating, especially when we needed help changing rooms due to the air conditioning issues. While they were friendly, we felt that some parts of the service, especially housekeeping, could have been quicker.
Location
7.0
The location is beautiful with direct beach access; however, a significant portion of the hotel was fenced off, impacting our experience.
Dining
7.0
Breakfast options were good with fresh omelettes and pastries, though it could benefit from some additional variety to enhance the experience.
Facilities
6.0
While the pool area was clean, the absence of a hot tub and some beach access was a letdown, affecting the resort-like experience we expected.
Reese
United Kingdom,
November
2024
7.0/10
My stay at the resort was quite a mixed bag. While I loved the spacious rooms and the breathtaking views from my balcony, I was disappointed by the damage still evident from the hurricane, which really hindered the overall experience. The service was incredibly attentive, which made me feel welcomed, but the breakfast options left much to be desired. Overall, I enjoyed a peaceful getaway with some lovely moments, but certain amenities simply weren't up to par.
Rooms
7.0
The rooms were spacious with stunning views from the balcony, but they felt slightly cramped due to ongoing renovations.
Service
9.0
The service was attentive and accommodating, making sure I had everything I needed during my stay.
Location
8.0
The location is beautiful, with easy access to the beach, though some areas were still closed off due to hurricane damage.
Dining
5.0
The breakfast was underwhelming, with limited options that didn't match the usual resort standard.
Facilities
6.0
I enjoyed the serene outdoor seating areas, but some promised amenities like the hot tub were not operational at the time of my visit.
Molly
United Kingdom,
September
2024
7.4/10
I had a lovely stay at this hotel during my Keys trip. I felt safe and comfortable here, and the staff went above and beyond to ensure I had a pleasant experience. While I enjoyed the beautiful beach and relaxing atmosphere, I found the dining options slightly lacking and the pool area could use some upkeep. Overall, I would say it's a great place for those looking for a relaxing getaway.
Rooms
7.0
The rooms were spacious and clean, although we had to switch to one without a balcony. The decor was a bit shabby but the bedding was delightful.
Service
9.0
The service was excellent; the staff were friendly and accommodating, making the stay even more enjoyable.
Location
9.0
The hotel was ideally situated near great dining options and had a beautiful private beach area for relaxation.
Dining
6.0
While the breakfast was adequate, with a simple ordering system, it could definitely use more variety.
Facilities
6.0
The beach was beautiful for relaxing, but the pool needed some attention as it was not very clean.
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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
is available in 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
FAQs
About Chesapeake Beach Resort
What are the check-in and check-out times at Chesapeake Beach Resort?
Check-in time is at 16:00, and check-out time is by 11:00.
How close is Chesapeake Beach Resort to the nearest airport?
The nearest airport is located approximately 80 km away.
What are some nearby attractions to Chesapeake Beach Resort?
Nearby attractions include the History of Diving Museum (0.5 km) and the Theater of the Sea (4 km).
Is there on-site dining available at Chesapeake Beach Resort?
The resort features an on-site restaurant that offers diverse dining options.
What amenities are available at the pool area of Chesapeake Beach Resort?
The pool area includes sun loungers, a heated pool, and ocean views.
Does Chesapeake Beach Resort provide free Wi-Fi?
Guests can access complimentary Wi-Fi throughout the property.
Are pets allowed at Chesapeake Beach Resort?
The resort is pet-friendly and allows pets with potential additional charges.
What room amenities can guests find at Chesapeake Beach Resort?
Rooms include a 37-inch flat-screen TV, air conditioning, and a small refrigerator.
What nearby restaurants can guests visit when staying at Chesapeake Beach Resort?
Nearby dining options include Whale Harbor Seafood Buffet, Wahoo's Bar and Grill, and Shuck N Dive, all within 0.5 km.
Does Chesapeake Beach Resort offer any recreational activities?
Guests can enjoy beach access, fishing, and board games on-site.
Is parking available at Chesapeake Beach Resort?
The hotel provides free on-site private parking for guests.
What languages do the staff speak at Chesapeake Beach Resort?