Chesapeake Beach Resort Islamorada Beach photoChesapeake Beach Resort Islamorada Exterior photoChesapeake Beach Resort Islamorada Exterior photo
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From149US$ /night
Check-in
03Jun2026Select date
Check-out
04Jun2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About Resort

83409 Overseas Highway, Islamorada, Florida, United States, 33036
-
Steps from Whale Harbor Marina
Great
8.6
9.1
/10
3.9
4.2
/5

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

Chesapeake Beach Resort offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Ocean View Two Queens
2 persons
345 sq. feet 
2 Double beds
Shower
Coffee machine
Ocean View King
2 persons
345 sq. feet 
1 King-size bed
Shower
Coffee machine
Deluxe King Suite
2 persons
595 sq. feet 
1 King-size bed
Shower
Coffee machine
ADA Ocean View Two Queens
2 persons
370 sq. feet 
2 Double beds
Shower
Coffee machine
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Facilities

Chesapeake Beach Resort offers amenities for your comfortable stay and unforgettable experiences
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
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Chesapeake Beach Resort Location

83409 Overseas Highway, Islamorada, Florida, United States, 33036
Map view
83409 Overseas Highway, Islamorada, Florida, United States, 33036
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
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
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
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
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
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
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
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
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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
Wireless 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
Property is also known as
chesapeake beach resort

Reviews and Ratings

Feedback about Chesapeake Beach Resort from previous guests about their experience.
Review score
Based on 1196 verified reviews
9.0/10
Perfect
89%
Recommend
Cleanliness
8.9/10
Comfort
8.9/10
Facilities
8.6/10
Free Wi-Fi
8.5/10
Location
9.0/10
Staff
8.5/10
Value for money
7.8/10
Pros
Ocean view
Private beach
Comfortable room
Helpful staff
Cons
Door issues
Cleaning service
Supply shortages
Guest reviews
based on 88 reviews
4/5
based on 762 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.
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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?
The staff primarily speaks English.

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Check-in
03Jun2026Select date
Check-out
04Jun2026Select date
Rooms and Guests2 Guests, 1 Room