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From149US$ /night
Check-in
07Feb2026Select date
Check-out
08Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

83409 Overseas Highway, Islamorada, Florida, United States, 33036
-
Close to the History of Diving Museum
Great
8.6
9.1
/10
3.1
4.2
/5

Chesapeake Beach Resort - An oceanfront villa resort with private beach access and water sports in Islamorada

Chesapeake Beach Resort offers newly renovated villas, suites, and rooms with private balconies overlooking the ocean or garden. Accommodations include plush bedding, rainfall showers, flat-screen TVs, and kitchenettes in select units. A daily resort fee covers cooked-to-order omelets, continental breakfast, high-speed Wi-Fi, water sports rentals, and access to two outdoor pools and a private beach. Situated in Islamorada, the resort is 1 km from the History of Diving Museum and 2 km from the Florida Keys History and Discovery Center. Nearby dining options include Wahoo's Bar and Grill, Whale Harbor Seafood Buffet, and Shuck N Dive. The Chesapeake Beach Resort also provides pet-friendly accommodations, group rates, and event planning services for weddings and reunions.

Pros

Private beach access and oceanfront views from rooms, suites, and villas.

Multiple water sports rentals are included, such as kayaks and paddleboards.

Pet-friendly accommodations with no weight restrictions.

Close proximity to Theater of the Sea (1.4 km) for dolphin encounters.

On-site outdoor pools with ocean views.

Cons

The $50 nightly resort fee is mandatory.

Some villas and suites require a short walk to reach the beach.

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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 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
Standard Queen Room
2 persons
315 sq. feet 
2 King Size Beds
Shower
Coffee machine
Hearing impaired Ocean view Two Queen Beds
2 persons
370 sq. feet 
2 King Size Beds
Shower
Coffee machine
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Facilities

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

General

  • No smoking on site
  • Free Wi-Fi
  • Free 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 Attractions and Activities
Top Attractions
Activities
Dining
Entertainment
History of Diving Museum
History of Diving Museum
12 minutes' walk
Diving artifacts and exhibits showcase the deep-rooted history of underwater exploration in Florida's waters.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
25 minutes' walk
Interactive exhibits highlight the cultural, natural, and historical aspects of the Florida Keys.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
25 minutes walking
Unique fossilized coral reefs offer scenic trails and educational programs about geology and history.
Snorkeling Tour
3 minutes' drive
A thrilling experience with colorful marine life. Tours available at nearby Whale Harbor Marina.
Yoga by the Sea
7 minutes' drive
Relaxing beachfront yoga classes cater to all skill levels. Registration required for group sessions.
Wahoo's Bar and Grill
Wahoo's Bar and Grill
3 minutes' walk
Casual Caribbean fare with fresh seafood, vibrant colors, and a laid-back atmosphere perfect for families.
Whale Harbor Seafood Buffet
Whale Harbor Seafood Buffet
3 minutes' walk
Bountiful seafood buffet featuring local specialties. Reservations recommended for larger groups.
Shuck N Dive
Shuck N Dive
3 minutes' walk
Lively atmosphere with live music and karaoke. Perfect for a fun night out with friends and family.
Morada Bay Beach Cafe
5 minutes' drive
Beachfront bar with occasional live music events, making it a great spot for sunset views.
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
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 is the distance from Chesapeake Beach Resort to Windley Key Fossil Reef Geological State Park?
Chesapeake Beach Resort is located 3 km from Windley Key Fossil Reef Geological State Park.
What is the check-in and check-out time at Chesapeake Beach Resort?
Check-in is at 16:00 and check-out is by 11:00.
Does Chesapeake Beach Resort offer free internet access?
Free Wi-Fi is provided to all guests in the hotel.
Is parking available at Chesapeake Beach Resort?
Complimentary private parking is available on-site.
Are pets allowed at Chesapeake Beach Resort?
Pets are allowed at the hotel for an additional charge.
What are some amenities available in the rooms at Chesapeake Beach Resort?
Each room includes air conditioning, a flat-screen TV, a refrigerator, and some rooms feature balconies.
What is the pool situation at Chesapeake Beach Resort?
Chesapeake Beach Resort boasts both an outdoor pool and a heated pool, complemented by ocean views.
Can guests arrange excursions while staying at Chesapeake Beach Resort?
The hotel can assist guests in arranging excursions to local attractions, including the Theater of the Sea, located just 4 minutes away by car.
How far is Chesapeake Beach Resort from the History of Diving Museum?
The hotel is located 0.3 km from the History of Diving Museum.
Is there a gym at Chesapeake Beach Resort?
A fitness center is available on-site for guests.
Check-in
07Feb2026Select date
Check-out
08Feb2026Select date
Rooms and Guests2 Guests, 1 Room
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