Chesapeake Beach Resort Islamorada Beach photoChesapeake Beach Resort Islamorada Exterior photoChesapeake Beach Resort Islamorada Exterior photo

Chesapeake Beach Resort, Islamorada

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From$149 /night
Check-in
12Aug
Check-out
13Aug
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

83409 Overseas Highway, Islamorada, 33036
-
Close to the History of Diving Museum
Great
8.5
9.1
/10
3.9
4.2
/5

Chesapeake Beach Resort - A family-friendly oceanfront resort with private beach access, water sports, and newly renovated villas

Chesapeake Beach Resort offers private beach access, oceanfront views, and a range of renovated accommodations including garden-view rooms, ocean-view suites, and multi-bedroom villas. Each room features plush bedding, a private balcony, and modern bathrooms with walk-in showers. The resort provides water sports rentals, including kayaks and paddleboards, along with an outdoor pool and beach lounge chairs. Guests can enjoy fresh seafood at nearby Wahoo's Bar & Grill, located 0.5 km away, or explore local attractions like Theater of the Sea (1.4 km), where dolphin encounters are available. The property is ADA-compliant, pet-friendly, and features complimentary Wi-Fi, self-parking, and a resort fee covering breakfast, water sports, and beach amenities.

Pros

Newly renovated rooms with private balconies and modern bathrooms.

Direct beach access with complimentary water sports rentals for guests.

Pet-friendly accommodations and ADA-compliant facilities.

Proximity to dining options like Wahoo's Bar & Grill and Theater of the Sea (1.4 km).

Cons

Some villas are nestled among foliage, limiting direct ocean views.

The resort fee ($50 per night), though covering multiple amenities, is an additional cost.

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
    32 sq. feet
    2 Double beds
    Air conditioning
    Balcony
  • Ocean View King
    2 persons
    32 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
  • Deluxe King Suite
    2 persons
    55 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
Show all rooms

Room Rates & Availability Calendar

Check availability and prices for your dates now!
August 2026 - August 2027
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Check-in/ Check-out

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
Show more

Chesapeake Beach Resort Location

83409 Overseas Highway, Islamorada, 33036
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
3 minutes' walk
Casual Caribbean fare with fresh seafood, vibrant colors, and a laid-back atmosphere perfect for families.
Whale Harbor Seafood Buffet
3 minutes' walk
Bountiful seafood buffet featuring local specialties. Reservations recommended for larger groups.
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
    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
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in the entire hotel 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

Reviews and Ratings

Feedback about Chesapeake Beach Resort from previous guests about their experience.
Review score
Based on 1063 verified reviews
9.0 /10
Perfect
89 %
Recommend
Cleanliness
8.9/10
Comfort
8.8/10
Facilities
8.6/10
Free WiFi
8.5/10
Location
9.0/10
Staff
8.6/10
Value for money
7.8/10
Pros
Comfortable bed
Helpful staff
Good breakfast
Free kayaking
Villa upgrade
Cons
Road noise
Limited privacy
Noisy neighbors
Guest reviews
based on 88 reviews
4/5
based on 727 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.
Open reviews
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.

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