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
01Sept
Check-out
02Sept
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

83409 Overseas Highway, Islamorada, 33036
-
Next to Whale Harbor Marina
Great
8.4
9.1
/10
3.9
4.2
/5

4-star oceanside resort in Islamorada

Amenities

Chesapeake Beach Resort offers private beach access along with outdoor pools facing the ocean. Guests can rent water sports equipment including kayaks and paddleboards on-site. A dedicated event venue provides a picturesque setting for weddings and corporate gatherings.

Accommodations

The hotel features newly renovated rooms, suites, and villas, each equipped with private balconies for ocean or garden views. Rooms include plush bedding and contemporary rainfall showers in spacious bathrooms. Select accommodations are designed to accommodate families and larger groups.

Location

Chesapeake Beach Resort is situated in the Sport Fishing Capital of the World, offering convenient access to numerous fishing spots. Guests might explore local attractions, seafood restaurants, and unique shopping experiences in Islamorada. The property is a short drive from renowned snorkeling and diving sites, enhancing outdoor adventures.

Dining

The resort provides a cooked-to-order breakfast featuring omelets and continental items at the Sunrise Room. Guests can also enjoy seafood at Wahoo's Bar & Grill, just steps from the property. Dining options nearby offer a variety of cuisines within walking distance.

Family-Friendly

Chesapeake Beach Resort provides various activities suitable for families, including beach games and water sports. Children can explore the outdoor pool or participate in seasonal resort activities. The spacious accommodations allow for comfortable family stays.

Highlights

Location: Sport Fishing Capital of the World

Amenities: Private beach access & outdoor pools

Rooms: Newly renovated suites with balconies

Dining: Cooked-to-order breakfast & local seafood

Water Sports: Kayak, paddleboard & fishing rentals

Family: Spacious accommodations & beach activities

Must-do experiences

  • Stop by Lorelei Restaurant for sunset views and live music.
  • Try the Key Lime Pie at Mrs. Mac's Kitchen - a local favorite!
  • Visit the History of Diving Museum for a unique underwater journey.
  • Explore the serene trails at the Windley Key Fossil Reef Geological State Park.
  • Join a guided eco-tour to see local wildlife in the tranquil waters.

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

Price and Room Availability Calendar

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

Facilities

Chesapeake Beach Resort offers amenities for your comfortable stay and unforgettable experiences
Facilities: Great
8.4/10Review 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 Highlights
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Whale Harbor Marina
Whale Harbor Marina
3 minutes walking
A vibrant marina offering fishing charters, boat rentals, and stunning sunset views. Ideal for water lovers.
History of Diving Museum
History of Diving Museum
12 minutes walking
This museum showcases the history of underwater exploration with engaging exhibits. A unique experience for history buffs.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
4 minutes drive
A geological wonder featuring fossilized coral reefs and nature trails. Perfect for nature enthusiasts and hikers.
Fishing Charters
3 minutes walking
Nearby charters provide deep-sea fishing experiences. Rentals and equipment are available for all skill levels.
Yoga at the Beach
5 minutes drive
Beachfront yoga sessions offer relaxation and stress relief with ocean views. Check for seasonal schedules and classes.
Wahoo's Bar and Grill
3 minutes walking
Casual dining with seafood specialties. Enjoy fresh catch and craft beers in a laid-back, welcoming atmosphere.
Whale Harbor Seafood Buffet
3 minutes walking
A seafood buffet with a wide array of dishes. Family-friendly with something for everyone, including gluten-free options.
Shuck N Dive
3 minutes walking
An upbeat bar known for live music and karaoke nights. Great for an evening out with friends or family.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
5 minutes drive
A family-friendly center showcasing the history of the Keys with interactive exhibits and educational programs.
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 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

Reviews and Ratings

Feedback about Chesapeake Beach Resort from previous guests about their experience.
Review score
Based on 1056 verified reviews
9.0 /10
Perfect
89 %
Recommend
Cleanliness
8.8/10
Comfort
8.7/10
Facilities
8.4/10
Free WiFi
9.3/10
Location
9.0/10
Staff
8.5/10
Value for money
7.7/10
Guest reviews
based on 88 reviews
4/5
based on 722 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.
Open reviews
FAQs
About Chesapeake Beach Resort
What is the check-in and check-out policy at Chesapeake Beach Resort?
Check-in is at 16:00 and check-out is by 11:00.
Is parking available at Chesapeake Beach Resort?
Private parking is available on-site for free, with a reservation needed.
What are some attractions near Chesapeake Beach Resort?
Nearby attractions include the History of Diving Museum (0.5 km), Theater of the Sea (3 km), and Windley Key Fossil Reef Geological State Park (3 km).
What amenities can guests enjoy at Chesapeake Beach Resort?
Amenities include free Wi-Fi, an outdoor swimming pool with ocean views, beach access, a Jacuzzi, and a fitness club.
What are the dining options available at Chesapeake Beach Resort?
The resort features an on-site restaurant and local dining options within walking distance, including Whale Harbor Seafood Buffet, Wahoo's Bar and Grill, and Shuck N Dive, all located 0.5 km away.
What room amenities are provided at Chesapeake Beach Resort?
Rooms come equipped with air conditioning, a flat-screen TV, a refrigerator, and complimentary toiletries.
Are there fitness facilities at Chesapeake Beach Resort?
There is a fitness club available for guests to use during their stay.
Can guests access any water sports activities at Chesapeake Beach Resort?
The resort offers complimentary kayaking and paddleboarding equipment rentals for guests.

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