Chesapeake Beach Resort in Islamorada, Florida Keys
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Key details
About the Property
83409 Overseas Highway, Islamorada, 33036,
-
Next to Whale Harbor Marina
Great
8.4
9.1
/10
3.9
4.2
/5
Loved by Chesapeake Beach Resort guests
Private beach atmosphere
Text service for requests
Complimentary kayaks
Continental breakfast ordered
Unique beachfront villas
"This resort served the best included breakfast we have had."
tmwyss from United States
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"The layout and I like that's acomplete boutique hotel unique great staff and absolutely great planned villas n rooms"
Ventura from United States
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"Resort is beautiful. Views, location. The beach was awesom3"
Adele 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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"Great location for being close to fishing charters and restaurants - nice new rooms with a relaxed energy and on site breakfast"
Cynthia R from United States
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Islamorada 3-star oceanfront resort with a private beach area
Private Beach & Complimentary Water Sports
Chesapeake Beach Resort offers a private beach area exclusive to guests, featuring loungers and beach chairs. Complimentary water sports equipment rentals include kayaks and paddleboards, available for guest use. Fishing poles are also available for rent on-site, with bait sold at the front desk.
Two-Bedroom Villas & Premium Rooms
The hotel offers spacious two-bedroom and premium villas with ocean views and kitchenettes. All rooms include a 37-inch flat-screen cable TV and a small refrigerator, with select rooms offering a balcony. A personalized breakfast delivery service is available, and daily housekeeping is provided in all room types.
Location & Nearby Attractions
Chesapeake Beach Resort is located in Islamorada, 2 miles from Windley Key Fossil Reef Geological State Park. The History of Diving Museum is a 3-minute walk away, and Theater of the Sea is a 4-minute drive from the property. Several local dining options, including Wahoo's and a Publix grocery store, are within walking distance.
Heated Outdoor Pools & Entertainment
Two heated outdoor swimming pools, including one with an ocean view, are open year-round with a fence around the pool for safety. The hotel offers live music performances and hosts live entertainment events on-site for guests. A snack bar is available, and the pools include a shallow end, sun loungers, and pool towels.
Pet-Friendly & Family-Friendly Amenities
The resort is pet-friendly, allowing guests to bring dogs, and offers allergy-free rooms upon request. Board games and puzzles are available for children, and a minimarket on site sells essentials. Regular guest check-ins via text allow families and couples to request additional needs during their stay.
Highlights
Private beach area exclusive to guests
Complimentary kayaking and paddleboarding
Two-bedroom and premium villas with ocean views
History of Diving Museum (3-minute walk)
Heated outdoor pool with ocean view
Pet-friendly accommodations
Must-do experiences
Visit the History of Diving Museum for a unique underwater journey.
Savor a stone crab sandwich at the iconic Hungry Tarpon restaurant.
Explore the serene Anne's Beach for stunning views and relaxation.
Take a sunset cruise with Islander Watersports for breathtaking sights.
Discover local art at the Green Turtle Inn's gallery space.
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
room details
Ocean View King
2 persons
32 sq. feet
1 King-size bed
Air conditioning
Balcony
room details
Deluxe King Suite
2 persons
55 sq. feet
1 King-size bed
Air conditioning
Balcony
room details
Show all rooms
Room Availability and Pricing Calendar
See today's rates and availability for your selected dates!
September 2026 - September 2027
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Check-in/ Check-out
Facilities
Chesapeake Beach Resort offers amenities for a comfortable stay and memorable Florida Keys 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
Private parking is possible on site for free.
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, 33036,
Explore Islamorada
Islamorada Activities and Dining
Top Attractions
Activities
Dining
Entertainment
History of Diving Museum
12 minutes' walk
Diving history exhibits showcase artifacts and stories. Family-friendly with interactive displays.
Florida Keys History and Discovery Center
25 minutes' walk
Regional history and culture highlighted in interactive exhibits. Great for learning about the area's heritage.
Windley Key Fossil Reef Geological State Park
25 minutes' walk
Unique geological features with trails showcasing fossilized coral reefs. Ideal for nature walks.
Snorkeling Tours
3 minutes' drive
Exciting snorkeling trips to vibrant coral reefs. Equipment rental often included, seasonal availability.
Yoga on the Beach
5 minutes' drive
Relaxing beach yoga sessions. Perfect for unwinding with calming ocean views.
Wahoo's Bar and Grill
3 minutes' walk
Casual dining with a tropical vibe. Known for seafood dishes and outdoor seating.
Whale Harbor Seafood Buffet
3 minutes' walk
Buffet featuring fresh local catches. Family-friendly atmosphere with extensive options.
Mango's Bar & Grill
7 minutes' drive
Vibrant nightlife spot with live music events. Ideal for casual dining and drinks.
Islamorada Brewery & Distillery
7 minutes' drive
Local brews and spirits with tastings. Family-friendly with outdoor seating and food trucks.
Local transportation
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
Ratings & Reviews
Read what previous guests have shared about their experience at Chesapeake Beach Resort.
Review score
Based on 1092 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
8.9/10
Staff
8.5/10
Value for money
7.7/10
Pros
Friendly staff
Clean rooms
Good breakfast
Cons
Expensive fees
Malfunctioning hot tub
Guest reviews
based on 88 reviews
4/5
based on 719 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.
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