What are the check-in and check-out times at Chesapeake Beach Resort?
Check-in is at 16:00 and check-out is by 11:00.
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Chesapeake Beach Resort, Islamorada
149US$
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Key details
About the Hotel
83409 Overseas Highway,
Islamorada,
Florida,
United States,
33036,
Florida
- Close to Whale Harbor Marina
Great
8.5
9.1
3.2
4.2
Loved by guests
"Villa was lovely, spacious and comfortable! Great location overlooking the sea."
"The beach is small but lovely."
"2 hours of included daily use of kayaks and paddle boards."
Chesapeake Beach Resort - Oceanfront Resort with Private Beach, Water Sports, and Two Outdoor Pools
Located along the Florida Keys coastline, this family-friendly Islamorada hotel features newly renovated accommodations with private balconies and ocean views. The resort offers rooms with plush bedding, premium villas with full kitchenettes, and spacious suites with separate living areas. Two outdoor swimming pools overlook the ocean, while the private beach provides lounge chairs and water sports equipment rentals including kayaks and paddleboards. A cooked-to-order breakfast service is available daily, accompanied by continental options. Chesapeake Beach Resort's location puts guests within walking distance of multiple seafood restaurants and bars. The property sits just 0.5 miles from Whale Harbor Marina and 0.5 miles from the History of Diving Museum.
Pros
Private beach access with complimentary water sports equipment rentals
Each accommodation includes a private balcony
Daily cooked-to-order breakfast included in resort fee
Pet-friendly policies allow families to travel with pets
Cons
Additional $50 nightly resort fee applies
Boat and trailer parking requires separate arrangements
“In my opinion, this oceanfront hotel certainly emphasizes family fun with its beach access and complimentary water sports; the airy villas, some right by the highway, could be perfect for longer stays, while others are undergoing construction. The breakfast setup felt cramped, yet the outdoor dining by the water seemed lovely. Overall, a mixed bag of great amenities alongside ongoing improvements, in my view.”
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Select your room type
Cozy rooms, spacious suites, and family-friendly homes, all with flexible cancellation policies & special deals
Ocean View King
2 persons
32 m²
1 King-size bed
Shower
Coffee machine
room details
Deluxe King Suite
2 persons
55 m²
1 King-size bed
Shower
Coffee machine
room details
Standard Queen Room
2 persons
29 m²
2 King Size Beds
Shower
Coffee machine
room details
Hearing impaired Ocean view Two Queen Beds
2 persons
34 m²
2 King Size Beds
Shower
Coffee machine
room details
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Price and room availability calendar
Check availability and rates for your selected dates!
Facilities
Enjoy premium amenities for a relaxing stay with your pet
General
- No smoking on site
- Free 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
- Patio
- 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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Location
83409 Overseas Highway,
Islamorada,
Florida,
United States,
33036,
Florida
Map view
83409 Overseas Highway,
Islamorada,
Florida,
United States,
33036,
Florida
City landmarks
Museum
History of Diving Museum
950 m
Landmark
Windley Key Fossil Reef Geological State Park
2.3
km
Gallery
Lobster Trap Art Gift Shop and Gallery
2.2
km
Museum
Florida Keys History and Discovery Center
2.3
km
Island
Upper Matecumbe Key
2.9
km
Island
Windley Key
2.4
km
Monument
Hurricane Monument
3.1
km
Gallery
Michelle Nicole Lowe Art Gallery
2.8
km
Landmark
Keys History & Discovery Center
2.4
km
Landmark
In the Doghouse Art Studio
3.0
km
Gallery
Pasta Pantaleo Signature Gallery
3.4
km
Gallery
Gallery Morada
3.4
km
Landmark
Carysfort Reef
3.0
km
Island
Plantation Key
3.0
km
Island
Raccoon Key
3.0
km
Church
Matecumbe United Methodist Church
3.1
km
Gallery
Elena Madden Studio Gallery
3.3
km
Gallery
Portside Studio & Gallery
3.4
km
Landmark
Cheeca Rocks
3.6
km
Landmark
Indian Key State Historic Site
4.1
km
Landmark
Lignumvitae Key Botanical State Park
4.1
km
Landmark
Rain Barrel Village
5.0
km
Landmark
FNX Club by Islamorada Fitness
4.4
km
Landmark
Rain Barrel Sculpture Gallery
5.0
km
Landmark
Crossland Gallery
4.6
km
Nearby
Marina
Whale Harbor Marina
210 m
Restaurants
Wahoo's Bar and Grill
190 m
83413 Overseas Hwy
Whale Harbor Seafood Buffet
210 m
83413 Overseas Hwy
The Sand Bar
210 m
83413 Overseas Hwy
Shuck N Dive
210 m
83413 Overseas Hwy
Casa Mar Seafood
560 m
97001 Oversea Hwy Islamorada
Ziggie & Mad Dog's
910 m
83000 Overseas Hwy
Explore Islamorada
Local Experiences
History of Diving Museum
12 minutes walking
Museum showcasing diving history with exhibitions and artifacts. Guided tours available for a deeper understanding.
Windley Key Fossil Reef Geological State Park
25 minutes walking, 4-minute drive
State park featuring fossilized coral reefs and nature trails. Ideal for hiking and exploring geological formations.
Florida Keys History and Discovery Center
25 minutes walking, 5-minute drive
Interactive exhibits highlighting the history and nature of the Florida Keys. Check for special events throughout the year.
Lobster Trap Art Gift Shop and Gallery
25 minutes walking, 4-minute drive
Gallery featuring local art and unique gifts made from recycled materials. A great spot to support local artists.
Wahoo's Bar and Grill
3 minutes walking
Casual eatery known for fresh seafood and tropical drinks. Outdoor seating available for a laid-back dining experience.
Whale Harbor Seafood Buffet
3 minutes walking
Buffet featuring a variety of seafood dishes. Family-friendly atmosphere and reservations recommended during weekends.
The Sand Bar
3 minutes walking
Charming spot with a relaxed vibe, serving burgers and cocktails. Perfect for enjoying a sunset by the water.
Getting around
Looking for exclusive early booking discounts?
Unlock special rates for your next adventure with your pet today!
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
How far is Chesapeake Beach Resort from Windley Key Fossil Reef Geological State Park?
The resort is 3 km from Windley Key Fossil Reef Geological State Park.
What amenities are included in the rooms at Chesapeake Beach Resort?
Rooms feature a 37-inch flat-screen cable TV, small refrigerator, and free Wi-Fi.
Does Chesapeake Beach Resort offer private beach access?
Guests have access to a private beach area with loungers.
Are there any on-site dining options at Chesapeake Beach Resort?
The resort has an on-site restaurant where guests can enjoy meals.
Is parking available at Chesapeake Beach Resort?
Free private parking is available on-site, but a reservation is needed.
What recreational activities are available at Chesapeake Beach Resort?
Guests can enjoy fishing, access to water sports, and an outdoor swimming pool.
Which notable nearby attractions can be visited from Chesapeake Beach Resort?
Nearby attractions include the History of Diving Museum (0.5 km) and the Theater of the Sea (6 km).
What services does Chesapeake Beach Resort offer for families?
The resort provides children's entertainment options, board games, and spacious family-friendly villas.
What languages do the staff at Chesapeake Beach Resort speak?
The staff can communicate in English and Spanish.
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