Can guests enjoy fishing directly from the beach?
10 November 2024
Fishing is permitted in the inlet area designated for that purpose.
75 photos
Chesapeake Beach Resort, Islamorada
149US$
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Up to 10% cheaper
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Key details
About the Resort
83409 Overseas Highway,
Islamorada,
Florida,
United States,
33036,
Florida
- Near Whale Harbor Marina
Perfect
8.6
9.1
3.2
4.2
Loved by guests
"Free kyacking ,paddle boards, you can fish on the property."
"We booked an ocean view room with 2 queens and as my wife stated from the moment we walked in and out to our balcony..'this looks like a postcard!'"
"The amenities make you feel like you are in an all-inclusive."
Chesapeake Beach Resort - Oceanfront Getaway near Windley Key
Chesapeake Beach Resort is located in Islamorada, between Everglades National Park and the Florida Strait. The resort offers a private beach, outdoor pools with ocean views, and water sports rentals, including kayaks, paddle boards, and fishing rods. Onsite dining options include fresh seafood and Italian cuisine. The resort accommodates events such as weddings, reunions, meetings, and retreats, offering group rates.
Additional perks of the hotel
Private beach access and lounge chairs
On-the-beach event venue
Wi-Fi in public areas and rooms
Boat and trailer parking available
Pet-friendly accommodations
Onsite water sports rentals: kayak, paddle board & fishing rod rentals
AAA and CAA member benefits
Cooked-to-order omelets and continental breakfast items included in resort fee
Welcome drink included in resort fee
Use of in-room robes and slippers
High speed internet
Pool/beach towels
Pool/beach lounge chairs
Two hours of water sports rentals per room, per night included in resort fee
Seasonal resort activities
Use of beach games
Use of fish cleaning stations
24 hour coffee and tea in lobby
Self-parking (excluding boats and trailers)
Local calls
Live entertainment (musicians, stilt walkers, acrobats, fire-eaters)
Rooms & Villas
The resort offers newly renovated rooms, suites, and villas, each with a private balcony. Room options include garden view rooms with plush bedding, ocean view rooms with king or queen beds, and one- or two-bedroom suites with separate living rooms and kitchenettes. Premium Ocean View Villas feature king-size beds, sleeper sofas, full-size refrigerators, stovetops, and dishwashers.
Other conveniences
Air conditioning
Private entrance
Walk-in shower
Hairdryer
Coffee machine
Wardrobe
Flat-screen TV with cable channels
Free toiletries
Rainfall shower
Mini refrigerators
Table & chairs
Balcony chairs & table
Blackout curtains
“What stood out to me at this Islamorada resort was the private beach access-a real perk, along with complimentary water sports-and the option for spacious villas perfect for families; regular text check-ins also add a nice touch. The ocean views and sunsets create a tranquil atmosphere. I would recommend it for a relaxing getaway.”
View all
Select your room type
The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and 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
Show all roomsLess
Price and Room Availability Calendar
Check availability and prices for your dates now!
Facilities
The hotel offers amenities for your comfortable stay and unforgettable experiences
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
- 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 Highlights
History of Diving Museum
12 minutes walking
Museum showcasing Florida's diving heritage with exhibits and artifacts. Offers guided tours and interactive displays.
Windley Key Fossil Reef Geological State Park
4 minutes drive
Natural park featuring ancient fossilized coral reefs. Ideal for hiking and educational walks through unique geological features.
Florida Keys History and Discovery Center
5 minutes drive
Offers insights into Keys' history with engaging exhibits on ecology and culture. Great for families and history buffs.
Lobster Trap Art Gift Shop and Gallery
4 minutes drive
Art gallery showcasing local artists and unique lobster trap art. Perfect for finding memorable souvenirs.
Wahoo's Bar and Grill
3 minutes walking
Casual dining with a tropical vibe serving fresh seafood and local favorites. Known for its vibrant cocktails and outdoor seating.
Whale Harbor Seafood Buffet
3 minutes walking
All-you-can-eat buffet featuring fresh seafood dishes and local flavors. Family-friendly atmosphere with options for everyone.
Getting around
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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
Questions of the users
About Chesapeake Beach Resort
Is it possible to bring dogs while staying at the resort?
15 December 2024
Yes, dogs are welcomed with a fee of $50 plus tax per pet, per night.
Are swimming and lounging allowed at the beach area?
5 January 2025
Absolutely! The private beach is open for swimming and offers beautiful views.
Do the rooms come equipped with kitchen facilities?
20 February 2025
Rooms feature mini refrigerators and coffee makers, but do not include full kitchen facilities.
Can dogs access the beach area?
30 March 2025
Yes, pets can enjoy the beach but must be leashed at all times.
Will guests have their own private balcony in their room?
10 April 2025
Each room is fitted with a separate, non-connected balcony for guests to enjoy.
If arriving early, can guests use the facilities before check-in?
25 May 2025
Early check-in is subject to availability, but guests can enjoy the pools and beach area before their room is ready.
What amenities can a small dog enjoy while on the resort?
15 June 2025
Small dogs can accompany guests in all public areas of the property, except for the pools, provided they are on a leash.
Have all renovations been completed in the guest rooms?
29 July 2025
All rentable rooms have been updated, though some areas of the property are still undergoing renovations.
Is there an on-site restaurant or bar available for guests?
18 August 2025
Currently, there is no food or beverage service on the property, but several restaurants are within a short walking distance.
Do you have any ground floor rooms available for guests with mobility concerns?
3 September 2025
There are standard double queen and king rooms available, but they are located seven steps up on the first floor.
Is boat parking and docking available for guests traveling by water?
27 October 2025
Yes, boat trailer parking and docking facilities are offered for a fee of $60 per day.Next best alternative
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