Chesapeake Beach Resort
Beachfront resort with ocean views and water sports in Islamorada.
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Chesapeake Beach Resort is a newly renovated oceanfront hotel in Islamorada, Florida. Set along white sand beaches, the property offers ocean views from its rooms, suites, and villas. Islamorada is known as the Sport Fishing Capital of the World and provides a year-round destination for water sports and coastal activities. The resort is suitable for couples, families, and groups seeking a relaxed coastal escape. On-site amenities include outdoor pools and private beach access, with water sports rentals available. The resort also features an oceanfront event venue for weddings and gatherings.
Should you book Chesapeake Beach Resort?
A newly renovated beachfront hotel with ocean views, balconies, and on-site water sports.
Best for
- Beachfront setting
- Water sports
- Pet-friendly stays
- Families and couples
Maybe not ideal for
- Rooms accessible only by stairs
Beachfront location
The resort sits directly on the beach in Islamorada, with powder white sand and ocean views. Lounge chairs are provided on the beach, and private beach access is available.
Rooms with balconies
Accommodations include rooms, suites, and standalone villas, all with balconies offering ocean or island views. Standard rooms are accessible by stairs only.
On-site pools
Two outdoor swimming pools with ocean views are available for guests. Pool towels and chairs are provided.
Water sports
The resort provides water sports rentals, such as kayaks and snorkeling gear. Two hours of rentals per room per night are included in the resort fee.
Rooms & rates
Standard Double Room
25.0 m² · 2 full beds
Balcony · Air conditioning · Attached bathroom · Flat-screen TV · Coffee machine · Free Wifi
Ocean View King
32.0 m² · 1 king bed
Balcony · Sea view · Pool view · Air conditioning · Attached bathroom · Flat-screen TV
ADA Ocean View King
34.0 m² · 1 king bed
Balcony · Sea view · Pool view · Air conditioning · Attached bathroom · Flat-screen TV
Ocean View Two Queens
32.0 m² · 2 full beds
Balcony · Sea view · Pool view · Air conditioning · Attached bathroom · Flat-screen TV
ADA Ocean View Two Queens
34.0 m² · 2 full beds
Balcony · Sea view · Pool view · Air conditioning · Attached bathroom · Flat-screen TV
Deluxe King Suite
55.0 m² · Bedroom 1: 1 queen bed Living room: 1 sofa bed
Private suite · Balcony · Sea view · Pool view · Air conditioning · Attached bathroom
ADA Deluxe Ocean View King
34.0 m² · 1 king bed
Private suite · Balcony · Sea view · Pool view · Air conditioning · Attached bathroom
Standard King Villa
1 king bed
Entire villa · Private kitchenette · Attached bathroom · Air conditioning · Dishwasher · Flat-screen TV
ADA King Efficiency Villa
1 king bed
Entire villa · Private kitchenette · Attached bathroom · Air conditioning · Dishwasher · Flat-screen TV
King Efficiency Villa
Bedroom 1: 1 king bed Living room: 1 sofa bed
Entire villa · Private kitchenette · Attached bathroom · Air conditioning · Dishwasher · Flat-screen TV
Premium Ocean View King Villa
Bedroom 1: 1 king bed Living room: 1 sofa bed
Entire villa · Private kitchenette · Attached bathroom · Sea view · Air conditioning · Dishwasher
Standard Queen Room
29.0 m² · 2 queen beds
Balcony · Garden view · Air conditioning · Attached bathroom · Flat-screen TV · Coffee machine
Hearing impaired Ocean view Two Queen Beds
34.0 m² · 2 queen beds
Balcony · Sea view · Pool view · Air conditioning · Attached bathroom · Flat-screen TV
Deluxe Queen Suite
55.0 m² · Bedroom 1: 2 queen beds Living room: 1 sofa bed
Private suite · Balcony · Sea view · Pool view · Air conditioning · Attached bathroom
Two-Bedroom Villa
Bedroom 1: 1 king bed Bedroom 2: 1 full bed Living room: 1 sofa bed
Entire villa · Private kitchenette · Attached bathroom · Garden view · Air conditioning · Dishwasher
Premium 1-Bedroom Ocean View Villa
Bedroom 1: 2 full beds Living room: 1 sofa bed
Entire villa · Private kitchenette · Attached bathroom · Sea view · Air conditioning · Dishwasher
What you'll enjoy
Gallery
Amenities & facilities
Most popular facilities
- 2 swimming pools
- Beachfront
- Free parking
- Facilities for disabled guests
- Non-smoking rooms
- Free Wifi
- Private beach area
- Wonderful Breakfast
Great for your stay
- Parking
- Private bathroom
- Air conditioning
- Pet friendly
- Free Wifi
- Free parking
- Non-smoking rooms
- Flat-screen TV
Private bathroom
- Toilet paper
- Towels
- Toilet
- Free toiletries
- Hairdryer
- Shower
Bedroom
- Linens
- Wardrobe or closet
- Alarm clock
Outdoors
- Outdoor furniture
- Beachfront
- Private beach area
Kitchen
- Coffee machine
- Microwave
- Refrigerator
Location
83409 Overseas Highway, Islamorada, FL 33036, United States, Islamorada, Florida
Chesapeake Beach Resort is located in Islamorada, Florida.
5 sights nearby, 1 of them within 0.5 mi; the closest is Whale Harbor Marina at 500 ft.
Things to do nearby
- Whale Harbor Marinamarina500 ft
- History of Diving Museummuseum0.6 mi
- Theater of the Seaattraction0.8 mi
- Quarry Stationhistoric site1.5 mi
- Windley Key Fossil Reef Geological State Parkpark1.5 mi
Straight-line distances from the property · data © OpenStreetMap contributors
What guests say
8.4 / 10 · Very good on Booking.com, from 722 guest reviews
Chesapeake Beach Resort earns strong praise for its prime Islamorada location, ocean views, included breakfast, and well-kept pools and beach — making it a genuinely appealing Keys retreat.
Reviews scoring 9–10: 15 · average 9
They wrote about: location, breakfast, room
Reviews scoring 7–9: 15 · average 7.7
They wrote about: breakfast, location, room
No reviews in the selected score range.
Good to know
House rules
- Check-in
From 4:00 PM to 11:00 PM
Guests are required to show a photo ID and credit card at check-in.
- Check-out
From 7:00 AM to 11:00 AM
- Cancellation/ prepayment
Cancellation and prepayment policies vary according to accommodation type. Enter your stay dates and check the conditions of your selected option.
- Age restriction
The minimum age for check-in is 18
- Pets
Pets are allowed. Charges may apply.
- Cards accepted at this property
Cash is not accepted
Frequently asked questions
What types of rooms are available?
The resort offers various rooms, suites, and standalone villas, including Standard Double and Queen rooms, Ocean View Kings and Two Queens (some ADA accessible), Deluxe Suites, and Standard, King, and Two-Bedroom Villas.
Does the hotel have parking?
Yes, the hotel provides free parking for guests. Accessible parking is also available.
Are pets allowed?
Yes, the hotel is pet-friendly, allowing pets in designated rooms.
Is there WiFi?
Yes, free WiFi is available for guests throughout the resort.
Does the hotel have a pool?
Yes, the hotel features two outdoor swimming pools with ocean views.
Are there rooms with a sea view?
Yes, several room types offer sea views, including Ocean View King, ADA Ocean View King, Ocean View Two Queens, ADA Ocean View Two Queens, Deluxe King Suite, ADA Deluxe Ocean View King, and various villas.
Can I fish from the property?
Fishing is available as an activity, possibly with an additional charge. The resort is located in Islamorada, the Sport Fishing Capital of the World.
What is the starting price?
The lowest displayed price is $235 for a Standard Double Room.
Is there an event venue?
Yes, the resort offers an oceanfront event venue suitable for weddings, reunions, meetings, and retreats.