In the heart of Matecumbe, Chesapeake Beach Resort offers a tranquil escape. Enjoy a leisurely breakfast, relax on the private beach with sun loungers and kayaking options or take a refreshing dip in one of the 2 outdoor pools. With multilingual staff and concierge services available to help plan your stay.
Reviews
9.09.0 out of 10
Wonderful
Popular amenities
Pet friendly
Non-smoking
24/7 front desk
Air conditioning
Main amenities (11)
Daily housekeeping
On a private beach
2 outdoor pools
Beach sun loungers
Beach towels
24-hour front desk
Air conditioning
Computer station
Multilingual staff
Concierge services
Kayaking
Feel at home (6)
Microwave
Private bathroom
Cable/satellite TV service
Daily housekeeping
Coffee/tea maker
Blackout drapes/curtains
The current price is $394
$394
includes taxes & fees
$350 per night
Mar 13 - Mar 14
Room options
Available filters for rooms
Showing 20 of 20 rooms
View all photos for 2-Bedroom Villa
2-Bedroom Villa
Highlights
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
646 sq ft
Resort view
Sleeps 6
1 King Bed, 1 Double Bed and 1 Double Sofa Bed
View all photos for Standard King
Standard King
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
272 sq ft
Sleeps 3
1 King Bed
View all photos for King Efficiency Villa
King Efficiency Villa
Highlights
Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
Dishwasher
517 sq ft
Resort view
Sleeps 4
1 King Bed and 1 Double Sofa Bed
View all photos for Standard Doubles
Standard Doubles
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
272 sq ft
Sleeps 4
2 Double Beds
View all photos for Standard King with Sleeper Sofa
Standard King with Sleeper Sofa
Highlights
Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout drapes/curtains
307 sq ft
Sleeps 4
1 King Bed and 1 Double Sofa Bed
View all photos for Hearing Impaired Ocean View Queens
Hearing Impaired Ocean View Queens
Highlights
Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
366 sq ft
Ocean view
Sleeps 4
2 Queen Beds
View all photos for Hearing Impaired Ocean View King Suite
Hearing Impaired Ocean View King Suite
Highlights
Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
540 sq ft
Ocean view
Sleeps 4
1 King Bed and 1 Queen Sofa Bed
View all photos for ADA King Efficiency Villa
ADA King Efficiency Villa
Highlights
Separate dining area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
HDTV
Hypo-allergenic bedding
517 sq ft
Resort view
Sleeps 3
1 King Bed
View all photos for Premium 1-Bedroom Ocean View Villa
Premium 1-Bedroom Ocean View Villa
Highlights
Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
Dishwasher
700 sq ft
Ocean view
Sleeps 6
2 Double Beds and 1 Double Sofa Bed
View all photos for Deluxe Ocean View Two Queen Suite
Windley Key Fossil Reef Geological State Park - 2 min drive - 1.8 km
Florida Keys Brewing Co. - 3 min drive - 3.5 km
Bud n' Mary's Dive Center - 6 min drive - 6.2 km
Getting around
Miami Intl. Airport (MIA) - 91 min drive
Restaurants
Lorelei Restaurant & Cabana Bar - 3 min drive
Hog Heaven - 3 min drive
Wahoo's Bar & Grill - 2 min walk
Florida Keys Brewing Co. - 3 min drive
Whale Harbor Restaurant Marina - 2 min walk
About this property
Chesapeake Beach Resort
Situated by the ocean, Chesapeake Beach Resort is a great choice for a stay in Islamorada. Guests can keep active with onsite kayaking. Fellow travelers say great things about the pool and helpful staff.
Languages
English, Spanish
At a glance
Hotel size
60 rooms
Arranged over 2 floors
Arriving/Leaving
Check-in start time: 4:00 PM; Check-in end time: midnight
Contactless check-in available
Early check-in subject to availability
Late check-in subject to availability
Minimum check-in age: 18
Check-out time is 11 AM
Contactless check-out available
Late check-out subject to availability
Special check-in instructions
Front desk staff will greet guests on arrival at the property
Required at check-in
Credit card required for incidental charges
Government-issued photo ID may be required
Minimum check-in age is 18
Minimum Spring Break check-in age is 21
Pets
Pets allowed (2 total, up to 50 lbs per pet)*
Service animals welcome
Restrictions apply*
Parking
Wheelchair-accessible parking on site
Onsite parking includes off-street options
Other information
Smoke-free property
Property amenities
Traveling with children
Pool gate
Outlet covers
Fence around the pool
What to do
On a private beach
Kayaking
Jet skiing nearby
Snorkeling nearby
Working away
Computer station
Services
24-hour front desk
Concierge services
Multilingual staff
Beach sun loungers
Beach towels
Pool loungers
Facilities
9 buildings/towers
Built in 2020
2 outdoor pools
Traditional architecture
Accessibility
Braille/raised signage
Wheelchair-accessible parking
Assistive listening devices available
Wheelchair-accessible public washroom
Wheelchair-accessible pool
Visual alarms in hallways
Handrails in hallways
Handrails in stairways
Closed captioned TV
Lever door handles
Upper floors accessible by stairs only
Well-lit path to entrance
Pool hoist on site
Room amenities
Be entertained
43-inch flat-screen TV
Cable TV channels
Home comfort
Air conditioning
Ceiling fan
Coffee/tea maker
Iron/ironing board
Sleep well
Hypo-allergenic bedding
Blackout drapes/curtains
Pillowtop mattress
Bed sheets provided
Freshen up
Private bathroom
Shower only
Designer toiletries
Hair dryer
Towels
Toilet paper
Stay connected
Laptop-friendly workspace
Free local calls
Food and drink
Microwave
More
Daily housekeeping
Access via exterior corridors
Fees & policies
Optional extras
Late check-out can be arranged for an extra charge (subject to availability)
Pets
Service animals exempt from fees
Pet deposit: USD 50.00 per stay
Pets are allowed for an extra charge of USD 50.00 per accommodation, per night
Pool, spa, & gym (if applicable)
Pool access available from 7:00 AM to 10:30 PM
Children under 16 years old are not allowed in the swimming pool without adult supervision
Policies
Construction is underway at a neighboring building and there may be noise disturbance from the construction work.
Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.
This property does not have elevators.
This property accepts credit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover
Also known as
Chesapeake Beach Islamorada
Chesapeake Beach Resort
Chesapeake Beach Resort Islamorada
Chesapeake Resort
Chesapeake Beach Hotel Islamorada
Chesapeake Beach Resort Hotel
Chesapeake Beach Resort Islamorada
Chesapeake Beach Resort Hotel Islamorada
Frequently asked questions
Does Chesapeake Beach Resort offer free cancellation for a full refund?
Yes, Chesapeake Beach Resort does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.
Is there a pool at Chesapeake Beach Resort?
Yes, there are 2 outdoor pools. Guests have pool access from 7:00 AM to 10:30 PM.
Are pets allowed at Chesapeake Beach Resort?
Yes, pets are welcome, with a limit of 2 total and maximum weight of 50 lbs per pet. There's a charge of USD 50.00 per accommodation, per night, and there's also a deposit of USD 50.00 per stay. Service animals are exempt from fees.
What are the check-in and check-out times at Chesapeake Beach Resort?
Check-in start time: 4:00 PM; Check-in end time: midnight. Check-out time is 11 AM. Late check-out is available for a charge (subject to availability). Contactless check-in and check-out are available.
What is there to do at Chesapeake Beach Resort and nearby?
Have fun during the warmer months with activities such as kayaking. Enjoy a swim in one of the 2 outdoor swimming pools or use the hotel's other amenities, which include a private beach.
What's the area around Chesapeake Beach Resort like?
Chesapeake Beach Resort is in Matecumbe, a short 11-minute walk from History of Diving Museum. Travelers give top marks for the hotel's prime location.
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Chesapeake Beach Resort Reviews
Reviews
9.0
Wonderful
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.More informationOpens in a new window
9.2/10
Cleanliness
9.2/10
Staff & service
8.8/10
Amenities
9.0/10
Property conditions & facilities
8.8/10
Eco-friendliness
Reviews
10/10 Exceptional
Feb 11, 2025
Great stay!
The breakfast at the shore was wonderful with friendly service and plenty of food choices.
Kim
Kim, 2-night trip
10/10 Exceptional
Mar 10, 2025
Most amazing views
Derick
Derick, 2-night trip
10/10 Exceptional
Feb 6, 2025
Beautiful place clean and enjoyable.. don’t hesitate to book in fl keys
Angel
Angel, 1-night trip
10/10 Exceptional
Jan 28, 2025
Island paradise
Great location, great beach, pools and staff.
Peter
Peter, 1-night trip
10/10 Exceptional
Feb 13, 2025
Excellent place
I love this place, every stay is truly a wonderful experience. The staff is always helpful and friendly. The grounds are really pretty as well.
cheryl
cheryl, 4-night trip
10/10 Exceptional
Feb 7, 2025
I enjoyed my stay. The breakfast was great and outdoor breakfast seating facing the ocean was a great way to start the day. Can’t beat the beach loungers scattered around the property.
kristie
kristie, 4-night trip
10/10 Exceptional
Feb 12, 2025
Fun place with excellent shoreline
The food and bar service near pool and shore line is staffed with excellent people that work hard to make our stay fun. We attended the Super bowl barbecue at the poolside and met new friends. A great place and we plan to visit again. Breakfast was included and the chefs were awesome.
Kim
Kim, 3-night trip
10/10 Exceptional
Feb 9, 2025
Loved it!
The resort is very clean and the staff are amazing. We encountered many staff during our stay and they were very friendly. Chef Chris in the Sunrise room created delicious made to order omelets. Breakfast was great.
Kathrine
Kathrine, 7-night trip
10/10 Exceptional
Dec 2, 2024
Good hotel
Felix
Felix, 1-night trip
8/10 Very good
Feb 19, 2025
Would stay again-loved the place!
Everything was great-we did have an issue with our a/c but we were only there two nights so we didn't worry with having them look at it. Just reported as we left the property. Loved the place overall!
Verified traveler
2-night trip
10/10 Exceptional
Nov 9, 2024
Absolutely gorgeous, clean, friendly staff, and great location
Amy
Amy, 4-night trip
10/10 Exceptional
Nov 30, 2024
Beautiful place , we was satisfied , beautiful beach .
Peter
Peter, 4-night trip
10/10 Exceptional
Nov 30, 2024
This was a really nice facility with wonderful staff and great amenities. Great place for a family
William
William, 2-night trip
10/10 Exceptional
Oct 15, 2024
Absolutely great place with beach access!
mariana
mariana, 3-night trip
10/10 Exceptional
Nov 3, 2024
Great place
Diana
Diana, 1-night trip
8/10 Very good
Jan 28, 2025
Weeding weekend
Went to a weeding in Islamorada and the option of the hotel was ideal
Verified traveler
1-night trip
10/10 Exceptional
Nov 22, 2024
Great Roadside location, clean & modern
Great location.
Friendly staff
Great room
Steve
Steve, 1-night trip
10/10 Exceptional
Dec 9, 2024
Nice grounds with good beach. Friendly staff
Leslie
Leslie, 3-night trip
10/10 Exceptional
Jan 25, 2025
First Class 👌
This was worth every penny. The room was spotless! The breakfast great! And the staff wonderful!! We will be back!
Anthony
Anthony, 2-night trip
10/10 Exceptional
Oct 18, 2024
Nice and quiet, Right on the water, Clean, neat,friendly staff, right next to food.
Christy
Christy, 1-night trip
10/10 Exceptional
Dec 1, 2024
Very well kept, clean and safe!
Melanie
Melanie, 1-night trip
6/10 Good
Jan 22, 2025
great stay, beautiful resort. AC didn’t work the best, didn’t love the barn door that didn’t lock in bathroom. Breakfast was great, but no indoor seating. One day was cool and rainy and no where to sit and eat. Pool and hot was nice
Lorie
Lorie, 2-night trip
10/10 Exceptional
Nov 23, 2024
We loved it here. Chef Chiris mskes the best omelets.
Carole
Carole, 5-night trip
10/10 Exceptional
Oct 6, 2024
Super nice hotel super good staff rooms super clean