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Chesapeake Beach Resort

3.5 star property
Islamorada beachfront hotel with 2 outdoor pools and bar/lounge

Choose dates to view prices

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

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi
  • Air conditioning

Main amenities (12)

  • Daily housekeeping
  • On a private beach
  • Marina
  • 2 outdoor pools
  • Free use of bicycles
  • Beach sun loungers
  • Beach towels
  • Bar/lounge
  • 24-hour front desk
  • Coffee/tea in a common area
  • Air conditioning
  • Computer station

Feel at home (6)

  • Microwave
  • Cable/satellite TV service
  • Daily housekeeping
  • Coffee/tea maker
  • Blackout drapes/curtains
  • 2 outdoor pools
The current price is CNY1,349
CNY1,900 total
includes taxes & fees
May 26 - May 27

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.6 out of 10
Exceptional
(51 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(100 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

8.6 out of 10
Excellent
(8 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

8.8 out of 10
Excellent
(20 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens | Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • Ocean view
  • 34 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(3 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View King Suite

43-inch flat-screen TV with cable channels, TV

Hearing Impaired Ocean View King Suite

8.8 out of 10
Excellent
(5 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Standard Queens

Standard Queens | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Queens

9.4 out of 10
Exceptional
(66 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Doubles

Standard Doubles | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(102 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King with Sleeper Sofa

9.2 out of 10
Wonderful
(25 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King

9.4 out of 10
Exceptional
(40 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

9.2 out of 10
Wonderful
(19 reviews)
  • Ocean view
  • 49 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

9.0 out of 10
Wonderful
(12 reviews)
  • Ocean view
  • 60 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds

View all photos for 2-Bedroom Villa

2-Bedroom Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 60 sq m
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King Villa

Standard King Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King Villa

  • Resort view
  • 30 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

King Efficiency Villa

9.6 out of 10
Exceptional
(4 reviews)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Premium 1-Bedroom Ocean View Villa

8.0 out of 10
Very good
(1 review)
  • Ocean view
  • 65 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa | Living area | 43-inch flat-screen TV with cable channels, TV

Premium Ocean View King Villa

  • Ocean view
  • 77 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Ocean View King Efficiency Villa

Ocean View King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • Ocean view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

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About the neighborhood

Map
83409 Overseas Hwy, Islamorada, FL, 33036

What's nearby

  • History of Diving Museum - 12 min walk - 1.1 km
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 2.0 km
  • Islamorada Brewery & Distillery - 2 min drive - 2.4 km
  • beach near Islamorada - 2 min drive - 2.7 km
  • Theater of the Sea - 2 min drive - 2.4 km

Getting around

  • Miami Intl. Airport (MIA) - 91 min drive

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Hog Heaven - ‬3 min drive
  • ‪Wendy's - ‬2 min drive
  • ‪Starbucks - ‬15 min walk

About this property

Chesapeake Beach Resort

A great choice for a stay in Islamorada, Chesapeake Beach Resort features a marina. After splashing around at the 2 outdoor pools, you can unwind with a drink at the bar/lounge. Fellow travelers say great things about the pool and helpful staff.

At a glance

DONE

Hotel size

    • 60 rooms
    • Arranged over 2 floors
DONE

Arriving/Leaving

    • Check-in start time: 4:00 PM; Check-in end time: 3:00 AM
    • Contactless check-in available
    • Late check-in subject to availability
    • Minimum check-in age: 18
    • Check-out time is 11 AM
    • Contactless check-out available
DONE

Special check-in instructions

    • Front desk staff will greet guests on arrival at the property
    • Information provided by the property may be translated using automated translation tools
DONE

Required at check-in

    • Credit card required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 18
DONE

Pets

    • Pets allowed (2 total, up to 50 lbs per pet)*
    • Service animals welcome
    • Restrictions apply*
WIFI

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms (speed: 100+ Mbps (good for 1–2 people or up to 6 devices))
LOCAL_PARKING

Parking

    • Wheelchair-accessible parking on site
    • Onsite parking includes off-street options
DONE

Other information

    • Smoke-free property

Property amenities

Food and drink

  • Free continental breakfast each morning 6:00 AM–10:00 AM
  • Bar/lounge
  • Coffee/tea in a common area

Traveling with children

  • Pool gate
  • Outlet covers
  • Fence around the pool

What to do

  • On a private beach
  • Kayaking
  • Boat tours
  • Fishing
  • Jet skiing nearby
  • Snorkeling nearby

Working away

  • Computer station

Services

  • 24-hour front desk
  • Concierge services
  • Multilingual staff
  • Free bicycle rentals
  • Beach sun loungers
  • Beach towels
  • Pool loungers

Facilities

  • 9 buildings/towers
  • Built in 2020
  • 2 outdoor pools
  • Marina
  • 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

  • Shower only
  • Designer toiletries
  • Hair dryer
  • Towels
  • Toilet paper

Stay connected

  • Laptop-friendly workspace
  • Free WiFi (speed of 100+ Mbps (good for 1–2 people or up to 6 devices))
  • Free local calls

Food and drink

  • Microwave

More

  • Daily housekeeping
  • Access via exterior corridors

Special features

Dining

Tiki Bar - Onsite bar.

Fees & policies

Optional extras

  • Late check-out can be arranged for an extra charge

Pets

  • Service animals exempt from fees
  • Pet deposit: USD 50.00 per night
  • Pets are allowed for an extra charge of USD 50.00 per accommodation, per night

Pool, spa, & gym (if applicable)

  • Pool access available from 8:00 AM to 6:00 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.

This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.

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.

Guests can rest easy knowing there's a fire extinguisher on site.

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 8:00 AM to 6:00 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 night. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

What are the check-in and check-out times at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM. Check-out time is 11 AM. Late check-out is available for a charge. Contactless check-in and check-out are available.

What is there to do at Chesapeake Beach Resort and nearby?

Have fun with onsite activities like kayaking, fishing, and cycling. 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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Reviews

Chesapeake Beach Resort Reviews

9.2

Wonderful

9.4

Cleanliness

9.0

Amenities

9.2

Staff & service

9.2

Property conditions & facilities

Guest review summary

What guests liked

  • The breakfast was excellent with a wide variety of options, including made-to-order hot dishes and plenty of continental choices. (202 reviews)
  • The beach area was calm, quiet, and nice with pleasant views and a private beach that was a rare find in the Keys. (175 reviews)
  • The pools were warm, well-maintained, and provided a relaxing atmosphere for guests. (116 reviews)
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From real guest reviews summarized by AI.

Popular mentions

Room
Service staff
View
Beach
Location
Breakfast
Restaurant
Kayaking
Bed
Hot Tub

Reviews

Verified

8/10 Very good

Great and friendly staff, perfect location.
Louis, 1-night trip
Verified

10/10 Exceptional

Breakfast was great, views were awesome, nice little private beach (rare in the keys) perfect location with plenty of night life walking distance and near by! Would stay again for sure!
Kenneth, 3-night trip
Verified

10/10 Exceptional

Great room, very clean and comfortable, pool heated and very nice area to relax. The private beach area is very nice.
Philip, 4-night trip
Verified

10/10 Exceptional

We enjoyed our stay. Nice staff, nice looking property, nice room, very good breakfast which was included and the omelette chef worked very hard to accommodate us and the other guests. Walked to a restaurant for dinner at Wahoos Seafood Bar and Grill, very good, about 200 yards from the resort.
Robert, 1-night trip
Verified

8/10 Very good

Outdoor areas was convenient after a long day running the Keys. Very relaxing.
Ryan, 5-night trip
Verified

10/10 Exceptional

Rooms are very clean. The beds are super comfortable. Plenty of loungers around the pool. Great location in Islamorada Central to bars and restaurants.
David, 3-night trip
Verified

8/10 Very good

Walls are a bit thin but not bad. This resort is family friendly.
Luke, 3-night trip
Verified

10/10 Exceptional

Staff is really friendly. Rooms are nice and you can bring your own drinks to the pool. Breakfast is delicious!
Christine, 1-night trip
Verified

10/10 Exceptional

Clean rooms, beautiful scenery, gorgeous sunrise, delicious breakfast. Loved this place.
Keely, 4-night trip
Verified

10/10 Exceptional

Great room, wonderful staff and good location
dian, 2-night trip
Verified

10/10 Exceptional

Great time from beginning to end. Beautiful water view.. the rooms are so costal and comfortable. Staff are great.. will definitely be back !
Kyra, 1-night trip
Verified

10/10 Exceptional

The view and location were great.
Melissa, 3-night trip
Verified

8/10 Very good

Nice place. Room and grounds were spotless
Greg, 1-night trip
Verified

10/10 Exceptional

Gorgeous view, very pleasant staff, clean room
Judy, 2-night trip
Verified

10/10 Exceptional

Wonderful breakfast with omelettes cooked to order, great pancakes, fresh fruit, etc. very pleasant staff and beautiful beach area.
Kurt, 2-night trip
Verified

8/10 Very good

Room was clean, lovely beach and lagoon with plenty of lounge chairs. Resort offers a good breakfast and there are a few nice places to eat within walking distance.
Rosalie, 2-night trip
Verified

10/10 Exceptional

Staff great, room very nice, beach and facilities were great
Melanie, 1-night trip
Verified

10/10 Exceptional

The staff was amazing! The pool/beach were delightful. Great location
MARY KAY, 3-night trip
Verified

10/10 Exceptional

Staff was great room was very clean
Harry, 2-night trip
Verified

10/10 Exceptional

Clean, great helpful staff, great breakfast. Lovely facility
Laura, 3-night trip
Verified

8/10 Very good

The hotel is in a perfect location, and offers so much on premise
Nancy, 3-night trip
Verified

10/10 Exceptional

Great staff, clean room, nice breakfast and convenient location. Enjoyed our week.
Warren, 6-night trip
Verified

10/10 Exceptional

Clean room, staff was incredibly nice and helpful. Amenities were also very good. Enjoyed the cooked to order breakfast, kayaks, and beautiful views!
Barry, 2-night trip
Verified

10/10 Exceptional

Clean, gorgeous view, amazing free breakfast, loved the robes!
Devon, 4-night trip
Verified

10/10 Exceptional

Great find! Wonderful beach area, very friendly staff, yummy breakfast, best robes ever, super clean!
Laura, 1-night trip