Chesapeake Beach Resort

Property class: 3.5
Islamorada beachfront hotel with 2 outdoor pools and bar/lounge

Choose dates to view prices

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.

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Free WiFi
  • Air conditioning
The current price is $151
$226 total
includes taxes & fees
Nov 4 - Nov 5

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for Ocean View Queens

A balcony with two blue chairs and a small table, overlooking a beach with palm trees and the ocean.

Ocean View Queens

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

View all photos for Ocean View King

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the outdoors through a sliding glass door.

Ocean View King

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

View all photos for ADA Ocean View King Suite

A balcony with a view of the ocean and palm trees, featuring a chair, a small table, and a bench.

ADA Ocean View King Suite

8.4 out of 10
Very good
(9 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the outdoors through a sliding glass door.

ADA Ocean View King

9.0 out of 10
Wonderful
(23 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View Queens

A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a balcony with a chair.

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

A hotel room with two beds, a desk, a TV, and a balcony with a view of palm trees.

Hearing Impaired Ocean View Queens

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

View all photos for Hearing Impaired Ocean View King Suite

A modern living room with a grey sofa, wooden chairs, a round coffee table, and a large TV on the wall.

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

A hotel room with two beds, a desk, a chair, a TV, and a ceiling fan.

Standard Queens

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

View all photos for Standard Doubles

A hotel room with two beds, a ceiling fan, an air conditioning unit, a TV, a desk with a chair, and a view of greenery through the windows.

Standard Doubles

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

View all photos for Standard King with Sleeper Sofa

A hotel room with a large bed, a ceiling fan, an air conditioning unit, a bedside table with a lamp, and a view of the outside through large windows.

Standard King with Sleeper Sofa

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

View all photos for Standard King

A hotel room with a large bed, a desk with a chair, a ceiling fan, and an air conditioning unit.

Standard King

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

View all photos for Ocean View King Suite

A modern bedroom with a large bed, a ceiling fan, bedside lamps, a bench, and a view through a sliding door.

Ocean View King Suite

9.4 out of 10
Exceptional
(24 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

A wooden balcony overlooking a beach with palm trees and a sunset.

Deluxe Ocean View Two Queen Suite

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

View all photos for 2-Bedroom Villa

A bedroom with a bed, bedside table, lamp, and a dresser with a mirror.

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

A neatly made bed in a hotel room with a wooden headboard, two bedside tables with lamps, and a door to the right.

Standard King Villa

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

View all photos for King Efficiency Villa

A neatly arranged hotel room with a large bed, a bedside table with a lamp, a chair, and a mirror.

King Efficiency Villa

8.8 out of 10
Excellent
(6 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

A bedroom with a bed, a sofa, a dresser, a TV, and a ceiling fan.

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 2 Full Beds, 1-Bedroom Villa

A hotel room with two beds, a large window with a view, and a ceiling with exposed beams.

2 Full Beds, 1-Bedroom Villa

7.0 out of 10
Good
(2 reviews)
  • 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

A spacious room with large windows offering a view of the beach and ocean.

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

A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

Ocean View King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)
  • 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
  • Theater of the Sea - 2 min drive - 2.4 km
  • Islamorada Brewery & Distillery - 2 min drive - 2.7 km
  • Anne's Beach - 16 min drive - 20.6 km

Getting around

  • Miami Intl. Airport (MIA) - 100 min drive

Restaurants

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

CHECK-IN
4:00pm
CHECK-OUT
11:00am

Hotel size

    • 60 rooms
    • Arranged over 2 floors

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

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

Required at check-in

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

Pets

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

Internet

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

Parking

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

Other information

    • Smoke-free property

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Reviews

Chesapeake Beach Resort Reviews

9.4

Exceptional

9.6

Cleanliness

9.2

Amenities

9.4

Staff & service

9.4

Property conditions & facilities

Guest review summary

What guests liked

  • Breakfast was consistently excellent with made-to-order options and delicious food. (364 reviews)
  • The property offers a private beach area with clear kayaks, paddle boards, and a beautiful view of the ocean. (223 reviews)
  • The pool was clean, well-maintained, and offered a great experience with amenities like a bar and complimentary activities. (150 reviews)
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From real guest reviews summarized by AI.
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Popular mentions

Room
Service staff
View
Beach
Location
Breakfast
Restaurant
Kayaking
Bed
Ocean

Reviews

Verified review

10/10 Exceptional

Wonderful Hotel Nice balconies, beautiful views Wonderful Beach, you can actually get into the ocean! Two pools a large, hot tub plenty of parking and wonderful staff definitely will return
Verified review

10/10 Exceptional

Beautiful property and great little breakfast!!
Verified review

10/10 Exceptional

Absolutely beautiful property. The front desk staff is friendly and as helpful as you could ask for. The breakfast provided was excellent. We definitely took the opportunity to use all the activity options we could in a one-night stay. I will recommend this place to anyone and everyone.
Verified review

10/10 Exceptional

The staff was excellent and the amenities were very convenient
Verified review

10/10 Exceptional

On arrival, was met by friendly staff, who made us very very welcome! Room was fantastic and very clean! Breakfast was amazing... overall had a great stay, in future will stay longer.
Verified review

10/10 Exceptional

Lovely place to stay in Islamorada. Beach and pools were great. Fantastic breakfast included with made to order omelettes. Parking was available. We stayed in the most basic room which was in the building by the office so we could hear traffic from the Overseas Highway but was it pretty quiet inside and we had no issues at night. There is a nice seating area out back too with private balcony and two chairs. The pool and beach are steps away so very easy to access.
Verified review

10/10 Exceptional

We arrived at 1AM and still were served a glass of champagne. A real welcoming. Room was clean and well appointed. Breakfast of omelets and pancakes, yogurt, fruit and juices. Above and beyond. Right on the water with comp gear, two swimming pools. Doesn't get any better. We shall return.
Verified review

10/10 Exceptional

Helpful and courteous staff. Clean. Very easy stay. Boat access and pool. Would come back if needed.
Verified review

8/10 Very good

Very nice property even though they have some remodeling going on, the place is agreeable. The staff in general was amazing, at least my experience was great. I visited the place few days after an accident with some limitations and my mother, an elderly person, they went an extra step to assist us and make our stay memorable at all times. My villa was spacious, clean and well located.
Verified review

10/10 Exceptional

The place was lovely. Great staff and breakfast! The pools on the beach were fantastic!
Verified review

10/10 Exceptional

Great stay. Helpful stay. Clean room. Excellent breakfast.
Verified review

10/10 Exceptional

Room was super clean. Staff was so nice and good breakfast
Verified review

10/10 Exceptional

Love the place very clean and peaceful
Verified review

8/10 Very good

The room was very clean, and was cleaned every day during our stay. Very good breakfast with made to order eggs, omelettes and pancakes.
Verified review

10/10 Exceptional

Very nice rooms, very important for us is having a good AC in the room and it was perfect. 2nd time I had stay in this hotel and I will stay again.
Verified review

10/10 Exceptional

Awesome staff. Great location. Nice property.
Verified review

10/10 Exceptional

Great place to stay, good location to restaurants and activities. Nice pool with tiki bar that mix a good drink. Full breakfast with made to order eggs and omelets which was a nice change from the normal continental breakfast. Stayed by the pool because Beach was full of sargassum but they work hard to clean it. Not much swimming room in the ocean…again a lot of seaweed.
Verified review

10/10 Exceptional

Resort is amazing. Gets better every year. Beach, 2 pools, water sports place is amazing.
Verified review

10/10 Exceptional

The hotel has a fabulous location on the beach the staff were very friendly and we were welcomed with a glass of fizz. Breakfast had a good choice the rooms were spotless you get 2 hours free water sports per day would definitely recommend
Verified review

10/10 Exceptional

Perfect place to stay and a super friendly and helpful staff...definitely staying here again
Verified review

10/10 Exceptional

Nice resort with great views and a nice beach area. The breakfast was awesome
Verified review

10/10 Exceptional

Everyone was friendly and room was nice.
Verified review

10/10 Exceptional

Wonderful place for family and friends. Breakfast is phenomenal. So many activities on site. Quiet location. No crowds. One of my favorites in the Keys!
Verified review

8/10 Very good

They do strive to provide great customer service and promised to have clean rooms but there were some minor things I noticed after the staff assured me they pay attention to great detail. The wall in bathroom had some mysterious staining and the toilet seat was super loose on the verge of falling off. Overall, this hotel was by far the one of the better ones around and had a professional and friendly staff. We stayed here because the hotel we booked initially down the road had bugs in the bed, so it was a relief to stay here last minute as a backup without the pests.
Verified review

10/10 Exceptional

The staff was so kind and eager to please! The breakfast had everything you could desire, very pleasant stay , absolutely would return !