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Chesapeake Beach Resort

3.5 star property

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Photo gallery for Chesapeake Beach Resort

A beach with palm trees and lounge chairs.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi

Explore the area

View in a map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, History of Diving Museum
    ‪12 min walk‬
  • Place, Theater of the Sea
    ‪2 min drive‬
  • Place, Islamorada Brewery & Distillery
    ‪2 min drive‬

Room options

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

9.6 out of 10
Exceptional
(52 reviews)
  • Ocean view
  • 366 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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
(103 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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

8.6 out of 10
Excellent
(8 reviews)
  • Ocean view
  • 540 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

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
(22 reviews)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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
  • 366 sq ft
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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
(3 reviews)
  • Ocean view
  • 366 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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
  • 540 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free WiFi

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
(73 reviews)
  • 307 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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
(109 reviews)
  • 272 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds
  • Free WiFi

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
(26 reviews)
  • 307 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

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
(41 reviews)
  • 272 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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
  • 527 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed
  • Free WiFi

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
(13 reviews)
  • Ocean view
  • 650 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds
  • Free WiFi

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
  • 646 sq ft
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed
  • Free WiFi

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
  • 323 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

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

8.4 out of 10
Very good
(5 reviews)
  • Resort view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

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
  • 517 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed
  • Free WiFi

View all photos for Premium 1-Bedroom Ocean View Villa

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

Premium 1-Bedroom Ocean View Villa

7.0 out of 10
Good
(2 reviews)
  • Ocean view
  • 700 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed
  • Free WiFi

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
  • 829 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

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
  • 517 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

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About the neighborhood

Islamorada

Located in Matecumbe within a short walk of History of Diving Museum, Chesapeake Beach Resort is within a mile (2 km) of Windley Key Fossil Reef Geological State Park. This 60-room, 3.5-star hotel has 2 outdoor pools along with a private beach and a marina.

What's nearby

  • History of Diving Museum - 12 min walk - 0.7 miles
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 1.3 miles
  • Theater of the Sea - 2 min drive - 1.5 miles
  • Islamorada Brewery & Distillery - 2 min drive - 1.7 miles
  • Anne's Beach - 15 min drive - 12.8 miles

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
  • ‪Wendy's - ‬2 min drive
  • ‪The Oceanview Inn & Sports Pub - ‬2 min drive

About this property

Chesapeake Beach Resort

Chesapeake Beach Resort features a private beach, a marina, and 2 outdoor pools. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and free use of bicycles.
43-inch flat-screen TVs come with cable channels, and guests can stay connected with free WiFi. Pillowtop beds grant a restful night's sleep, and bathrooms offer hair dryers and designer toiletries. Other standard amenities include microwaves, coffee makers, and free local calls.
A private beach, a marina, and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.

Children under 16 years old are not allowed in the swimming pool without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

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Property amenities

Internet

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

Parking and transportation

  • Wheelchair-accessible parking available
  • Onsite parking includes off-street options

Food and drink

  • Free continental breakfast available daily 6:00 AM to 10:00 AM
  • A bar/lounge
  • Coffee and tea in common areas

Restaurants on site

  • Tiki Bar

Things to do

  • 2 outdoor pools
  • Boat tours
  • Fishing
  • Free bicycle rentals
  • Kayaking

Family friendly

  • 2 outdoor pools
  • Fenced pool
  • In-room microwave
  • Pool gate

Conveniences

  • 24-hour front desk

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Multilingual staff

Business services

  • Computer station

Outdoors

  • Beach loungers
  • Beach towels
  • Marina
  • On a private beach
  • Pool loungers

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Assistive listening devices
  • Braille/raised signage
  • Handrails in hallways
  • Handrails in stairways
  • Lever door handles
  • Pool hoist on site
  • Upper floors accessible by stairs only
  • Visual alarms in hallways
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking
  • Wheelchair-accessible pool
  • Wheelchair-accessible public washroom

More

  • 2 floors
  • 9 buildings
  • Built in 2020
  • Smoking not allowed
  • Traditional architecture

Room amenities

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Designer toiletries
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • 43-inch flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Microwave

More

  • Access via exterior corridors
  • Air conditioning
  • Ceiling fan
  • Free local calls
  • Iron/ironing board
  • Laptop workspace
  • Phone

Policies

Check-in

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

Check-out before 11 AM
Contactless check-out available
A late check-out fee will be charged

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

Access methods

Staffed front desk

Pets

  • This property welcomes pets for USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per night
  • 2 total (50 lbs is the maximum weight per pet)
  • Restrictions apply
  • For more information, guests can reach out to the property at the number on the booking confirmation
  • Service animals exempt from fees

Property payment types

Important information

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

  • Pet deposit: USD 50.00 per night
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • A late check-out fee will be charged

This list may not be comprehensive. Fees and deposits might not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
Safety features at this property include a fire extinguisher
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
  • Check-in: 4:00 PM
  • Check-out: 11 AM
  • Minimum check-in age: 18
The front desk is open 24 hours a day.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A credit card for incidental charges and a government-issued photo ID may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards. Cash is not accepted. 
  • Onsite safety features include a fire extinguisher.

Additional information about polices, regulations, and more:

  • Pool access available from 8:00 AM to 6:00 PM.
  • Some facilities may be restricted. For more details, contact the property. Contact information can be found on your booking confirmation.
  • Nearby construction work may cause some noise disturbance.
  • There are no elevators.
  • No rollaway or extra beds are available.

Property is 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

Is free cancellation available at Chesapeake Beach Resort?

Chesapeake Beach Resort offers free cancellation on select room rates. For more details, take a look at the cancellation policy on our site.

How much does it cost to stay at Chesapeake Beach Resort?

As of Jul 22, 2026, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Aug 19, 2026 start from $221, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What can I see close to Chesapeake Beach Resort?

This hotel is situated in Matecumbe within a short 11-minute walk of History of Diving Museum. You'll also find Islamorada Brewery & Distillery and Florida Keys Brewing Co. within a short drive.

Is there parking available at Chesapeake Beach Resort?

Yes, there is wheelchair-accessible parking available.

Does Chesapeake Beach Resort include a casino at the property?

No, Chesapeake Beach Resort doesn't have a casino.

Will I find an indoor pool at Chesapeake Beach Resort?

No, this hotel doesn't have an indoor pool; however, there are 2 outdoor pools. Guests have pool access between 8:00 AM and 6:00 PM.

Is Chesapeake Beach Resort a good place to stay for couples?

There are plenty of amenities for couples at this hotel, including a private beach, 2 outdoor pools, and a bar/lounge.

Does Chesapeake Beach Resort have a hot tub?

No, this hotel doesn't have a spa tub.

Does Chesapeake Beach Resort have a restaurant with a breakfast menu?

Yes, Chesapeake Beach Resort serves free continental breakfast at Tiki Bar each morning.

Will Chesapeake Beach Resort allow pets to stay for free?

Although they can't stay for free, pets are welcome at Chesapeake Beach Resort for a fee of USD 50.00 per accommodation, per night. A deposit of USD 50.00 per night is collected.

Does Chesapeake Beach Resort have connecting rooms available?

No, this hotel doesn't feature connecting guestrooms.

Are there rooms with balconies at Chesapeake Beach Resort?

Yes, some guestrooms at this hotel offer either a balcony and a deck/patio where guests can enjoy ocean and garden views.

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1311 out of 1752 reviews
Rating 8 - Good. 279 out of 1752 reviews
Rating 6 - Okay. 90 out of 1752 reviews
Rating 4 - Poor. 42 out of 1752 reviews
Rating 2 - Terrible. 30 out of 1752 reviews

9.6/10

Cleanliness

9.4/10

Staff & service

9.2/10

Amenities

9.4/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

mary agnes

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The place was lovely. Great staff and breakfast! The pools on the beach were fantastic!
Stayed 3 nights in Jul 2026
Verified

10/10 Excellent

Nathan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Perfect place to stay and a super friendly and helpful staff...definitely staying here again
Stayed 1 night in Apr 2026
Verified

8/10 Good

Louis

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great and friendly staff, perfect location.
Stayed 1 night in Apr 2026
Verified

8/10 Good

Christopher

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent breakfast options, lovely setting.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Brittany

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean, amazing breakfast, lovely staff.
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Joseph Donald

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was spacious and cool.The breakfast was great! There was a great variety of cereal, bagels, muffins and coffee. The ladies cooked pancakes and eggs made to order! The only thing was I wish the sargassum was cleaned up off the beach..Other than that everything was great!
Stayed 5 nights in Jun 2026
Verified

10/10 Excellent

NIDAL

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast is very good Staff is amazing Private beach with a walk to sandbar is Beautiful
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Kenneth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Jerrod

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and beautiful beach
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

sarah

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was good and peaceful I definitely recommend this property
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Philip

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great room, very clean and comfortable, pool heated and very nice area to relax. The private beach area is very nice.
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

Patrick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome beachfront clean rooms walk to restaurants
Stayed 1 night in Mar 2026
Verified

8/10 Good

Mauricio

Liked: Staff & service, amenities
Nice hotel, second time we stay there. Nice pool and jacuzzi.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Matthew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was great!
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Monica

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful facility. Great breakfast
Stayed 3 nights in Apr 2026
Verified

8/10 Good

Rick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We enjoyed our stay. Amenities were goo
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Steven

Liked: Cleanliness, amenities, property conditions & facilities
Great modern resort, very clean, very friendly.
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Paul

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely loved it here. It was clean, beautiful and the made to order eggs/pancakes/french toast every morning was a huge plus. Our room had an amazing ocean view. Will definitely be staying here again when we go back to the keys
Stayed 4 nights in Mar 2026
Verified

8/10 Good

Mariola

warm pool, beautiful view at the beach, pleasant front desk and breakfast staff
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Wasim

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, access to the water front. Very nice and quiet atmosphere. Excellent made to order breakfast and other options.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Jordan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location. Beautiful grounds felt very private.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

celso

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
clean-staff very friendly and helpful-place is paradise
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

dian

Liked: Cleanliness, staff & service, amenities
Great room, wonderful staff and good location
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Roger

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful ocean view from our room staff was very helpful very clean room
Stayed 1 night in Feb 2026