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Chesapeake Beach Resort

Property class: 3.5

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Photo gallery for Chesapeake Beach Resort

A beach with palm trees and lounge chairs. - Chesapeake Beach Resort (Islamorada)
A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window. - Chesapeake Beach Resort (Islamorada)
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees. - Chesapeake Beach Resort (Islamorada)
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence. - Chesapeake Beach Resort (Islamorada)
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool. - Chesapeake Beach Resort (Islamorada)
Consider a stay at Chesapeake Beach Resort and take advantage of free continental breakfast, a marina, and a bar. This hotel is a great place to bask in the sun with a private beach, sun loungers, and kayaking. Enjoy onsite activities like boat tours and fishing. Guests can connect to free in-room WiFi.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi

Off-peak, on budget: 30% or more off select hotels in our fall sale

Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

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

9.6 out of 10
Exceptional
(54 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
(110 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
(3 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
(76 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 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
  • 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

About the neighborhood

Located on a private beach, Chesapeake Beach Resort is in Matecumbe, a neighborhood in Islamorada. Hurricane Monument and Indian Key Historic State Park are local landmarks, and some of the area's activities can be experienced at Islamorada Brewery & Distillery and Florida Keys Brewing Co.. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven. With jet skiing and snorkeling nearby, you'll find plenty of adventures in the water. Visit our Islamorada travel guide
Map
83409 Overseas Hwy, Islamorada, FL, 33036

What's nearby

  • A building with a blue facade, a large mural of a diving scene, and a statue of a diver.
    History of Diving Museum
    12 min walk - 0.7 miles
  • An archaeological site with stone structures and metal machinery.
    Windley Key Fossil Reef Geological State Park
    2 min drive - 1.3 miles
  • A waterfall at SeaWorld, with text reading "I eat the sea" and "Marine Mammal Park, Islamorada, Florida".
    Theater of the Sea
    2 min drive - 1.5 miles
  • A beach with a wooden structure, clear blue sky, and dense green foliage.
    Anne's Beach
    15 min drive - 12.8 miles
  • Islamorada Brewery & Distillery
    2 min drive - 1.7 miles

Getting around

  • Miami Intl. Airport (MIA)
    91 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

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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

Pets allowed for an extra charge of USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per night
Service animals are welcome, and are exempt from fees
2 total (up to 50 lbs per pet)
Restrictions apply; for more information contact the property at the number on the booking confirmation

Children and extra beds

Children are welcome
Rollaway/extra beds are not available

Property payment types

  • American Express
  • Discover
  • Mastercard
  • Visa

Important information

Optional extras

  • 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

The above list may not be comprehensive. Fees and deposits may 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

We should mention

This property does not have elevators
Pool access available from 8:00 AM to 6:00 PM
Some facilities may have restricted access; guests can contact the property for details using the contact information on the booking confirmation
Construction is underway at a neighboring building and there may be noise disturbance from the construction work
Children under 16 years old are not allowed in the swimming pool without adult supervision

Frequently asked questions

Does Chesapeake Beach Resort have a pool?

Yes, this property has 2 outdoor pools. Pool access is from 8:00 AM–6:00 PM.

Is Chesapeake Beach Resort pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 50 lbs per pet. There's a deposit of USD 50.00 per night and a fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM. Late check-in is available during limited hours.

What time is check-out at Chesapeake Beach Resort?

Check-out is at 11 AM. Late check-out is available for a fee.

Where is Chesapeake Beach Resort located?

Nestled on the beach, this Matecumbe hotel is within 1 mi (2 km) of History of Diving Museum and Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Lorelei Restaurant & Cabana Bar are also within 2 mi (3 km).

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Chesapeake Beach Resort Reviews

9.2

Wonderful

9.6

Cleanliness

9.2

Amenities

9.4

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 1338 out of 1791 reviews
Rating 8 - Good. 283 out of 1791 reviews
Rating 6 - Okay. 95 out of 1791 reviews
Rating 4 - Poor. 45 out of 1791 reviews
Rating 2 - Terrible. 30 out of 1791 reviews

Reviews

Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent location, nice breakfast.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice pool, great breakfast with seating outside with nice views
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing breakfast, clean room and very friendly staff.
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This resort was beautiful & very well maintained. The view from my room was absolutely breathtaking. I will definitely stay here again when I go back to the Keys
Stayed 3 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very quiet and peaceful stay. Amazing water and beach views from the balcony.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the view and the private beach
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone was friendly and we had a good time.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great beach for the keys and great breakfast! The bar food is minimal and they don’t always open but Wahoo next door is amazing. Would definitely come back to this hotel.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, we loved having the little beach area and swimming in the pool looking at the ocean. Apparently it's dog friendly too and we loved that, may come down with the pups next time! Also it smelled great and clean without smelling like actual cleaners. The staff was also very friendly as well, and there is a bar right next to the pool too!
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I always stay here with my sisters & mom for our girls trip! Always so relaxing!!
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the kayak, and breakfast and the view! Everything!
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful ocean view from balcony. Small pool could use resurfacing. Overall a beautiful pace for a place to stay, and enjoy the Keys.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The views were great and the location was perfect. The staff was friendly and helpful.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A great place to stay and very well located. Breakfast staff was wonderful and very accommodating. Check in staff as well. A beautiful property,
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was bery nice great location, its pet friendly staff was great and the breakfast was amazing...You have restaurants right next to the property that you dont need to drive anywhere...would be there again 🙏🙏
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff Omar was very helpful The Hotel has been recently renovated. Was very clean. Would definitely stay again.
Stayed 1 night in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, amenities, property conditions & facilities
I like the view of the ocean and everything
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Spectacular, beautiful view, excellent amenities, a quiet and beautiful place, very attentive staff, and the breakfast is exquisite—I’ll be back as soon as I can
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Hotel is right on the ocean. Was a large room and shower. Plenty of pool towels. Had 2 pools. Could also bike and kayak. Breakfast was good. Great location for many activities and restaurants.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was very clean, unexpectedly our bed was made up everyday and fresh towels. Cooked to order breakfast was a nice surprise. Staff was great. Will definitely return when in the Keys!
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is my second time going there and I love it. Perfect for family or just your self and friends. I recommend…
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love the place very clean and peaceful
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
10/10 recommend! We will be back again! We love coming here and bringing the boat. Staff is great and properly/rooms are so clean.
Stayed 6 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, property conditions & facilities
The room was very clean, and was cleaned every day during our stay. Very good breakfast with made to order eggs, omelettes and pancakes.
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean rooms. The continental breakfast is more then just continental. They make fresh omelettes right infront of you, water front view and a small dock to come in and out with your boat. All around amazing for the price and friendly staff. Highly recommended
Stayed 3 nights in Jul 2026