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Chesapeake Beach Resort

3.5 star property
Travelers relax on sun-kissed beaches or take refreshing swims in outdoor pools at this peaceful Florida Keys resort with private waterfront access

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels - Chesapeake Beach Resort (Islamorada)
Private beach, white sand, sun loungers, beach towels - Chesapeake Beach Resort (Islamorada)
Exterior - Chesapeake Beach Resort (Islamorada)
Beach/ocean view - Chesapeake Beach Resort (Islamorada)
Reception - Chesapeake Beach Resort (Islamorada)
Chesapeake Beach Resort offers a quiet escape in Matecumbe. Start your day with a leisurely breakfast, then head to the private beach with sun loungers and kayaking. Enjoy two outdoor pools, while multilingual staff and concierge services help plan the perfect stay.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi

Room options

Available filters for rooms
Showing 20 of 20 rooms

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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

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Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

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

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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

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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

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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

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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

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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

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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
(20 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

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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
(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.. 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

  • History of Diving Museum
    History of Diving Museum
    12 min walk - 0.7 miles
  • Windley Key Fossil Reef Geological State Park
    Windley Key Fossil Reef Geological State Park
    2 min drive - 1.3 miles
  • Theater of the Sea
    Theater of the Sea
    2 min drive - 1.5 miles
  • Islamorada Brewery & Distillery
    2 min drive - 1.5 miles
  • beach near Islamorada
    2 min drive - 1.7 miles

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

Hotel located in Matecumbe
Free continental breakfast, a marina, and a bar are just a few of the amenities provided at Chesapeake Beach Resort. With a private beach, sun loungers, and fishing, this hotel is the perfect place to soak up some sun. Enjoy onsite activities like kayaking and boat tours. Stay connected with free in-room WiFi.
You'll also enjoy the following perks during your stay:
  • 2 outdoor pools along with sun loungers
  • Free bicycle rentals, coffee/tea in the lobby, and a computer station
  • Multilingual staff, a 24-hour front desk, and smoke-free premises
  • Beach towels and concierge services
  • Guest reviews give top marks for the breakfast, beach locale, and pool
Room features
All 60 rooms offer comforts such as laptop-friendly workspaces and air conditioning, in addition to perks like free WiFi. Guest reviews speak positively of the clean, spacious rooms at the property.
More amenities include:
  • Hypo-allergenic bedding and pillowtop mattresses
  • Designer toiletries, showers, and hair dryers
  • 43-inch HDTVs with cable channels
  • Wardrobes/closets, microwaves, and coffee/tea makers

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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

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 Keys History & Discovery Center 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

9.4

Cleanliness

9.0

Amenities

9.4

Staff & service

9.2

Property conditions & facilities
Rating 10 - Excellent. 1277 out of 1720 reviews
Rating 8 - Good. 275 out of 1720 reviews
Rating 6 - Okay. 96 out of 1720 reviews
Rating 4 - Poor. 41 out of 1720 reviews
Rating 2 - Terrible. 31 out of 1720 reviews

Reviews

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

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

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

Jerrod

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

Patrick

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

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

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

Jerry

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice breakfast served - omelets, pancakes, French toast and many other items. Outdoor pool was nice as was the ocean beach. Friendly staff.
Stayed 2 nights in Apr 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

Steven

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

10/10 Excellent

Lyle

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The people were helpful & friendly. Accommodations were superb. The free breakfast selections were more than you get at most hotel chains. The area was very picturesque with the turquoise waters, cool breezes, and multiple swimming pools for a relaxed, calm days.
Stayed 4 nights in Apr 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

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

Isabel

Liked: Cleanliness, amenities, property conditions & facilities
This place was perfect for my family. The continental breakfast saved us a lot of money on food, the staff was friendly and the resort was clean. Will 100% be back here.
Stayed 5 nights in Apr 2026
Verified

8/10 Good

Beth

Liked: Cleanliness, staff & service, amenities
Nice grounds beautiful view
Stayed 3 nights in Mar 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
Verified

10/10 Excellent

Emil

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was very helpful!
Stayed 2 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

Douglas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful property! Every staff member was friendly, the room was clean and spacious, breakfast was cooked to order as we ate outside overlooking the water. We had a small dog and she was welcome everywhere. I would definitely stay here again!
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Alice

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The ocean was visible from our room and the balcony was wonderful!
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Melissa

Liked: Cleanliness, amenities, property conditions & facilities
The view and location were great.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Sara

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything about our stay here was fantastic! The staff were all very friendly and accommodating. Fresh-made omelets with friendly smiles to start every day! Everything was very clean. We will be back!
Stayed 5 nights in Mar 2026
Verified

6/10 Okay

Lori

The free breakfast was excellent. We upgraded to an ocean view room. The room was dated and not cleaned daily. The location was nice right on the beach with two pools.
Stayed 4 nights in Apr 2026