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Chesapeake Beach Resort

2.5 star property
Beachside hotel to enjoy 2 outdoor swimming pools and white sand beach

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your current months are May, 2024 and June, 2024.
May 2024
June 2024

Chesapeake Beach Resort

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Water view
ADA King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace
Premium Ocean View King Villa | Living area | 43-inch flat-screen TV with cable channels, TV
Premium Ocean View King Villa | Water view

Overview of Chesapeake Beach Resort

Reviews
9.0

Wonderful

Popular amenities

  • PoolPoolPool
  • On private beachOn private beachOn private beach
  • Pet friendlyPet friendlyPet friendly
  • Air conditioningAir conditioningAir conditioning
  • HousekeepingHousekeepingHousekeeping
  • Business servicesBusiness servicesBusiness services
The price is $199
$264 total
includes taxes & fees
May 5 - May 6

Explore the neighborhood

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Popular LocationHistory of Diving Museum11 min walk
  • Popular LocationTheater of the Sea2 min drive
  • Popular LocationFlorida Keys Brewing Co.3 min drive
  • AirportMiami, FL (MIA-Miami Intl.)91 min drive
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Room options

View all photos for 2-Bedroom Villa

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

2-Bedroom Villa

Highlights

Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • 646 sq ft
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King

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

Standard King

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 272 sq ft
  • 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

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
Dishwasher
  • 517 sq ft
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

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

Standard Doubles

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 272 sq ft
  • 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

Highlights

Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout drapes/curtains
  • 307 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Hearing Impaired Ocean View Queens

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 366 sq ft
  • Ocean view
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 540 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen 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

Highlights

Separate dining area
Air conditioning
Free cribs/infant beds
Full-sized refrigerator/freezer
Dining table
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 517 sq ft
  • Resort view
  • 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

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
Dishwasher
  • 700 sq ft
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 650 sq ft
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout drapes/curtains
  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 527 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
  • 517 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

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

Standard Queens

Highlights

Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 307 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

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

Standard King Villa

Highlights

Air conditioning
Free cribs/infant beds
Full-sized refrigerator/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
Pillowtop bed
  • 323 sq ft
  • Resort view
  • Sleeps 3
  • 1 King 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

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Full-sized refrigerator/freezer
Dining table
HDTV
  • 829 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

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

ADA Ocean View Queens

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 540 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 364 sq ft
  • Sleeps 3
  • 1 King Bed

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9.0 out of 10, Wonderful, (1004)
The price is $287
$378 total
includes taxes & fees
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About the neighborhood

Islamorada

Located on a private beach, Chesapeake Beach Resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park. Looking to get your feet wet? Jet skiing, snorkeling and boat tours adventures can be found near the property.
Visit our Islamorada travel guideOpens in a new window

What's nearby

  • History of Diving Museum - 11 min walk
  • Theater of the Sea - 2 min drive
  • Windley Key Fossil Reef Geological State Park - 2 min drive
  • Florida Keys Brewing Co. - 3 min drive
  • Founders Park - 5 min drive

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
  • Starbucks - 14 min walk
  • Whale Harbor Restaurant Marina - 2 min walk

About this property

Chesapeake Beach Resort

Transformed hotel, renovated in 2020 and located in Matecumbe
Chesapeake Beach Resort provides everything you need. With a private beach, sun loungers, and kayaking, this hotel is the perfect place to soak up some sun.
You'll also enjoy the following perks during your stay:
  • Swimming pool with sun loungers
  • 2 outdoor pools, multilingual staff, and beach towels
  • Concierge services, a computer station, and a 24-hour front desk
  • Smoke-free premises
  • Guest reviews give good marks for the beach locale, overall value, and pool
Room features
All 60 rooms include comforts such as laptop-friendly workspaces and air conditioning. Guest reviews speak well of the clean, spacious rooms at the property.
More amenities include:
  • Hypo-allergenic bedding and pillowtop mattresses
  • Bathrooms with designer toiletries and showers
  • 43-inch HDTVs with cable channels
  • Wardrobes/closets, microwaves, and coffee/tea makers

Languages

English, Spanish

Property amenities

Parking and transportation

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

Things to do

  • 2 outdoor pools
  • 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
  • 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
  • Renovated entire property - January 2020
  • Smoke-free property
  • Traditional architecture

Room amenities

Bedroom

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

Bathroom

  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels

Entertainment

  • 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: midnight
Early check-in subject to availability
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
Late check-out subject to availability
A late check-out fee will be charged

Special check-in instructions

Front desk staff will greet guests on arrival

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 stay
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

Fees

You'll be asked to pay the following charges at the property:

  • Resort fee: USD 40 per accommodation, per night
The resort fee includes:
  • Beach access
  • Beach loungers
  • Beach towels
  • Breakfast
  • Internet access
  • Phone calls
  • Pool access
  • Self parking
  • Sporting facilities or equipment

We have included all charges provided to us by the property.

Optional extras

  • Pet deposit: USD 50.00 per stay
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • Late check-out is available for a fee (subject to availability)

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
Minimum Spring Break check-in age is 21 years old
This property accepts credit cards; cash is not accepted

We should mention

This property does not have elevators
Pool access available from 7:00 AM to 10:30 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

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

Does Chesapeake Beach Resort have a pool?

Yes, this property has 2 outdoor pools. Pool access is from 7:00 AM–10:30 PM.

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

As of May 2, 2024, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on May 5, 2024 start from $199.0, excluding 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.

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 stay and a fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: midnight. 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 (subject to availability).

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. Matecumbe United Methodist Church and Florida Keys Brewing Co. are also within 3 mi (5 km).

Chesapeake Beach Resort Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 840 out of 1301 reviews" "
Rating 8 - Good. 271 out of 1301 reviews" "
Rating 6 - Okay. 107 out of 1301 reviews" "
Rating 4 - Poor. 46 out of 1301 reviews" "
Rating 2 - Terrible. 37 out of 1301 reviews" "

9.0/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.8/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

10/10 Excellent

Helen

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing!
Stayed 1 night in Apr 2024

8/10 Good

Sharleen

Traveled with partner
Liked: Cleanliness, staff & service
Disliked: Amenities
Photos of the room we booked which was garden view were not really garden view more like parking lot view, however, we were "upgraded" to a villa anyways. The "villa" was at the back of the property which was right up against the main road. Incredibly noisy all day and night. Absolutely horrible place for a room and right next to the garbage and housekeeping area. No bar service at all just a guy selling a few types of beers. They have no liquor license. Not a vacation spot in the keys. Will not be back.
Stayed 2 nights in Apr 2024

10/10 Excellent

Vytautas

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice hotel
Stayed 2 nights in Apr 2024

10/10 Excellent

Beatriz

Liked: Property conditions & facilities
Stayed 1 night in Apr 2024

10/10 Excellent

Kelly Ann

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean and updated property...convenient to get to any of the othet keys...love Wahoos next door to eat ..staff was very nice..its right on the ocean. Really great gem that was peaceful and i slept like a baby in their comfortably beds. I will definitely return.
Stayed 3 nights in Apr 2024

6/10 Okay

Marci, Kennett Square

Traveled with family
The room was nice but definitely not worth the 500 and some dollars per night. I was woken up early by that God awful beeping sound that moving machinery makes. To make it even worse, it went on all day for each of the 2 days we were there. Apparently maintenance was being done on the soffits. The room air conditioner sounded like a train. The beds squeaked every time you moved. I also woke up both mornings with bites all over my legs. Bedbugs? I’m not sure but I did inform management to check out the room. I don’t believe I would stay there again after this experience. It frankly was hugely over priced for what you got.
Stayed 2 nights in Apr 2024

8/10 Good

Brittney

Traveled with family and small children, Traveled with group, Traveled with family
Liked: Cleanliness
The hotel is super convenient location and right on the beach. We were disappointed that We had to wait until 4 pm to get into our room. We called for early check in but they kept saying call back. We never got early check in. When my daughter was playing in the pool she scraped her knee on the broken tiles!!! How can you have a “resort” and charge $350 a night and have broken tiles in the pool in multiple areas. The pool floor is slippery as well! The pool was HOTTTTT. It was not refreshing… my 4 year old daughter that gor her knee cut by the tile in the pool kept saying the pool felt like a huge warm bath! My son slipped on the outside flooring because it’s slick! Very disappointed in the pool miantenance.
Stayed 1 night in Apr 2024

10/10 Excellent

Edwin

Traveled with pets, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is my first time on the property since the remodel. It was a great stay and very clean. Love what they did with the place. The staff was great, super attentive, and super nice. The price for the hotel was great for what you get. And better than other hotels in the area which do not look as good as this. The only item I would like to see improved is the boat dock area. They should put some funds into this area so people can park their boats temporarily. I have booked my Memorial trip already and will be back. :)
Stayed 1 night in Apr 2024

10/10 Excellent

Jeffrey

Traveled with group
Liked: Property conditions & facilities
Property was updated. Beautiful area. Would stay again
Stayed 1 night in Apr 2024

10/10 Excellent

Laura

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Shakeitha Vanessa Anthony Eric and the women that grabbed our paddle boards were all wonderful! great place
Stayed 2 nights in Apr 2024

General hotel information

Reasons to Book
Property Cleanliness & Room Cleanliness
Check-In Time
4:00 PM
Check-Out Time
11:00 AM
Star Rating
2.5