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Chesapeake Beach Resort

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

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Water view
Hypo-allergenic bedding, pillowtop beds, laptop workspace
Premium Ocean View King Villa | Living area | Flat-screen TV
Premium Ocean View King Villa | Water view

Reviews

9.0

Wonderful

Popular amenities

  • On private beach
  • Pool
  • 24/7 front desk
    24/7 front desk24/7 front desk
  • Pet friendly
    Pet friendlyPet friendly
  • Housekeeping
    HousekeepingHousekeeping
  • Air conditioning
    Air conditioningAir conditioning

Check-in time

4:00 PM

Check-out time

11:00 AM

Explore the area

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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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 hotel has in-room conveniences like microwaves, coffee makers, and flat-screen TVs.

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

  • The preferred airport is Miami Intl. Airport (MIA): 91-min drive, 77.5 mi/124.8 km.

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Hog Heaven - ‬3 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min walk
  • ‪The Whistle Stop - ‬2 min drive

About this property

Chesapeake Beach Resort

Beachside hotel to enjoy 2 outdoor swimming pools and white sand beach
Features of Chesapeake Beach Resort include a private beach, 2 outdoor pools, and a computer station. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area.
Flat-screen TVs come with cable channels. 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.
2 outdoor swimming pools are on site along with a private beach.

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.

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
  • 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 provided

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

  • This property welcomes pets for USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
  • 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 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)

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

  • 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.
  • The minimum check-in age for Spring Break is 21 years old.
  • This property accepts credit cards. Cash is not accepted. 
  • Contactless check-in and contactless check-out are available.

Additional information about polices, regulations, and more:

  • Pool access available from 7:00 AM to 10:30 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 27, 2024, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Jul 31, 2024 start from $179.0, 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.

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 Founders Park and Islamorada County Park within a short drive.

Is there parking available at Chesapeake Beach Resort?

Yes, there is 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 7:00 AM and 10:30 PM.

Is Chesapeake Beach Resort good for couples?

Couples staying at this hotel will appreciate amenities like a pillowtop mattress as well as a private beach and 2 outdoor pools.

Are there hot tubs at Chesapeake Beach Resort?

No, there isn't a spa tub at this hotel.

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

No, Chesapeake Beach Resort doesn't have a restaurant that serves breakfast.

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 stay is collected.

Are there connecting rooms at Chesapeake Beach Resort?

No, this hotel doesn't feature connecting guestrooms.

Are there rooms with balconies that I can book at Chesapeake Beach Resort?

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

Chesapeake Beach Resort Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 897 out of 1368 reviews" "
Rating 8 - Good. 279 out of 1368 reviews" "
Rating 6 - Okay. 112 out of 1368 reviews" "
Rating 4 - Poor. 47 out of 1368 reviews" "
Rating 2 - Terrible. 33 out of 1368 reviews" "

9.2/10

Cleanliness

9.0/10

Staff & service

8.6/10

Amenities

9.0/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

10/10 Excellent

Yvonne

Traveled with group, Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful resort
Stayed 2 nights in Jul 2024

10/10 Excellent

Rolf

Traveled with group, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved the location, the spaciousness of the room, and the resort activities that were included in our stay. The AC in our room was very loud though, even on the lowest level, so much that it was hard to sleep with it on. Overall however, we enjoyed our stay at Chesapeake Beach Resort.
Stayed 2 nights in Jul 2024

10/10 Excellent

Steven

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great
Stayed 1 night in Jul 2024

10/10 Excellent

Cindy

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing resort! Also Chris, Nari and Renee were wonderful at breakfast service. Spectacular views of the ocean and peaceful.
Stayed 2 nights in Jul 2024

10/10 Excellent

Sadaf

Stayed 1 night in May 2024

10/10 Excellent

camille

Traveled with partner
Excellent service, impecable rooms , kind and polite people, good amenities, beautiful place and gorgeous view
Stayed 4 nights in May 2024

6/10 Okay

Cristina, Miami

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in May 2024

2/10 Terrible

Anita

Traveled with partner, Traveled with pets
Disliked: Staff & service, amenities
Where can I start? Checkin took 20 mins although we were the only ones there. They charged us a pet fee for every night even though we have registered emotional support dogs. No other hotel in the keys has charged us this fee. No one told us where our room was, or that there was breakfast, or a bar, or that we could rent a boat or rent paddle boards/kayaks etc. we were given ZERO information about the property. We had to search and find the hidden waste disposal for our pet waste. There was very loud construction starting before 8am every morning. After additional fees that weren’t part of the booking and pet fees for our 2 emotional support dogs, we ended up paying more than we would have at the Islander resort, which we stayed at the previous night as we’d gotten in earlier than anticipated and the Chesapeake was fully booked. Worst experience in the Keys in all our years of going.

10/10 Excellent

alex

Stayed 2 nights in Apr 2024

10/10 Excellent

Margarita

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night 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

10/10 Excellent

Walt

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great stay!
It was a one night stay on my way to Key West with my brothers. Room was great and we even were able to check in early. Close enough to walk to a couple restaurants and bars, so after spending the afternoon looking around we were able to park the car and enjoy the evening on the water.
Stayed 1 night in Apr 2024

8/10 Good

kevin

Stayed 1 night 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

8/10 Good

Randall

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Apr 2024

10/10 Excellent

Katelyn

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We has a very good experience with the team service….employees were very helpful and friendly… I would recommend it 💯
Stayed 1 night in Apr 2024

10/10 Excellent

Nicole

Traveled with family
We only stayed for one night while traveling on our way to Key West. The property was absolutely beautiful. We utilized the pool and the hot tub, and also the game area out by the beach. The room was spotless, and the beds were very comfy. The bathroom was large and included all necessary toiletries. I wish we were staying longer than one night!
Stayed 1 night in Apr 2024

10/10 Excellent

Tami

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful, updated room. Great balcony. Free parking. Bathrobes and slippers for use in rooms. Right on the water. Lovely beach area. Will stay here again!!
Stayed 1 night in Apr 2024

10/10 Excellent

Alan

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our ocean front room was awesome! The views were spectacular. The entire staff was so polite and helpful. If I had to say one negative comment the breakfast was very week. The gentleman who ran the breakfast more than made up for it with his personal charm. I HIGHLY recommend this facility.
Stayed 2 nights in Apr 2024

10/10 Excellent

Brian

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Relaxation
This was a beautiful and calming location to relax after several days at Universal Studios. No need to search for a beach, since you have one within walking distance. We enjoyed paddle boarding and kaying (free with the stay). Definitely on our list to revisit in the future!
Stayed 4 nights in Apr 2024