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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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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

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

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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Room options

View all photos for 2-Bedroom Villa

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

2-Bedroom Villa

  • 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

9/10 Wonderful
  • 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

  • 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

9.2/10 Wonderful
  • 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

8.3/10 Very Good
  • 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

  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View King Suite

Flat-screen TV

Hearing Impaired Ocean View King Suite

  • 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

  • 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

  • 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

8/10 Very Good
  • 650 sq ft
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.6/10 Exceptional
  • 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

10/10 Exceptional
  • 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

9.5/10 Exceptional
  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

  • 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

8.8/10 Excellent
  • 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

  • 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 | Flat-screen TV

Premium Ocean View King Villa

  • 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

  • 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

  • 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

8.2/10 Very Good
  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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9.0 out of 10, Wonderful, (1007)
The price is $254
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$341 total
includes taxes & fees
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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
  • Starbucks - 14 min walk
  • Whale Harbor Restaurant Marina - 2 min walk

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
  • 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

  • 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

Fees

You'll be asked to pay these 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

These are all of the charges provided to us by the property.

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 Jun 3, 2024, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Jun 9, 2024 start from $238.49, 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 Florida Keys Brewing Co. and Founders Park within a short drive.

Is parking available on site 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 a good place to stay 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 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. 866 out of 1334 reviews" "
Rating 8 - Good. 276 out of 1334 reviews" "
Rating 6 - Okay. 111 out of 1334 reviews" "
Rating 4 - Poor. 46 out of 1334 reviews" "
Rating 2 - Terrible. 35 out of 1334 reviews" "

9.0/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

9.0/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

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

6/10 Okay

Nicole

Traveled with group
Liked: Cleanliness, staff & service
The room was clean and as pictured and the staff was very nice. However, the property gave me "motel" vibes when we pulled up. It's certanly not a resort. The property is tiny, with a tiny pool and a tiny undesirable waterside area that can not be called a beach.
Stayed 1 night in Feb 2024

10/10 Excellent

Robert

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay. Love the location, property conition and above all, the staff. Great job folks !!
Stayed 4 nights in Feb 2024

10/10 Excellent

Rayla

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 4 nights in Feb 2024

10/10 Excellent

Patrick

Traveled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
There is a big difference between the regular rooms in the main buildings and the Villas. I definitely suggest staying in the Villas. It’s the only beach in the area and it’s completely private. Right on the water.
Stayed 2 nights in Mar 2024

6/10 Okay

Wesley

Liked: Cleanliness, property conditions & facilities
Nice place, just lacking a place to get a drink and have some beachfront amenities that we expected. It was a nice,well kept place
Stayed 2 nights in Feb 2024

10/10 Excellent

Aline

Traveled with family
Beautiful grounds, clean rooms and beach. Good breakfast and very friendly staff. In a convenient location. Love the tables and chairs on the water. Could look at the view forever.
Stayed 2 nights in Feb 2024