See all properties

Chesapeake Beach Resort

2.5 star property
Beachfront hotel with 2 outdoor pools in Islamorada

Choose dates to view prices

your current months are December, 2024 and January, 2025.
December 2024
January 2025

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Water view
Aerial view
ADA King Efficiency Villa
Private beach, white sand, sun loungers, beach towels

Reviews

9.0 out of 10

Wonderful

Popular amenities

  • Pool
    Pool
  • 24/7 front desk
    24/7 front desk
  • On private beach
    On private beach
  • Pet-friendly
    Pet-friendly
  • Housekeeping
    Housekeeping
  • Air conditioning
    Air conditioning

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • History of Diving Museum
    11 min walk
  • Theater of the Sea
    2 min drive
  • Windley Key Fossil Reef Geological State Park
    2 min drive

Room options

View all photos for 2-Bedroom Villa

2-Bedroom Villa

2-Bedroom Villa

  • 60 sq m
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King

Standard King

  • 25 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa

King Efficiency Villa

  • 48 sq m
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

  • 25 sq m
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

  • 29 sq m
  • 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

  • 34 sq m
  • 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

  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

  • 48 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

  • 65 sq m
  • 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

  • 60 sq m
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

  • 34 sq m
  • 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

  • 49 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

  • 48 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

Standard Queens

Standard Queens

  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

  • 30 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa | Living area

Premium Ocean View King Villa

  • 77 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

ADA Ocean View Queens

  • 34 sq m
  • 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

  • 50 sq m
  • 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

  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

Similar properties

Outdoor pool
Amara Cay Resort
On private beach
Pool
Pet-friendly
Parking included
4.4 out of 5, Excellent, (1211)
The price is CA $235
per night
CA $357 total
includes taxes & fees
5 Dec - 6 Dec
Amara Cay Resort

About the area

Islamorada

On the beach.With a stay at this Matecumbe hotel, you'll be within half a mile (1 km) of History of Diving Museum and 2 miles (3 km) of Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Keys History & Discovery Center are also within 2 miles (3 km).

What's nearby

  • History of Diving Museum - 11 min walk - 1.0 km
  • Theater of the Sea - 2 min drive - 1.8 km
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 1.8 km
  • Florida Keys Brewing Co. - 3 min drive - 3.5 km
  • Bud n' Mary's Dive Center - 6 min drive - 6.2 km

Getting around

  • Miami Intl. Airport (MIA) - 91 min drive

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Hog Heaven - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Florida Keys Brewing Co. - ‬3 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min walk

About this property

Chesapeake Beach Resort

Beachfront hotel with 2 outdoor pools in Islamorada
Simply walk outside to smell the salt air and watch the ocean waves from the white sand beach. Cool off in one of the 2 outdoor swimming pools at Chesapeake Beach Resort, and enjoy summer activities like kayaking.

A complete renovation of Chesapeake Beach Resort was completed in January 2020.

This Islamorada hotel is smoke free.

  • 60 guestrooms or units
  • 2 levels
  • 9 buildings
  • Built in 2020
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Front desk (24 hours)
  • Staff is multilingual
  • Concierge
  • Computer for guest use
  • No smoking on site
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels.

Bathrooms include showers, complimentary toiletries, and hair dryers. Business-friendly amenities include phones along with free local calls (restrictions may apply). Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

Languages

English, Spanish

Property amenities

Family friendly

  • 2 outdoor pools
  • Fence around the pool
  • Microwave
  • Pool gate

Parking and transportation

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

Things to do

  • 2 outdoor pools
  • Kayaking

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • This property does not have elevators
  • Assistive listening devices available
  • Braille 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 parking
  • Wheelchair-accessible pool
  • Wheelchair-accessible public washroom
  • Wheelchair accessible (may have limitations)

Room amenities

Entertainment

  • 43-inch flat-screen TV
  • Cable channels

Bedroom

  • Air conditioning
  • Bed sheets
  • Blackout drapes/curtains
  • Ceiling fan
  • Hypo-allergenic bedding
  • Pillow-top mattress

Bathroom

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

Food and drink

  • Coffee/tea maker
  • Microwave

More

  • Access via exterior corridors
  • Free local calls
  • Iron/ironing board
  • Laptop-friendly 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: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.

Property payment types

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • 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 may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Minimum Spring Break check-in age is 21 years old. This property accepts Visa, Mastercard, American Express, and Discover. Cash is not accepted. 

We should mention

  • Pool access available from 7:00 AM to 10:30 PM.
  • Certain facilities might have restricted access. For details, you can contact the property at the number on the booking confirmation.
  • Guests may experience noise disturbance due to nearby construction work.
  • To make arrangements to bring your pet, contact the property directly at the number on your booking confirmation (please see the Fees section for related charges).

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

Chesapeake Beach Resort Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 931 out of 1367 reviews" "
Rating 8 - Good. 253 out of 1367 reviews" "
Rating 6 - Okay. 105 out of 1367 reviews" "
Rating 4 - Poor. 47 out of 1367 reviews" "
Rating 2 - Terrible. 31 out of 1367 reviews" "

9.2/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

9.0/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

10/10 Excellent

Brian

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Really nice place. Room and staff were great. Chris the chef was awesome!
Stayed 1 night in Oct 2024

10/10 Excellent

Cabrina

Liked: Cleanliness, staff & service, property conditions & facilities
Very nice and clean
Stayed 1 night in Oct 2024

10/10 Excellent

Brooke

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2024

10/10 Excellent

Rafael

Travelled with partner
Liked: Staff & service, property conditions & facilities
We loved everything in this place. The people at reception desk were courteous and welcomed us with a glass of refreshing champagne. The room was great. Clean and quiet. The breakfast was awesome, the lady who cooked our breakfast omellete ( included in our price) was caring and very friendly with us. The beach is the best thing. Day or night. We loved the privacy here. I would only suggest a little bit of improvements on the gardens / green areas but I can understand its tough to maintain due to damages caused by storms etc… thanks for an unforgettable experience!!
Stayed 1 night in Aug 2024

10/10 Excellent

Stacey

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Paradise
Nothing not to love. We would definitely come back!
Stayed 1 night in Aug 2024

8/10 Good

Andrew

Travelled with partner
Liked: Cleanliness, staff & service
Disliked: Amenities
The staff were wonderful - cheerful and helpful. There is a big difference between staying in a room with a view (new building) and not with a view (roadside motel). The beach was peaceful and quiet. There were some issues with the room, but they were quickly resolved by staff. Very homey environment - not luxurious, but perfect for those who just want to relax and spend quiet time together without all the bells and whistles.
Stayed 2 nights in Aug 2024

4/10 Poor

Chanel

Liked: Staff & service
Disliked: Cleanliness, amenities
The pictures made it nicer than it really was in person. It’s an average hotel.
Stayed 1 night in Aug 2024

10/10 Excellent

Daisy

Travelled with family, Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything about this resort is good. Location, resort, pool and scenery
Stayed 1 night in Aug 2024

10/10 Excellent

Jennifer

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2024

10/10 Excellent

Sandra

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My favorite thing about this hotel is the breakfast. Room was clean and comfortable. Had a small fridge and microwave. Had two pools and one Jacuzzi. A small beach area with access to kayaks and paddle boards. It was great for a relaxing weekend.
Stayed 1 night in Aug 2024

10/10 Excellent

NICOLE

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Aug 2024

10/10 Excellent

Juan

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2024

8/10 Good

Paola

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

8/10 Good

Leilani

Travelled with family
Liked: Staff & service, property conditions & facilities, room comfort
Stayed 1 night in Jul 2024

10/10 Excellent

Benjamin

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Convenient quiet spot. Great amenities. Serene vibes. Family had a great time.
Stayed 2 nights in Aug 2024

4/10 Poor

Laura

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities
When we checked in, there was a $50 per night room fee. Did not know this! We were supposed to get a welcome drink but they were out of it, really??? Staff was very nice & breakfast was good, chef was very friendly! The place where breakfast was served only had high top tables but no chairs! A little odd, there were tables outside but it was too windy so no chairs there either.
Stayed 2 nights in Aug 2024

10/10 Excellent

andrew

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The customer service was amazing!
Stayed 3 nights in Aug 2024

10/10 Excellent

Amy Mileen, Shawnee

Stayed 5 nights in Jul 2024

10/10 Excellent

Raymond

Stayed 3 nights in Aug 2024

10/10 Excellent

Daniel

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Me encantó, súper limy una excelente ubicación
Stayed 1 night in Aug 2024

10/10 Excellent

Stacy

Liked: Amenities
My family had a wonderful time here. There was just enough to do on property in the evenings after we had fun doing other activities all day. There was lots of little critters in the water and on land for my kid to watch and have fun with. Also, the water pressure was great in the shower! Free breakfast every morning was great too! We were all able to eat well before starting our day. We would definitely come back.
Stayed 5 nights in Jul 2024

10/10 Excellent

Kevin

Stayed 1 night in Aug 2024

10/10 Excellent

Michela

Stayed 1 night in Jul 2024

2/10 Terrible

Guzman

Travelled with partner
Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service, amenities
The manager was rude and not helpful at all. I had an issue with a payment made to a third party booking agency that never made it there. All she kept telling me was that it wasn't her problem but mine....very unprofessional.
Stayed 4 nights in Jul 2024

10/10 Excellent

Troy Steven

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect!
Stayed 4 nights in Jul 2024