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Chesapeake Beach Resort

2.5 star property

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Balcony
Hypo-allergenic bedding, pillowtop beds, laptop workspace
Water view
Aerial view

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Pet friendly
  • Housekeeping
  • 24/7 front desk
  • 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 | Hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

  • Resort view
  • 646 sq ft
  • 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

  • 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

  • Resort view
  • 517 sq ft
  • 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

  • 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

  • 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

  • Ocean view
  • 366 sq ft
  • 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

  • Ocean view
  • 540 sq ft
  • 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

  • Resort view
  • 517 sq ft
  • 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

  • Ocean view
  • 700 sq ft
  • 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

  • Ocean view
  • 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

  • Ocean view
  • 364 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

  • Ocean view
  • 527 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

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

Ocean View King Efficiency Villa

  • Ocean view
  • 517 sq ft
  • 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

  • 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

  • Resort view
  • 323 sq ft
  • 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

  • Ocean view
  • 829 sq ft
  • 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

  • Ocean view
  • 366 sq ft
  • 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

  • Ocean view
  • 540 sq ft
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

  • Ocean view
  • 364 sq ft
  • Sleeps 3
  • 1 King Bed

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Exterior

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  • Parking included
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The price is $489
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$616 total
includes taxes & fees
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About this property

Chesapeake Beach Resort

Hotel in Matecumbe
At Chesapeake Beach Resort, relax by one of the 2 outdoor swimming pools or spend the day at the private white sand beach where you can enjoy kayaking.
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.

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.

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 total renovation of this property was completed in January 2020.

Chesapeake Beach Resort is a smoke-free property.

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 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: 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 at the property

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

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

Chesapeake Beach Resort Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 1016 out of 1453 reviews
Rating 8 - Good. 247 out of 1453 reviews
Rating 6 - Okay. 106 out of 1453 reviews
Rating 4 - Poor. 49 out of 1453 reviews
Rating 2 - Terrible. 35 out of 1453 reviews

9.2/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

10/10 Excellent

Jeannie, Girard

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the location, beach area, breakfast and STAFF
Stayed 4 nights in Dec 2024

10/10 Excellent

Amy

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

10/10 Excellent

Viorel

Liked: Cleanliness, staff & service, property conditions & facilities
Great front desk staff, clean property overall. Some things never change fortunately.
Stayed 1 night in Nov 2024

10/10 Excellent

Viorel

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I'm a routine guest at this property for over 25 years. One of the best in the Keys, price and money. Great location, nearby Whale Harbour, the Sandbar, Boat rentals, 3 restaurants and one rooftop bar within a 1 minute walk, and Islamorada attractions just over the bridge. Great front desk staff, clean property overall. Some things never change fortunately.
Stayed 1 night in Dec 2024

8/10 Good

Luca

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Great beach and clean big well furnished rooms
Stayed 2 nights in Dec 2024

10/10 Excellent

Samara

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful
Stayed 1 night in Sep 2024

10/10 Excellent

Bing Yi

Stayed 1 night in Dec 2024

10/10 Excellent

Jack

Liked: Staff & service, property conditions & facilities
Loved our room & view (Ocean-view King suite) and LOVED the hot tub. It saved our trip! It rained A LOT during our trip - and we very much enjoyed going from the hot tub to the heated swimming pool during the rain : )
Stayed 3 nights in Dec 2024

4/10 Poor

Lori

Traveled with family
Disliked: Cleanliness, staff & service
Very disappointing, considering hotel rate. No room for bags, no room for towels in bathroom, stains on sheets. Had to call front desk twice and then had to go to reception for change of sheets. Balcony looked out on parking area. What do you want for 700/per night. Total rip-off.
Stayed 2 nights in Dec 2024

8/10 Good

Verified traveler

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

10/10 Excellent

Saravanan

Liked: Cleanliness, staff & service, property conditions & facilities
Good
Stayed 1 night in Dec 2024

6/10 Okay

Michele

Disliked: Property conditions & facilities
We stayed one night at CHESAPEAKE BEACH resort en route to the keys and I would not recommend to fellow travelers. The hotel is right off a very busy road so you will hear traffic if you are situated near the front of the property. More problematic are the paper thin walls that allow you to hear every word of the conversation in the room next door as well as their 6:30 am alarm and 3:30 pm margarita party. There was very limited hot water - my husband took a cold shower and I opted to wait until our next stop as I don't enjoy a cold plunge shower. My son and I walked over to breakfast at 7 am only to be told they had run out of eggs so the "make your personalized omelette" was not in order. We had cold cereal out of plastic cups (no bowls) and a piece of toast. Upon checking out, I was informed "you'll get a receipt from Expedia" - no thank you, no how was your stay, no common courtesy. I would definitely NOT recommend this resort to others. Especially with a $600/night price tag over the holidays.
Stayed 1 night in Dec 2024

10/10 Excellent

Jason

Traveled with family
Booked online with just pictures as reference. The staff and resort in its entirety went beyond expectations. Breakfast was excellent and pool and water activities were enjoyable!!! A must must must if looking to stay in Islamorada. Will be returning!!!
Stayed 4 nights in Dec 2024

10/10 Excellent

OVEE

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

8/10 Good

Rashmi

Liked: Cleanliness
Disliked: Staff & service
Rooms were very clean and big. Our room faced the ocean which was the best thing. Nice and calm atmosphere with easy access to area amenities. There can be more in-resort amenities. Staff could be more welcoming and friendly. The person at the front desk and the breakfast area were very rude. Will be nice if they can be more cordial and nice.
Stayed 2 nights in Dec 2024

10/10 Excellent

Sam

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicely renovated property. 5 star room with a nice resort feel.
Stayed 1 night in Dec 2024

10/10 Excellent

Maria Liliana

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice job
Stayed 1 night in Dec 2024

8/10 Good

Deeptha

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent beach . Friendly and efficient staff . Prompt service.
Stayed 1 night in Dec 2024

10/10 Excellent

adriana

Stayed 1 night in Nov 2024

10/10 Excellent

Tim

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Loved it.
Stayed 2 nights in Dec 2024

10/10 Excellent

Pamela

Stayed 1 night in Nov 2024

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff is always warm and friendly.
Stayed 3 nights in Dec 2024

10/10 Excellent

Allan

Stay one night in December for a half marathon. Room was clean and comfortable
Stayed 1 night in Dec 2024

8/10 Good

Mary Beth

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

10/10 Excellent

Charles

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean, maintained. Attention to detail obvious. Office staff very friendly & responsive. Great breakfast choices and service. Nice property... would definitely recommend.
Stayed 5 nights in Nov 2024