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Chesapeake Beach Resort

3.5 star property

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Outdoor spa tub
Water view
Balcony
1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Windley Key Fossil Reef Geological State Park
    ‪2 min drive‬
  • Theater of the Sea
    ‪2 min drive‬
  • Florida Keys Brewing Co.
    ‪4 min drive‬

Room options

View all photos for 2-Bedroom Villa

2-Bedroom Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • 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 | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King

9.8 out of 10
Exceptional
(27 reviews)
  • 272 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • 517 sq ft
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Standard Doubles | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(80 reviews)
  • 272 sq ft
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King with Sleeper Sofa

9.0 out of 10
Wonderful
(18 reviews)
  • 307 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(2 reviews)
  • 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

8.6 out of 10
Excellent
(4 reviews)
  • 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 | 1 bedroom, 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 | 1 bedroom, 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

8.8 out of 10
Excellent
(9 reviews)
  • 650 sq ft
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(77 reviews)
  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

9.4 out of 10
Exceptional
(13 reviews)
  • 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

9.8 out of 10
Exceptional
(41 reviews)
  • 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 | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Queens

9.4 out of 10
Exceptional
(50 reviews)
  • 307 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Standard King Villa | 1 bedroom, 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 | 43-inch flat-screen TV with cable channels, 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 | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • 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

10.0 out of 10
Exceptional
(2 reviews)
  • 540 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

8.6 out of 10
Excellent
(16 reviews)
  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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Exterior

Amara Cay Resort

  • On private beach
  • Pool
  • Pet friendly
  • Restaurant
4.4 out of 5, Excellent, (1224)
$310 nightly
The price is $310 total
includes taxes & fees
Amara Cay Resort

About this property

Chesapeake Beach Resort

3.5-star hotel in Matecumbe
At Chesapeake Beach Resort, you can relax at one of the 2 outdoor swimming pools, play on the private white sand beach, or spend the day at a marina.
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.

This Islamorada hotel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). 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.

A private beach, a marina, and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.

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 amenities like a marina and complimentary bicycles.

A complimentary breakfast is offered each morning. A bar/lounge is on site where guests can unwind with a drink. A computer station is located on site and wireless Internet access is complimentary. A total renovation of this property was completed in January 2020.

Chesapeake Beach Resort is a smoke-free property.

A complimentary continental breakfast is served each morning between 6:00 AM and 10:00 AM.
Tiki Bar - Onsite bar.

Languages

English, Spanish

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • In-room WiFi speed: 100+ Mbps (good for 1–2 people or up to 6 devices)
  • Available in some public areas: Free WiFi

Parking and transportation

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

Food and drink

  • Free continental breakfast available daily 6:00 AM to 10:00 AM
  • A bar/lounge
  • Coffee and tea in common areas

Restaurants on site

  • Tiki Bar

Things to do

  • 2 outdoor pools
  • Boat tours
  • Fishing
  • Free bicycle rentals
  • 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
  • Marina
  • 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
  • Smoking not allowed
  • Traditional architecture

Room amenities

Bedroom

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

Bathroom

  • Designer toiletries
  • Hair dryer
  • 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: 3:00 AM
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
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
  • A late check-out fee will be charged

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
This property accepts credit cards; cash is not accepted
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

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

9.2

Wonderful

Rating 10 - Excellent. 1064 out of 1482 reviews
Rating 8 - Good. 249 out of 1482 reviews
Rating 6 - Okay. 93 out of 1482 reviews
Rating 4 - Poor. 41 out of 1482 reviews
Rating 2 - Terrible. 35 out of 1482 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

10/10 Excellent

Patricia

Stayed 2 nights in Apr 2025

10/10 Excellent

phil

Liked: Cleanliness, staff & service, property conditions & facilities
very nice hotel
Stayed 2 nights in Apr 2025

6/10 Okay

Adel

Traveled with family
Disliked: Staff & service
The chef at the breakfast was so rude and hostile When I complained to the front desk (Venessa she did not care even I told her he yelled at me in front of other guests. Venessa and that breakfast chef are very unprofessional hence I will never go there again On the other hand, another person at the reception was very kind and professional and her name is Adriana
Stayed 2 nights in Apr 2025

10/10 Excellent

Hari

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great experience on our anniversary. Sunrise view was great.
Stayed 1 night in Apr 2025

10/10 Excellent

Mauricio

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful hotel, always great to be in the Florida Keys.
Stayed 1 night in Apr 2025

10/10 Excellent

Tijana

Stayed 1 night in Mar 2025

10/10 Excellent

Nathan

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The views are beautiful
Stayed 2 nights in Apr 2025

10/10 Excellent

David, Pembroke Pines

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place with a great staff.
Stayed 4 nights in Mar 2025

10/10 Excellent

Sandra

Liked: Cleanliness, staff & service, property conditions & facilities
Great place!
Stayed 2 nights in Dec 2024

10/10 Excellent

Lindsey

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We enjoyed our stay at the Chesapeake very much. The ocean view suite was well maintained and spacious for our family. The location is fabulous within 1-2 miles of fabulous dining and adventurous activities. We chose not to have daily service in our room, but staff texted each day to see what we needed. Would highly recommend!
Stayed 6 nights in Mar 2025

10/10 Excellent

Kim

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 3 nights in Mar 2025

10/10 Excellent

Manuel

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent
Stayed 1 night in Mar 2025

10/10 Excellent

Margaret

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Beautiful property, lots to do. Food was delicious. Staff are kind and helpful
Stayed 1 night in Nov 2024

8/10 Good

valerie

Liked: Cleanliness, staff & service, property conditions & facilities
The view from my room was awesome. The public areas (to beach, pools, breakfast) were extremely convenient to get to. The only negative comment I have concerns the room amenities. There should be a dresser for more drawer space and a few more hooks or racks in bathroom for towels. Other than that it was a fantastic resort that I would highly recommend
Stayed 5 nights in Mar 2025

8/10 Good

Scot

Traveled with family
Liked: Cleanliness, property conditions & facilities, room comfort
Very nice location and grounds.
Stayed 2 nights in Mar 2025

10/10 Excellent

jay

Stayed 4 nights in Mar 2025

10/10 Excellent

rancel

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Mar 2025

8/10 Good

Peyton

Stayed 1 night in Mar 2025

10/10 Excellent

Melissa

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful pool, beach and hot tub. My son loved the waffle guy at breakfast.
Stayed 1 night in Mar 2025

8/10 Good

Carlos

Stayed 2 nights in Mar 2025

10/10 Excellent

Maria, Jupiter

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We were very happy here. Had almost everything except fine dining which we did not mind! Plenty of places to go!
Stayed 1 night in Mar 2025

8/10 Good

Jamie, Bloomington

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 5 nights in Mar 2025

10/10 Excellent

Federico

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Mar 2025

8/10 Good

Ashley

Liked: Cleanliness
Stayed 2 nights in Mar 2025

2/10 Terrible

Michael

Traveled with family
Disliked: Cleanliness, staff & service, amenities, property conditions & facilities
This is not a resort. It is a motor lodge sandwiched between the highway and the water. You literally park under your room. There is a tiny pool. The “beach” is a joke. It’s not sand, but white dirt, and it’s a tiny area. The water is shallow and the bottom is weedy and rocky. I am a cheap person, but my wife and kid and I all decided to leave shortly after checking in (no refund despite the deceptive advertising) and go back to Eden ROC in Miami. Better room, real resort amenities, and less expensive. Chesapeake motor lodge felt like a prison.
Stayed 4 nights in Mar 2025