See all properties

Chesapeake Beach Resort

3.5 star property

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Property preview
Hypo-allergenic bedding, pillowtop beds, laptop workspace
Outdoor spa tub
Water view

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi
$280
includes taxes & fees
Jan 25 - Jan 26, 2026

Explore the area

View in a map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Place, History of Diving Museum
    ‪12 min walk‬
  • Place, Theater of the Sea
    ‪3 min drive‬
  • Place, Islamorada Brewery & Distillery
    ‪3 min drive‬

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.6 out of 10
Exceptional
(45 reviews)
  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

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

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

8.0 out of 10
Very good
(4 reviews)
  • 540 sq ft
  • 1 bedroom
  • 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

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

View all photos for ADA Ocean View Queens

ADA Ocean View Queens | Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • 366 sq ft
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View Queens

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
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Standard Queens

Standard Queens | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Queens

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

View all photos for Standard Doubles

Standard Doubles | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(92 reviews)
  • 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

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

View all photos for Standard King

Standard King | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King

9.4 out of 10
Exceptional
(32 reviews)
  • 272 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

9.4 out of 10
Exceptional
(16 reviews)
  • 527 sq ft
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen 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
(10 reviews)
  • 650 sq ft
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for 2-Bedroom Villa

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

2-Bedroom Villa

10.0 out of 10
Exceptional
(1 review)
  • 646 sq ft
  • 2 bedrooms
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King Villa

Standard King Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King Villa

  • 323 sq ft
  • 1 bedroom
  • Resort view
  • 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

10.0 out of 10
Exceptional
(2 reviews)
  • 517 sq ft
  • 1 bedroom
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double 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
  • 1 bedroom
  • 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
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa 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
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Ocean View King Efficiency Villa

  • 517 sq ft
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Similar properties

Exterior
Lime Tree Bay Resort
  • On private beach
  • Pool
  • Hot tub
  • Pet friendly
4.6 out of 5, Wonderful, 1,114 reviews
Lime Tree Bay 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.

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
Information provided by the property may be translated using automated translation tools

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. 1168 out of 1604 reviews
Rating 8 - Good. 267 out of 1604 reviews
Rating 6 - Okay. 98 out of 1604 reviews
Rating 4 - Poor. 42 out of 1604 reviews
Rating 2 - Terrible. 29 out of 1604 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness

Reviews

10/10 Excellent

Hermes

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent recommendation for a small budget.
Stayed 3 nights in Sep 2025

10/10 Excellent

Annia

Traveled with family and small children, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing location grounds are very well maintained. Staff is beyond amazing Vanessa and Jose
Stayed 1 night in Sep 2025

8/10 Good

Britnee

Liked: Amenities
Beautiful resort with easy going staff
Stayed 1 night in Sep 2025

10/10 Excellent

Carl

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful property, breakfast was awesome
Stayed 1 night in Sep 2025

10/10 Excellent

Roger

Stayed 2 nights in Sep 2025

10/10 Excellent

francine

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The front desk and staff was very helpful, courteous, and professional. Will definitely be back. Property was beautiful. The rooms were clean, exquisite and comfortable.
Stayed 2 nights in Sep 2025

10/10 Excellent

Annie

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

8/10 Good

Yoel

Stayed 2 nights in Sep 2025

4/10 Poor

David

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Anything extra is very expensive, especially beverages in the lobby ! Price gouging !
Stayed 2 nights in Sep 2025

10/10 Excellent

nancy Rioseco

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
The breakfast was fresh and hot with a nice selection of fruits and drink. The staff was amazing. Would definitely recommend this resort. The pools were clean and the beach was beautiful.
Stayed 2 nights in Sep 2025

10/10 Excellent

Yvette

Traveled with partner
Liked: Staff & service, amenities, property conditions & facilities
Everything was perfect and beautiful
Stayed 1 night in Sep 2025

2/10 Terrible

Kelly

Traveled with partner
Liked: Cleanliness, staff & service, amenities
We arrived on Friday September 12, our room had no dresser to put all our clothes in which I found very strange then on Saturday around 3pm the electricity went out, we waited a couple hours then we called the front desk and the girl said it would be out for a while so I was having sinus issues plus asthma so I went to the office to speak with the receptionist and she apologized but didn’t know when the electric would be restored so do to my condition we had to go back home to Miami , we were not offered a different room first, check the office video , we would like , Saturday and Sunday nights refund back to us since we left on Saturday.
Stayed 3 nights in Sep 2025

10/10 Excellent

Shakene

Stayed 3 nights in Sep 2025

10/10 Excellent

RUBEN

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

10/10 Excellent

Deborah

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean property, good breakfast included and the views are spectacular!! Beautiful beach location!! Would go back anytime!!
Stayed 3 nights in Sep 2025

10/10 Excellent

Osvaldo

Stayed 2 nights in Sep 2025

10/10 Excellent

Logan

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

10/10 Excellent

April

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Relaxation 😌

Such a relaxing and fun spot. Enjoyed snorkeling every day at sunrise and sunset 😍 Can't wait for my next stay 🤗
Stayed 2 nights in Sep 2025

2/10 Terrible

Ori

Disliked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Sep 2025

10/10 Excellent

mariela tumene

Liked: Cleanliness, staff & service, property conditions & facilities
amazing everything
Stayed 1 night in Sep 2025

10/10 Excellent

Gregory

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great clean beautiful resort, but the road noise!

Centrally located in Islamorada and spotless property. Not a piece of trash anywhere. Comfortable beds, great towels. Resort seems newly built. Beautiful oceanside pool or second more private pool. Lots of loungers and umbrellas all along the beach. Accessible by boat with private lagoon. You can see and probably paddle to the sandbar from there. Only downside to me was highway noise, and neighbor noise. Seems like no soundproofing. You hear the trucks and your neighbors clearly all night long if you are in the cheaper rooms that are non-ocean front/view up closer to the roadway. Bring earplugs. Staff everywhere cleaning and fixing things up. Lots of different room and little “house” options. Property is huge. Kayaks, paddleboards there for a fee.
Stayed 4 nights in Sep 2025

6/10 Okay

David, Village of Lakewood

Traveled with family and small children
Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
I don’t know how this property has a rating of “wonderful”. We checked in during a heavy thunderstorm only to find out that the building our room was located in had no elevator. Upon learning this I told the front desk we are a family of 4 (two young kids) with 4 suitcases and that lugging these up slippery stone stairs in the middle of a storm was a really bad idea. So even though it was not offered, I asked to be moved to a building with an elevator! I was told that would be an extra $200 for the night. I passed and lugged them up with my wife. Then the room was poop. Bathroom door didn’t close all the way - the girls in your family will love that! Shower knob nearly pulled off the wall unless braced with your other hand, no water bottles in the room (paid or otherwise). Pedestal sink with no place to put toiletries, unless on top of the friggen toilet! GM called later that night offering to let us move rooms. Too late- already did the work ourselves and only staying for one night. The right move would have been monetary compensation at this point.
Stayed 1 night in Sep 2025

10/10 Excellent

Joe

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

8/10 Good

Luis

Liked: Cleanliness, staff & service
It was ok
Stayed 1 night in Aug 2025

10/10 Excellent

Arlettis

Liked: Amenities
All good
Stayed 1 night in Sep 2025