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Chesapeake Beach Resort

3.5 star property

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
43-inch flat-screen TV with cable channels, TV
Hypo-allergenic bedding, pillow-top beds, laptop workspace
Deluxe Ocean View Two Queen Suite | Balcony
Water view

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Breakfast included
  • Free Wi-Fi
  • Restaurant

Explore the area

View 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
(46 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(88 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • 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

8.4 out of 10
Very good
(5 reviews)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

8.6 out of 10
Excellent
(17 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

ADA Ocean View Queens

9.0 out of 10
Wonderful
(7 reviews)
  • Ocean view
  • 34 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(2 reviews)
  • Ocean view
  • 34 sq m
  • 1 bedroom
  • 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)
  • Ocean view
  • 50 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Standard Queens

Standard Queens

Standard Queens

9.4 out of 10
Exceptional
(60 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

9.2 out of 10
Wonderful
(95 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

9.2 out of 10
Wonderful
(24 reviews)
  • 29 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King

Standard King

9.6 out of 10
Exceptional
(35 reviews)
  • 25 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

9.2 out of 10
Wonderful
(17 reviews)
  • Ocean view
  • 49 sq m
  • 1 bedroom
  • 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

9.0 out of 10
Wonderful
(11 reviews)
  • Ocean view
  • 60 sq m
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds

View all photos for 2-Bedroom Villa

2-Bedroom Villa

2-Bedroom Villa

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

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

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

View all photos for King Efficiency Villa

King Efficiency Villa

King Efficiency Villa

10.0 out of 10
Exceptional
(2 reviews)
  • Resort view
  • 48 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

  • Resort view
  • 48 sq m
  • 1 bedroom
  • 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

  • Ocean view
  • 65 sq m
  • 1 bedroom
  • 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

Premium Ocean View King Villa

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

Ocean View King Efficiency Villa

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

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About the area

Islamorada

Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park. .This beach hotel is 1.2 mi (2 km) from Islamorada Brewery & Distillery and 1.7 mi (2.8 km) from Keys History & Discovery Center.

What's nearby

  • History of Diving Museum - 12 min walk - 1.1 km
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 2.0 km
  • Islamorada Brewery & Distillery - 2 min drive - 2.4 km
  • Theater of the Sea - 2 min drive - 2.4 km
  • Bud n' Mary's Dive Center - 5 min drive - 7.3 km

Getting around

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

Restaurants

  • ‪Tiki Bar - ‬13 min walk
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Hog Heaven - ‬3 min drive
  • ‪Wendy's - ‬2 min drive

About this property

Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools
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.

Make yourself at home in one of the 60 air-conditioned rooms featuring microwaves and flat-screen televisions. Your room comes with a pillowtop bed. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, designer toiletries, and hair dryers.
Spend the day on the private beach or dip into one of the 2 outdoor pools. This hotel also features complimentary wireless internet access and concierge services.
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM.
Featured amenities include a computer station, a 24-hour front desk, and multilingual staff.
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 transport

  • 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 bathroom

More

  • 2 floors
  • 9 buildings
  • Built in 2020
  • Smoke-free property
  • 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

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. 1225 out of 1675 reviews
Rating 8 - Good. 277 out of 1675 reviews
Rating 6 - Okay. 100 out of 1675 reviews
Rating 4 - Poor. 43 out of 1675 reviews
Rating 2 - Terrible. 30 out of 1675 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

Reviews

8/10 Good

James

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great breakfast very well kept grounds
Stayed 6 nights in Nov 2025

6/10 Okay

Ross

Stayed 2 nights in Oct 2025

10/10 Excellent

Diana

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Room was extremely clean and well equipped. Robes and slippers were an added bonus. Beautiful nicely kept resort. Pools and beach beautiful. Breakfast was great and Chef Chris seems to love his job. All the staff are great!
Stayed 1 night in Nov 2025

10/10 Excellent

Robbie, Rock Hill

Stayed 3 nights in Nov 2025

10/10 Excellent

Yudith

Liked: Cleanliness, amenities, property conditions & facilities
Especial as always
Stayed 2 nights in Nov 2025

8/10 Good

haley

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
breakfast was very good, but it was totally self service clean up as well. The beach in the keys is nothing special. The kayak was included for one hour if you want a fishing rod or two hours with two people only no fishing rod.
Stayed 1 night in Nov 2025

8/10 Good

Angela

Stayed 4 nights in Oct 2025

8/10 Good

Rhonda

Liked: Cleanliness, amenities, property conditions & facilities
Nice place, good location, friendly staff, clean room, good food, beat views, easy access to pool and beach.
Stayed 3 nights in Nov 2025

10/10 Excellent

Cheryl

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Our room was beautiful and spotless. The staff was always polite, handling any inquiry or request. The location is ideal, located on the beach with easy access to the main road. They provide a nice breakfast from 6 to 10 every morning with a variety of options to choose from on top of 24-hour coffee.
Stayed 3 nights in Nov 2025

10/10 Excellent

Laurie

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Beautiful location. The room was very comfortable and clean. The ocean view room with a balcony was perfect. The continental breakfast was great. I would highly recommend staying here.
Stayed 5 nights in Nov 2025

10/10 Excellent

Jeff

Liked: Cleanliness, amenities, property conditions & facilities
Very friendly staff. Nice clean rooms. Property was well maintained. I would definitely stay here again
Stayed 2 nights in Nov 2025

10/10 Excellent

Carlos Alberto

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to relax.
Stayed 5 nights in Aug 2025

8/10 Good

Cody Douglas

Liked: Cleanliness, amenities, property conditions & facilities
Room was very clean, staff very friendly. The resort was nice and well taken care of. A very nice resort to stay without the resort up charges! My wife and I would come back again. Chef Chris, handling the breakfast in the morning is the man!
Stayed 4 nights in Nov 2025

10/10 Excellent

Kimberly

Stayed 6 nights in Nov 2025

8/10 Good

Nancy

Liked: Cleanliness, amenities, property conditions & facilities
The room is always very clean. The only thing that I always have an issue with is there is no vanity space in the bathroom for toiletries. A shelf or something would be a nice addition to store toiletries.
Stayed 2 nights in Nov 2025

10/10 Excellent

Karl

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
The room was very nice, AC worked well, breakfasts were very good - my commendations to the man that cooked omelets in the morning. We spent most of our time on the beach overlooking the ocean.
Stayed 4 nights in Oct 2025

10/10 Excellent

Robin

Liked: Cleanliness, staff & service, amenities
Our room was very clean and the property was beautifully kept. The location was very quite and convient.
Stayed 3 nights in Oct 2025

10/10 Excellent

Andrew, Charlotte

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location right on the beach with 2 pools. Entire place looks to have been totally renovated in the last year or two, and the rooms and fixtures all look brand new. Easy parking, nice breakfast included
Stayed 1 night in Nov 2025

8/10 Good

ELIZABETH

Stayed 2 nights in Nov 2025

10/10 Excellent

Kelli

Travelled with family
Liked: Staff & service, amenities
Our standard queen room was spacious. It was spotless, great amenities and a wonderful polite staff. Housekeeping was great. The complementary breakfast was delicious. Chefs Krystal and Mr. Chris whipped up delicious omelets and pancakes.
Stayed 3 nights in Nov 2025

10/10 Excellent

Kendra

Liked: Cleanliness, property conditions & facilities
We ended up there because the Air BnB that we had booked was having the floors painted our last night. We had to find something else at the last minute. Chesapeake Beach Resort was beautiful! There was so much to do. We wish we would have stayed there our whole trip. We will definitely be staying again if we go back to the Keys!
Stayed 1 night in Nov 2025

6/10 Okay

Faye

Travelled with partner, Travelled with group
Liked: Cleanliness
Disliked: Amenities
The room was beautiful and the staff was great. However, both of the pools were dirty inside and on the patio around the pools. The tiki bar wasn't finished with unfinished plywood on top. The breakfast was excellent until the last two days when they ran out of fruit and eggs. There's no beach to speak of ... only rocks. I wouldn't recommend it.
Stayed 3 nights in Nov 2025

10/10 Excellent

Kelley

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything about the property was impressive. It was a great stay, and we would stay there again.
Stayed 2 nights in Nov 2025

10/10 Excellent

Alex, fort myers

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Feom start to finsh i have nothing but 100 stars for this place! Check in was a breeze, view was perfect. Privacy, quiet, except noise from main road but once you close the sliding door and curtains good night! The complimentary breakfast was a hit and definitely filling, you eat and can sit right next to the water and watch the fish and sunrise! Pleanty of charis on beach! Parking was perfect and covered! Bed was comphy and shower was amazing!
Stayed 3 nights in Nov 2025

8/10 Good

Dwight

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Clean room, friendly staff, perfect setting, good breakfast
Stayed 7 nights in Oct 2025