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Chesapeake Beach Resort

Property class: 3.5

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Photo gallery for Chesapeake Beach Resort

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

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free Wi-Fi

Explore the area

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

Room options

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

9.6 out of 10
Exceptional
(51 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
(99 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

8.6 out of 10
Excellent
(8 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

8.8 out of 10
Excellent
(20 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 | Hypo-allergenic bedding, pillow-top beds, laptop workspace

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
(3 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

8.8 out of 10
Excellent
(5 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 | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Queens

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

View all photos for Standard Doubles

Standard Doubles | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard Doubles

9.2 out of 10
Wonderful
(102 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 | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King with Sleeper Sofa

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

View all photos for Standard King

Standard King | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Standard King

9.6 out of 10
Exceptional
(39 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
(19 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 | Hypo-allergenic bedding, pillow-top beds, laptop workspace

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

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

King Efficiency Villa

9.6 out of 10
Exceptional
(4 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 | Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA King Efficiency Villa

10.0 out of 10
Exceptional
(1 review)
  • 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 | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Premium 1-Bedroom Ocean View Villa

8.0 out of 10
Very good
(1 review)
  • 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 | 43-inch flat-screen TV with cable channels, TV

Premium Ocean View King Villa

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

View all photos for Ocean View King Efficiency Villa

Ocean View King Efficiency Villa | Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Efficiency Villa

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

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About this property

Chesapeake Beach Resort

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 features coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include a shower, complimentary toiletries and hairdryers.

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 telephones along with free local calls (restrictions may apply). Additionally, rooms include an iron/ironing board and a ceiling fan. Housekeeping is offered on a daily basis 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 aged 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.

The free breakfast at Chesapeake Beach Resort gets high marks from our customers. During your stay, you'll be within walking distance of History of Diving Museum. Enjoy features like free WiFi in public areas, plus 2 outdoor pools and a marina.
  • Free continental breakfast served daily
  • Free Wi-Fi (speed: 100+ Mbps (good for 1–2 people or up to 6 devices))
  • Enjoy drinks at the bar/lounge
  • Take a swim in the 2 outdoor pools
  • Amenities include a computer, multilingual staff and coffee/tea in a common area
  • On-site recreation includes a private beach, complimentary bicycles and kayaking
  • Guests really like the accommodation for the cleanliness and spaciousness
  • 11 minutes on foot from History of Diving Museum and a 2-minute drive from Windley Key Fossil Reef Geological State Park
  • Pets welcome for a fee (restrictions apply)
Simply walk outside to smell the salty 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 such as a marina and complimentary bicycles.

Free breakfast is available daily. You can enjoy a drink at the bar/lounge. A computer station is on site and WiFi is free in public spaces.

This 3.5-star Islamorada hotel is smoke free.

Guests are served a free continental breakfast daily from 6:00 AM to 10:00 AM.
Tiki Bar – On-site 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 and check-out are available
Late check-in subject to availability
Minimum check-in age - 18

Check-out

Check-out before 11 AM
Contactless check-out
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: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per night
  • Maximum 2 (weight limit: 50 lb 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.

Payment types at the property

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 night
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • A late check-out fee will be charged

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

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Front desk staff will greet guests on arrival at the property.

We should mention

  • Pool access available from 8:00 AM to 6:00 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

9.2

Wonderful

Rating 10 - Excellent. 1266 out of 1713 reviews
Rating 8 - Good. 277 out of 1713 reviews
Rating 6 - Okay. 97 out of 1713 reviews
Rating 4 - Poor. 42 out of 1713 reviews
Rating 2 - Terrible. 31 out of 1713 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

Reviews

10/10 Excellent

Diane

Liked: Cleanliness, staff & service, amenities
I had a wonderful time Beautiful place. Great staff
Stayed 4 nights in Jan 2026

10/10 Excellent

Lauren, St. Louis

Liked: Cleanliness, amenities, property conditions & facilities
Love!!!!! The private beach, and the two polols and the personalized breakfast bar and the views were all perfect. Looking forward to stay again.
Stayed 1 night in Jan 2026

8/10 Good

Yu mi

Stayed 1 night in Jan 2026

10/10 Excellent

Rodney

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Friendly and helpful staff. Beautiful setting. Very nice breakfast included with made-to-order omelets. Great base to explore other things the Keys has to offer. Restaurants in walking distance.
Stayed 2 nights in Jan 2026

10/10 Excellent

Konrad

Stayed 1 night in Jan 2026

10/10 Excellent

Nadine

Liked: Cleanliness, staff & service, amenities
Clean room. Nice staff. Champagne on arrival. Two warm pools right on the ocean. A nice guitar guy for entertainment on Saturday. Breakfast was included. Made to order omelette, pancake, etc. watched them make a Mickey pancake for a little girl who smiled from ear to ear.
Stayed 1 night in Jan 2026

8/10 Good

ANNA

Liked: Cleanliness, staff & service, amenities
.
Stayed 1 night in Jan 2026

10/10 Excellent

dian

Liked: Cleanliness, staff & service, amenities
Great room, wonderful staff and good location
Stayed 2 nights in Jan 2026

10/10 Excellent

Alicia

Liked: Cleanliness, amenities, property conditions & facilities
Great stay clean room lots of resort amenities included. Champagne at check in was a nice touch
Stayed 2 nights in Jan 2026

10/10 Excellent

Jacqueline

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
This is our second time staying there and we really like it!! It is so cute, very clean and the location is close to many bars and restaurants. Uber/Lyft is very accessible too. The breakfast is also nice and you get a nice view of the water too.
Stayed 2 nights in Dec 2025

10/10 Excellent

Diane

Liked: Cleanliness, amenities, property conditions & facilities
Beautiful beach area. Friendly staff.
Stayed 1 night in Jan 2026

10/10 Excellent

Michelle Marie

Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
The room was clean and bright, the view was amazing, and the staff were always friendly, helpful and courteous! The breakfast with fresh made omelets was also a pleasure!
Stayed 6 nights in Jan 2026

10/10 Excellent

Nancy

Liked: Cleanliness, amenities, property conditions & facilities
Staff was very nice. Nice to use the complimentary clear bottom kayaks. Breakfast was good, Didi made a great omelette!
Stayed 2 nights in Jan 2026

10/10 Excellent

Donna

Liked: Cleanliness, amenities, property conditions & facilities
The workers were excellent. The breakfast staff were wonderful. Chris, Didi,Emily. The were so helpful. You have a great bunch of workers. I can't say enough about the staff.
Stayed 7 nights in Jan 2026

10/10 Excellent

Zohreh, edmonds

Liked: Cleanliness, amenities, property conditions & facilities
Room was very clean newly remodeled Staff were very nice Nice breakfast and amenities Beautiful view The property has two buildings There is one building on the beach which has very nice view ,but the other building is near a busy highway with highway noise When I was making the reservation for the beach front rooms once I would pay they would switch the room and say the beach front were no longer available although the site still listed them as available It was like bait and switch which I thought was dishonest I am not sure it was the fault of the Expedia app that still showed the beach front rooms were available or the hotel But they were nice to switch me to the beach front rooms the next day I would definitely stay there again
Stayed 2 nights in Jan 2026

2/10 Terrible

Hugo

Liked: Cleanliness
Disliked: Staff & service, amenities
Tuve una muy mala esperiencia en el check in me hicieron esperar 2 horas, también en la mañana un empleado de mantenimiento abrió la puerta sin avisar invadiendo minorivacidad
Stayed 1 night in Jan 2026

10/10 Excellent

Mayra

Stayed 2 nights in Jan 2026

8/10 Good

Tracy

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 6 nights in Dec 2025

8/10 Good

Susan E

Travelled with family
Liked: Staff & service, property conditions & facilities
Same toothpaste smear on sink when we arrived, still there for 4 days. I cleaned around it myself just to see. Very disappointed. I chlorox wiped the whole room. Fortunately, that was the only issue. This was my second stay. I would come back and I will recommend you.
Stayed 8 nights in Jan 2026

10/10 Excellent

Kurt

Liked: Cleanliness, staff & service, property conditions & facilities
Wonderful breakfast with omelettes cooked to order, great pancakes, fresh fruit, etc. very pleasant staff and beautiful beach area.
Stayed 2 nights in Jan 2026

10/10 Excellent

Harry

Travelled with family
Liked: Cleanliness, staff & service
Staff was great room was very clean
Stayed 2 nights in Jan 2026

10/10 Excellent

Fritz

Liked: Cleanliness, amenities, property conditions & facilities
Yes and yes!
Stayed 1 night in Jan 2026

10/10 Excellent

Annie

Liked: Cleanliness, amenities, property conditions & facilities
Wonderful nice and clean staff 👌 very nice special specially staff Vanessa she very helpful and sweet. Is nice place to stay we will come again. Thank you Vanessa again.
Stayed 1 night in Jan 2026

6/10 Okay

Matthew

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Staff was courteous. We arrived late in the evening and our room was next to the lobby. The rooms are ok, nothing great. It was a colder evening in January and the room was cold. The front desk offered us extra blankets but it would have been nice to have directions on how to control the heating in the room. A decent value for the price, we were only there overnight so room was adequate.
Stayed 1 night in Jan 2026

10/10 Excellent

Victor, HIALEAH

Stayed 1 night in Jan 2026