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
Water view
1 bedroom, hypo-allergenic bedding, pillow-top beds, laptop workspace
Outdoor spa tub
Balcony

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

2-Bedroom Villa

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

Standard King

9.4 out of 10
Exceptional
(28 reviews)
  • 25 sq m
  • Sleeps 3
  • 1 King Bed

King Efficiency Villa

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

Standard Doubles

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

Standard King with Sleeper Sofa

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

Hearing Impaired Ocean View Queens

10.0 out of 10
Exceptional
(2 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Hearing Impaired Ocean View King Suite

8.6 out of 10
Excellent
(4 reviews)
  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

ADA King Efficiency Villa

  • 48 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

Premium 1-Bedroom Ocean View Villa

  • 65 sq m
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

Deluxe Ocean View Two Queen Suite

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

Ocean View King

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

Ocean View King Suite

9.4 out of 10
Exceptional
(13 reviews)
  • 49 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

Ocean View Queens

9.8 out of 10
Exceptional
(42 reviews)
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

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

Standard Queens

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

Standard King Villa

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

Premium Ocean View King Villa

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

ADA Ocean View Queens

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

ADA Ocean View King Suite

8.0 out of 10
Very good
(3 reviews)
  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed

ADA Ocean View King

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

Similar properties

About this property

Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools
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. A complete renovation of Chesapeake Beach Resort was completed in January 2020.

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.

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 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
  • 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
  • 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

Access methods

Staffed front desk

Pets

  • Pets: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
  • 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 stay
  • 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
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.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

We should mention

  • Pool access available from 7:00 AM to 10:30 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. 1070 out of 1487 reviews
Rating 8 - Good. 249 out of 1487 reviews
Rating 6 - Okay. 93 out of 1487 reviews
Rating 4 - Poor. 41 out of 1487 reviews
Rating 2 - Terrible. 34 out of 1487 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

david

Stayed 2 nights in Apr 2025

8/10 Good

John

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

10/10 Excellent

Jen

Stayed 1 night in Apr 2025

10/10 Excellent

Dianelis

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excelent
Stayed 1 night in Mar 2025

8/10 Good

Nicole

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful view from room , breakfast included is nice due to price of room
Stayed 4 nights in Apr 2025

8/10 Good

Tom

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

10/10 Excellent

jamie

Stayed 2 nights in Apr 2025

10/10 Excellent

Yoxaris

Stayed 4 nights in Apr 2025

8/10 Good

Kurt, Miami

Travelled with family
We made a stop over at this place on our way from Miami to Ley West. A convienient, nice place with good restaurants near by.
Stayed 1 night in Apr 2025

10/10 Excellent

Kirstin

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property location was good. The views were beautiful. Lots of lounge chairs and space for everyone. We went during the week and felt like we were in an exclusive place. Front desk staff were beyond excellent. Restaurant next door was fabulous. Fresh fish and great drinks. The bed in the Villa was super comfy. Plenty of towels and amenities. I give it a great recommendation .
Stayed 4 nights in Apr 2025

10/10 Excellent

Jennifer

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great views, easy beach and pool access. 2 hours of included daily use of kayaks and paddle boards. Quiet, relaxing, friendly staff. Great location between Miami and Key West.
Stayed 5 nights in Apr 2025

10/10 Excellent

Steven

Liked: Cleanliness, staff & service, property conditions & facilities
This is a wonderful spot. The staff was welcoming and our room was wonderful. We’ll be back!
Stayed 2 nights in Apr 2025

10/10 Excellent

Cory

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very friendly staff that was extra accommodating to us! Clean, quiet, beautiful grounds! Would definitely stay again!
Stayed 1 night in Apr 2025

10/10 Excellent

Pamela, Dunkirk

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such a nice hidden gem in the keys! Lots of beach space, 2 pools, breakfast included was a nice bonus.
Stayed 1 night in Apr 2025

10/10 Excellent

Jan

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Apr 2025

10/10 Excellent

WD

Stayed 1 night in Apr 2025

8/10 Good

Amy

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

Nice Resort for the Money

I was looking for a one night stay in Islamorada that wouldn't break the bank, but still be comfortable and clean. The Chesapeake Resort fit the bill! Rooms have been updated and resort was clean and quiet. It has a nice area for sunning and two pools. There isn't a restaurant or bar on site, but they do offer a very good continental breakfast with made to order eggs and a bar cart with quality liquor, beer, and wine. Also, two restaurants are within walking distance.
Stayed 1 night in Mar 2025

10/10 Excellent

Brian

Liked: Cleanliness, staff & service, property conditions & facilities
The property was clean and and everything was well maintained.
Stayed 4 nights in Apr 2025

4/10 Poor

Angelina

Disliked: Cleanliness, property conditions & facilities
Stayed 2 nights in Apr 2025

10/10 Excellent

Tammy M.

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely heaven on Earth! Gorgeous grounds beautiful room. The property was beyond exceptional in everyday!
Stayed 2 nights in Apr 2025

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

Travelled 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

Travelled 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

Travelled 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