Chesapeake Beach Resort

3.5 star property
Hotel on the beach, with 2 outdoor pools

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

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

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk
  • Breakfast included

Explore the area

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

Room options

Ocean View Queens

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

Ocean View King

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

ADA Ocean View King Suite

8.0 out of 10
Very good
(3 reviews)
  • 540 sq ft
  • 1 bedroom
  • Ocean view
  • Sleeps 4
  • 1 King Bed

ADA Ocean View King

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

ADA Ocean View Queens

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

Hearing Impaired Ocean View Queens

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

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

Standard Queens

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

Standard Doubles

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

Standard King with Sleeper Sofa

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

Standard King

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

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

Deluxe Ocean View Two Queen Suite

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

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

Standard King Villa

  • 323 sq ft
  • 1 bedroom
  • Resort view
  • Sleeps 3
  • 1 King Bed

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

ADA King Efficiency Villa

  • 517 sq ft
  • 1 bedroom
  • Resort view
  • Sleeps 3
  • 1 King Bed

Premium 1-Bedroom Ocean View Villa

  • 700 sq ft
  • 1 bedroom
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

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

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About the neighborhood

Islamorada

Located in Matecumbe within a short walk of History of Diving Museum, Chesapeake Beach Resort is within a mile (2 km) of Windley Key Fossil Reef Geological State Park. This 60-room, 3.5-star hotel has 2 outdoor pools along with a private beach and a marina.

What's nearby

  • History of Diving Museum - 12 min walk - 0.7 miles
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 1.3 miles
  • Theater of the Sea - 2 min drive - 1.5 miles
  • Islamorada Brewery & Distillery - 2 min drive - 1.5 miles
  • Florida Keys Brewing Co. - 4 min drive - 2.5 miles

Getting around

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

Restaurants

  • ‪Tiki Bar - ‬13 min walk
  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Wendy's - ‬2 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Starbucks - ‬15 min walk

About this property

Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools
Chesapeake Beach Resort features a private beach, a marina, and 2 outdoor pools. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and free use of bicycles.
43-inch flat-screen TVs come with cable channels, and guests can stay connected with free WiFi. Pillowtop beds grant a restful night's sleep, and bathrooms offer hair dryers and designer toiletries. Other standard amenities include microwaves, coffee makers, and free local calls.
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.

Similar properties

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

  • This property welcomes pets for USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
  • 2 total (50 lbs is the maximum weight per pet)
  • Restrictions apply
  • For more information, guests can reach out to the property at the number on the booking confirmation
  • Service animals exempt from fees

Property payment types

Important information

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

  • 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 list may not be comprehensive. Fees and deposits might 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
  • Check-in: 4:00 PM
  • Check-out: 11 AM
  • Minimum check-in age: 18
The front desk is open 24 hours a day.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A credit card for incidental charges and a government-issued photo ID may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards. Cash is not accepted. 

Additional information about polices, regulations, and more:

  • Pool access available from 7:00 AM to 10:30 PM.
  • Some facilities may be restricted. For more details, contact the property. Contact information can be found on your booking confirmation.
  • Nearby construction work may cause some noise disturbance.
  • There are no elevators.
  • No rollaway or extra beds are available.

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

Frequently asked questions

Is free cancellation available at Chesapeake Beach Resort?

Chesapeake Beach Resort offers free cancellation on select room rates. For more details, take a look at the cancellation policy on our site.

How much does it cost to stay at Chesapeake Beach Resort?

As of Oct 29, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Nov 2, 2025 start from $114.49, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What can I see close to Chesapeake Beach Resort?

This hotel is situated in Matecumbe within a short 11-minute walk of History of Diving Museum. You'll also find Founders Park and Islamorada County Park within a short drive.

Will I be able to park at Chesapeake Beach Resort?

Yes, there is accessible parking available.

Does Chesapeake Beach Resort include a casino at the property?

No, Chesapeake Beach Resort doesn't have a casino.

Will I find an indoor pool at Chesapeake Beach Resort?

No, this hotel doesn't have an indoor pool; however, there are 2 outdoor pools. Guests have pool access between 7:00 AM and 10:30 PM.

What do couples enjoy most about Chesapeake Beach Resort?

There are plenty of amenities for couples at this hotel, including a private beach, 2 outdoor pools, and a bar.

Does Chesapeake Beach Resort have a hot tub?

No, there isn't a spa tub at this hotel.

Does Chesapeake Beach Resort have a restaurant with a breakfast menu?

Yes, Chesapeake Beach Resort serves free continental breakfast at Tiki Bar each morning.

Will Chesapeake Beach Resort allow pets to stay for free?

Although they can't stay for free, pets are welcome at Chesapeake Beach Resort for a fee of USD 50.00 per accommodation, per night. A deposit of USD 50.00 per stay is collected.

Are there connecting rooms at Chesapeake Beach Resort?

No, there aren't connecting guestrooms at this hotel.

Are there rooms with balconies at Chesapeake Beach Resort?

Yes, some guestrooms at this hotel offer either a balcony or a deck where guests can enjoy ocean or garden views.

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1127 out of 1548 reviews
Rating 8 - Good. 259 out of 1548 reviews
Rating 6 - Okay. 93 out of 1548 reviews
Rating 4 - Poor. 40 out of 1548 reviews
Rating 2 - Terrible. 29 out of 1548 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

Edgardo

Liked: Amenities
It was new, loved the balcony. Beach sports were nice but needed more lifejacket sizes. Pool amenities were great. Breakfast was good.
Stayed 1 night in Jul 2025

10/10 Excellent

Francisco

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Best breakfast ever right on the ocean 😋
Stayed 1 night in Jul 2025

8/10 Good

vickie

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Ac. Was not great at all. Wish there was more of a variety for food at bar area. We were starving had to order pizza. That was one reason for picking this resort. The breakfast was wonderful tho
Stayed 1 night in Jul 2025

10/10 Excellent

Nicholas

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel is wonderful
Stayed 2 nights in Jul 2025

10/10 Excellent

Adam

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We just got bk from 3 nts here: 2adults 1 child. We absolutely loved this hotel, it was clean, the staff were friendly and the rooms were very clean and the AC was perfect for escaping from the Florida heat and humidity. The breakfast offerings were plentiful, huge shout out to the chef for his waffles for the kids. The outdoor brekfast area was perfect for sitting and staring out to sea and the Islamorada lighthouse. Make sure you check out the entry to the little marina where it narrows at thebentey from the sea - looking into the crystal clear water at dawn and dusk we saw Nurse Sharks, Eels, Horseshoe crabs and so many small and media sized coloured fish. Get up early one morning to checkout the sunrise too!! So worth it! Would highly recommend and we will use again when we are next in Islamorada. A wonderful place to stay.
Stayed 3 nights in Jul 2025

10/10 Excellent

jonathan

Traveled with partner, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Front desk girl i didn't remember her name but she was very kind and proffesional and gave us a beautiful upgrade. Our second time here and will continue to come back.
Stayed 1 night in Jul 2025

10/10 Excellent

Donis

Traveled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Its not to close or to far
Stayed 1 night in Jul 2025

8/10 Good

Jason David

Traveled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
I loved the ocean views! Awesome pool location!
Stayed 2 nights in Jul 2025

10/10 Excellent

Michael

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

Chesapeake is Amazing - Gets better every trip

We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is a GREAT option!
Stayed 4 nights in Jul 2025

10/10 Excellent

Liu M

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
One of my favorite places to have a relaxing trip with the family
Stayed 1 night in Jun 2025

10/10 Excellent

Rachel

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful staff. Vanessa was awesome! We will return
Stayed 2 nights in Jul 2025

6/10 Okay

Mayra

Traveled with family
Stayed 1 night in Jul 2025

10/10 Excellent

Michael

Stayed 1 night in Jul 2025

8/10 Good

Maria

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We were not able to enjoy the beach as it was full of algae, wild plants, and very uncomfortable
Stayed 1 night in Jul 2025

10/10 Excellent

Gabriel

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this property. It had inclusive breakfast and watersports available
Stayed 1 night in Jul 2025

10/10 Excellent

Robert

Stayed 4 nights in Jun 2025

10/10 Excellent

Cody

Liked: Cleanliness, staff & service, property conditions & facilities
Great view! Sweet ppl that work there!
Stayed 1 night in Jul 2025

10/10 Excellent

yumi, vancouver

Liked: Cleanliness, staff & service, property conditions & facilities
Nice hotel, friendly staff. Clean, safe. Good amenities. The free breakfast is nice. A little close to the highway, so you can hear the traffic noise depending on your room location. But all in all, a good place to stay
Stayed 2 nights in Jul 2025

10/10 Excellent

Kristine

Stayed 1 night in Jul 2025

10/10 Excellent

Paco

Traveled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
Great staff friendly as hell. Had a great time relaxed and the place is A1 highly recommend it. I’ll probably be going next week again.
Stayed 2 nights in May 2025

8/10 Good

Luis, BRONX

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

10/10 Excellent

Evelyn

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Absolutely liked everything about this hotel. From delicious breakfast options to cozy rooms with stunning views, everything exceeded my expectations.
Stayed 2 nights in Jul 2025

10/10 Excellent

ANTHONY

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Omar helped us with everything. Great staff. Clean bathroom and great room. Perfectly fine and my 15 year old daughter is picky..of course. Would come again.
Stayed 1 night in Jul 2025

10/10 Excellent

Mehtap

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Excellent!
Stayed 1 night in Jul 2025

10/10 Excellent

jennifer

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

Our New Favorite on the Keys

Stayed 4 nights in Jul 2025