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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
Hypo-allergenic bedding, pillowtop beds, laptop workspace
Water view
Balcony
Outdoor spa tub

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Bar
  • 24/7 front desk

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

9.8 out of 10
Exceptional
(43 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
(3 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
(21 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
(31 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
(9 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

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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
  • Theater of the Sea - 3 min drive - 1.3 miles
  • Windley Key Fossil Reef Geological State Park - 3 min drive - 1.3 miles
  • Islamorada Brewery & Distillery - 3 min drive - 1.7 miles
  • Bud n' Mary's Dive Center - 10 min drive - 4.8 miles

Getting around

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

Restaurants

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

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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

  • 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 Dec 12, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Jan 5, 2026 start from $171.49, 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 Florida Keys Brewing Co. and Founders Park within a short drive.

Is parking available on site 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 amenities will couples enjoy at Chesapeake Beach Resort?

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

Are there hot tubs at Chesapeake Beach Resort?

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.

Does Chesapeake Beach Resort have connecting rooms?

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

Are there rooms with balconies that I can book 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.

Reviews

Chesapeake Beach Resort Reviews

9.2

Wonderful

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

9.0/10

Eco-friendliness
Rating 10 - Excellent. 1155 out of 1588 reviews
Rating 8 - Good. 267 out of 1588 reviews
Rating 6 - Okay. 95 out of 1588 reviews
Rating 4 - Poor. 42 out of 1588 reviews
Rating 2 - Terrible. 29 out of 1588 reviews

Reviews

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

8/10 Good

Lester

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

Nice...

Very nice staff throughout. The room was nice but has an a/c that runs on the wall all the time. There was also a half in gap on the door to the room that alloeed you to hear all the road noise outside. Breakfast staff and food was great, lagoon kayaking was fun but water not easily accessible except for a thin sand path out into the ocean. Pool was well kept and property very nice.
Stayed 2 nights in Aug 2025

10/10 Excellent

Evelin

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
All is clean the service is nice 💕
Stayed 1 night in Aug 2025

10/10 Excellent

Felipe

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

8/10 Good

Summer

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

10/10 Excellent

Shelby

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice resort, clean quiet, two very nice pools!! Great hot tub!! Paddle boards, and kayaks to use staff was very nice!! highly recommend
Stayed 5 nights in Aug 2025

8/10 Good

Gloria

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent view and nice people
Stayed 2 nights in Aug 2025

10/10 Excellent

NICOLA

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was absolutely amazing! Decorated extremely tasteful, immaculate condition, breakfast was lovely sat outside. Would love to return here.
Stayed 1 night in Aug 2025

8/10 Good

Victoria

Traveled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, clean rooms, great amenities and the staff is very friendly.
Stayed 3 nights in Aug 2025

10/10 Excellent

Elizabeth

Business traveler
Liked: Property conditions & facilities
I enjoyed my stay. I would stay at this hotel again
Stayed 1 night in Aug 2025

10/10 Excellent

Thomas

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was welcoming and accommodating
Stayed 1 night in Aug 2025

10/10 Excellent

Daniel

Liked: Cleanliness, staff & service, property conditions & facilities
Great place
Stayed 1 night in Aug 2025

10/10 Excellent

Denice

Traveled with family
Stayed 2 nights in Aug 2025

10/10 Excellent

Richard

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

Great location

Awesome resort. Lots of amenities. Great for a weekend getaway. Good restaurants nearby
Stayed 2 nights in Aug 2025

10/10 Excellent

Ernesto

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

Perfect Gateway

I would like to thank Venessa for a wonderful seem less check and the champagne welcome and being greated by name was very welcoming the room was very comfortable and the complimentary breakfast was a plus as well as the fact that it is pet friendly with a reasonable fee. I will definitely come back again.
Stayed 2 nights in Aug 2025

10/10 Excellent

Heather

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

Villa 1 was Beautiful!

Amazing stay at Villa 1 at the Chesapeake Resort in Islamorado! Beautiful!
Stayed 2 nights in Aug 2025

10/10 Excellent

Dawn, Auburn

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautifully updated property. Staff is very friendly. They are a bit old school in all the paperwork they require however.
Stayed 3 nights in Aug 2025

10/10 Excellent

Carlos

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

10/10 Excellent

Alan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Overall amazing experience 😊
Stayed 1 night in Aug 2025

10/10 Excellent

Brendon

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

8/10 Good

Linda

Traveled with partner
Liked: Staff & service
Disliked: Cleanliness, amenities, property conditions & facilities
The room given was right by the main road so when you opened door to balcony you could only hear the sounds of the passing cars. Then there was done wall AC unit right about the bed headboard that was blowing hard and there was a thick layer of built up dust over 1 cm thick but when pointed out to front desk nobody could care less. They were not even full my guess is about 20 percent full if that. Other wise a very nice facility that has two pools, private beach and very nice water temp that we were able to really enjoy floating on the kayak
Stayed 1 night in Aug 2025

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