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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
Water view
Deluxe Ocean View Two Queen Suite | Balcony
Hypo-allergenic bedding, pillowtop beds, laptop workspace
43-inch flat-screen TV with cable channels, TV

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Breakfast included
  • Free WiFi
  • Restaurant

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
(46 reviews)
  • Ocean view
  • 366 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.6 out of 10
Exceptional
(88 reviews)
  • Ocean view
  • 364 sq ft
  • 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
  • 540 sq ft
  • 1 bedroom
  • 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)
  • Ocean view
  • 364 sq ft
  • 1 bedroom
  • 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)
  • Ocean view
  • 366 sq ft
  • 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)
  • Ocean view
  • 366 sq ft
  • 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
  • 540 sq ft
  • 1 bedroom
  • 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
(60 reviews)
  • 307 sq ft
  • 1 bedroom
  • 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
(95 reviews)
  • 272 sq ft
  • 1 bedroom
  • 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

9.2 out of 10
Wonderful
(24 reviews)
  • 307 sq ft
  • 1 bedroom
  • 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

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

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

9.2 out of 10
Wonderful
(17 reviews)
  • Ocean view
  • 527 sq ft
  • 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
  • 650 sq ft
  • 1 bedroom
  • 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)
  • Resort view
  • 646 sq ft
  • 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, pillowtop beds, laptop workspace

Standard King Villa

  • Resort view
  • 323 sq ft
  • 1 bedroom
  • 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)
  • Resort view
  • 517 sq ft
  • 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, pillowtop beds, laptop workspace

ADA King Efficiency Villa

  • Resort view
  • 517 sq ft
  • 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, pillowtop beds, laptop workspace

Premium 1-Bedroom Ocean View Villa

  • Ocean view
  • 700 sq ft
  • 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
  • 829 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Ocean View King Efficiency Villa

  • Ocean view
  • 517 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

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Exterior

Islander Resort

Matecumbe
  • On private beach
  • Pool
  • Pet friendly
  • Parking included
9.2 out of 10, Wonderful, 1,011 reviews
$410 nightly
The price is $461
Mar 2 - Mar 3
Total with taxes and fees
Islander Resort

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
  • Islamorada Brewery & Distillery - 2 min drive - 1.5 miles
  • Theater of the Sea - 2 min drive - 1.5 miles
  • Bud n' Mary's Dive Center - 5 min drive - 4.6 miles

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 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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  • On private beach
  • Pool
  • Pet friendly
  • Parking included
9.2 out of 10, Wonderful, 1,170 reviews
$343 nightly
The price is $386
Mar 1 - Mar 2
Total with taxes and fees
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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
  • 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 Feb 11, 2026, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Feb 12, 2026 start from $352.49, 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 Windley Key Fossil Reef Geological State Park and Florida Keys Brewing Co. 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.

Is Chesapeake Beach Resort good for couples?

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, this hotel doesn't have a spa tub.

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. 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

Nafeeza

Stayed 2 nights in Dec 2025

8/10 Good

James

Traveled 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

Traveled 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

Traveled 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

Traveled 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

Traveled 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

Traveled 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

Traveled 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

Traveled 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

Traveled 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

Traveled with group, Traveled with partner
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

Traveled 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

Traveled 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

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