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

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi

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
(49 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
(98 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

8.6 out of 10
Excellent
(8 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

8.8 out of 10
Excellent
(19 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
(3 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
(62 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
(100 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
(25 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
(37 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
(19 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

9.4 out of 10
Exceptional
(3 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

View all photos for Ocean View King Efficiency Villa

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

Ocean View King Efficiency Villa

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

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  • Pool
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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
  • 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

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

About this property

Chesapeake Beach Resort

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
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8.8 out of 10, Excellent, 1,263 reviews
$291 nightly
The price is $328
Apr 20 - Apr 21
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
Safety features at this property include a fire extinguisher
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. 
  • Onsite safety features include a fire extinguisher.

Additional information about polices, regulations, and more:

  • Pool access available from 8:00 AM to 6:00 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 Apr 5, 2026, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on May 4, 2026 start from $287, including 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 there parking available at Chesapeake Beach Resort?

Yes, there is wheelchair-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 8:00 AM and 6:00 PM.

Is Chesapeake Beach Resort a good place to stay for couples?

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

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.

Does Chesapeake Beach Resort have connecting rooms available?

No, this hotel doesn't feature connecting guestrooms.

Are there rooms with balconies at Chesapeake Beach Resort?

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

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1246 out of 1682 reviews
Rating 8 - Good. 267 out of 1682 reviews
Rating 6 - Okay. 96 out of 1682 reviews
Rating 4 - Poor. 42 out of 1682 reviews
Rating 2 - Terrible. 31 out of 1682 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

9.0/10

Amenities

9.2/10

Property conditions & facilities

Reviews

10/10 Excellent

Robert

Stayed 2 nights in Dec 2025

10/10 Excellent

Andre

Stayed 3 nights in Jan 2026

6/10 Okay

Briana

Liked: Cleanliness
Stayed 2 nights in Jan 2026

10/10 Excellent

Benny

Liked: Cleanliness
Stayed 2 nights in Dec 2025

10/10 Excellent

Gerta

Liked: Cleanliness, staff & service, property conditions & facilities
One of the most beautiful hotel I have ever stayed. It's on the pricey side, but worth staying it. We loved everything about it.
Stayed 2 nights in Dec 2025

10/10 Excellent

Nelly

Traveled with family
Liked: Cleanliness, staff & service, amenities
Yadira at the front desk greeted us with glass of champagne. The room attendant brought us extra towels immediately and the rooms are fantastic. Comfortable beds and huge bathrooms. The resort feels like a high end resort. Too bad we’re only staying one night!!
Stayed 1 night in Jan 2026

6/10 Okay

Brianna

Traveled with family
Liked: Cleanliness, staff & service, amenities
Pros: staff is very friendly and hardworking, the pool area was great, location was close to lots of shops and restaurants, loved the ability to rent fishing poles, kayaks/paddleboards, and bikes for up to 2 hours a day for free. Cons: the room we had only had one bed and a pullout couch which was super uncomfortable, you could feel the springs no matter where you layed. We ran out of toilet paper and lotion and had to call multiple times before someone came to restock. Very expensive for what you get.
Stayed 5 nights in Dec 2025

10/10 Excellent

Navya

Very clean room and friendly staff. They were very eager to answer our questions about the area/amenities and quick to get our sink fixed, even though it was late at night! Would definitely recommend them in you're spending a day in the area.
Stayed 1 night in Dec 2025

8/10 Good

Kory

Liked: Cleanliness, staff & service, property conditions & facilities
Good location and a nice resort all in all. However, the rooms are very noisy. You can hear everything being said in the rooms around you.
Stayed 2 nights in Dec 2025

10/10 Excellent

Shankar B

Liked: Cleanliness, amenities, property conditions & facilities
Room was spotless. Great breakfast. Amazing view of the sunrise.
From our balcony
Stayed 1 night in Jan 2026

10/10 Excellent

David

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Eggs to order fresh.
Stayed 6 nights in Dec 2025

10/10 Excellent

Donghyun

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Breakfast omr
Stayed 2 nights in Dec 2025

8/10 Good

Dionicio

Stayed 1 night in Dec 2025

10/10 Excellent

Julie

Traveled with pets, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Entire resort was clean and beautiful. Quiet location with beautiful rooms. We will return.
Stayed 2 nights in Dec 2025

8/10 Good

DAWNE, Tampa

Traveled with partner
Liked: Property conditions & facilities
Staff was wonderful
Stayed 3 nights in Dec 2025

10/10 Excellent

Kunfeng

Traveled with family and small children, Traveled with group, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
They have warm swim pool and hot tub! Nice and clean.
Stayed 4 nights in Dec 2025

10/10 Excellent

Changyi

Stayed 4 nights in Dec 2025

10/10 Excellent

venkat

Traveled with group, Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Great little place on highway 1 in Islamorada. Renovated, clean great bathrooms, balconies, 2 heated pools and a jacuzzi, wonderful breakfast excellent and friendly staff and a welcome champagne drink 😃. Wait did i forget to mention amazing ocean views with ample beach chairs and umbrellas. They have free fishing and kayaking activities. Two families of 4 stayed and had a great time. This place is a gem.
Stayed 2 nights in Dec 2025

6/10 Okay

Kait

Overall, our stay was okay!
Stayed 3 nights in Dec 2025

6/10 Okay

Pamela, West Palm Bch

We arrived at 3:15 there was no room available for us. So we got in a bad mood. We had to wait for the turtle club (slowwww)to clean it we finally were in our room 2 hours later. Check in time is 4pm it was after 5 by the time we we could get keys was very frustrating Breakfast was ok amenities were just ok.
Stayed 3 nights in Dec 2025

10/10 Excellent

Jordan

Stayed 3 nights in Dec 2025

10/10 Excellent

James

Stayed 2 nights in Dec 2025

8/10 Good

Sreenivasa Reddy

Stayed 4 nights in Dec 2025

10/10 Excellent

Maira

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great breakfast.... they had everything that i liked in particular. They had healthy options.. not a big place so it didnt seem overwhelmed with options just the right amount of options. Place i staid had an amazing ocean view :)
Stayed 1 night in Dec 2025

10/10 Excellent

Noemy

Traveled with family
Liked: Cleanliness, staff & service, amenities
Front desk help were Amazing, everyone working there were very friendly. Clean room, Super great breakfast, which is free and sitting outside to enjoy the beautiful scenery💝
Stayed 1 night in Dec 2025

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