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Chesapeake Beach Resort

3.5 star property
3.5-star beachfront hotel with 2 outdoor pools

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

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

Reviews

9.2 out of 10
Wonderful

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

View all photos for 2-Bedroom Villa

2-Bedroom Villa | Private kitchenette | Microwave, coffee/tea maker

2-Bedroom Villa

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

View all photos for Standard King

Standard King | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King

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

View all photos for King Efficiency Villa

King Efficiency Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

King Efficiency Villa

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

View all photos for Standard Doubles

Standard Doubles | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Doubles

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

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King with Sleeper Sofa

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

View all photos for Hearing Impaired Ocean View Queens

1 bedroom, 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
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA King Efficiency Villa

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

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Premium 1-Bedroom Ocean View Villa

  • 700 sq ft
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double 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
(8 reviews)
  • 650 sq ft
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

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

View all photos for Ocean View King Suite

Ocean View King Suite | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

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

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

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

Ocean View King Efficiency Villa

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

View all photos for Standard Queens

Standard Queens | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Queens

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

View all photos for Standard King Villa

Standard King Villa | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King Villa

  • 323 sq ft
  • Resort view
  • Sleeps 3
  • 1 King 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
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens | 1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View Queens

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

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

10.0 out of 10
Exceptional
(2 reviews)
  • 540 sq ft
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View King

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

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About the neighborhood

Islamorada

On the beach.With a stay at this Matecumbe hotel, you'll be within half a mile (1 km) of History of Diving Museum and 2 miles (3 km) of Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Keys History & Discovery Center are also within 2 miles (3 km).

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

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Hog Heaven - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Florida Keys Brewing Co. - ‬3 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min walk

About this property

Chesapeake Beach Resort

3.5-star beachfront hotel with 2 outdoor pools
Simply walk outside to smell the salt 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 like 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.

  • 60 guestrooms or units
  • 2 levels
  • 9 buildings
  • Built in 2020
  • Continental breakfast (free)
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Coffee in lobby
  • Front desk (24 hours)
  • Staff is multilingual
  • Concierge
  • Computer for guest use
  • No smoking on site
  • Bar or lounge
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include showers, complimentary toiletries, and hair dryers.

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 phones along with free local calls (restrictions may apply). Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

Languages

English, Spanish

Similar properties

Exterior

Amara Cay Resort

  • On private beach
  • Pool
  • Pet friendly
  • Restaurant
4.4 out of 5, Excellent, 1,218 reviews
$261 nightly
The price is $293
Jul 6 - Jul 7
Total includes taxes and fees
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Property amenities

Family friendly

  • 2 outdoor pools
  • Fenced pool
  • In-room microwave
  • Pool gate

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

Things to do

  • 2 outdoor pools
  • Boat tours
  • Fishing
  • Free bicycle rentals
  • Kayaking

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

Room amenities

Entertainment

  • 43-inch flat-screen TV with cable channels

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

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

  • Pets: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
  • Maximum 2 (weight limit: 50 lbs 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.

Property payment types

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

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
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    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. This property accepts Visa, Mastercard, American Express, and Discover. Cash is not accepted. 

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

Frequently asked questions

How close is Chesapeake Beach Resort to the airport?

Chesapeake Beach Resort is 77.5 mi (91-min drive) away from the Miami Intl. Airport (MIA) airport, the closest popular airport to the property.

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

As of Jun 23, 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Jul 1, 2025 start from $203.49, 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.

Does Chesapeake Beach Resort have an airport shuttle?

Airport shuttle services are not available at Chesapeake Beach Resort.

How close is Chesapeake Beach Resort to the beach?

This hotel is on a private beach. Don't forget your sunscreen!

Does Chesapeake Beach Resort offer free breakfast?

Chesapeake Beach Resort offers free continental breakfast every day from 6:00 AM to 10:00 AM.

Is there a casino at Chesapeake Beach Resort?

No, there is no casino at this hotel.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: 3:00 AM.

Is there free parking at Chesapeake Beach Resort?

Free parking is not available at this hotel.

Does Chesapeake Beach Resort have a pool?

Chesapeake Beach Resort features 2 outdoor pools. Guests can enjoy pool access from 7:00 AM to 10:30 PM.

Does Chesapeake Beach Resort have a spa?

There are no spa services available at this hotel.

How close is Chesapeake Beach Resort to downtown Islamorada?

Chesapeake Beach Resort is 1.2 mi away from Islamorada.

Chesapeake Beach Resort Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 1058 out of 1474 reviews
Rating 8 - Good. 245 out of 1474 reviews
Rating 6 - Okay. 93 out of 1474 reviews
Rating 4 - Poor. 44 out of 1474 reviews
Rating 2 - Terrible. 34 out of 1474 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

VIANA

Stayed 2 nights in May 2025

10/10 Excellent

Jennifer

Traveled 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

8/10 Good

Jamie, Bloomington

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 5 nights in Mar 2025

10/10 Excellent

Federico

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

8/10 Good

Ashley

Liked: Cleanliness
Stayed 2 nights in Mar 2025

2/10 Terrible

Michael

Traveled with family
Disliked: Cleanliness, staff & service, amenities, property conditions & facilities
This is not a resort. It is a motor lodge sandwiched between the highway and the water. You literally park under your room. There is a tiny pool. The “beach” is a joke. It’s not sand, but white dirt, and it’s a tiny area. The water is shallow and the bottom is weedy and rocky. I am a cheap person, but my wife and kid and I all decided to leave shortly after checking in (no refund despite the deceptive advertising) and go back to Eden ROC in Miami. Better room, real resort amenities, and less expensive. Chesapeake motor lodge felt like a prison.
Stayed 4 nights in Mar 2025

10/10 Excellent

Lisandra

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean, very beautiful. Sea on the back side love it.
Stayed 1 night in Mar 2025

6/10 Okay

James

Liked: Cleanliness
Stayed 1 night in Mar 2025

10/10 Excellent

Jessica

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful property, comfy, and clean room and excellent service!
Stayed 1 night in Mar 2025

8/10 Good

Jim

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Convenient
Stayed 5 nights in Mar 2025

10/10 Excellent

Christopher

Stayed 1 night in Mar 2025

10/10 Excellent

Keziah

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
So accommodating. Love this place. I could be there all day
Stayed 1 night in Mar 2025

10/10 Excellent

Michelle

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property fit all of our needs. Our Villa was immaculately clean. All the staff was extremely accommodating and went out of their way to be polite and warming. The arrival champagne glass was so nice after our trip and the beach was great, the water was amazing. I will definitely book this resort when we come back down to the Keys and that won’t be long because we live in Florida. If you want to stay in Islamorada, you should absolutely put this place in your top 3. They serve drinks and has two poles and people were snorkeling and just have a great time. Everyone that we spoke to absolutely loved this place. Robes and the shoes were so nice. I would absolutely give this place five stars out of five. For a 10 out of 10 experience for your trip in the Florida Keys trust me your hotel or resort you should not have any concerns or questions or drama.
Stayed 2 nights in Mar 2025

10/10 Excellent

theodore

Stayed 4 nights in Mar 2025

10/10 Excellent

Heike

Stayed 1 night in Mar 2025

10/10 Excellent

Liang Eva

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
We had a great spring break. The resort is clean, conveniently located.
Stayed 5 nights in Mar 2025

8/10 Good

Robert

Liked: Cleanliness, staff & service, property conditions & facilities
Nice people, quiet resort.
Stayed 3 nights in Mar 2025

10/10 Excellent

max

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay, clean room!
Stayed 2 nights in Mar 2025

10/10 Excellent

Gladys

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Secluded quiet, excellent to relax
Stayed 1 night in Mar 2025

10/10 Excellent

Tracy

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff are super friendly. Our room was clean and well laid out. Make sure to use the 2 hours free paddle boarding that comes with your reservation, we seen sharks, manatees and lots of fish and hermit crabs. The breakfast in the morning is fresh and a great selection.
Stayed 2 nights in Mar 2025

10/10 Excellent

Rebecca, Okeechobee

Liked: Cleanliness, staff & service, property conditions & facilities
I love this place! Lovely maintained grounds, very clean and modern rooms. The sunrises are amazing. Front desk, cleaning staff, breakfast staff and bar staff were friendly and very accommodating. I am going to miss the great cooked to order omelets and drinks by the pool and beach. I would recommend this resort to anyone with families or adults only. We enjoyed the beautiful grounds which are lush and well maintained. The chess, checkers and kayak rentals plus the tiki boat rentals to the sandbar are an added bonus. This was betterthan an all inclusive resort in the Caribbean for us. Paradise in the Keys- close to shopping and great restaurants. Better than traveling south where it gets a little crazy for us. We plan to come back as often as we can.
Stayed 3 nights in Mar 2025

8/10 Good

Darlis

Stayed 2 nights in Feb 2025

10/10 Excellent

Sue Ellen

Liked: Cleanliness, staff & service, property conditions & facilities
We asked for & received early check-in. The staff was friendly & helpful & everything was immaculate! Wonderful breakfast included! Nice beach area with lots to do. We will definitely stay here again!
Stayed 1 night in Mar 2025

10/10 Excellent

Derick

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Most amazing views
Stayed 2 nights in Feb 2025

10/10 Excellent

Patrick

Liked: Cleanliness, amenities
Love this place
Stayed 2 nights in Feb 2025