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Chesapeake Beach Resort

2.5 star property
Beachfront hotel with 2 outdoor pools in Islamorada

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Water view
ADA King Efficiency Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace
Premium Ocean View King Villa | Living area | Flat-screen TV
Premium Ocean View King Villa | Water view
Reviews
9.0

Wonderful

Popular amenities

  • Pet friendlyPet friendlyPet friendly
  • Pool
  • On private beachOn private beachOn private beach
  • HousekeepingHousekeepingHousekeeping
  • Air conditioningAir conditioningAir conditioning
  • Business servicesBusiness servicesBusiness services

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Popular LocationHistory of Diving Museum11 min walk
  • Popular LocationTheater of the Sea2 min drive
  • Popular LocationFlorida Keys Brewing Co.3 min drive
  • AirportMiami, FL (MIA-Miami Intl.)91 min drive

Room options

View all photos for 2-Bedroom Villa

2-Bedroom Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

  • 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 | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard King

9/10 Wonderful
  • 272 sq ft
  • 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

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

View all photos for Standard Doubles

Standard Doubles | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Doubles

9.2/10 Wonderful
  • 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

8.3/10 Very Good
  • 307 sq ft
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Hearing Impaired Ocean View Queens

  • 366 sq ft
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View King Suite

Flat-screen TV

Hearing Impaired Ocean View King Suite

  • 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 | 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 | 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

8/10 Very Good
  • 650 sq ft
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

9.6/10 Exceptional
  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King Suite

10/10 Exceptional
  • 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

9.5/10 Exceptional
  • 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 | Hypo-allergenic bedding, pillowtop beds, laptop workspace

Standard Queens

8.8/10 Excellent
  • 307 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Standard King Villa | 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 | Flat-screen 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 | Hypo-allergenic bedding, pillowtop beds, laptop workspace

ADA Ocean View Queens

  • 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

  • 540 sq ft
  • 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

8.2/10 Very Good
  • 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 - 11 min walk
  • Theater of the Sea - 2 min drive
  • Florida Keys Brewing Co. - 3 min drive
  • Founders Park - 5 min drive
  • Bud n' Mary's Dive Center - 6 min drive

Getting around

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

Restaurants

  • Lorelei Restaurant & Cabana Bar - 3 min drive
  • Wahoo's Bar & Grill - 2 min walk
  • Hog Heaven - 3 min drive
  • Starbucks - 14 min walk
  • Whale Harbor Restaurant Marina - 2 min walk

About this property

Chesapeake Beach Resort

Beachfront hotel with 2 outdoor pools in Islamorada
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 summer activities like kayaking.

A complete renovation of Chesapeake Beach Resort was completed in January 2020.

This Islamorada hotel is smoke free.

  • 60 guestrooms or units
  • 2 levels
  • 9 buildings
  • Built in 2020
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Front desk (24 hours)
  • Staff is multilingual
  • Concierge
  • Computer for guest use
  • No smoking on site
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. Flat-screen televisions come with cable channels.

Bathrooms include showers, complimentary toiletries, and hair dryers. 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

Property amenities

Family friendly

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

Parking and transportation

  • Wheelchair-accessible parking available
  • Onsite parking includes off-street options

Things to do

  • 2 outdoor pools
  • 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

  • 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

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: midnight
Early check-in subject to availability
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
Late check-out subject to availability
A late check-out fee will be charged

Special check-in instructions

Front desk staff will greet guests on arrival

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

Fees

Guests will be asked to pay the following charges at the property:

  • Resort fee: USD 40 per accommodation, per night
The resort fee includes:
  • Beach access
  • Beach loungers
  • Beach towels
  • Breakfast
  • Internet access
  • Phone calls
  • Pool access
  • Self parking
  • Sporting facilities or equipment

We've listed all charges provided to us by the property.

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
  • Late check-out is available for a fee (subject to availability)

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
Minimum Spring Break check-in age is 21 years old
This property accepts credit cards; cash is not accepted
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.
    Minimum Spring Break check-in age is 21 years old. 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 May 24, 2024, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on May 29, 2024 start from $229.0, 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 does not offer free breakfast.

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: midnight.

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

9.0

Wonderful

Rating 10 - Excellent. 856 out of 1326 reviews" "
Rating 8 - Good. 275 out of 1326 reviews" "
Rating 6 - Okay. 111 out of 1326 reviews" "
Rating 4 - Poor. 47 out of 1326 reviews" "
Rating 2 - Terrible. 37 out of 1326 reviews" "

9.0/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

9.0/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

10/10 Excellent

Cheryl

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Derrick was amazing customer service. If we ever come back we will definitely stay here. Chesapeake Beach Resort was the best hotel to stay at. All employees were very polite and accommodating. Thanks Again for a very enjoyable stay.
Stayed 2 nights in May 2024

10/10 Excellent

Douglas

Liked: Property conditions & facilities
Stayed 1 night in Apr 2024

10/10 Excellent

Karen

Wonderful staff, amenities and nearby dining…breakfast choices all same daily, kinda boring. Clean and lovely balcony, too!
Stayed 4 nights in Feb 2024

10/10 Excellent

William

Traveled with partner, Traveled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful waterfront property with so many picturesque spots thruout the property. Staff were extraordinary from the front desk to the breakfast room bringing a bowl of iced water to our dog. We’ll be back. No question!!!
Stayed 2 nights in Feb 2024

10/10 Excellent

Eric

Stayed 3 nights in Feb 2024

10/10 Excellent

Paul, Ajax

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved this place. Beautiful spot on the water and a top notch hotel. Staff was amazing and the grounds and the beach perfect.
Stayed 2 nights in Feb 2024

2/10 Terrible

Giovanni

Traveled with partner, Traveled with family
Liked: Staff & service
Disliked: Cleanliness, amenities, property conditions & facilities
This place is super expensive for how crappy everything is! Staff is subpar! Never staying here!
Stayed 2 nights in Feb 2024

8/10 Good

John C

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I liked the villa we had along with the view. I would stay there again. It was a great experience
Stayed 4 nights in Feb 2024

10/10 Excellent

Cynthia

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Great location. Villa was roomy and bright. Property grounds very nice. Not crowded. Would recommend.
Stayed 2 nights in Feb 2024

10/10 Excellent

FRANCISCO

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice quite resort
Stayed 2 nights in Jan 2024