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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
Balcony
Aerial view
Hypo-allergenic bedding, pillowtop beds, laptop workspace
Water view

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Pet-friendly
  • 24/7 front desk
  • Housekeeping
  • Air conditioning

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • History of Diving Museum
    ‪11 min walk‬
  • Theater of the Sea
    ‪2 min drive‬
  • Windley Key Fossil Reef Geological State Park
    ‪2 min drive‬

Room options

View all photos for 2-Bedroom Villa

2-Bedroom Villa

2-Bedroom Villa

  • 60 sq m
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King

Standard King

  • 25 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa

King Efficiency Villa

  • 48 sq m
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

  • 25 sq m
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

  • 29 sq m
  • 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

  • 34 sq m
  • 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

  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

  • 48 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

  • 65 sq m
  • 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

  • 60 sq m
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillowtop beds, laptop workspace

Ocean View King

  • 34 sq m
  • 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

  • 49 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

  • 48 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

Standard Queens

Standard Queens

  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

  • 30 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa | Living area

Premium Ocean View King Villa

  • 77 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

ADA Ocean View Queens

  • 34 sq m
  • 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

  • 50 sq m
  • 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

  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

Similar properties

Exterior

Islander Resort

  • On private beach
  • Pool
  • Pet-friendly
  • Parking included
4.5 out of 5, Wonderful, (1006)
The price is CA $902
per night
CA $1,105 total
includes taxes & fees
7 Mar - 8 Mar
Islander Resort

About the area

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
  • Windley Key Fossil Reef Geological State Park - 2 min drive
  • Florida Keys Brewing Co. - 3 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
  • ‪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

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. 43-inch 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
  • Fence around the pool
  • 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.
  • This property does not have elevators
  • Assistive listening devices available
  • Braille 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 parking
  • Wheelchair-accessible pool
  • Wheelchair-accessible public washroom
  • Wheelchair accessible (may have limitations)

Room amenities

Entertainment

  • 43-inch flat-screen TV
  • Cable channels

Bedroom

  • Air conditioning
  • Bed sheets
  • Blackout drapes/curtains
  • Ceiling fan
  • Hypo-allergenic bedding
  • Pillow-top 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
  • Free local calls
  • Iron/ironing board
  • Laptop-friendly 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 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
  • 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.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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

Chesapeake Beach Resort Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 981 out of 1407 reviews
Rating 8 - Good. 237 out of 1407 reviews
Rating 6 - Okay. 106 out of 1407 reviews
Rating 4 - Poor. 48 out of 1407 reviews
Rating 2 - Terrible. 35 out of 1407 reviews

9.2/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.0/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

10/10 Excellent

Carole

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved it here. Chef Chiris mskes the best omelets.
Stayed 5 nights in Nov 2024

10/10 Excellent

Steve

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great Roadside location, clean & modern
Great location. Friendly staff Great room
Stayed 1 night in Nov 2024

10/10 Excellent

Jacqueline

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Staff was very accommodating. The room was clean and equipped with a microwave, refrigerator, and very comfortable Robes. We loved the view and the peacefulness.
Stayed 3 nights in Nov 2024

10/10 Excellent

Mary

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This wonderful, boutique-like resort deserves more than a five star rating. From the front desk personnel to the kitchen staff, everyone was warm and friendly, and made us feel so very welcome. I'd like to give a special shout out to Derrick, who made it possible for us to have the vacation of my dreams. I can't thank you enough!
Stayed 2 nights in Oct 2024

10/10 Excellent

Julie

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Beautiful views
We had a great stay. The view was amazing. The breakfast was better than we expected. Nary in the sunrise room was so friendly and went above and beyond. We will definitely come back.
Stayed 2 nights in Nov 2024

8/10 Good

ADRIAN

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice place, nice beach, very clean property
Changed the room because the front door has gaps , not well insonorized
Stayed 1 night in Nov 2024

10/10 Excellent

colleen

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful views. Spacious rooms.
Stayed 2 nights in Nov 2024

10/10 Excellent

John

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing property! We had a reservation at a different place and were not happy with it so decided to push on. We couldn’t be happier. The staff is amazing, breakfast is great and there is a private beach. We are so happy we extended our stay.
Stayed 1 night in Nov 2024

10/10 Excellent

David

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beach access!
Stayed 3 nights in Nov 2024

10/10 Excellent

Amy

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a wonderful time. Every morning we had an omelette made by Nary and Chris. The other breakfast options were delicious as well. The rooms were very clean. The views were gorgeous. And it was a nice drive to get to Key West. I will be going back.
Stayed 4 nights in Nov 2024

10/10 Excellent

Amy

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely gorgeous, clean, friendly staff, and great location
Stayed 4 nights in Nov 2024

10/10 Excellent

Kaliany

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Nov 2024

8/10 Good

James, HOLLYWOOD

Liked: Cleanliness, property conditions & facilities
Stayed 2 nights in Nov 2024

10/10 Excellent

Shayan

Liked: Cleanliness, staff & service, property conditions & facilities
Amazing resort and beautiful view. Great staff and very clean. Definitely come back here again. Perfect for staycation .
Stayed 1 night in Nov 2024

10/10 Excellent

Diana

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place
Stayed 1 night in Nov 2024

8/10 Good

Yudimay

Stayed 2 nights in Oct 2024

10/10 Excellent

AMNERYS

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Es un hotel maravilloso de relax y para descansar en familia.
Stayed 1 night in Oct 2024

10/10 Excellent

Amanda

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We booked the ocean view room and our room was beautiful. The room was very clean and the view from the balcony was lovely! Our facorite part was breakfast, where they had an omlete station and they were delicious!! The dining area outside was incredible with awesome ocean views. The hot tub was nice and warm and the views from there were just as incredible as all of the others. The only thing that was a little upsetting was the deposit that i had to put down (the whole cost of my booking) but the good thing is it was refunded the next day.
Stayed 1 night in Oct 2024

10/10 Excellent

Brad

Liked: Cleanliness, property conditions & facilities, room comfort
Good price and nice and clean
Stayed 3 nights in Oct 2024

10/10 Excellent

ROLANDO

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The beautiful prosperity and good staf
Stayed 3 nights in Oct 2024

10/10 Excellent

Mayer

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Excellent
Excellent!
Stayed 1 night in Oct 2024

8/10 Good

Ignas

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 5 nights in Oct 2024

10/10 Excellent

Sara

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I grew up vacationing in Islamorada with my family. It was special to be back with my husband and daughter 20 years later. * Breakfast was delicious!
Stayed 2 nights in Oct 2024

10/10 Excellent

Cristian

Stayed 1 night in Sep 2024

10/10 Excellent

Elyse

Stayed 1 night in Oct 2024