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Chesapeake Beach Resort

2.5 star property
Beachfront hotel with 2 outdoor pools in Islamorada

Choose dates to view prices

your current months are October, 2024 and November, 2024.
October 2024
November 2024

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Aerial view
Balcony
Water view
Hypo-allergenic bedding, pillowtop beds, laptop workspace

Reviews

9.0 out of 10

Wonderful

Popular amenities

  • On private beach
  • Pool
  • 24/7 front desk
    24/7 front desk
  • Pet-friendly
    Pet-friendly
  • Housekeeping
    Housekeeping
  • Air conditioning
    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

Flat-screen 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

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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
Chesapeake Beach Resort offers its guests 2 outdoor swimming pools and a private beach. Chesapeake Beach Resort also features multilingual staff and concierge services.

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
  • 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

  • Cable channels
  • Flat-screen TV

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

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. 921 out of 1383 reviews" "
Rating 8 - Good. 272 out of 1383 reviews" "
Rating 6 - Okay. 108 out of 1383 reviews" "
Rating 4 - Poor. 49 out of 1383 reviews" "
Rating 2 - Terrible. 33 out of 1383 reviews" "

9.2/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

9.0/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

10/10 Excellent

Sonia

Stayed 2 nights in Jun 2024

10/10 Excellent

Karina

Stayed 1 night in Jun 2024

10/10 Excellent

Courtney

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Jun 2024

8/10 Good

Ryan

Stayed 1 night in Jun 2024

10/10 Excellent

Jonathan

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Jun 2024

8/10 Good

DIUSMARY

Liked: Cleanliness, staff & service, property conditions & facilities
Muy buena experiencia muy amable todo el servicio
Stayed 1 night in Jun 2024

10/10 Excellent

Danielle

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved it here! Very clean and convenient. The staff was amazing and helpful.
Stayed 4 nights in Jun 2024

10/10 Excellent

Carlos

Travelled with family, Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
All of the above!!
Stayed 2 nights in Jun 2024

10/10 Excellent

Arianna

Liked: Cleanliness, staff & service, property conditions & facilities
The personal very professional. The room is nice and clean, remodeled but the bathroom is small. Free kayak and convenient located close to restaurants and ice cream place.
Stayed 2 nights in Jun 2024

10/10 Excellent

Kelly

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Honeymooners special
Stayed 4 nights in Jun 2024

10/10 Excellent

Deborah

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Favorite getaway
We love this property. We come back every year. Each year they make improvements. Staff is super nice.
Stayed 2 nights in Jun 2024

10/10 Excellent

Fanni

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Jun 2024

10/10 Excellent

joyce

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We have stayed at this property several times. They’ve made some very nice improvements including a nice fresh breakfast (omelettes, waffles, fruits, cereals, etc.) room, updates to the buildings ( fresh and new). We were granted an upgrade to a one bedroom unit with a balcony and oceanview. It’s also close to many restaurants. We will return.
Stayed 3 nights in Jun 2024

10/10 Excellent

Heather

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We went back for a second time , the resort is honestly one the most welcoming small resorts we've been to. The rooms are clean. The staff is very accommodating and we had a beautiful stay. We will keep going back ❤️
Stayed 4 nights in Jun 2024

8/10 Good

Rob

Liked: Cleanliness, staff & service, property conditions & facilities
the rooms are small& and that is an issue.
Stayed 2 nights in Jun 2024

8/10 Good

Timothy

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice gem on the highway...
Great little place we picked on our trip to Key West. We wanted to be a bit closer to Key West when we came from the Miami Airport - we didn't want to travel from MIA to Key West on the same day we came in. This was a nice place and wish we had more time to spend there. Reasonably priced and convenient for us. The breakfast was great.
Stayed 1 night in May 2024

10/10 Excellent

West

Travelled with family
Liked: Staff & service, amenities, property conditions & facilities
Great location clean friendly staff
Stayed 4 nights in Jun 2024

8/10 Good

Brittany

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was very quiet and peaceful and the beach view was beautiful. Very clean rooms as well a plus for me and complementary breakfast.
Stayed 2 nights in Jun 2024

10/10 Excellent

Hansel

Stayed 5 nights in Mar 2024

8/10 Good

Randy

Liked: Cleanliness, staff & service, property conditions & facilities
Nice place
Stayed 2 nights in Jun 2024

8/10 Good

Jose

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We really enjoyed our stay. There are 2 pools. One has a hot tub. The room was spacious and had a great view of the ocean. There is a beach area, but lots of seaweed kept us from swimming in the area. The breakfast in the morning was great. Lots of food to choose from. We had omelettes most mornings and I had waffles as well. We saw 2 manatees in the cove next to the breakfast area as well as a dolphin on another day. There is a marina within walking distance where you can book fishing trips. It is a quiet property. I would definitely recommend this property.
Stayed 5 nights in Jun 2024

4/10 Poor

Jessica

Travelled with family
Liked: Property conditions & facilities
False advertising
The website shows a resort and this is not a resort it’s a nice hotel with a pool like a holiday inn. Breakfast was awful in a random room. VERY overpriced for what it is. Would not recommend or return
Stayed 5 nights in Feb 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great room. Big. Clean. Nice set up. Beach is 30 sec walk
Stayed 1 night in Jun 2024

10/10 Excellent

Brian

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Great place
Stayed 2 nights in Jun 2024

4/10 Poor

Susan

There was a $50 nonoptional resort fee I didn’t know about. I slept in the room and didn’t do anything else. When I asked it be removed, they said it was standard and ‘included’. Well it wasn’t included on my booking!
Stayed 1 night in Jun 2024