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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 November, 2024 and December, 2024.
November 2024
December 2024

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Water view
Hypo-allergenic bedding, pillowtop beds, laptop workspace
Premium Ocean View King Villa | Living area | 43-inch flat-screen TV with cable channels, TV
Premium Ocean View King Villa | Water view

Reviews

9.0 out of 10

Wonderful

Popular amenities

  • Pool
    Pool
  • 24/7 front desk
    24/7 front desk
  • On private beach
    On private beach
  • 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 | 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

  • 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

  • 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

  • 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

43-inch flat-screen TV with cable channels, 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

  • 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

  • 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

  • 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

  • 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

  • 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 | 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 | 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

  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed
Pool
Islander Resort
On private beach
Pool
Pet friendly
Parking included
4.5 out of 5, Wonderful, (1007)
The price is $288
per night
$379 total
includes taxes & fees
Nov 10 - Nov 11
Islander Resort

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
  • 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
  • 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

  • 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: 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

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 Oct 27, 2024, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on Nov 5, 2024 start from $159.0, 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.

Reviews

9.0

Wonderful

Rating 10 - Excellent. 925 out of 1371 reviews" "
Rating 8 - Good. 260 out of 1371 reviews" "
Rating 6 - Okay. 105 out of 1371 reviews" "
Rating 4 - Poor. 48 out of 1371 reviews" "
Rating 2 - Terrible. 33 out of 1371 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

Brian

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Really nice place. Room and staff were great. Chris the chef was awesome!
Stayed 1 night in Oct 2024

10/10 Excellent

Cabrina

Liked: Cleanliness, staff & service, property conditions & facilities
Very nice and clean
Stayed 1 night in Oct 2024

2/10 Terrible

Sean

Liked: Room comfort
Disliked: Property conditions & facilities
Stayed 2 nights in Jul 2024

10/10 Excellent

adam

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay while in the Keys. Clean rooms and friendly staff.
Stayed 1 night in Mar 2024

8/10 Good

Matthew

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is a very quaint property that is low key and relaxing. The “beach” area was constructed very nicely to give that sand beach feeling, given that it is the keys which is naturally rocky. Rooms were clean and modern and spacious. Will definitely return again.
Stayed 2 nights in Jul 2024

10/10 Excellent

Renee

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Amazing views and beautiful property! The complimentary breakfast was delicious with an omelet bar. Everyone who worked there was willing to help and very kind. We will definitely go back!
Stayed 1 night in Jul 2024

10/10 Excellent

Susan

Traveled with family
Liked: Cleanliness, property conditions & facilities, room comfort
Great place for the whole family
This is a wonderful place to stay for both adults and children. There are 2 nice pools and a very pleasant beach area. My 5 year old granddaughter was thrilled and the rest of the family enjoyed our stay thoroughly.
Stayed 5 nights in Jul 2024

10/10 Excellent

mary

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property was very nice. We had beautiful ocean views from our room. The pools were clean and plenty of loungers, very relaxing. The beach was terrific. Breakfast was included and very good with much variety. The staff was absolutely fantastic. Friendly, helpful and welcoming.
Stayed 2 nights in Jul 2024

10/10 Excellent

Brad

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
What a surprise! This place was amazing. The beach was great, had no idea it was so big and accessible.
Stayed 1 night in Jul 2024

6/10 Okay

Sebastian

Traveled with family
Liked: Staff & service, amenities, property conditions & facilities
Smelly room , either it was from fresh paint or detergent they use to wash sheets . Bathroom door was constantly opening ( sliding door ) . Easy fix , used rolled piece of paper under to keep it closed . Small beach on plus side , also kayaks and surf boards available. Very nice staff . Breakfast available but seemed like they ran out of food very quickly. We went there around 9:45 am ( it was served from 6am to 11 am ) and most of the food was gone . Chef was making omelets for those who wanted to wait in line . Would I stay there again ? Not sure …
Stayed 5 nights in Jul 2024

10/10 Excellent

Anastasiya

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Amazing rooms with awesome accommodations
Vanessa at the front desk was friendly and helpful. Our room was clean and had a modern style and good accommodations around. Kayaks and bicycles rent is included in your stay. We would love to stay again.
Stayed 1 night in Jul 2024

8/10 Good

Norma

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
A quick stop
We were there for a very short time. The site is beautiful and relaxing. The beach was not really a swimming beach but I could dunk and the two lovely pools made up for it. Breakfast was good and eating with that view was priceless.
Early morning breakfast
Our view
Stayed 1 night in Jul 2024

10/10 Excellent

Mahesh

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beach in the back. Very Quiet. Relaxing place
Stayed 1 night in Jul 2024

8/10 Good

Jessica

Liked: Cleanliness, staff & service, property conditions & facilities
I believe it is over priced for the room and the hotel. Double room are full beds, uncomfortable for 2 adults to share a bed.
Stayed 1 night in Jul 2024

10/10 Excellent

Thomas

Stayed 1 night in Jul 2024

10/10 Excellent

Obed

Traveled with family and small children, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 3 nights in Jul 2024

10/10 Excellent

Jason

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful place with a very nice beach. I felt very safe and secluded. Love it and will be back
Stayed 1 night in May 2024

10/10 Excellent

Melissa

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Superb establishment
Stayed 1 night in Jul 2024

10/10 Excellent

Andrew

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely love this resort . Vanessa and chris the manageress were amazing. Cannot fault this resort . Wonderful breakfast bar amazingvfacilities
Stayed 4 nights in Jun 2024

10/10 Excellent

William

Stayed 1 night in Jul 2024

8/10 Good

Michael

Traveled with family and small children, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Pros: The room was immaculate. Both pools were clean and convenient. Staff at the check-in desk were very helpful. Very convenient to visit with little kids. Cons: There was a $50-something "resort" fee that was not disclosed by Expedia. The "chef" at breakfast was not pleasant. Towels at the pool were not re-stocked on regular basis.
Stayed 1 night in Jul 2024

10/10 Excellent

Nicolas

Traveled with family
Liked: Staff & service
Stayed 3 nights in Jul 2024

10/10 Excellent

kevin

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
I will be staying here again!
This is a great place to stay. The amenities make you feel like you are in an all-inclusive. The beach area and pools are beautiful. There are a couple Great restaurants within walking distance.
Stayed 1 night in Jul 2024

10/10 Excellent

Leidy Johanna

Traveled with family and small children, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I LOVED! staying here. It was quite calm and super relaxing. The rooms were super clean. And best of all the breakfast included. The cooks were amazing especially Nattie she was amazing. We will be back as soon as we can. The pool area can use a bit more light at night, but still overall a wonderful place.
Stayed 3 nights in Jun 2024

10/10 Excellent

Anna

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Jul 2024