Chesapeake Beach Resort

2.5 star property
Beachside hotel to enjoy 2 outdoor swimming pools and a white sand beach

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Water view
Hypo-allergenic bedding, pillow-top beds, laptop workspace
Premium Ocean View King Villa | Living area
Premium Ocean View King Villa | Water view
Reviews
9.0

Wonderful

Popular amenities

  • 24/7 front desk24/7 front desk24/7 front desk
  • Pool
  • On private beachOn private beachOn private beach
  • Pet-friendlyPet-friendlyPet-friendly
  • HousekeepingHousekeepingHousekeeping
  • Air conditioningAir conditioningAir conditioning

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

2-Bedroom Villa

Highlights

Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • 60 sq m
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

Standard King

9/10 Wonderful

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 25 sq m
  • Sleeps 3
  • 1 King Bed

King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 48 sq m
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Standard Doubles

9.2/10 Wonderful

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 25 sq m
  • Sleeps 4
  • 2 Double Beds

Standard King with Sleeper Sofa

8.3/10 Very good

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Sofa bed - double
  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Hearing Impaired Ocean View Queens

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Hearing Impaired Ocean View King Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

ADA King Efficiency Villa

Highlights

Separate dining area
Air conditioning
Free cots/infant beds
Full-sized fridge/freezer
Dining table
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 48 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

Premium 1-Bedroom Ocean View Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 65 sq m
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

Deluxe Ocean View Two Queen Suite

8/10 Very good

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 60 sq m
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

Ocean View King

9.6/10 Exceptional

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Sofa bed - double
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

Ocean View King Suite

10/10 Exceptional

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 49 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

Ocean View Queens

9.5/10 Exceptional

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
  • 48 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

Standard Queens

8.8/10 Excellent

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

Standard King Villa

Highlights

Air conditioning
Free cots/infant beds
Full-sized fridge/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
Separate bedroom
  • 30 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

Premium Ocean View King Villa

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Full-sized fridge/freezer
Dining table
HDTV
  • 77 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

ADA Ocean View Queens

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

ADA Ocean View King Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed

ADA Ocean View King

8.2/10 Very good

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

Similar properties

About the area

Islamorada

At Chesapeake Beach Resort you'll be within a 15-minute walk of History of Diving Museum and 1.8 km (1.1 mi) from Windley Key Fossil Reef Geological State Park. Highlights at this beachfront hotel include 2 outdoor swimming pools and a private beach. .This beach hotel offers concierge services, a 24-hour front desk and a computer station. Plus you'll find multilingual staff. .With a stay at this Matecumbe hotel, you'll be 2 km (1.2 mi) from Islamorada Brewery & Distillery and 2.7 km (1.7 mi) from Keys History & Discovery Center.

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
  • Founders Park - 5 min drive

Getting around

  • Miami International 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

Beachside hotel to enjoy 2 outdoor swimming pools and a white sand beach
Simply walk outside to smell the salty 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 such as 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 members are 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 features coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. Flat-screen televisions come with cable channels.

Bathrooms include a shower, complimentary toiletries and hairdryers. Business-friendly amenities include telephones along with free local calls (restrictions may apply). Additionally, rooms include an iron/ironing board and a ceiling fan. Housekeeping is offered on a daily basis and hypo-allergenic bedding can be requested.

Languages

English, Spanish

Property amenities

Parking and transport

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

Things to do

  • 2 outdoor pools
  • Kayaking

Family friendly

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

Conveniences

  • 24-hour front desk

Guest services

  • Concierge services
  • Daily housekeeping
  • Multilingual staff

Business services

  • Computer station

Outdoors

  • Beach loungers
  • Beach towels
  • On a private beach
  • Pool loungers

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

More

  • 2 floors
  • 9 buildings
  • Built in 2020
  • Renovated entire property - January 2020
  • Smoke-free property
  • Traditional architecture

Room amenities

Bedroom

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

Bathroom

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

Entertainment

  • Flat-screen TV with cable channels

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 and check-out are available
Late check-in subject to availability
Minimum check-in age - 18

Check-out

Check-out before 11 AM
Contactless check-out
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 lb 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.

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

What is the cancellation policy at Chesapeake Beach Resort?

Chesapeake Beach Resort offers free cancellation on select room rates. Check out the cancellation policy for more info.

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

As of 31 May 2024, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 16 June 2024 start from AU$395.40, including 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.

Are there any beaches close to Chesapeake Beach Resort?

The closest beach to Chesapeake Beach Resort is Anne's Beach (16.1 km).

Does Chesapeake Beach Resort have a pool?

Yep, and guests recommend it! Chesapeake Beach Resort has 2 outdoor swimming pools. Grab your bathers and lounge poolside while enjoying on a lounger. The pool is open 7:00 AM to 10:30 PM.

What makes Chesapeake Beach Resort a romantic place to stay?

A private beach, plus pillowtop beds in the guestrooms, help set the scene for a romantic weekend at Chesapeake Beach Resort.

Is there a free airport shuttle available at Chesapeake Beach Resort?

No, Chesapeake Beach Resort does not offer an airport shuttle service.

What time are check-in & check-out at Chesapeake Beach Resort?

Check-in begins at 4:00 PM. Check-out time is 11 AM.

Chesapeake Beach Resort Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 865 out of 1333 reviews" "
Rating 8 - Good. 276 out of 1333 reviews" "
Rating 6 - Okay. 111 out of 1333 reviews" "
Rating 4 - Poor. 46 out of 1333 reviews" "
Rating 2 - Terrible. 35 out of 1333 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

6/10 Okay

Wesley

Liked: Cleanliness, property conditions & facilities
Nice place, just lacking a place to get a drink and have some beachfront amenities that we expected. It was a nice,well kept place
Stayed 2 nights in Feb 2024

10/10 Excellent

Aline

Travelled with family
Beautiful grounds, clean rooms and beach. Good breakfast and very friendly staff. In a convenient location. Love the tables and chairs on the water. Could look at the view forever.
Stayed 2 nights in Feb 2024

10/10 Excellent

Dariusz

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We love the resort's friendly crew, everyone was helpful, always smiling and happy to answer any questions we had. We were treated with a complimentary room upgrade, from a small room to a villa! That was awesome! The resort has been just completely remodeled, sits literally on the beach, gorgeous views of the ocean, swimming pools, hot tub, kayaking, bicycles, complimentary breakfast, couple of minutes walk to a few local restaurants... just perfect!
Stayed 3 nights in Feb 2024

10/10 Excellent

Janet

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Don’t hesitate to stay here!
Perfect location. Rooms clean and beautiful. Staff was so friendly and helpful. Loved the beach the pool and hot tub. Kayak and paddle boards available for free. Fabulous vacation spot.
Stayed 3 nights in Feb 2024

10/10 Excellent

John

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 6 nights in Feb 2024

10/10 Excellent

DIANE

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful property, staff were helpful, and it was beautiful, the availability of the kayaks and paddle boards was a bonus. We will be back.
Stayed 1 night in Feb 2024

10/10 Excellent

Catherine

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was beautiful. Staff was accommodating. They did a great job on recent renovation. We stayed in villa that was clean and charming. We will definitely come back and stay again.
Stayed 2 nights in Feb 2024

10/10 Excellent

Jessica

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Pool, beach area were great
Stayed 4 nights in Feb 2024

4/10 Poor

LeAnn

Travelled with family
Liked: Property conditions & facilities, room comfort
Disliked: Cleanliness, staff & service
Pretty resort, poor staffing and service
We stayed two nights at Chesapeake Beach Resort as the midway stretch of two weeks traveling around Florida from Orlando, to the Everglades, to the Keys and continuing North along the Atlantic coast. The stay had some positives but unfortunately more negatives. First of all the positives were that the resort itself is extremely aesthetically pleasing. If you love posting on instagram this is your perfect destination. We had a two queen bed suite on the third floor which was extremely spacious and again beautiful in appearance. The view was amazing. Another positive that deserves mentioning is the gentleman running the water sports rental and bar was quite friendly and outgoing. Really the only positive staff encounter we had. When we first arrived the encounter with the front desk staff was possibly the most awkward we’ve ever had. A young man and young lady were both at the desk but said nothing when we walked in and I would not say they were outwardly rude, but definitely dismissive in demeanor. My husband and I felt like we were doing them a disservice by checking into our room. They literally said nothing beyond handing us a form to fill out in regards to our vehicle. We had to ask about the water sports rental which also seemed like it pained them to have to explain. Beyond that there was no obvious staff. The pool towels were set out and then not maintained during the day the dirty bin overflowed as did the trashes. Just not $500+ a night worthy service.
Stayed 2 nights in Feb 2024

10/10 Excellent

David

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean and quiet
Stayed 2 nights in Feb 2024