See all properties

Chesapeake Beach Resort

2.5 star property
Beachfront hotel with 2 outdoor pools in Islamorada

Choose dates to view prices

Photo gallery for Chesapeake Beach Resort

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

Reviews

9.0 out of 10
Wonderful

Popular amenities

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

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • Theater of the Sea
    ‪2 min drive‬
  • Windley Key Fossil Reef Geological State Park
    ‪2 min drive‬
  • Florida Keys Brewing Co.
    ‪3 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

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 - 1.0 km
  • Theater of the Sea - 2 min drive - 1.8 km
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 1.8 km
  • Florida Keys Brewing Co. - 3 min drive - 3.5 km
  • Bud n' Mary's Dive Center - 6 min drive - 6.2 km

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

Similar properties

Exterior

Amara Cay Resort

  • On private beach
  • Pool
  • Pet-friendly
  • Parking included
4.4 out of 5, Excellent, 1,214 reviews
The price is CA $451
CA $603 total
includes taxes & fees
30 Mar - 31 Mar
Amara Cay Resort

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 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. 989 out of 1413 reviews
Rating 8 - Good. 236 out of 1413 reviews
Rating 6 - Okay. 105 out of 1413 reviews
Rating 4 - Poor. 48 out of 1413 reviews
Rating 2 - Terrible. 35 out of 1413 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

Carol

Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
Never disappointing. Wonderful Stay
Stayed 2 nights in Feb 2025

10/10 Excellent

Pamela

Stayed 1 night in Nov 2024

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff is always warm and friendly.
Stayed 3 nights in Dec 2024

10/10 Excellent

Allan

Stay one night in December for a half marathon. Room was clean and comfortable
Stayed 1 night in Dec 2024

8/10 Good

Mary Beth

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

10/10 Excellent

Eric

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

10/10 Excellent

Christopher

Stayed 1 night in Nov 2024

10/10 Excellent

Leslie

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice grounds with good beach. Friendly staff
Stayed 3 nights in Nov 2024

10/10 Excellent

Kelley

Stayed 1 night in Nov 2024

6/10 Okay

Randy

Liked: Cleanliness, staff & service, property conditions & facilities
Fees not included???
Booked hotel and it stated a price with tax and fees, however, the hotel charged an additional $56 per night "resort fee". Don't understand that. Room was clean, quiet, had a great view and breakfast was excellent.
Stayed 2 nights in Dec 2024

10/10 Excellent

Ronall

Travelled with family, Travelled with family and small children
Liked: Cleanliness, staff & service, property conditions & facilities
All good!
Stayed 1 night in Nov 2024

10/10 Excellent

Joseph

Travelled with family, Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Chesapeake Beach Resort is an excellent choice for family vacation or couple’s gate-away. This was our second time staying at the resort. This time we brought our kids and they absolutely loved it here. The exclusiveness, the private beach, water activities, two pools, and courteous resort staff. My family was welcomed warmly by Charlsie. Charlsie made my family feel welcomed and granted my wife’s request and upgraded us to a villa facing the ocean. This trip was my wife’s 40th birthday and Charlsie made it extra special for our family. I want to take this time to thank all the staff of Chesapeake Resort. The front desk staff, the grounds keep, the breakfast crew and their engagements with the kids, and the housekeeping crew. All pleasant staff. Thank you.
Stayed 7 nights in Nov 2024

10/10 Excellent

Cirma

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Dec 2024

8/10 Good

Nicole

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

10/10 Excellent

Diane

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Very clean, modern property. Staff very nice, rooms are newly renovated. Nice pool, great location to shops and restaurants. Champagne upon arrival, and breakfast is included with an omelet station. Also robes and slippers in room, nice touch. Not much of a beach and water here has grass growing in it, so not good for swimming if that's your thing. Pool is very nice, free kayak and paddle board. Would stay again
Stayed 1 night in Dec 2024

2/10 Terrible

Gabriela

Travelled with family
Liked: Staff & service
Disliked: Cleanliness, property conditions & facilities
The walls are paper thin and you can hear EVERYTHING going on in the next room. Also our room was infested with mosquitoes which is a public safety hazard. We checked in and had to leave the same day. Awful experience.
Stayed 2 nights in Nov 2024

10/10 Excellent

Felix

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

10/10 Excellent

Melanie

Travelled with family, Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very well kept, clean and safe!
Stayed 1 night in Nov 2024

10/10 Excellent

Connie

Liked: Cleanliness, property conditions & facilities, room comfort
Great get away
Room was comfortable .. not much storage for clothing in drawers, bathroom not any space to set you bathroom extras on . But has 2 great pools and a hot tub . Breakfast in the morning .
Stayed 3 nights in Nov 2024

4/10 Poor

Joseph

Stayed 1 night in Nov 2024

10/10 Excellent

Michael

Travelled with partner
Liked: Amenities
Facilities were clean. Staff very friendly and helpful. Including Mary and Chris the breakfast chefs. Small pools. We did miss swimming in the ocean due to alleged sharks. Tons restaurants close to chose from.
Stayed 5 nights in Nov 2024

10/10 Excellent

Paul, McKinney

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I highly recommend this resort! It’s not very big, which I loved. The Ocean view room was fantastic! There are two pools, which have plenty of seating and umbrellas. The free breakfast is a must, the omelette were great. The staff were wonderful, and always pleasant. The amenities, kayaks and paddle boards were a plus! Bottom line is I haven’t had a more relaxing time for quite some time, and we enjoyed every minute.
Stayed 4 nights in Nov 2024

10/10 Excellent

Peter

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful place , we was satisfied , beautiful beach .
Stayed 4 nights in Oct 2024

10/10 Excellent

William

Liked: Cleanliness, property conditions & facilities
This was a really nice facility with wonderful staff and great amenities. Great place for a family
Stayed 2 nights in Nov 2024

10/10 Excellent

Melissa

Stayed 1 night in Nov 2024