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Chesapeake Beach Resort

2.5 star property
Hotel on the beach, with 2 outdoor pools

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your current months are January, 2025 and February, 2025.
January 2025
February 2025

Photo gallery for Chesapeake Beach Resort

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

Reviews

9.0 out of 10

Wonderful

Popular amenities

  • Pet-friendly
  • 24/7 front desk
  • Housekeeping
  • Air conditioning
The price is €222
includes taxes & fees
8 Jan - 9 Jan

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for 2-Bedroom Villa

2-Bedroom Villa

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

View all photos for Standard King

Standard King

Standard King

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

View all photos for King Efficiency Villa

King Efficiency Villa

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

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

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

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

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

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillow-top beds, laptop workspace

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

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

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

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

Highlights

Separate dining area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
HDTV
Hypo-allergenic bedding
  • 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

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

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

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

View all photos for Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

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

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

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

View all photos for Ocean View Queens

Terrace/patio

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

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

View all photos for Standard Queens

Standard Queens

Standard Queens

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

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

Highlights

Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 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

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
  • 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

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Separate bedroom
  • 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

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

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

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

Exterior

Amara Cay Resort

On private beach
Pool
Pet-friendly
Parking included
8.8 out of 10, Excellent, (1219)
The price is €344
includes taxes & fees
13 Jan - 14 Jan
Amara Cay Resort
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About the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036

What's nearby

  • History of Diving Museum - 11 min walk
  • Theater of the Sea - 2 min drive
  • Florida Keys Brewing Co. - 3 min drive
  • Founders Park - 5 min drive
  • Bud n' Mary's Dive Center - 6 min drive

Getting around

  • Miami International 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

Transformed hotel, renovated in 2020 and located in Matecumbe
Chesapeake Beach Resort provides everything that you need. With a private beach, sunloungers and kayaking, this hotel is the perfect place to soak up some sun.
You'll also enjoy the following perks during your stay:
  • 2 outdoor pools with sunloungers
  • Beach towels, multilingual staff and concierge services
  • Smoke-free property, a 24-hour front desk and a computer station
  • Guest reviews give top marks for the breakfast, beach locale and pool
Room features
All 60 rooms feature comforts, such as laptop-friendly workspaces and air conditioning. Guest reviews speak positively of the cleanliness, size rooms at the property.
Other amenities include:
  • Hypo-allergenic bedding and pillowtop mattresses
  • Bathrooms with designer toiletries and showers
  • 43-inch HDTVs with cable channels
  • Wardrobes/cupboards, microwaves and coffee/tea makers

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
  • Housekeeping (daily)
  • 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 bathroom

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 provided

Entertainment

  • 43-inch 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 are allowed for an extra charge of USD 50.00, per accommodation, per night, plus a deposit of USD 50.00 per stay
Service animals are welcome, and are exempt from fees
2 total (up to 23 kg per pet)
Restrictions apply; for more information contact the property on the number on the booking confirmation

Children and extra beds

Children are welcome
Rollaway/extra beds are not available.

Payment types at the property

Important information

Optional extras

  • 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)

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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

We should mention

This property does not have any lifts
Pool access available from 7:00 AM to 10:30 PM
Some facilities may have restricted access; guests can contact the property for details using the contact information on the booking confirmation
Construction is underway at a neighbouring building and there may be noise disturbance from the construction work
Children under 16 years old are not allowed in the swimming pool without adult supervision

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

Does Chesapeake Beach Resort have a pool?

Yes, this property has 2 outdoor pools. Pool access is from 7:00 AM to 10:30 PM.

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

As of 7 Jan 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 8 Jan 2025 start from €222.04, 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.

Is Chesapeake Beach Resort pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 23 kg per pet. There's a deposit of USD 50.00 per stay and a fee of USD 50.00 per accommodation, per night. Service animals are exempt from fees.

What time is check-in at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; check-in end time: midnight. Late check-in is available during limited hours.

What time is check-out at Chesapeake Beach Resort?

Checkout is at 11 AM. Late checkout is available for a fee (subject to availability).

Where is Chesapeake Beach Resort located?

Nestled on the beach, this Matecumbe hotel is within 1 mi (2 km) of History of Diving Museum and Windley Key Fossil Reef Geological State Park. Islamorada Brewery & Distillery and Keys History & Discovery Center are also within 2 miles (3 km).

Chesapeake Beach Resort Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 958 out of 1392 reviews" "
Rating 8 - Good. 248 out of 1392 reviews" "
Rating 6 - Okay. 105 out of 1392 reviews" "
Rating 4 - Poor. 49 out of 1392 reviews" "
Rating 2 - Terrible. 32 out of 1392 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

claudia

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The rooms, including the bathroom, were recently renovated and were very clean. The staff were very friendly. I received a text shortly after check in to make sure my room was ok and if we needed anything to let them know- nice touch! They had a breakfast room with pancakes, waffles, omelets made to order, yogurts and fruits, bagels, toast, coffee and teas, cereals etc all complimentary. And speaking of complimentary, they had bikes, kayaks, paddle boards etc for your use. I would definitely recommend Chesapeake Beach Resort.
Stayed 2 nights in Dec 2024

10/10 Excellent

Marli da

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 2 nights in Jan 2025

10/10 Excellent

Margaret

Liked: Property conditions & facilities
Really lovely property, nice updated room. Bathroom could use improved lighting for mirrors, but overall very nice! Front desk staff seemed a bit frazzled & slightly unprofessional, but some customer service training could easily improve that. The bar/breakfast service and staff were very good! Cleaning and ground crew really friendly and helpful.
Stayed 2 nights in Dec 2024

10/10 Excellent

Jeannie, Girard

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the location, beach area, breakfast and STAFF
Stayed 4 nights in Dec 2024

10/10 Excellent

Viorel

Liked: Cleanliness, staff & service, property conditions & facilities
Great front desk staff, clean property overall. Some things never change fortunately.
Stayed 1 night in Nov 2024

10/10 Excellent

Viorel

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I'm a routine guest at this property for over 25 years. One of the best in the Keys, price and money. Great location, nearby Whale Harbour, the Sandbar, Boat rentals, 3 restaurants and one rooftop bar within a 1 minute walk, and Islamorada attractions just over the bridge. Great front desk staff, clean property overall. Some things never change fortunately.
Stayed 1 night in Dec 2024

8/10 Good

Luca

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Great beach and clean big well furnished rooms
Stayed 2 nights in Dec 2024

10/10 Excellent

Samara

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

4/10 Poor

Lori

Travelled with family
Disliked: Cleanliness, staff & service
Very disappointing, considering hotel rate. No room for bags, no room for towels in bathroom, stains on sheets. Had to call front desk twice and then had to go to reception for change of sheets. Balcony looked out on parking area. What do you want for 700/per night. Total rip-off.
Stayed 2 nights in Dec 2024

10/10 Excellent

Saravanan

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

6/10 Okay

Michele

Disliked: Property conditions & facilities
We stayed one night at CHESAPEAKE BEACH resort en route to the keys and I would not recommend to fellow travelers. The hotel is right off a very busy road so you will hear traffic if you are situated near the front of the property. More problematic are the paper thin walls that allow you to hear every word of the conversation in the room next door as well as their 6:30 am alarm and 3:30 pm margarita party. There was very limited hot water - my husband took a cold shower and I opted to wait until our next stop as I don't enjoy a cold plunge shower. My son and I walked over to breakfast at 7 am only to be told they had run out of eggs so the "make your personalized omelette" was not in order. We had cold cereal out of plastic cups (no bowls) and a piece of toast. Upon checking out, I was informed "you'll get a receipt from Expedia" - no thank you, no how was your stay, no common courtesy. I would definitely NOT recommend this resort to others. Especially with a $600/night price tag over the holidays.
Stayed 1 night in Dec 2024

10/10 Excellent

Jason

Travelled with family
Booked online with just pictures as reference. The staff and resort in its entirety went beyond expectations. Breakfast was excellent and pool and water activities were enjoyable!!! A must must must if looking to stay in Islamorada. Will be returning!!!
Stayed 4 nights in Dec 2024

8/10 Good

Rashmi

Liked: Cleanliness
Disliked: Staff & service
Rooms were very clean and big. Our room faced the ocean which was the best thing. Nice and calm atmosphere with easy access to area amenities. There can be more in-resort amenities. Staff could be more welcoming and friendly. The person at the front desk and the breakfast area were very rude. Will be nice if they can be more cordial and nice.
Stayed 2 nights in Dec 2024

10/10 Excellent

Sam

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicely renovated property. 5 star room with a nice resort feel.
Stayed 1 night in Dec 2024

8/10 Good

Deeptha

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent beach . Friendly and efficient staff . Prompt service.
Stayed 1 night in Dec 2024

10/10 Excellent

adriana

Stayed 1 night in Nov 2024

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

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

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