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Chesapeake Beach Resort

2.5 star property
Islamorada hotel with 2 outdoor pools and private beach

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Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun loungers, beach towels
Hypo-allergenic bedding, pillowtop beds, laptop workspace
Balcony
Water view
Aerial view
In the heart of Matecumbe, Chesapeake Beach Resort offers a tranquil escape. Enjoy a leisurely breakfast, relax on the private beach with sun loungers and kayaking options or take a refreshing dip in one of the 2 outdoor pools. With multilingual staff and concierge services available to help plan your stay.

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Pet friendly
  • Non-smoking
  • 24/7 front desk
  • Air conditioning

Main amenities (11)

  • Daily housekeeping
  • On a private beach
  • 2 outdoor pools
  • Beach sun loungers
  • Beach towels
  • 24-hour front desk
  • Air conditioning
  • Computer station
  • Multilingual staff
  • Concierge services
  • Kayaking

Feel at home (6)

  • Microwave
  • Private bathroom
  • Cable/satellite TV service
  • Daily housekeeping
  • Coffee/tea maker
  • Blackout drapes/curtains
The current price is $394
includes taxes & fees
$350 per night
Mar 13 - Mar 14

Room options

Available filters for rooms
Showing 20 of 20 rooms

View all photos for 2-Bedroom Villa

2-Bedroom Villa | Hypo-allergenic bedding, pillowtop beds, laptop workspace

2-Bedroom Villa

Highlights

Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • 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

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 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

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
Dishwasher
  • 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

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 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

Highlights

Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout drapes/curtains
  • 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

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 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

Highlights

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

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dining table
Dishwasher
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 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

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout drapes/curtains
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 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

Highlights

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

Ocean View King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
Dishwasher
HDTV
  • 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

Highlights

Deck/patio
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 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

Highlights

Air conditioning
Free cribs/infant beds
Kitchenette
Full-sized refrigerator/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 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

Highlights

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

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 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

Highlights

Balcony
Separate sitting area
Air conditioning
Free cribs/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 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

Highlights

Balcony
Air conditioning
Free cribs/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 364 sq ft
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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About the neighborhood

Map
83409 Overseas Hwy, Islamorada, FL, 33036

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

Situated by the ocean, Chesapeake Beach Resort is a great choice for a stay in Islamorada. Guests can keep active with onsite kayaking. Fellow travelers say great things about the pool and helpful staff.

Languages

English, Spanish
VISIBILITY

At a glance

Hotel size

    • 60 rooms
    • Arranged over 2 floors

Arriving/Leaving

    • Check-in start time: 4:00 PM; Check-in end time: midnight
    • Contactless check-in available
    • Early check-in subject to availability
    • Late check-in subject to availability
    • Minimum check-in age: 18
    • Check-out time is 11 AM
    • Contactless check-out available
    • Late check-out subject to availability

Special check-in instructions

    • Front desk staff will greet guests on arrival at the property

Required at check-in

    • Credit card required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 18
    • Minimum Spring Break check-in age is 21

Pets

    • Pets allowed (2 total, up to 50 lbs per pet)*
    • Service animals welcome
    • Restrictions apply*

Parking

    • Wheelchair-accessible parking on site
    • Onsite parking includes off-street options

Other information

    • Smoke-free property

Property amenities

Traveling with children

  • Pool gate
  • Outlet covers
  • Fence around the pool

What to do

  • On a private beach
  • Kayaking
  • Jet skiing nearby
  • Snorkeling nearby

Working away

  • Computer station

Services

  • 24-hour front desk
  • Concierge services
  • Multilingual staff
  • Beach sun loungers
  • Beach towels
  • Pool loungers

Facilities

  • 9 buildings/towers
  • Built in 2020
  • 2 outdoor pools
  • Traditional architecture

Accessibility

  • Braille/raised signage
  • Wheelchair-accessible parking
  • Assistive listening devices available
  • Wheelchair-accessible public washroom
  • Wheelchair-accessible pool
  • Visual alarms in hallways
  • Handrails in hallways
  • Handrails in stairways
  • Closed captioned TV
  • Lever door handles
  • Upper floors accessible by stairs only
  • Well-lit path to entrance
  • Pool hoist on site

Room amenities

Be entertained

  • 43-inch flat-screen TV
  • Cable TV channels

Home comfort

  • Air conditioning
  • Ceiling fan
  • Coffee/tea maker
  • Iron/ironing board

Sleep well

  • Hypo-allergenic bedding
  • Blackout drapes/curtains
  • Pillowtop mattress
  • Bed sheets provided

Freshen up

  • Private bathroom
  • Shower only
  • Designer toiletries
  • Hair dryer
  • Towels
  • Toilet paper

Stay connected

  • Laptop-friendly workspace
  • Free local calls

Food and drink

  • Microwave

More

  • Daily housekeeping
  • Access via exterior corridors
MONETIZATION_ON

Fees & policies

Optional extras

  • Late check-out can be arranged for an extra charge (subject to availability)

Pets

  • Service animals exempt from fees
  • Pet deposit: USD 50.00 per stay
  • Pets are allowed for an extra charge of USD 50.00 per accommodation, per night

Pool, spa, & gym (if applicable)

  • Pool access available from 7:00 AM to 10:30 PM
  • Children under 16 years old are not allowed in the swimming pool without adult supervision

Policies

Construction is underway at a neighboring building and there may be noise disturbance from the construction work.
Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.
This property does not have elevators.
This property accepts credit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover

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 offer free cancellation for a full refund?

Yes, Chesapeake Beach Resort does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.

Is there a pool at Chesapeake Beach Resort?

Yes, there are 2 outdoor pools. Guests have pool access from 7:00 AM to 10:30 PM.

Are pets allowed at Chesapeake Beach Resort?

Yes, pets are welcome, with a limit of 2 total and maximum weight of 50 lbs per pet. There's a charge of USD 50.00 per accommodation, per night, and there's also a deposit of USD 50.00 per stay. Service animals are exempt from fees.

What are the check-in and check-out times at Chesapeake Beach Resort?

Check-in start time: 4:00 PM; Check-in end time: midnight. Check-out time is 11 AM. Late check-out is available for a charge (subject to availability). Contactless check-in and check-out are available.

What is there to do at Chesapeake Beach Resort and nearby?

Have fun during the warmer months with activities such as kayaking. Enjoy a swim in one of the 2 outdoor swimming pools or use the hotel's other amenities, which include a private beach.

What's the area around Chesapeake Beach Resort like?

Chesapeake Beach Resort is in Matecumbe, a short 11-minute walk from History of Diving Museum. Travelers give top marks for the hotel's prime location.

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Chesapeake Beach Resort Reviews

Reviews

9.0

Wonderful

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 Exceptional

Great stay!
The breakfast at the shore was wonderful with friendly service and plenty of food choices.
Kim, 2-night trip

10/10 Exceptional

Most amazing views
Derick, 2-night trip

10/10 Exceptional

Beautiful place clean and enjoyable.. don’t hesitate to book in fl keys
Angel, 1-night trip

10/10 Exceptional

Island paradise
Great location, great beach, pools and staff.
Peter, 1-night trip

10/10 Exceptional

Excellent place
I love this place, every stay is truly a wonderful experience. The staff is always helpful and friendly. The grounds are really pretty as well.
cheryl, 4-night trip

10/10 Exceptional

I enjoyed my stay. The breakfast was great and outdoor breakfast seating facing the ocean was a great way to start the day. Can’t beat the beach loungers scattered around the property.
kristie, 4-night trip

10/10 Exceptional

Fun place with excellent shoreline
The food and bar service near pool and shore line is staffed with excellent people that work hard to make our stay fun. We attended the Super bowl barbecue at the poolside and met new friends. A great place and we plan to visit again. Breakfast was included and the chefs were awesome.
Kim, 3-night trip

10/10 Exceptional

Loved it!
The resort is very clean and the staff are amazing. We encountered many staff during our stay and they were very friendly. Chef Chris in the Sunrise room created delicious made to order omelets. Breakfast was great.
Kathrine, 7-night trip

10/10 Exceptional

Good hotel
Felix, 1-night trip

8/10 Very good

Would stay again-loved the place!
Everything was great-we did have an issue with our a/c but we were only there two nights so we didn't worry with having them look at it. Just reported as we left the property. Loved the place overall!
2-night trip

10/10 Exceptional

Absolutely gorgeous, clean, friendly staff, and great location
Amy, 4-night trip

10/10 Exceptional

Beautiful place , we was satisfied , beautiful beach .
Peter, 4-night trip

10/10 Exceptional

This was a really nice facility with wonderful staff and great amenities. Great place for a family
William, 2-night trip

10/10 Exceptional

Absolutely great place with beach access!
mariana, 3-night trip

10/10 Exceptional

Great place
Diana, 1-night trip

8/10 Very good

Weeding weekend
Went to a weeding in Islamorada and the option of the hotel was ideal
1-night trip

10/10 Exceptional

Great Roadside location, clean & modern
Great location. Friendly staff Great room
Steve, 1-night trip

10/10 Exceptional

Nice grounds with good beach. Friendly staff
Leslie, 3-night trip

10/10 Exceptional

First Class 👌
This was worth every penny. The room was spotless! The breakfast great! And the staff wonderful!! We will be back!
Anthony, 2-night trip

10/10 Exceptional

Nice and quiet, Right on the water, Clean, neat,friendly staff, right next to food.
Christy, 1-night trip

10/10 Exceptional

Very well kept, clean and safe!
Melanie, 1-night trip

6/10 Good

great stay, beautiful resort. AC didn’t work the best, didn’t love the barn door that didn’t lock in bathroom. Breakfast was great, but no indoor seating. One day was cool and rainy and no where to sit and eat. Pool and hot was nice
Lorie, 2-night trip

10/10 Exceptional

We loved it here. Chef Chiris mskes the best omelets.
Carole, 5-night trip

10/10 Exceptional

Super nice hotel super good staff rooms super clean
NELSON, 2-night trip

10/10 Exceptional

Love the resort
lorraine, 2-night trip