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731 reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, 33036, Florida, United States

Reservations:

+1-833-728-2041

Choose dates to view prices

Beachfront

Private beach area

Outdoor swimming pool

Free Private Parking

Free wifi

Beach

Air conditioning

Private entrance

Chesapeake Beach Resort

Welcome to Chesapeake Beach Resort, a charming 3-star resort located in Islamorada, Florida. Our resort is situated right on the beautiful beachfront, offering stunning ocean views and a private beach area for our guests to enjoy. With a total of 731 reviews, our resort is highly rated by fellow travelers for its exceptional service and amenities.

Conveniently located just 1.2mi from the city center, Chesapeake Beach Resort provides easy access to all the attractions and activities that Islamorada has to offer. Whether you want to relax on the beach, take a dip in the outdoor swimming pool, or soak in the hot tub, our resort has something for everyone. Our pet-friendly policy allows you to bring your furry friends along for an extra charge.

Each room at Chesapeake Beach Resort is equipped with modern amenities such as air conditioning, a private bathroom, and a kitchenette with kitchenware. For your convenience, we offer free WiFi and private parking. Other amenities include a 24-hour front desk, a convenience store on-site, and daily housekeeping services.

With its prime location, excellent reviews, and a range of amenities, Chesapeake Beach Resort is the perfect choice for a relaxing and enjoyable stay in Islamorada, Florida. Prices start from $248, so book your stay with us today and experience the best of beachfront living.

At Chesapeake Beach Resort, we know that pets are part of the family too, which is why we are delighted to welcome your furry friends. Our pet-friendly policy allows you to bring your beloved pets along for an additional charge. So, no need to leave them behind while you enjoy the sun, sand, and ocean breeze. Let them explore the beautiful beachfront with you and create unforgettable memories together.

When it's time to cool off and have a splash, we have not one but two outdoor pools available exclusively for adults. Our pools are heated, ensuring a comfortable swim no matter the season. Take a dip in the refreshing water or lounge by the poolside and soak up the rays. With shallow ends and stunning views of the ocean, our pools provide the perfect setting for relaxation and rejuvenation. So grab your favorite book, find a cozy spot, and let the worries of everyday life melt away.

At Chesapeake Beach Resort, we want to make your stay as convenient as possible. That's why we accept major credit cards, including Visa, Discover, Mastercard, and American Express. Say goodbye to the hassle of finding an ATM or worrying about carrying cash. With our accepted payment methods, you can focus on enjoying your vacation. So go ahead and indulge in delicious meals, shop for souvenirs, or treat yourself to a spa treatment without a worry. We've got you covered!

Come and experience the best of beachfront living at Chesapeake Beach Resort. With our pet-friendly policy, two stunning pools, and hassle-free payment options, we've got all you need for a truly enjoyable stay. Book your beach getaway today and prepare to make memories that will last a lifetime.

Most popular amenities

Beachfront

Private beach area

Outdoor swimming pool

Free Private Parking

Free wifi

Beach

Air conditioning

Private entrance

Parking On Site

24-hour front desk

Ocean view

Non-smoking rooms

Wheelchair accessible

Beach chairs/Loungers

Kitchenware

Kitchenette

Elevator

Upper floors accessible by elevator

Balcony

Free toiletries

Rooms

Show 7 photos

Efficiency Villa, Accessible

1 King Size Bed

0 sqft

Kitchenette

Microwave

Flat-screen TV

Refrigerator

+

More details

Featuring a private entrance, this air-conditioned villa is consisted of of 1 living room, 1 separate bedroom and 1 bathroom with a walk-in shower and a hairdryer. The well-equipped kitchenette has a stovetop, a refrigerator, a dishwasher and kitchenware. This wheelchair accessible villa features a coffee machine, a seating area with a flat-screen TV and a roll-in shower. The unit offers 1 bed.

Hearing Impaired Ocean View King Suite in Chesapeake Beach Resort

Show 8 photos

Suite, Accessible, Ocean View

1 King Size Bed

1 Sofa Bed

590 sqft

Ocean view

Private Bathroom

Balcony

Private entrance

+

More details

This spacious suite is consisted of of 1 living room, 1 separate bedroom and 1 bathroom with a walk-in shower and free toiletries. The air-conditioned suite offers a flat-screen TV with cable channels, a private entrance, a coffee machine, a seating area as well as sea views. The unit offers 2 beds.

Ocean View King  in Chesapeake Beach Resort

Show 11 photos

King Room, Ocean View

1 King Size Bed

345 sqft

Ocean view

Private Bathroom

Balcony

Private entrance

+

More details

Ocean View King (1 King Bed) is 366 square feet and includes a king-size bed 150-183 width plus cable tv.

King Efficiency Villa in Chesapeake Beach Resort

Show 6 photos

Efficiency Villa

1 King Size Bed

1 Sofa Bed

0 sqft

Private Bathroom

Kitchenette

Kitchenware

Private entrance

+

More details

Stay in our luxurious King Efficiency Villa, where you'll find a private entrance, fully equipped kitchenette, and a spacious living area with a comfortable sofa. Enjoy a restful night's sleep on the king size bed, and take advantage of amenities such as a flat-screen TV, air conditioning, and free toiletries. With space for three adults and a prime location on the ground floor, our villa is the perfect retreat for your vacation.

Ocean View Two Queens in Chesapeake Beach Resort

Show 6 photos

Room - 2 Queen, Ocean View

2 Double Beds

345 sqft

Ocean view

Private Bathroom

Balcony

Private entrance

x4

+

x3

More details

Experience the perfect getaway in our Ocean View Two Queens room - a spacious and comfortable double room with stunning ocean views, private balcony, and all the amenities you need for a memorable stay, including a microwave, coffee machine, and flat-screen TV. Ideal for families, this room can accommodate 2 adults and 2 children, offering a memorable vacation where you can relax and soak in the beauty of the ocean.

Standard Double Room in Chesapeake Beach Resort

Show 8 photos

Room - 2 Queen

2 Double Beds

270 sqft

Private Bathroom

Balcony

Private entrance

Microwave

x4

+

x3

More details

The spacious double room features air conditioning, a private entrance, as well as a private bathroom boasting a walk-in shower and a hairdryer. Featuring a balcony, this double room also provides a coffee machine, a wardrobe and a flat-screen TV with cable channels. The unit has 2 beds.

Deluxe King Suite in Chesapeake Beach Resort

Show 20 photos

Deluxe Suite, King

1 Queen Size Bed

1 Sofa Bed

590 sqft

Ocean view

Private Bathroom

Balcony

Private entrance

+

More details

Indulge in the spacious comfort of our Deluxe King Suite, boasting stunning ocean views from your private balcony. This suite features a queen-size bed, sofa bed, and modern amenities including a flat-screen TV, microwave, and coffee machine, ensuring a relaxing stay for up to two adults and two children.

Two-Bedroom Villa in Chesapeake Beach Resort

Show 7 photos

Villa, 2 Bedroom

1 Double Bed

1 Sofa Bed

1 King Size Bed

645 sqft

Private Bathroom

Kitchenette

Kitchenware

Private entrance

x20

+

x13

More details

2-Bedroom Villa (1 King Bed, 1 Double Bed and 1 Double Sofa Bed) is 646 square feet and includes either a double bed 131-150 width or a king-size bed 150-183 width plus cable tv.

Premium 1-Bedroom Ocean View Villa in Chesapeake Beach Resort

Show 7 photos

Premium Villa, 1 Bedroom, Ocean View

2 Double Beds

1 Sofa Bed

0 sqft

Ocean view

Private Bathroom

Kitchenette

Kitchenware

+

More details

Boasting a private entrance, this air-conditioned villa features 1 living room, 1 separate bedroom and 1 bathroom with a walk-in shower and a hairdryer. The fully equipped kitchenette has a stovetop, a refrigerator, a dishwasher and kitchenware. The villa features a coffee machine, a seating area, a wardrobe, a flat-screen TV with cable channels, as well as sea views. The unit has 3 beds.

Standard King Room in Chesapeake Beach Resort

Show 6 photos

King Room

1 King Size Bed

1 Sofa Bed

310 sqft

Private Bathroom

Balcony

Private entrance

Microwave

+

More details

Experience true comfort and relaxation in our spacious Standard King Room, boasting a generous 269 sqft of stylishly furnished space. Unwind on your private balcony or catch up on your favorite shows with our flat-screen TV, all while enjoying the convenience of amenities like a microwave, coffee machine, and refrigerator. Enjoy a restful night's sleep in our luxurious king-size bed and wake up feeling refreshed and ready for a day of adventures.

Premium Ocean View King Villa in Chesapeake Beach Resort

Show 9 photos

Premium Villa, Ocean View

1 King Size Bed

1 Sofa Bed

830 sqft

Ocean view

Private Bathroom

Kitchenette

Kitchenware

+

More details

Experience breathtaking ocean views from our Premium Ocean View King Villa. This spacious villa features a private bathroom, kitchenette, and a comfortable king size bed. Enjoy the convenience of a flat-screen TV, air conditioning, and free toiletries. Discover true relaxation with the sounds of the waves and the stunning ocean right at your doorstep.

ADA Deluxe Ocean View King  in Chesapeake Beach Resort

Show 6 photos

Deluxe, King, Accessible, Ocean View

1 King Size Bed

365 sqft

Ocean view

Private Bathroom

Balcony

Private entrance

+

More details

Experience the ultimate oceanfront luxury in our ADA Deluxe Ocean View King suite. With stunning views, a private balcony, and top-notch amenities like a microwave and flat-screen TV, this is the perfect retreat for a family getaway.

Guest reviews

8

731 reviews

Categories of assessments

Cleanliness

Comfort

Location

Facilities

Staff

Value for money

WiFi quality

Breakfast

Featured reviews:

🇺🇸

Stapleton

8.2

May 2023

Although the resort has obviously been there for awhile, everything has been upgraded - brand new. The decor of the lobby and rooms was beautiful and very clean. Parked right in front of my room. Like staying in a newly opened resort. Restaurant/bar within walking distance

No one told me at check in that I needed to reserve the complimentary breakfast and so there was none for me.

🇺🇸

Paula

9.1

July 2023

There is a private beach at the resort that is absolutely beautiful. You can swim at the ocean, there is a clear space from the seaweeds, it's so beautiful. You can have 2 hours / day to use the kayaks and the stand up paddle, which is pretty convenient. If you take the ocean view room, the view is amazing. The room is also very comfortable. Parking is super easy. They don't have a restaurant at the property, but walking less than 2 minutes there is an amazing all you can eat seafood restaurant. You can also take the car and 2-3 minutes away you'll find amazing restaurants. The lady who was in the front desk welcoming the guests was adorable, very polite and kind.

The complimentary breakfast could be a little better - there is a boxed breakfast with few options to pick, we had it for the first day but from the second day we preferred to go to Publix and buy some breakfast items. This is not something related to the property, but some guests are not polite at all. Throwing garbage at the beach, leaving their things behind on the beach chairs, not good at all.

🇬🇧

Claire

8.2

August 2023

Parking: Open resort with plenty of parking close to the rooms. Rooms: were fairly spacious breakfast: was delivered to room in the morning, selected the night before from a list Beds were doubles, so not overly big, but they were fairly comfortable. Aircon: worked well, along with fan Balcony and view: Ocean view room with a reasonable sized balcony and two comfortable chairs Pools: Two good sized pools to choose from, neither were busy, Loungers/seatingL Plenty of seats near the sea and pool to choose from, some with parasols. Always plenty free to use. 2 hour free water sports: We were told that we could have 2 hours free water sports during our stay

Room: sometimes there was a bad smell (possibly from the drains). Beds: were doubles, so not overly big, but they were fairly comfortable. Aircon: was a little loud but worked well. View: ocean view rather than ocean facing - no option to select later Pools area: there is no pool bar/service available at this hotel 2 hour free water sports: We were told that we could have 2 hours free water sports during our stay but there was never anyone near to the kayaks, etc. to ask about it.

🇺🇸

Gyöngy

8.2

April 2023

We thought our room was ocean view, but unfortunately it wasn't. However, we received an upgrade to the villas, and opening the door during breakfast it was an 'oceanview' :D. Very comfy villa with kitchen. The breakfast was good too, grab and go: got a list of items every evening we checked the things we wanted next morning (no limit, whatever we wated from the list). The breakfast sandwiches were frozen, we were lucky to have a stove to warm them up. Others with a microwave.... not so much. The beds were comfy, clean. The beach area was very nice. We had a windy day, but we still liked the resort. The staff was kind and helpful. We didn't have sheets for the sofa bed, but asking at the front desk we received what we needed. Free parking. Great restaurant right next door (Wahoo's), very good food and the best home-made Keylime cake.

A bit expensive.

🇺🇸

Dawn

9.1

May 2022

it was close to everything, quite. like the hot tub . the view of the water was awesome.

lack of counter space in bathroom, shower was great ! didn’t care for same choices on breakfast for 4 days .

🇬🇧

Steph

8.2

November 2022

The property was in a beautiful location. It was well equipped with two pools and a hot tub. The room was also kitted out with a decent size fridge and microwave. The beds were comfy and rooms clean and stylish, one of the nicest rooms we’ve stayed in during our travels through Florida. You could sunbathe on the beds on the beach. Breakfast was provided as part of our stay which you picked each day for the following day. A choice of drink, fruit, cereal/bar and breakfast sandwich were provided.

You had to request your bed making although we didn’t require toiletries or expect/want a change of towels it would have been nice to have our beds made. However I must add that had I asked for this I had no doubt whatsoever it would have been made. You do get daily texts asking if everything is ok or if you require anything.

🇺🇸

Travis

10

August 2023

This is our 6th time visiting. Always great. I would suggest stocking the rooms with a small dust pan and broom. Since room service isn't coming each day. My wife always comments about wishing there was a broom to deal with the sand. This may also help keep the rooms cleaner for when your team comes to service and make it easier for them.

Feel like a general location to take trash from the room would be helpful

🇺🇸

Michael

9.1

May 2023

Location is great. Close to lots of restaurants and bars, shopping and boutique stores. 2 fantastic swimming pools and hot tub. Very comfortable room with balcony and views of the ocean and private beach. This was our 3rd time staying here and will be back again.

Need bigger pillows

🇺🇸

Jennifer

10

July 2023

My husband picked this resort to spend his birthday. The pictures looked lovely but surely don't do it justice. It was beautiful. We rented a 2 bedroom villa with a full kitchen. Even our children were in love with the place. The beach and 2 pools were just a few feet from the villa which was perfect and the staff was lovely and helpful and so professional. I am definitely coming back!

🇬🇧

Benjamin

8.2

February 2023

clean, modern and great location

staff could be a little friendlier, but nonetheless they were helpful. stayed in large ocean room with two queen beds and a pull out sofa for family of 5. no additional bedding / sheets etc were available for the pull out sofa and had not been properly clean under. rest of property and ground were immaculate and super faculties.

Points of Interest Around Chesapeake Beach Resort

Attractions

Flamingo Visitor Center

24.1mi

Everglades National Park

30.1mi

Pools

Location

  • Outdoor

Features

  • Heated
  • Shallow end
  • With view

Age restrictions

  • Adults only

Availability

  • All season

Amenities of Chesapeake Beach Resort

Beachfront

Private beach area

Outdoor swimming pool

Free Private Parking

Free wifi

Beach

Air conditioning

Private entrance

Parking On Site

24-hour front desk

Ocean view

Non-smoking rooms

Wheelchair accessible

Beach chairs/Loungers

Kitchenware

Kitchenette

Elevator

Upper floors accessible by elevator

Balcony

Free toiletries

Stay rules - Chesapeake Beach Resort

  • Check-in / Check-out

  • Pets

  • Internet

  • Age restrictions

  • Curfew

  • Parking

  • Reservations

  • Children and beds

  • Cards accepted at this property

Frequently Asked Questions - Chesapeake Beach Resort

Is it possible to stay with my pet at Chesapeake Beach Resort?

Absolutely! You are more than welcome to stay with your furry friend at Chesapeake Beach Resort. They allow pets and may apply charges for accommodating them. Enjoy your stay together!

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

Chesapeake Beach Resort offers check-in timings from 04:00 PM to 11:00 PM. Make sure to check out by 11:00 AM.

Can guests park for free at Chesapeake Beach Resort?

Yes, there is parking available at Chesapeake Beach Resort. The parking is free, private, and located on-site. However, it is important to note that a parking reservation is required.

How much does a stay at Chesapeake Beach Resort cost?

Rooms at Chesapeake Beach Resort are available starting from $248. Prices might vary according to room availability and chosen dates. To see the current rates, please add your travel dates.

Which room categories can I book at Chesapeake Beach Resort?

Chesapeake Beach Resort offers a variety of rooms including villas, doubles, and suites. The occupancy ranges from 2 to 5 adults, with some rooms accommodating children as well. Smoking is not allowed in any of the rooms. The bed sizes vary with options such as double, queen, and king size beds. Room sizes range from 269 sqft to 592 sqft.

Where can guests find entertainment in Chesapeake Beach Resort?

Guests at Chesapeake Beach Resort can spend their time at the hotel enjoying a range of leisure amenities. The hotel features a beachfront and a private beach area, allowing guests to relax by the ocean and soak up the sun. In addition, the hotel offers outdoor swimming pools, perfect for taking a refreshing dip or lounging by the water.

There are two pools available, both heated and with a shallow end. These pools also offer a view, adding to the tranquil and relaxing ambiance. It is worth noting that the pools have age restrictions and are for adults only.

For guests who enjoy fishing, the hotel also offers this activity as an amenity. Additionally, board games and puzzles are available for those who prefer indoor entertainment. With these leisure amenities, guests can ensure a fun and enjoyable stay at Chesapeake Beach Resort.

Can guests use a pool at Chesapeake Beach Resort?

The Chesapeake Beach Resort has two pools available. Both pools are open all year round and are located outdoors. However, there are age restrictions as only adults are allowed to use the pools. The pools are heated, have a shallow end, and offer a view.

Does Chesapeake Beach Resort accept credit cards and cash payments?

No, Chesapeake Beach Resort does not accept cash payments. They only accept payment through Visa, Discover, Mastercard, and American Express credit cards.