919 reviews
From
$49283409 Overseas Highway, Islamorada, 33036, Florida, United States
919 reviews
1/94
Beachfront
Private beach area
Outdoor swimming pool
Free Private Parking
Free wifi
Beach
Air conditioning
Private entrance
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 919 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 $492, 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.
Beachfront
Private beach area
Outdoor swimming pool
Free Private Parking
Free wifi
Beach
Air conditioning
Private entrance
Parking On Site
24-hour front desk
Non-smoking rooms
Wheelchair accessible
Beach chairs/Loungers
Kitchenware
Kitchenette
Elevator
Upper floors accessible by elevator
Balcony
Free toiletries
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.
Show 8 photos
Suite, Accessible, Ocean View
1 King Size Bed
1 Sofa Bed
595 sqft
Balcony
Microwave
Flat-screen TV
Refrigerator
+
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.
Show 11 photos
King Room, Ocean View
1 King Size Bed
345 sqft
Private Bathroom
Balcony
Private entrance
Microwave
+
More details
Ocean View King (1 King Bed) is 366 square feet and includes balcony, satellite tv , cable tv, hairdryer, tea and coffee making facilities , ironing set, and safe.
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.
Show 6 photos
Room - 2 Queen, Ocean View
2 Double Beds
345 sqft
Private Bathroom
Balcony
Private entrance
Microwave
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.
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.
Show 20 photos
Deluxe Suite, King Size
1 Queen Size Bed
1 Sofa Bed
590 sqft
Private Bathroom
Balcony
Private entrance
Microwave
+
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.
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 balcony, satellite tv , cable tv, hairdryer, tea and coffee making facilities , ironing set, and safe.
Show 7 photos
Premium Villa, 1 Bedroom, Ocean View
2 Double Beds
1 Sofa Bed
0 sqft
Private Bathroom
Kitchenette
Kitchenware
Private entrance
+
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.
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.
Show 9 photos
Premium Villa, Ocean View
1 Sofa Bed
1 King Size Bed
830 sqft
Private Bathroom
Kitchenette
Kitchenware
Private entrance
+
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.
Show 6 photos
Deluxe, King Size, Accessible, Ocean View
1 King Size Bed
365 sqft
Private Bathroom
Balcony
Private entrance
Microwave
+
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.
8.1
919 reviewsCategories 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.
Bonnie
10
December 2024
The rooms were very comfortable and clean. The staff serving breakfast was super friendly and helpful. Actually all the staff (office, chamber maid) was very accommodating. Beach was very nice and we had plenty of sitting. Was nice that there were paddleboards and kayaks to use. Pool/spa was perfect and we enjoyed both! We enjoyed our stay enough that my friend is going to bring her family back. We all would stay here again!
We had trouble with our coffee maker and they brought another one and that one had issues too. Oh well, they had coffee available at bkft.
Johanna
8.2
December 2024
Private pool, private beach. Excellent omlette from chef!
The room door didn’t close properly from the very first entering to rhe room. Noticed some break-in marks on it. Notified the staff about it and they changed our room immediately. Then this other weird thing happened: we woke up in the middle of the night because the main light shined bright down to us in our room, even thow we were asleep and for sure didn’t put it on ourselves. So we had to deal with founding the switch in the middle of the night while it was very hard to find and while being upset about this weird event.
Maddalone
10
May 2024
Breakfast included and good 👍 you can walk next door for two restaurants and an all you can eat seafood buffet. I went with myself and two adult children. The food was good at restaurants. For 3 with cocktails lunch or dinner all meals were with tip $80 to $100 . Just expect that . Drinks pricey though hotel has happy hour drinks for $7. Free kyacking ,paddle boards, you can fish on the property. 1 hour 45 in early am to key west . Great location . Very impressed by all staff at the hotel and restaurants. I was upgraded to a villa . We loved it . Full fridge, stove top, microwave , sink , dishes and silverware. Fishing charters all around the area . We did a charter at Robbie’s a really cool spot to hang out at .
Really I can say I have no complaints at all .
Megan
10
November 2023
The room was beautiful and ocean front. Vey comfortable beds! The balcony was spacious as was the bathroom. The beachfront was stunning and the pools were a lot of fun! Complimentary water sports was such a wonderful bonus and the breakfast was great with many options and open for such a long span of time. Oh and at check in they offered you champagne. The staff was exceptional the whole time checking in on our needs and it was a very busy week as we stayed over the holiday.
Honestly, I can’t really say that there was anything we didn’t like. They ran out of towels in the pool area a couple times but if you called, texted, or asked a staff member they got them immediately. Like I said it was a busy holiday week we visited so I would have expected more hiccups but they really have this facility well managed. I have a pretty high bar, we travel the world and I barely ever give reviews. This is well deserved exceptional review.
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.
Christine
8.2
December 2024
Location next to the beach was great - however maybe did not live up to our ‘resort’ expectations. Freshly cooked omelettes in the morning were great! Lovely view to wake up to. Comfy beds. Mostly pleasant staff. Good location to visit the Keys. Fabulous seafood buffet next door on Christmas Day!
No glassware or plates etc in room. Would recommend others to be aware. No ‘little milks’ in room for a cup of tea. Very busy road - but possibly time of year.
Giovanni
10
June 2024
This is our place to go when my wife and I need to take a break from our stressful routine. We land in key west, rent a car (buy some wine and other groceries) and drive to our favorite refuge. We always get the ocean view room. Rooms are clean, beds very comfy and cozy, the view from the balcony is stunning and refreshing! The resort is quiet and peaceful with a relaxed vibe, two pools, a hot tub and a private beach. All you have to do is enjoy the sun and forget about the rest of the world!
Michelle
10
November 2024
Beautiful location, clean and comfortable rooms, helpful staff (especially the delightful Nari who made us delicious omelets), lovely little beach area complete with complimentary water sports, clean and accommodating pool areas, a proper included breakfast, and, last but not least, yummy bathrobes and slippers.
I’m always looking for more hooks in the bathroom to hang the bath towels for a family of four. And, given the beach location, a drying rack for swimsuits, etc.
Schnelle
8.2
October 2023
Property was nice waited long time to have are room ready after sending them messages we were looking for early check in waited 4 hours from arrival time to room was available on Anniversary not a great start !
The water sports equipment old and beat up need to be upgraded the Iquana’s are all around pool areas very invasive and poop near pool not a good look some of concrete on balconies cracked as a building inspector that’s concerning had cones and tape in certain areas safety code violations!
Attractions
Flamingo Visitor Center
24.1miEverglades National Park
30.1miAttractions
Flamingo Visitor Center
24.1miEverglades National Park
30.1miLocation
Features
Age restrictions
Availability
Beachfront
Private beach area
Outdoor swimming pool
Free Private Parking
Free wifi
Beach
Air conditioning
Private entrance
Parking On Site
24-hour front desk
Non-smoking rooms
Wheelchair accessible
Beach chairs/Loungers
Kitchenware
Kitchenette
Elevator
Upper floors accessible by elevator
Balcony
Free toiletries
Accessibility
Entire unit located on ground floor
Entire unit wheelchair accessible
Hearing accessible
Toilet with grab rails
Upper floors accessible by elevator
Upper floors accessible by stairs only
Visual aids (Braille)
Wheelchair accessible
Activities
Beach
Fishing
Bathroom
Free toiletries
Hairdryer
Private Bathroom
Shower
Toilet
Toilet paper
Towels
Bedroom
Alarm clock
Linens
Wardrobe or closet
Cleaning Services
Daily housekeeping
Entertainment & Family Services
Board games/Puzzles
Food & Drink
Wine/Champagne
Food & drink safety
Breakfast to-go containers
Delivered food covered securely
Front Desk Services
24-hour front desk
Baggage storage
Concierge
Invoice provided
Private check-in/out
General
Air conditioning
Convenience store on site
Elevator
Facilities for disabled guests
Heating
Hypoallergenic room available
Interconnecting room(s) available
Non-smoking rooms
Pet Friendly
Private entrance
Smoke-free property
Tile/Marble floor
Internet
Free wifi
Kitchen
Coffee machine
Dining table
Kitchenette
Kitchenware
Microwave
Refrigerator
Stovetop
Toaster
Living Area
Sitting area
Sofa
Media & Technology
Cable channels
Flat-screen TV
Telephone
TV
Outdoors
Balcony
Beachfront
Outdoor furniture
Private beach area
Parking
Free Private Parking
Parking On Site
Physical distancing
Cashless payment available
Room Amenities
Clothes rack
Fan
Iron
Socket near the bed
Sofa bed
Safety & security
Carbon monoxide detector
Fire extinguishers
Key card access
Security alarm
Smoke alarms
Safety features
First aid kits available
Services
Wake-up service
Wake-up service/Alarm clock
Spa
Beach chairs/Loungers
Outdoor swimming pool
View
Pool view
From 16:00
Until 23:00
Guests are required to show a photo identification and credit card upon check-in
From 07:00
Until 11:00
Pets are allowed. Charges may apply.
WiFi is available in all areas and is free of charge.
The minimum age for check-in is 18
Come and go whenever you want
Free private parking is available on site (reservation is needed).
Child policies
Children of all ages are welcome.
Children 12 and above will be charged as adults at this property.
To see correct prices and occupancy info, add the number and ages of children in your group to your search.
Crib and extra bed policies
No capacity for extra beds or cribs.
Cash
Discover,
American Express,
Mastercard,
Visa
This property does not accept cash.
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 $492. 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.
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