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Chesapeake Beach Resort
2 stars

Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, FL 33036, United States
+1 305 664 4662
C$ 213

rate per night


based on 883 reviews

Chesapeake Beach Resort
Thu 20/6
Fri 21/6
Room type
Nightly total
Standard Room
C$ 213
Double room
C$ 343
King room
C$ 393

About Chesapeake Beach Resort

  • Resort Room
    Enjoy the many amenities of the resort
  • Freebies
    This stay includes Wi-Fi, Breakfast, and Parking for free

Chesapeake Beach Resort is located in Islamorada and is close to Hurricane Monument. It has a spa and wellness center, as well as a Jacuzzi, a sun deck and a private beach.

Chesapeake Beach Resort Islamorada treats guests to an outdoor pool, outdoor tennis courts and a bike rental service. Guests have access to a terrace and a barbecue area.

The resort features 65 rooms, all of which are filled with a variety of facilities to ensure an enjoyable stay.

Chesapeake Beach Resort is situated amongst the area's well-known sightseeing attractions, including Theater of the Sea, which is a short walk away. Guests are able to visit Key Largo and Long Key, situated a short drive away from the property.

Photos of Chesapeake Beach Resort

Latest deals for Chesapeake Beach Resort

Thu 20/6
Fri 21/6
Queen room
1 queen bed
2 queen beds
1 queen bed
Double room
2 double beds
2 double beds
bed type unknown
King room
bed type unknown
bed type unknown
bed type unknown
Standard Room
2 double beds
bed type unknown
bed type unknown
Deluxe room
bed type unknown
2 queen beds
2 queen beds
*Total includes estimated local taxes & fees payable on check out.
Prices are based on 1 night including GST, excluding local taxes and fees.

Amenities at Chesapeake Beach Resort

  • Private beach
  • Outdoor pool
  • Room service
  • Bicycle rental
  • Tennis
  • Free Wi-Fi
  • Coffee machine
  • Free parking
  • Wi-Fi available in all areas
  • Flat-screen TV

Accessibility and suitability

  • Entire unit located on ground floor
  • Entire unit wheelchair accessible
  • Pets allowed on request. Charges may apply.
  • Disabled Access
  • Roll-in shower
  • Elevator
  • Accessible by elevator
  • Hypoallergenic
  • Allergy-free room
  • No smoking
  • Lowered sink
  • Non-feather pillow
  • Toilet with grab rails
  • Upper floors accessible by elevator
  • Upper floors accessible by stairs
  • Private entrance


  • Free Wi-Fi
  • Wi-Fi available in all areas
  • Internet
  • Linens
  • Towels
  • Fan
  • Fire extinguisher
  • Free toiletries
  • Shampoo
  • Smoke alarms
  • Heating
  • Body soap
  • Air-conditioned
  • Trash cans
  • Conditioner


  • Window
  • Sea view
  • Seating area
  • Interconnected room(s) available
  • Sofa
  • Telephone
  • Tile/marble floor
  • Pool view
  • Storage available


  • Dishwasher
  • Microwave
  • Kitchenware
  • Stovetop
  • Toaster
  • Refrigerator
  • Coffee machine
  • Kitchenette

Services and conveniences

  • Wake-up service
  • Concierge service
  • Mini-market on site
  • Room service
  • Key access
  • Key card access
  • Private check-in/check-out
  • 24hr front desk


  • Shower
  • Shower cap
  • Hairdryer
  • Toilet
  • Toilet paper
  • Private bathroom
  • Walk-in shower

Pool and spa

  • Heated pool
  • Spa
  • Hot tub
  • Outdoor pool
  • Pool towels
  • Pool with a view


  • Socket near the bed
  • Alarm clock
  • Sofa bed
  • Clothes rack
  • Wardrobe or closet


  • Beach towels
  • Balcony
  • Outdoor furniture
  • Private beach

Media and entertainment

  • Flat-screen TV
  • Cable or satellite TV
  • TV

Things to do

  • Bicycle rental
  • Fishing
  • Board games/puzzles

Parking and transportation

  • Free parking
  • Private parking


  • Laundry facilities
  • Iron and ironing board

Health and safety

  • Daily housekeeping
  • Safe


  • Dining table

Family friendly

  • Complimentary breakfast


  • Tennis

Reviews of Chesapeake Beach Resort

All reviews are collected from real users with a verified booking made with KAYAK or one of our trusted external partners.

Very goodBased on 883 verified guest reviews

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4.0 Mediocre
6.8 Okay
Pros:The view and well kept grounds were incredible. The view of sunrise and sunset were breathtaking. The tiki bar with local beers was a plus.
Cons:Unfortunately we arrived and immediately jumped in the shower. The shower was not cleaned property with black long hair all over the shower wall. This was not s good start to our stay. Also, the shower and bathroom could be updated to reflect the beauty of the locale and the price of the rooms.
5.4 Fair
Pros:Breakfast awesome fresh
Cons:Construction all day next door, no food at property. The have a bar/tiki but it is closed. Rug in rooms very clammy. Only to sleep and leave.
7.4 Good
Pros:Great waterfront view from our room, heated pools, and nice harbor for the boats. Covered parking was nice and the staff was also very friendly.
Cons:You are charged a daily resort fee not included in the original cost, but I have to say it's less of a resort and more of a hotel.
5.7 Fair
Pros:We liked the views and proximity to water and water sports. Breakfast was good. Plenty of outdoor seating to relax. Good location.
Cons:Our bed was so tough to sleep in, and we tried both beds in the room. We woke up with sore backs and tossed all night. So we were tired a lot of the trip from barely sleeping. We are young too so this is not regular for us. Other than that, the room could have been cleaner, specifically the shower. And we wished for a tiki bar for drinks on resort.
8.5 Very good
Pros:Just ONE catamaran is not ready for sailing. Lack some important accessories for normal sailing.
10.0 Wonderful
Pros:We stayed in one of the cottages. Nice screened in porch and beds were very comfy. Sitting on top of the tiki hut was awesome in the breeze watching the motor sports on the water. Really nice place.
Cons:We saw a sign that said no taking wildlife from the lagoon so we didn't fish off the dock. The dock was full of snapper but we could only fish off the beach were there were no fish.
9.7 Wonderful
Pros:i liked the location of the resort. The activities like kayaking, biking and sailing were of no extra charge. Breakfast was included. The views and grounds were very attractive. Our college aged daughter and friends joined us for an overnight, and really loved the resort.
9.4 Wonderful
Pros:We upgraded from a regular room to a suite 702, and was thrilled with the accommodations, could not have asked for a better view. Felt like royalty for 3 days. PS Breakfast is included I think with most rooms was acceptable
9.3 Wonderful
Pros:Staff was very helpful in getting our room upgraded to a king room. We were even able to upgrade to a king suite with ocean view. We did have to pay more, but it was discounted for us. Very quiet and relaxing with a beautiful view!
Cons:Our room at first had 2 double beds and we wanted a king.


83409 Overseas Highway, Islamorada, FL 33036

What's nearby

  • History of Diving Museum0.9 km
  • Theater of the Sea1.4 km
  • Blu Bamboo Salon and Day Spa2.2 km
  • Lobster Trap Art Gallery2.2 km
  • Hooked on Books2.8 km
  • Cheeca Lodge & Spa3.1 km
  • Matecumbe United Methodist Church3.1 km
  • Hurricane Monument3.1 km
  • Island Body & Sol Spa3.3 km
  • The Rain Barrel Artisan Village5 km
  • Bud n' Mary's Fishing Marina6.2 km
  • Bud n' Mary's Dive Center6.2 km



Check in anytime after 4:00 PM, check out anytime before 11:00 AM


Cancellation/prepayment policies vary by room type and provider.

Essential information about Chesapeake Beach Resort

Low season


High season


Average price (weeknight)

C$ 428

Average price (weekend night)

C$ 444
Cheapest month to stay with an average 51% drop in price.
Most expensive month to stay with an average 44% rise in price.
Average Sun. - Thu. price over the last 2 weeks.
Average Fri. & Sat. price over the last 2 weeks.

When to book a room at Chesapeake Beach Resort

Price per night. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for your stay at Chesapeake Beach Resort

  • If you’re after a cheap room at Chesapeake Beach Resort, then you should consider staying during the low season. The cheapest deals can generally be found in October and November.
  • Prices can also vary depending on which day of the week you stay. For the best room deals at Chesapeake Beach Resort, plan to stay on a Saturday or Thursday. The most expensive day is usually Sunday.
  • How long should you stay at Chesapeake Beach Resort? KAYAK users usually book their rooms here for 5 days.

FAQs when booking at Chesapeake Beach Resort

  • What is the best way to get to Chesapeake Beach Resort from the airport?

    Travelers who have landed at Reagan Washington (DCA) Airport and need to spend their entire holiday at Chesapeake Beach Resort need not worry. This resort is around 29.7 miles from the airport, and you can reach comfortably at this place by using the car rentals at the airport. It would take around 50 minutes to reach the resort from DCA airport. Apart from the car rental, you use a taxi at the airport's Main terminal at an affordable cost. If you are at the History of Diving Museum, it will take around 15 minutes to cover 0.6 miles to get to Chesapeake Beach Resort.

  • Why should I stay at Chesapeake Beach Resort instead of other hotels?

    You will never regret staying at Chesapeake Beach Resort during your vacation holiday. It is one of the hotels located on a private beach in the Upper Florida Keys. You will enjoy the heated pool and hot tubs while staying in this place. You will also enjoy having the sea views while on the balconies of this hotel. There are canoes, Kayaks, and bikes available. On the site, you can engage in several activities, such as playing tennis and shuffle boarding with friends. You can even visit and learn more at the Windley Key Fossil Reef Geological State Park at the resort.

  • What options does Chesapeake Beach Resort give me when I travel with my kids?

    If you consider bringing your child and staying at Chesapeake Beach Resort, you will be in the right and safe spot. You can think about using the indoor pool instead of the outdoor one for the safety of the children. A children's camp and childcare services are also provided. The on-site restaurants offer meals suitable for children to soothe their stomachs. Several kid-friendly amenities are available, including arcade games on the hotel computers, cartoon channels on the flat-screen TVs in the rooms, a water park with a water slide, a railroad trail, and a gift shop.

  • How is parking at Chesapeake Beach Resort?

    You won't spend a single coin for parking while staying at Chesapeake Beach Resort. The parking lot at this place uses the precast structural system that includes a center ramp design, allowing a level facade on four sides with driven foundations. You can decide to use private parking or public parking depending on your choice once at the resort.

  • Why should I eat at Chesapeake Beach Resort?

    Chesapeake Beach Resort is a place with several restaurants that offers varieties of delicious meals that you will never miss tasting. You will enjoy all the meals delivered from the ten restaurant locations. For seafood at affordable prices, you can consider getting to Rod and Reel, Traders Seafood Steak, or Broadway Café restaurants. For Mexican dishes, you can consider getting them at Plaza Mexico Restaurant. You can consider getting Italian dishes at Ledo Pizza, Mama Lucia, or Neptune's Seafood Pub restaurants when you need them.

  • Where is Chesapeake Beach Resort located?

    Chesapeake Beach Resort is located at 83409 Overseas Highway, 2 km from the centre of Islamorada. History of Diving Museum is the closest landmark to Chesapeake Beach Resort.

  • When is check-in time and check-out time at Chesapeake Beach Resort?

    Check-in time is 4:00 PM and check-out time is 11:00 AM at Chesapeake Beach Resort.

  • Does Chesapeake Beach Resort offer free Wi-Fi?

    Yes, Chesapeake Beach Resort offers free Wi-Fi.

  • Does Chesapeake Beach Resort offer free parking?

    Yes, Chesapeake Beach Resort offers free parking.

  • How far is Chesapeake Beach Resort from the airport?

    Chesapeake Beach Resort is 100.2 km from Miami. Chesapeake Beach Resort is 112.2 km from Miami Opa Locka.

  • Does Chesapeake Beach Resort have a pool?

    Yes, Chesapeake Beach Resort has a pool on-site.

  • How does KAYAK find such great Chesapeake Beach Resort hotel deals?

    KAYAK scours the web for all room deals available at Chesapeake Beach Resort in Islamorada and lets you compare them to find the best rate for your stay. Many different travel sites will offer discounts or deals at different times for rooms at Chesapeake Beach Resort and KAYAK will provide you with prices from a huge range of travel sites. That means that you can always find a great deal for Chesapeake Beach Resort.

Nearby hotels and places to stay

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Southern Diversion Estate Islamorada see our winter discounts1.08 kmPrivate pool, Kitchen, terrace/patioC$ 2,218+
Radiant Suite With Ocean View And Resort Amenities1.33 kmBalcony, air-conditioned, Coffee machineC$ 986+
Alluring Accessible Suite with Ocean Views1.33 kmBalcony, air-conditioned, Coffee machineC$ 975+
3-star hotel
20% cheaperHadley Resort and Marina7 Good (1,216 reviews)1.51 kmSnorkeling, Outdoor pool, Free Wi-FiC$ 262+
Special Summer Sale Rates May-July!!0.71 kmPrivate beach, Outdoor pool, Hot tubC$ 397+
Relax in this updated townhome while overlooking the sparkling Atlantic Ocean1.38 kmPool, Kitchen, BalconyC$ 401+
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay1.89 kmKitchen, Tennis, terrace/patioC$ 438+
4-star hotel
The Islands of Islamorada8.1 Excellent (15 reviews)1.33 kmPrivate beach, snorkelling, Outdoor poolC$ 796+
3-star hotel
20% cheaperHadley Resort and Marina7 Good (1,216 reviews)1.51 kmSnorkeling, Outdoor pool, Free Wi-FiC$ 262+
Radiant Suite With Ocean View And Resort Amenities1.33 kmBalcony, air-conditioned, Coffee machineC$ 986+
Cozy Cottage in the Heart of Islamorada1.84 kmKitchen, Balcony, air-conditionedC$ 773+

Good to know

Value for money


Distance to downtown

2.0 km