Search
About
Rooms
Amenities
Reviews
Location
When to book
Tips & FAQs
Nearby stays
Chesapeake Beach Resort
2 stars

Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, FL 33036, United States
+1 305 664 4662
From
$155
Cheapest

rate per night

8.0
Great

based on 857 reviews

Chesapeake Beach Resort
Thu 5/2
-
Fri 5/3
Room type
Provider
Nightly total
Standard room
Double room
Queen room

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 5/2
Fri 5/3
King room
bed type unknown
bed type unknown
1 king bed
Queen room
1 queen bed
1 queen bed
2 queen beds
Double room
2 double beds
2 double beds
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, not including 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.
  • Increased accessibility
  • 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

Basics

  • 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

General

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

Kitchen

  • 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

Bathroom

  • 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

Bedroom

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

Outdoor

  • 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

  • Laundry facilities
  • Iron and ironing board

Health and safety

  • Daily housekeeping
  • Safe

Dining

  • Dining table

Family friendly

  • Complimentary breakfast

Fitness

  • 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.

8.0
Very goodBased on 857 verified guest reviews
8.2Friends
7.9Families
8.1Couples
8.0Solo

Pros +
Cons -

Traveler type:
Time of Year:
Show reviews that mention
Traveler rating:
Sort by:
A
4.0 Mediocre
Pros:Location.
A
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.
A
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.
A
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.
A
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.
A
8.5 Very good
Pros:Just ONE catamaran is not ready for sailing. Lack some important accessories for normal sailing.
L
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.
A
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.
T
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
A
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.

Location

83409 Overseas Highway, Islamorada, FL 33036

What's nearby

  • History of Diving Museum0.6 mi
  • Theater of the Sea0.9 mi
  • Blu Bamboo Salon and Day Spa1.4 mi
  • Lobster Trap Art Gallery1.4 mi
  • Hooked on Books1.7 mi
  • Cheeca Lodge & Spa1.9 mi
  • Matecumbe United Methodist Church1.9 mi
  • Hurricane Monument1.9 mi
  • Island Body & Sol Spa2.1 mi
  • The Rain Barrel Artisan Village3.1 mi
  • Bud n' Mary's Fishing Marina3.8 mi
  • Bud n' Mary's Dive Center3.8 mi

Policies

Check-in/Check-out

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

Cancellation/prepayment

Cancellation/prepayment policies vary by room type and provider.

Essential information about Chesapeake Beach Resort

Low season

August

High season

July

Average price (weeknight)

$312

Average price (weekend night)

$424
Cheapest month to stay with an average 30% drop in price.
Most expensive month to stay with an average 42% 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 August and October.
  • 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 Monday. The most expensive day is usually Tuesday.
  • The cheapest price a room at Chesapeake Beach Resort was booked for on KAYAK in the last 2 weeks was $263, while the most expensive was $498.
  • How long should you stay at Chesapeake Beach Resort? KAYAK users usually book their rooms here for 2 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, 1.2 miles from the center 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 62.3 miles from Miami. Chesapeake Beach Resort is 69.7 miles from Miami Opa Locka.

  • Does Chesapeake Beach Resort have a pool?

    Yes, Chesapeake Beach Resort has a pool onsite.

  • 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

Rental
Beacon Reef Condo Oceanfront Islamorada - Free Boat Dockage - Water, Elec0.44 miPrivate beach, Outdoor pool, Hot tub$268+
Rental
Southern Diversion Estate Islamorada see our winter discounts0.67 miPrivate pool, Kitchen, terrace/patio$1,726+
Rental
Radiant Suite With Ocean View And Resort Amenities0.83 miBalcony, air-conditioned, Coffee machine$906+
Rental
Alluring Accessible Suite with Ocean Views0.83 miBalcony, air-conditioned, Coffee machine$906+
3-star hotel
46% cheaperHadley Resort and Marina7 Good (1,258 reviews)0.94 miSnorkeling, Outdoor pool, Free Wi-Fi$135+
3-star hotel
23% cheaperFisher Inn Resort & Marina7.9 Good (1,073 reviews)1.31 miPrivate beach, snorkeling, Outdoor pool$192+
3-star hotel
16% cheaperSunset Inn8.6 Excellent (839 reviews)1.37 miOutdoor pool, Free Wi-Fi, Tea/coffee maker$211+
Rental
Beacon Reef Condo Oceanfront Islamorada - Free Boat Dockage - Water, Elec0.44 miPrivate beach, Outdoor pool, Hot tub$268+
Rental
3 Bedroom Private Oceanfront House - Sol10 Excellent (2 reviews)1.25 miOutdoor pool, Kitchen, wifi$1,146+
3-star hotel
16% cheaperSunset Inn8.6 Excellent (839 reviews)1.37 miOutdoor pool, Free Wi-Fi, Tea/coffee maker$211+
4-star hotel
The Islands of Islamorada8.4 Excellent (18 reviews)0.83 miPrivate beach, snorkeling, Outdoor pool$731+
3-star hotel
Casa Morada8 Excellent (1 review)1.38 miBar/Lounge, Room service, Free Wi-Fi$303+

Good to know

Value for money

7.5

Distance to city center

1.2 mi