Chesapeake Beach Resort Accommodation in Islamorada, Florida
Book on our site
up to 10% cheaper
than Booking.com
Key details
About the Hotel
83409 Overseas Highway, Islamorada, 33036,
-
Steps from Whale Harbor Marina
Great
8.4
9.1
/10
3.9
4.2
/5
Loved by Chesapeake Beach Resort guests
Private beach atmosphere
Text service
Complimentary kayaks
Unique villas
Continental breakfast
"The room was lovely, super clean, very modern style with an ocean view."
Ernesto from United States
read full review
"Breakfast on the sea is a plus."
Masal9 from Italy
read full review
"Freshly cooked omelettes in the morning were great!"
Christine from Australia
read full review
"Perfect location in Islamorada with nice views of the water."
Cindy G from United States
read full review
"Free use of kayaks if weather permits."
Esta K from United States
read full review
Oceanfront resort in Islamorada with private beach access
Amenities & Activities
The resort offers a private beach area exclusive to guests with loungers and umbrellas. Guests receive complimentary access to kayaking and paddleboarding equipment for up to two hours daily. Two heated outdoor pools with ocean views and a hot tub are available, along with Friday yoga classes.
Rooms & Accommodations
Spacious two-bedroom villas and premium suites are available, some with full kitchens and ocean-view balconies. Each room includes a 37-inch flat-screen cable TV and a small refrigerator. Select villas feature kitchenettes, and the hotel offers personalized breakfast delivery service to the room.
Dining
A complimentary breakfast is served daily from 6am to 10am with made-to-order omelets, pancakes, and French toast prepared by chefs Chris and Jose. The on-site snack bar offers drinks and light meals, including burgers and hot dogs. Guests also receive a welcome champagne drink upon arrival.
Location & Nearby Attractions
The resort is located on the oceanfront in Islamorada, within a 3-minute walk to the History of Diving Museum. Windley Key Fossil Reef Geological State Park is 2 miles away, and Theater of the Sea is a 4-minute drive. Many local dining options are within walking distance, including a rooftop bar next door.
Family & Pet-Friendly Features
The resort welcomes pets with a fee of $50 per pet per night. Children enjoy board games, giant chess and checkers, cornhole, and free use of fishing poles and bikes. Daily housekeeping and regular guest check-ins via text ensure a smooth stay for families.
Highlights
Beachfront: Private beach area with loungers and umbrellas
Rooms: Two-bedroom villas with kitchenettes and ocean views
Activities: Complimentary kayaking, paddleboarding, and fishing
Dining: Made-to-order omelet breakfast and welcome champagne
Pet Policy: Pets allowed for $50 per pet per night
Check-in Perks: Personalized breakfast delivery and daily guest check-in texts
Must-do experiences
Snorkel at the John Pennekamp Coral Reef State Park for stunning views.
Savor the conch fritters at Mike's Kitchen, a local favorite.
Visit the Florida Keys History and Discovery Center for culture.
Take a sunset cruise with Islander Watersports for breathtaking sights.
Explore the hidden treasures at the Islander Watersports market.
Select your room type
Chesapeake Beach Resort offers a range of rooms across the Sunshine State — from double rooms to family suites — complete with breakfast, flexible cancellations, and seasonal deals for your Florida stay
Ocean View Two Queens
2 persons
32 sq. feet
2 Double beds
Air conditioning
Balcony
room details
Ocean View King
2 persons
32 sq. feet
1 King-size bed
Air conditioning
Balcony
room details
Deluxe King Suite
2 persons
55 sq. feet
1 King-size bed
Air conditioning
Balcony
room details
Show all rooms
Price and Room Availability Calendar
Check availability and prices for your dates now!
September 2026 - September 2027
Sun
Mon
Tue
Wed
Thu
Fri
Sat
September 2026
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
October 2026
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
November 2026
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
December 2026
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
January 2027
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2027
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
March 2027
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
April 2027
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
May 2027
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
June 2027
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
July 2027
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
August 2027
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
Choose dates to see prices
Check-in/ Check-out
Amenities
Chesapeake Beach Resort offers amenities for your Florida getaway, from theme park days to coastal escapes
Facilities: Great
8.4/10Review score
General
No smoking on site
Wi-Fi
Parking
24-hour reception
VIP check-in/ -out
Pets allowed
Rooms/ Facilities for disabled
Wheelchair access
Security
Luggage storage
Private beach
Allergy-free rooms
Lift
Smoke detectors
Fire extinguishers
Key card access
Sports & Fitness
Yoga class
Fishing
Guest Parking
Private parking is possible on site for free.
Services
Housekeeping
Shops/Commercial services
Welcome drink
Dining
Snack bar
Children
Board games
Facilities for people with disabilities
Toilet for disabled
Bathroom for disabled
Spa & Leisure
Heated swimming pool
Outdoor swimming pool
Beach access
Sun loungers
Live entertainment
Pool with view
Shallow end
Room features
Air conditioning
Heating
Sitting area
Garden furniture
Dining table
Bathroom
Free toiletries
Sink
Self-catering
Cookware/ Kitchen utensils
Media
Flat-screen TV
AM/FM alarm clock
Show more
Chesapeake Beach Resort Location
83409 Overseas Highway, Islamorada, 33036,
Explore Islamorada
Explore the Flavors and Fun
Top Attractions
Activities
Dining
Entertainment
History of Diving Museum
12 minutes' walk
Museum showcasing the history of diving and underwater exploration. Unique exhibits and informative tours offer rich insights.
Lobster Trap Art Gift Shop and Gallery
4 minutes' drive
Gallery featuring local artists' work and unique crafts. A great spot to find souvenirs and enjoy the artistic vibe of the Keys.
Florida Keys History and Discovery Center
5 minutes' drive
Interactive exhibits on the history and ecology of the Florida Keys. Educational programs and workshops enhance the experience.
Snorkeling at Carysfort Reef
5 minutes' drive
Thrilling snorkeling adventure to see vibrant coral reefs and diverse marine life. Rentals available nearby; guided tours recommended.
Yoga at FNX Club
10 minutes' drive
Relaxing yoga sessions offered with beautiful ocean views. Classes suitable for all levels; check for schedule and pricing.
Wahoo's Bar and Grill
3 minutes' walk
Casual eatery with fresh seafood and tropical drinks. Enjoy outdoor seating and the famous fish tacos in a laid-back atmosphere.
Whale Harbor Seafood Buffet
3 minutes' walk
Seafood buffet featuring local catches and diverse dishes. Family-friendly atmosphere with ample options for every palate.
Islander Watersports
3 minutes' walk
Live music and entertainment at a vibrant waterfront venue. Regularly hosts events, including open mic nights and local bands.
Getting around Florida
City Centre
Islamorada 24 min · 1.2 mi
Bus
Bus stop 8 min · 3.3 mi
Want to Unlock an Early Booking Rate for Your Florida Stay?
Get exlusive rates right now!
Check Rates
Property information and rules
Check-in
from 16:00-23:00
Check-out
from 07:00-11:00
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in the entire hotel for free.
Breakfast
A full breakfast is served at the price of USD 0.1 per person.
Children & extra beds
There are no extra beds provided in a room. There are no cots provided in a room.
Pets
Pets are allowed on request.
Year renovated:
2008
Number of rooms:
45
Reviews and Ratings
Feedback about Chesapeake Beach Resort from previous guests about their experience.
Review score
Based on 1092 verified reviews
9.0 /10
Perfect
89 %
Recommend
Cleanliness
8.8/10
Comfort
8.7/10
Facilities
8.4/10
Free WiFi
9.3/10
Location
8.9/10
Staff
8.5/10
Value for money
7.7/10
Pros
Friendly staff
Clean rooms
Good breakfast
Cons
Expensive fees
Guest reviews
based on 88 reviews
4/5
based on 721 reviews
8.4/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
Guest reviews
Bayside Villas By Islander Resort
Bayside Inn Key Largo
Islander Resort
Sunshine Key Rv Resort & Marina
Gilbert'S Resort & Marina
Seafarer Key Largo Resort And Beach
Ambrosia Key West
Caloosa Cove Resort By Coolvacay
Best Western Gateway To The Keys - Florida City, Homestead, Everglades
Westwinds Inn
Blackfin Resort And Marina
Sea Dell Motel - Marathon