Chesapeake Beach Resort Islamorada Beach photoChesapeake Beach Resort Islamorada Exterior photoChesapeake Beach Resort Islamorada Exterior photo

Chesapeake Beach Resort

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Check rooms and rates
From$149 /night
Check-in
01Sept
Check-out
02Sept
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

83409 Overseas Highway, Islamorada, 33036
-
Near Whale Harbor Marina
Great
8.4
9.1
/10
3.9
4.2
/5

3-star Islamorada oceanfront resort with private beach access

Rooms & Villas

Chesapeake Beach Resort offers two-bedroom and premium villas that include a well-equipped kitchen and ample space for families. Select rooms and suites have a balcony overlooking the ocean or the property. Each room comes with a 37-inch flat-screen cable TV and a small refrigerator.

Private Beach & Pools

The resort has a private beach area reserved exclusively for guests, with sun loungers and beach chairs available. Two heated outdoor pools offer ocean views, and one has a shallow end and a fence around it for safety. Complimentary kayaking and paddleboarding equipment rentals are provided, along with fishing poles and limited bike use.

Breakfast & Dining

A complimentary breakfast is served daily with made-to-order omelets and pancakes, plus fresh fruit, yogurt, bagels, and cereal. Guests can eat at outdoor tables overlooking the water or take the meal back to their room. A snack bar and a bar selling canned drinks and wine are available on-site.

Activities & Entertainment

Live music and performance events take place on-site, and guests can use board games and puzzles in common areas. Yoga classes are offered, and the beach area has giant chess, checkers, and cornhole sets. The hotel is 3 minutes' walk from the History of Diving Museum and 4 minutes' drive from Theater of the Sea.

Pet-Friendly & Accessibility

The resort allows dogs with a per-pet nightly fee and provides designated pet waste disposal areas. Wheelchair-accessible rooms include grab rails, raised toilets, and lower bathroom sinks, along with visual aids such as Braille signage. Accessible parking is available at no extra charge.

Highlights

Private beach: Exclusive guest-only area with loungers

Breakfast: Made-to-order omelets, pancakes & fresh fruit included

Water sports: Free kayaks, paddleboards, fishing poles

Location: Walk to History of Diving Museum, drive to Theater of the Sea

Pools: Two heated outdoor pools with ocean views

Pet policy: Dogs welcome with nightly fee

“This Islamorada resort strikes a pleasing balance, especially for families. The private beach and complimentary water sports add real value. It's a solid choice for those seeking a relaxed oceanfront experience, with spacious villas catering particularly well to longer stays.”
Hotel logo
James DavidEditor-in-Chief at Dogfriendly-hotels

Select your room type

The hotel provides many room choices—family rooms, doubles, and pet-friendly suites—with breakfast, free cancellation, and special offers
  • Ocean View Two Queens
    2 persons
    32 m²
    2 Double beds
    Air conditioning
    Balcony
  • Ocean View King
    2 persons
    32 m²
    1 King-size bed
    Air conditioning
    Balcony
  • Deluxe King Suite
    2 persons
    55 m²
    1 King-size bed
    Air conditioning
    Balcony
Show all rooms

Rates & availability calendar

See current prices and availability for your chosen dates!
August 2026 - August 2027
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Check-in/ Check-out

Facilities

Hotels feature amenities designed to keep both you and your pet comfortable
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

  • Cookware/ Kitchen utensils

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

Location

83409 Overseas Highway, Islamorada, 33036
Explore Islamorada
Explore the Area
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
History of Diving Museum
History of Diving Museum
12 minutes walking
Museum showcasing the history of diving with artifacts and exhibits. Special exhibits and guided tours available.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
4 minutes driving
Unique fossil reef park featuring hiking trails and geological displays. Great for nature lovers and history buffs.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
5 minutes driving
Center offering insights into the rich history and ecology of the Florida Keys with engaging exhibits and artifacts.
Snorkeling at Carysfort Reef
5 minutes driving
Exciting snorkeling opportunities at Carysfort Reef, ideal for thrill-seekers. Rentals and guided tours available.
Yoga on the Beach
3 minutes walking
Relaxing beach yoga sessions offered nearby, perfect for rejuvenation and connecting with nature. Classes available daily.
Wahoo's Bar and Grill
3 minutes walking
Casual spot known for fresh seafood and vibrant atmosphere. Try their famous fish tacos and outdoor seating.
Whale Harbor Seafood Buffet
3 minutes walking
Buffet offering a variety of seafood dishes in a family-friendly environment. A local favorite for seafood lovers.
Islander Watersports
3 minutes walking
Recreation area with live music and themed events. Family-friendly, featuring activities for all ages throughout the week.
Morada Way Arts & Cultural District
5 minutes driving
Local art and culture hub with galleries and occasional live performances. Experience local art events and exhibitions.
Local transport and travel tips
  • City Centre
    Islamorada 24 min  ·  2 km
  • Bus
    Bus stop 8 min  ·  5.3 km
Want access to early-bird pet-friendly hotel deals?
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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 1056 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
9.0/10
Staff
8.5/10
Value for money
7.7/10
Pros
Oceanfront room
Comfortable beds
Private beach
Complimentary watersports
Cons
Unfriendly staff
Poor breakfast
Guest reviews
based on 88 reviews
4/5
based on 722 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.
Open reviews
FAQs
About Chesapeake Beach Resort
What is the distance between Chesapeake Beach Resort and the nearest attractions?
Chesapeake Beach Resort is located 0.5 km from Whale Harbor Marina and 1 km from the History of Diving Museum.
What amenities are available at Chesapeake Beach Resort?
The resort features an outdoor swimming pool, a private beach, free Wi-Fi, and air conditioning in all rooms.
What are the check-in and check-out times at Chesapeake Beach Resort?
Check-in is at 16:00 and check-out is at 11:00.
Is parking available at Chesapeake Beach Resort?
Chesapeake Beach Resort offers free private parking on-site, with prior reservation required.
What room amenities can guests expect at Chesapeake Beach Resort?
Rooms come equipped with free Wi-Fi, a 37-inch flat-screen TV, a small refrigerator, and air conditioning.
Does Chesapeake Beach Resort offer any recreational activities?
Guests can enjoy access to the private beach, fishing, and complimentary water sports equipment rentals.
Which attractions are located near Chesapeake Beach Resort?
Popular nearby attractions include the Theater of the Sea, located 4 minutes by car, and the Windley Key Fossil Reef Geological State Park, which is about 3 km away.
What additional services does Chesapeake Beach Resort provide?
The resort offers a 24-hour reception, luggage storage, and a fitness club on-site.
Are there any family-friendly amenities at Chesapeake Beach Resort?
Chesapeake Beach Resort features board games and offers a children's playground.
What features does the pool at Chesapeake Beach Resort have?
The pool is heated, open year-round, and provides ocean views along with sun loungers.

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