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

Chesapeake Beach Resort, All-Inclusive in Islamorada

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From$149 /night
Check-in
19Jul
Check-out
20Jul
Rooms and Guests2 Guests, 1 Room
Key details

About This Resort

83409 Overseas Highway, Islamorada, 33036
-
Close to the History of Diving Museum
Great
8.6
9.1
/10
3.9
4.2
/5

Chesapeake Beach Resort - Oceanfront resort with private beach, 0.3 miles from Whale Harbor Marina

Located between Everglades National Park and Florida Strait in Islamorada. The resort features an outdoor pool with ocean views, private beach access, and water sports equipment rentals (kayaks, paddleboards, fishing rods). On-site facilities include event venues for weddings and meetings, fish cleaning stations, and boat parking. Resort fee ($50/night) includes made-to-order breakfast, two hours of water sports rentals per room, beach chairs, and Wi-Fi. Theater of the Sea, offering dolphin swimming experiences, is 0.9 miles away. Alligator Reef snorkeling site is located 5.8 miles offshore.

Additional perks of the hotel

24-hour coffee and tea service in lobby

Welcome drink upon arrival

Seasonal resort activities and beach games

Group rates available for events

Pet-friendly accommodations

ADA compliant facilities

Full Moon Party access at Pierre's Restaurant

Italian and seafood restaurants within walking distance

Rooms and Suites

Standard rooms feature balconies with pool or ocean views, walk-in showers, and 37-inch flat-screen TVs. Ocean View Suites include separate living rooms with dining tables seating four, and sleeper sofas. Villas offer kitchenettes with full-size refrigerators, two-burner stovetops, and dishwashers. ADA accessible rooms available with roll-in showers. Two-bedroom suites feature master bedrooms with king beds and direct balcony access.

Other conveniences

Air conditioning and heating

Coffee makers and mini-refrigerators

Balcony furniture

In-room safes

Blackout curtains

Wardrobes

Free toiletries

AM/FM alarm clocks

Complimentary robes and slippers

Tiled floors in villas

“This Islamorada resort emphasizes relaxation, especially for families who want a private beach experience. Complimentary water sports add value, and the spacious villas suit longer stays. I think it's a particularly appealing venue for beachfront weddings, given the setting.”
Hotel logo
Madeline ScottChief Content Curator at Allinclusiveresorts

Choose Your Ideal Room

Choose from suites, family rooms, and more—breakfast, free cancellation, and exclusive perks included
  • Ocean View Two Queens
    2 persons
    32 sq. feet
    2 Double beds
    Air conditioning
    Balcony
  • Ocean View King
    2 persons
    32 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
  • Deluxe King Suite
    2 persons
    55 sq. feet
    1 King-size bed
    Air conditioning
    Balcony
Show all rooms

Rates and Room Availability by Date

Find available dates and compare today’s prices
July 2026 - July 2027
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Choose dates to see prices
Check-in/ Check-out

Resort Features & Services

Unmatched comfort, unforgettable experiences—all built into your stay
Facilities: Great
8.6/10Review score

General

  • No smoking on site
  • Wi-Fi
  • Free 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' walk
Diving artifacts and exhibits; highlights the evolution of scuba diving with engaging displays and interactive elements.
Windley Key Fossil Reef Geological State Park
Windley Key Fossil Reef Geological State Park
25 minutes walking
Unique fossilized coral reefs and hiking trails; offers a glimpse into prehistoric marine life with guided tours available.
Florida Keys History and Discovery Center
Florida Keys History and Discovery Center
25 minutes walking
Extensive local history exhibits; explore the cultural heritage of the Keys with various themed galleries and free admission days.
Water Sports at Whale Harbor Marina
3 minutes' walk
Thrilling jet ski rentals, kayaking, and fishing charters; ideal for adventure seekers wanting to explore the waters.
Yoga Sessions at FNX Club
10 minutes' drive
Relaxation-focused yoga classes; a perfect way to unwind while enjoying a calming atmosphere in a fitness community.
Wahoo's Bar and Grill
3 minutes' walk
Casual atmosphere with seafood specialties; try the grilled fish tacos or fresh catch of the day.
Whale Harbor Seafood Buffet
3 minutes' walk
Buffet-style dining featuring a variety of seafood dishes; perfect for families, with kids' options available.
Live Music at The Sand Bar
3 minutes' walk
Lively atmosphere with local bands performing; enjoy a mix of genres and a family-friendly vibe.
Shuck N Dive
3 minutes' walk
Casual bar with a fun setting; hosts local events and trivia nights that cater to all ages.
Transportation Options & Local Travel
  • City Centre
    Islamorada 24 min  ·  1.2 mi
  • Bus
    Bus stop 8 min  ·  3.3 mi
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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 US$0.10 per person per day.
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

Guest Reviews & Star Ratings

Hear from Guests Who’ve Stayed Before
Review score
Based on 993 verified reviews
8.9 /10
Great
89 %
Recommend
Cleanliness
9.0/10
Comfort
8.9/10
Facilities
8.6/10
Free WiFi
8.5/10
Location
9.0/10
Staff
8.6/10
Value for money
7.9/10
Pros
Sheltered dock
Private beach
Easy snorkeling
Comfortable room
Cons
Noisy traffic
Uncomfortable pillows
Lukewarm shower
Construction noise
Guest reviews
based on 88 reviews
4/5
based on 734 reviews
8.6/10
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 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?
Private parking is available on-site for free, but a reservation is needed.
What recreational facilities does Chesapeake Beach Resort offer?
The hotel features a heated outdoor pool with ocean views, private beach access, and complimentary fishing equipment.
Which amenities are included in the guest rooms at Chesapeake Beach Resort?
Rooms offer air conditioning, a 37-inch flat-screen TV, a small refrigerator, and free Wi-Fi.
How far is Chesapeake Beach Resort from the History of Diving Museum?
The History of Diving Museum is just a 3-minute walk from the hotel.
What nearby attractions can guests visit from Chesapeake Beach Resort?
Nearby attractions include Windley Key Fossil Reef Geological State Park (3 km) and Theater of the Sea (6 km).
Is breakfast available at Chesapeake Beach Resort?
Breakfast is available at an additional charge.
What types of views can guests expect from their rooms at Chesapeake Beach Resort?
Rooms offer views of the ocean or patio.
What leisure activities are available at Chesapeake Beach Resort?
Leisure activities include beach access, fishing, and use of outdoor sun loungers.

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