Chesapeake Beach Resort – Islamorada Resort Review
Last updated: August 28, 2026
Choose Chesapeake Beach Resort if...
- You want a classic oceanfront resort with a private Atlantic beach at mid-range rates
- You're a family wanting beachfront villas with kitchens and a low-key vibe
- You're an angler wanting an on-site fishing dock without a full marina
Skip Chesapeake Beach Resort if...
- You want modern, contemporary design — this is a traditional Keys aesthetic
- You expect on-site dining, spa, or fitness center — none on property
- You want nightlife — Islamorada evenings are quiet and resort-centered
AskTheKeys Traveler Match
How well does Chesapeake Beach Resort fit your trip?
Before you book — the one trade-off
Chesapeake leans into classic Keys character over modern polish — you get a private beach and fishing dock, but no on-site dining or spa.
AskTheKeys Decision SummaryChesapeake Beach Resort is best for couples, families, and anglers wanting an oceanfront resort with private Atlantic beach, fishing dock, and classic Keys lodge character in Islamorada at upper-mid pricing. It is not ideal for guests wanting modern design, walkable dining, or full-service spa amenities.
Choose Chesapeake Beach if you want a classic oceanfront resort with a private Atlantic beach at mid-range rates. Skip it if you want modern design, on-site dining and spa, or nightlife.
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Before You Book
The details that matter after you've narrowed down your options.
Best for
- Couples seeking a classic oceanfront resort with private beach and Atlantic views at mid-range rates
- Families wanting beachfront villas with kitchens and a low-key, kid-friendly atmosphere
- Anglers who want an on-site fishing dock without needing a full marina property
- Repeat Keys visitors who prefer established lodge character over contemporary design
Not ideal for
- Guests wanting modern or contemporary design — the resort has a traditional Keys aesthetic
- Travelers expecting on-site dining, spa, or fitness center — none are available on-property
- Nightlife seekers — Islamorada has no nightlife district; evenings are quiet and resort-centered
Quick facts
| Address | 83409 Overseas Highway, Islamorada, FL 33036 |
|---|---|
| Phone | (305) 664-4662 |
| Check-in / Out | 3:00 PM / 11:00 AM |
| Parking | On-site (complimentary) |
| Pets | No |
| Beach access | Yes |
| Pool(s) | Yes |
| Spa | No |
| EV charging | No |
Location & nearby
Chesapeake Beach Resort is located in Upper Matecumbe Key within Islamorada.
What's nearby
- Whale Harbor Channel(0.5 mi, 10 min walk)
- Theater of the Sea(3 mi, 60 min walk)
- Robbie's Marina (Tarpon Feeding)(3.5 mi, 70 min walk)
- Islamorada Fish Company(1 mi, 20 min walk)
- History of Diving Museum(2 mi, 40 min walk)
- Hurricane Monument(1.5 mi, 30 min walk)
- Founders Park(2.5 mi, 50 min walk)
- Bud N' Mary's Marina(0.3 mi, 6 min walk)
Amenities overview
Property highlight features
- Private Atlantic oceanfront beach
- On-site fishing dock
- Heated oceanfront pool
- Hotel rooms and multi-bedroom villas with kitchens
- Direct Atlantic snorkeling access
- Complimentary kayaks and paddleboards
Pricing positioning
Typical nightly pricing tends to fall in the $$$ range, depending on season and room type.
upper-mid-range oceanfront resort with fishing dock
Compare current room availability and secure member-only pricing.
We handle our lodging checks through Expedia's network engine so you can lock in hidden seasonal discounts and stack your One Key™ rewards points across different island brands.
Independent Decision Engine
Florida Keys Resorts operates as a fully objective, crowdsourced review system. We do not accept paid placements from hotels to alter their scoring records. Instead, we use standardized API connections to provide transparent third-party rate checks for our community.
How Chesapeake Beach Resort Compares to Other Islamorada Resorts
Chesapeake Beach Resort vs Cheeca Lodge & Spa
- Chesapeake Beach Resort wins:classic oceanfront lodge with fishing dock, private beach, and villa options at lower rates
- Cheeca Lodge & Spa wins:flagship luxury resort with spa, golf, marina, fine dining, and comprehensive family programming
Chesapeake Beach Resort vs Islander Resort
- Chesapeake Beach Resort wins:oceanfront lodge with fishing dock, heated pool, and hotel-plus-villa mix near Whale Harbor
- Islander Resort wins:24-acre oceanfront-to-bayside resort with bungalows, four dining venues, seaside sports, and pet-friendly policy
Chesapeake Beach Resort vs La Siesta Resort & Villas
- Chesapeake Beach Resort wins:classic oceanfront lodge with fishing dock and hotel-plus-villa mix near Whale Harbor
- La Siesta Resort & Villas wins:Islamorada Resort Collection member with on-site dining, marina, water taxi, and Tulum-inspired oceanfront cottages and villas
FAQs
Does Chesapeake Beach Resort have a beach?
Yes. Chesapeake Beach Resort has a private Atlantic oceanfront beach with loungers, direct snorkeling access, and views across the shallow reef flats. It is one of the few Islamorada properties with a genuine sand beach.
Does Chesapeake Beach Resort have a fishing dock?
Yes. The resort has an on-site fishing dock where guests can fish directly or arrange charter pickups. The dock connects to Islamorada's Whale Harbor fishing corridor and is within walking distance of Bud N' Mary's Marina.
Does Chesapeake Beach Resort have a restaurant?
No. There is no on-site restaurant. Villas include full kitchens for self-catering. Islamorada Fish Company, Whale Harbor Seafood, and other restaurants are within a 1–2 mile drive.
What types of rooms does Chesapeake Beach Resort offer?
The resort offers standard oceanfront hotel rooms and multi-bedroom villas with full kitchens. Villas are suited for families or extended stays; hotel rooms work for couples and short trips.
Is Chesapeake Beach Resort good for families?
Yes. The private beach, heated pool, villas with kitchens, and fishing dock make it a solid family choice. There are no organized kids' programs — for structured family activities, consider Cheeca Lodge.
How does Chesapeake Beach Resort compare to Cheeca Lodge?
Chesapeake is smaller, less expensive, and more casual than Cheeca Lodge. Cheeca offers a full spa, golf course, marina, and fine dining. Chesapeake offers a fishing dock, private beach, and classic lodge character at lower rates.
Is Chesapeake Beach Resort pet-friendly?
No. Chesapeake Beach Resort does not allow pets. Pet-friendly Islamorada options include Cheeca Lodge & Spa and Islander Resort.
Do you need a car at Chesapeake Beach Resort?
Yes. Islamorada is car-dependent. The resort provides free on-site parking. Self-catering kitchens in villas reduce dining trips, but a car is needed for restaurants, groceries, and attractions.