Pros & cons
PROS
- Oceanfront setting with two pools and private beach access
- All rooms feature balconies with ocean or island views
- Cooked-to-order breakfast and two hours of water sports included
CONS
- $50 nightly resort fee
- No on-site laundry; you’ll need a nearby service
Overview
Fresh off a 2025 renovation, this Islamorada resort sits right on the Overseas Highway with the vibe people come here for: sunrise over the Atlantic, palms swaying, and enough on-site fun that you don’t have to leave if you don’t want to. Every room has a balcony (ocean or garden), and the property fronts a sandy beach with two ocean-view pools.
What You’ll Do
- Start with the included cooked-to-order breakfast (omelets, plus continental items) served 6:00–10:00 AM.
- Paddle or pedal: kayaks and paddleboards are on site, and two hours of water-sports rentals per room per night are included in the resort fee. Fishing off the property and clear kayaks are available, and sunset tiki cruises depart from the marina.
- Laze on the beach or by the pools, then wander to nearby eateries or book a charter—this is the Sport Fishing Capital after all.
Need-to-Know
- Check-in is 4:00 pm; check-out is 11:00 am.
- Resort fee is $50/night and covers breakfast, a welcome drink, robes/slippers, high‑speed internet, pool/beach towels and loungers, two hours of water-sports gear, seasonal activities and beach games, fish-cleaning stations, 24‑hour lobby coffee/tea, self‑parking (boats/trailers extra), and local calls.
- Pet-friendly: dogs are allowed with a per‑night fee; cats aren’t permitted.
- Parking for boats and trailers carries additional charges. No on‑site laundry (there’s a service down the road).
Nearby & Nature
You’re an easy walk (about 11 minutes) from the History of Diving Museum, and a short drive from reefs and mangroves where you can spot dolphins, manatees, sea turtles, and loads of tropical fish. The resort’s calm shoreline is a good launch for paddling when winds are light.
Why It’s Worth It
If you want an easy Keys base where the sunrise is your alarm clock and your day’s activities are steps away, this place nails the brief. The included breakfast and gear time add real value, especially for families.
Best Time to Visit
- Weekdays for thinner crowds.
- Sunrise for glassy water, cooler temps, and the best light from ocean-view balconies.
- Late afternoon golden hour is great on the beach; book sunset cruises a bit ahead on busy weekends.
Where it is
24.9356, -80.6135Tips for Chesapeake Beach Resort
- 01Book an oceanfront balcony if sunrise views matter to you.
- 02Budget for the $50 resort fee—it covers breakfast and two hours of gear.
- 03Grab kayaks or paddleboards early for the calmest water.
- 04If you’re trailering a boat, expect extra parking charges.
- 05Walk to the History of Diving Museum instead of driving.
Amenities
Near Chesapeake Beach Resort
All places →All trails →
0.1 mi awayFlagler StationWaterfront steakhouse for sunset dinners on the Overseas HighwayRestaurant · Food
0.6 mi awayHistory of Diving MuseumA compact museum charting diving’s evolution with jaw-dropping helmetsExhibit · Parking
0.8 mi awayTheater of the SeaClassic Keys marine park with dolphin swims and lush lagoonsParking · Restroom
1.4 mi awayDrop Anchor Resort & MarinaOld-Keys lodge with ocean views, pool, and a handy boat rampLodging · Parking
1.9 mi awayWindley Key Quarry TrailShort loop among coral-quarry walls with fossil coral up closeEasy · 0.4 mi · 30 min
1.9 mi awayWindley Key Hammock TrailShady 0.6 mile loop through Keys hammock and fossil reef historyEasy · 0.6 mi · 30 min
2.6 mi awayGreen Turtle Hammock Nature TrailShady 0.4 mile loop through rare Keys rockland hammock.Easy · 0.4 mi · 30 min
10 mi awayAnne's Beach BoardwalkFlat mangrove boardwalk to shallow Keys water and shaded pavilionsEasy · 0.5 mi · 30 min
