Chesapeake Beach Resort rates, Islamorada

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Dates and guests	Current price	Customer link
Nov 20 to Nov 22, 2026 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details
Nov 13 to Nov 15, 2026 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details
Dec 8 to Dec 10, 2026 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details
Dec 11 to Dec 13, 2026 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details
Dec 25 to Dec 28, 2026 · 3 nights · 3 adults	Get current price for this stay	Customer link — Open hotel details
Jan 8 to Jan 10, 2027 · 2 nights · 2 adults	Get current price for this stay	Customer link — Open hotel details
Feb 26 to Feb 27, 2027 · 1 night · 4 adults	Get current price for this stay	Customer link — Open hotel details

Axel's take: 8.6/10

A strong waterfront pick for pools and breakfast, less convincing for beach swimming. a relaxed 3-star oceanfront resort in Islamorada, scored for what it is.

Chesapeake Beach Resort is a relaxed 3-star oceanfront resort that delivers well on the essentials: comfortable renovated rooms, two pools and a waterfront setting. Recent Tripadvisor, Expedia and Hotels.com guests repeatedly praise the staff, cleanliness and cooked-to-order breakfast. We'd choose an ocean-view room here for an easygoing Keys break rather than expect a full-service luxury resort.

The beach is better for lounging than effortless swimming: coral underfoot and seasonal seaweed can make water access disappointing. Onsite dining beyond breakfast is limited, and guests mention inconsistent bar hours. The mandatory nightly resort fee covers breakfast, ordinary self-parking and limited watersports use; boating facilities cost extra. Expedia also currently flags construction at a neighboring building, so check the noise situation before booking. We'd skip it if a reliably swimmable beach or extensive resort dining tops your list.

Best for: couples seeking waterfront downtime; families who prioritize pools; travelers exploring the Upper Keys
Watch out for: Coral shoreline and seasonal seaweed; Mandatory resort fee and limited onsite dining; Neighboring construction flagged by Expedia
Location: Oceanfront in Islamorada, with nearby restaurants and convenient access to Upper Keys attractions.
Rooms: Renovated rooms draw strong comfort feedback; book an ocean-view category rather than assume every balcony faces the sea.
Cleanliness: Strong overall feedback across recent reviews, despite occasional housekeeping misses.
Service: Friendly front-desk and breakfast staff are consistent strengths across review sites.
Amenities: Two outdoor pools, private beach area and watersports; breakfast and limited equipment use are covered by the resort fee.
Fees and surprises: Mandatory nightly resort fee; boating services cost extra, no elevators, and Expedia flags neighboring construction.

Axel's opinion of Chesapeake Beach Resort, from the hotel's website and recent guest reviews. Sources: Hotel website · Tripadvisor · Expedia · Hotels.com. Reviewed Oct 23, 2026.

About Chesapeake Beach Resort

Property type: Resort
3-star hotel
83409 Overseas Hwy, Islamorada
Amenities: Computer, Air conditioning, 24-hour reception, Smoke-free property, Heating, Garden, Terrace, All Spaces Non-Smoking (public and private), Non-smoking rooms, Room service, Fridge, Cable TV
Check-in from: 16:00:00
Check-out by: 11:00:00
City page: Hotels in Islamorada

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3-star hotel · 83409 Overseas Hwy, Islamorada

Check-in from 16:00:00 · Check-out by 11:00:00

Computer · Air conditioning · 24-hour reception · Smoke-free property · Heating · Garden · Terrace · All Spaces Non-Smoking (public and private) · Non-smoking rooms · Room service · Fridge · Cable TV

Hotels in Islamorada

Axel's take

a relaxed 3-star oceanfront resort in Islamorada

8.6/10

A strong waterfront pick for pools and breakfast, less convincing for beach swimming.

Best for

couples seeking waterfront downtime
families who prioritize pools
travelers exploring the Upper Keys

Watch out for

Coral shoreline and seasonal seaweed
Mandatory resort fee and limited onsite dining
Neighboring construction flagged by Expedia

Location: Oceanfront in Islamorada, with nearby restaurants and convenient access to Upper Keys attractions.
Rooms: Renovated rooms draw strong comfort feedback; book an ocean-view category rather than assume every balcony faces the sea.
Cleanliness: Strong overall feedback across recent reviews, despite occasional housekeeping misses.
Service: Friendly front-desk and breakfast staff are consistent strengths across review sites.
Amenities: Two outdoor pools, private beach area and watersports; breakfast and limited equipment use are covered by the resort fee.
Fees and surprises: Mandatory nightly resort fee; boating services cost extra, no elevators, and Expedia flags neighboring construction.

Axel's opinion, from the hotel's website and recent guest reviews, scored for what the hotel is. Sources: Hotel website · Tripadvisor · Expedia · Hotels.com. Reviewed Oct 23, 2026.

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