
Upper Matecumbe Key Vacation Packages
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Top rated hotels for your Upper Matecumbe Key vacation package

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
The price is $322 per night
$322
includes taxes & fees
$286 per night
May 11 - May 12
Features of Chesapeake Beach Resort include a private beach, 2 outdoor pools, and a computer station. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area.
On private beach
Pool

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.09 mi from city center
The price is $359 per night
$359
includes taxes & fees
$319 per night
May 5 - May 6
Cheeca Lodge & Spa features a private beach, a golf course, and a full-service spa. Free valet and self parking are available, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
On private beach
Pool

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
1.88 mi from city center
The price is $310 per night
$310
includes taxes & fees
$276 per night
May 8 - May 9
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a gym. You can take advantage of free parking, along with a free area shuttle. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include WiFi in public areas, a meeting room, and a terrace.
On private beach
Pool
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View all propertiesLowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.