Deals on vacations and trips to Upper Matecumbe Key
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Upper Matecumbe Key flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
The Balfour
South Beach
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. WiFi in public areas is free. Valet parking, dry cleaning, and luggage storage are also offered.
B Ocean Resort Fort Lauderdale Beach
East Fort Lauderdale
Save 100% on your flight
per person
Aug 7 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the business center, express check-out, and valet parking.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
Top Upper Matecumbe Key hotels deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$251 nightly
The price is $283 total per night
$283 total
Jun 2 - Jun 3
Total includes taxes and fees
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a playground, and families will appreciate the onsite laundry facilities.
On private beach
Pool
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$208 nightly
The price is $235 total per night
$235 total
Jun 2 - Jun 3
Total includes taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at the bar/lounge and enjoy perks like free continental breakfast and free WiFi.
On private beach
Pool
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$249 nightly
The price is $281 total per night
$281 total
Jun 16 - Jun 17
Total includes taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle. You'll appreciate the gym, poolside bar, and laundry facilities.
On private beach
Pool
La Siesta Resort & Villas
80241 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$261 nightly
The price is $293 total per night
$293 total
Jun 4 - Jun 5
Total includes taxes and fees
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, and a 24-hour front desk and wedding services are also provided.
On private beach
Pool
Islander Resort
82100 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$258 nightly
The price is $291 total per night
$291 total
Jun 24 - Jun 25
Total includes taxes and fees
This hotel features a private beach, a golf course, and 3 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families will appreciate the mini golf and complimentary bicycles.
On private beach
Pool
Hadley Resort and Marina
82749 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$138 nightly
The price is $155 total per night
$155 total
Jun 1 - Jun 2
Total includes taxes and fees
This traditional hotel's private beach and marina are among the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. Families will appreciate the playground and barbecue grills.
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.
Popular places to visit
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
History of Diving Museum
4.5/5(51 reviews)
Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.
Hurricane Monument
4/5(66 reviews)
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
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