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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.
![Hilton Cabana Miami Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/18200/18107/ff01dffb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Hilton Cabana Miami Beach Resort
Mid Beach
Save 100% on your flight
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
This smoke-free hotel features a private beach, 2 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the 24-hour gym and perks like free WiFi.
![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5f494a59_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
1 Hotel South Beach
South Beach
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus.
![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/2638eb6b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) 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.
![Hotel Riu Plaza Miami Beach](https://images.trvl-media.com/lodging/1000000/80000/74600/74574/9a7e80e8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Hotel Riu Plaza Miami Beach
Mid Beach
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
![Mayfair House Hotel & Garden](https://images.trvl-media.com/lodging/1000000/30000/24400/24311/8140bb16_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Mayfair House Hotel & Garden
Coconut Grove
Save 100% on your flight
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 12 conference rooms and valet parking. You'll appreciate the 24-hour gym, poolside bar, and rooftop terrace.
Top Upper Matecumbe Key hotels deals
![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/c393a7d6_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $229 per night
$229
per night
Jun 30 - Jul 1
This smoke-free 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](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $209 per night
$209
per night
Jun 23 - Jun 24
This smoke-free hotel's private beach and 2 outdoor pools are some of the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. There's a computer station and multilingual staff can provide around-the-clock assistance.
On private beach
Pool
![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/fb068024_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Islander Resort
82100 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $179 per night
$179
per night
Jun 23 - Jun 24
This hotel features a private beach, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the 24-hour gym and perks like free self parking and free WiFi.
On private beach
Pool
![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/7a012acc_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $266 per night
$266
per night
Jul 8 - Jul 9
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 free perks like free self parking and an area shuttle. You'll appreciate the gym, poolside bar, and laundry facilities.
On private beach
Pool
![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/f8fc560f_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
La Siesta Resort & Villas
80241 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $239 per night
$239
per night
Jul 8 - Jul 9
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
![Hadley Resort and Marina](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/5ccef8c8_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hadley Resort and Marina
82749 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $151 per night
$151
per night
Jun 26 - Jun 27
A marina and an outdoor pool are featured at this traditional hotel. Enjoy the free on-the-go breakfast each morning. A business center, a terrace, and a garden are also on offer.
Pool
Breakfast included
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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.
Photos of local treasures
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![Islamorada showing a beach bar](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191196-Islamorada.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)
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