Upper Matecumbe Key flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel
South Beach
Save 100% on your flight
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This hotel features free WiFi in public areas, concierge services, and valet parking. Enjoy the free cooked-to-order breakfast each morning. A terrace, a garden, and luggage storage are also on offer.
1 Hotel South Beach
South Beach
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
May-Dee Suites
Hollywood Hills
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Miami (MIA)
An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on offer.
Hilton Cabana Miami Beach Resort
Mid Beach
Save 100% on your flight
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. Enjoy the free cooked-to-order breakfast each morning. Valet parking, a terrace, and express check-out are also offered.
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
The price is $229 per night
$229
per night
Jul 9 - Jul 10
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
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
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
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $266 per night
$266
per night
Jul 9 - Jul 10
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
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
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.
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