Deals on vacations and trips to Upper Matecumbe Key

Save when you book Upper Matecumbe Key package deals

Choose two or more items and save on your trip:

Upper Matecumbe Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Park Royal Miami Beach managed by Accor

Park Royal Miami Beach managed by Accor

2.5 out of 5
North Beach
Save 100% on your flight
Price was $1,053, price is now $574 per person
$574
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
An outdoor pool, self parking, and laundry facilities are featured at this hotel. A terrace, a garden, and concierge services are also on offer.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $17,345, price is now $8,653 per person
$8,653
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
This aparthotel 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.
ABAE Hotel by Eskape Collection

ABAE Hotel by Eskape Collection

3.5 out of 5
South Beach
Save 100% on your flight
Price was $1,360, price is now $794 per person
$794
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
A restaurant and an outdoor pool are featured at this hotel. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Save 100% on your flight
Price was $1,618, price is now $947 per person
$947
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
A full-service spa, 2 restaurants, and 4 outdoor pools are all featured at this smoke-free resort. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the gym, poolside bar, and concierge services.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Save 100% on your flight
Price was $1,410, price is now $840 per person
$840
per person
Nov 27 - Dec 2
found 24 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like full breakfast and WiFi in public areas. Valet parking, a terrace, and luggage storage are also offered.

Top Upper Matecumbe Key hotels deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$214 nightly
The price is $241 total per night
$241 total
Sep 15 - Sep 16
Total with 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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $178 total per night
$178 total
Oct 5 - Oct 6
Total with 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

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$211 nightly
The price is $237 total per night
$237 total
Sep 23 - Sep 24
Total with taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Enjoy the gym and visit the 3 bars/lounges and poolside bar for drinks.
On private beach
Pool
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$243 nightly
The price is $273 total per night
$273 total
Sep 22 - Sep 23
Total with taxes and fees
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families will appreciate the mini golf and complimentary bicycles.
On private beach
Pool
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$237 nightly
The price is $266 total per night
$266 total
Sep 7 - Sep 8
Total with 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
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $110 total per night
$110 total
Sep 7 - Sep 8
Total with taxes and fees
A marina and an outdoor pool are featured at this aparthotel. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Upper Matecumbe Key
View all properties
Lowest 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.

Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.
See properties

Frequently asked questions

How much are vacation packages to Upper Matecumbe Key?
With vacation packages on offer from just $574, you won't need to drain your bank balance for your getaway to Upper Matecumbe Key. Travelocity is here to help. Bundle hotels, flights and tours into a package and score some exciting discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Upper Matecumbe Key?
It's hard to top Travelocity when it comes to piecing together your Upper Matecumbe Key package deal. There are at least 400 air carriers and 1,000,000 properties around the world to choose from. Book your trip now and get ready to tick another exciting destination off your travel bucket list.
Why should I purchase my Upper Matecumbe Key vacation bundle with Travelocity?
Because you'll never roam alone if you lock in your trip through us, and we offer round-the-clock support and top-notch service to boot. Add to that our Price Match Guarantee and a massive range of destinations to choose from. It's our job to help you jet off on the vacation of a lifetime.
Can I save money on my Upper Matecumbe Key car rental if I book it with hotels and flights?
Combining your bookings into an Upper Matecumbe Key vacation package will save you some serious money. Book a car and flight; a flight, car and hotel; or a car and hotel. There's no better way to discover the greater Upper Matecumbe Key area than with your own rental car. You can also add activities and experiences to your Travelocity package.

Photos of local treasures

Browse Upper Matecumbe Key vacation photos for more inspiration

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
A pier extending into calm waters with a covered seating area and a sandy beach.
A pelican standing on a wooden dock.
A pier with birds perched on poles, a sign, and a bridge in the background.
A calm lake with a reflection of trees and a cloudy sky.

Explore More Ways to Travel with Travelocity