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.
President Hotel

President Hotel

3.5 out of 5
South Beach
Price was $1,399, price is now $679 per person
$679
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features an outdoor pool and a bar/lounge. WiFi in public areas is free. Valet parking, a terrace, and a garden are also offered.
Avi Lux Stay

Avi Lux Stay

4.5 out of 5
East Fort Lauderdale
Price was $2,165, price is now $878 per person
$878
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8 hot tubs, an outdoor pool, and a gym are all featured at this smoke-free aparthotel. WiFi in public areas is free. Valet parking, a 24-hour business center, and luggage storage are also offered.
501 First Studio Balcony by Palermo Home

501 First Studio Balcony by Palermo Home

2 out of 5
Downtown Miami
Price was $1,816, price is now $868 per person
$868
per person
Jan 17 - Jan 23
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
An outdoor pool is featured at this apartment, along with valet parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
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 $29,984, price is now $14,450 per person
$14,450
per person
Dec 31 - Jan 4
found 2 days ago
Roundtrip flight included
Boston (BOS) 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.
Miami Vacation Rentals Downtown with Pool

Miami Vacation Rentals Downtown with Pool

2.5 out of 5
Downtown Miami
Price was $2,682, price is now $1,368 per person
$1,368
per person
Jan 17 - Jan 23
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A poolside bar, a coffee shop, and a terrace are also provided.

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
$232 nightly
The price is $261 total per night
$261 total
Dec 1 - Dec 2
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
$186 nightly
The price is $209 total per night
$209 total
Nov 2 - Nov 3
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
$220 nightly
The price is $248 total per night
$248 total
Nov 15 - Nov 16
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
$303 nightly
The price is $340 total per night
$340 total
Nov 1 - Nov 2
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
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$123 nightly
The price is $138 total per night
$138 total
Nov 3 - Nov 4
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
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$208 nightly
The price is $234 total per night
$234 total
Nov 8 - Nov 9
Total with taxes and fees
A private beach and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A garden, a picnic area, and concierge services are also on offer.
On private beach
Pool
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 $679, 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