Upper Matecumbe Key Vacation Packages 2025/2026 from $548

Upper Matecumbe Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach

South Beach

$548

per person

Jan 28 - Feb 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,149

per person

Jan 28 - Feb 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$11,401

per person

Dec 30 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

The Penguin Hotel

South Beach

$618

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. WiFi in public areas is free. Valet parking, a terrace, and a garden are also offered.

EAST Miami Residences

Brickell

$1,427

per person

Jan 22 - Jan 27

found 3 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This luxury hotel features 2 restaurants, 4 outdoor pools, and a 24-hour gym. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and concierge services.

Top Upper Matecumbe Key hotels deals

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$166 total

Nov 20 - Nov 21

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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$301 nightly

$339 total

Nov 20 - Nov 21

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

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$205 nightly

$231 total

Nov 30 - Dec 1

Total with taxes and fees

A private beach and a restaurant are 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 outdoor pool and visit the 3 bars/lounges and poolside bar for drinks.

On private beach

Pool

Islander Resort

82100 Overseas Highway Islamorada FL

$277 nightly

$312 total

Nov 20 - Nov 21

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

Hadley Resort and Marina

82749 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$116 total

Nov 20 - Nov 21

Total with 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

Pines & Palms Resort

80401 Old Hwy Islamorada FL

$188 nightly

$212 total

Dec 2 - Dec 3

Total with taxes and fees

The private beach and marina are among the highlights at this hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Enjoy the outdoor pool and perks like free self parking and free WiFi.

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.

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.

Frequently asked questions

How much are vacation packages to Upper Matecumbe Key?

With vacation packages on offer from just $548, 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.