Upper Matecumbe Key Vacation Packages 2026 from $514

Upper Matecumbe Key flight + hotel vacation packages

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

MirabileCondoDwntown MIA Brickell w PRKG

Downtown Miami

Save 100% on your flight

$514

per person

Jul 24 - Jul 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This apartment features a restaurant, an indoor pool, and a bar/lounge. WiFi in public areas is free. Self parking and a coffee shop are also offered on site.

Casablanca Miami Beach

North Beach

$2,402

per person

Jul 23 - Jul 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$551

per person

Aug 22 - Aug 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$5,681

per person

Jul 26 - Jul 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Hotel Riu Plaza Miami Beach

Mid Beach

$996

per person

Aug 22 - Aug 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. You'll appreciate the gym, poolside bar, and snack bar/deli.

Top Upper Matecumbe Key hotels deals

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$269 total

Jun 16 - Jun 17

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

$278 nightly

$313 total

Jul 5 - Jul 6

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

Islander Resort

82100 Overseas Highway Islamorada FL

$316 nightly

$356 total

Jun 21 - Jun 22

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.

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$255 nightly

$287 total

Jun 28 - Jun 29

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.

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$241 nightly

$271 total

Jul 6 - Jul 7

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.

Bayside Villas by Islander Resort

81450 Overseas Highway Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$280 nightly

$315 total

Jun 23 - Jun 24

Total with taxes and fees

This hotel features 3 restaurants, a bar/lounge, and an outdoor pool. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free area shuttle. A terrace, a picnic area, and barbecue grills are also on offer.

Pool

Pet friendly

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

Bud n' Mary's Dive Center

4.5/5(142 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 family-friendly area.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

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 $514, 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.