Upper Matecumbe Key Vacation Packages 2026 from $410

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

$410

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.

Hollywood 6980

Driftwood

$765

per person

Jul 15 - Jul 19

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

An outdoor pool, free self parking, and barbecue grills are featured at this vacation home. WiFi in public areas is free. A garden is also provided.

The W - Bayshore Unit 1003

East Fort Lauderdale

$604

per person

Jul 2 - Jul 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and valet parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Casablanca Miami Beach

North Beach

$2,445

per person

Aug 21 - Aug 25

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) 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.

Hollywood 1811

Hollywood Hills

$692

per person

Jul 12 - Jul 16

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.

Top Upper Matecumbe Key hotels deals

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$224 nightly

$252 total

Jun 2 - Jun 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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$336 nightly

$378 total

Jun 14 - Jun 15

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

Free Cancellation

Reserve now, pay when you stay

$274 nightly

$309 total

Jun 23 - Jun 24

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

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$272 nightly

$306 total

Jun 1 - Jun 2

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

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$255 nightly

$287 total

Jun 1 - Jun 2

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

Hadley Resort and Marina

82749 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$194 total

Jun 29 - Jun 30

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

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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

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

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 $410, 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?

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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.