Upper Matecumbe Key Vacation Packages 2026 from $586

Upper Matecumbe Key flight + hotel vacation packages

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

Family Pool Home by Hollywood Beach

Hollywood Hills

$586

per person

Jul 9 - Jul 12

found 11 hours ago

Roundtrip flight included

New York (JFK) 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.

3BR Pool House Sleeps 8

Driftwood

$633

per person

Jul 9 - Jul 12

found 11 hours ago

Roundtrip flight included

New York (JFK) 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.

Brickell Bay 3304

Brickell

$593

per person

Jul 15 - Jul 18

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Casablanca Miami Beach

North Beach

$3,981

per person

Jul 12 - Jul 19

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Brickell Bay 3318

Brickell

$607

per person

Jun 19 - Jun 22

found 11 hours ago

Roundtrip flight included

Chicago (ORD) to Miami (MIA)

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

Top Upper Matecumbe Key hotels deals

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$232 nightly

$261 total

May 10 - May 11

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

$337 nightly

$379 total

Apr 29 - Apr 30

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.

Islander Resort

82100 Overseas Highway Islamorada FL

$276 nightly

$311 total

May 19 - May 20

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

$249 nightly

$280 total

May 11 - May 12

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

$237 nightly

$266 total

May 13 - May 14

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.

Hadley Resort and Marina

82749 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$185 total

May 5 - May 6

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.

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.

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.

Frequently asked questions

How much are vacation packages to Upper Matecumbe Key?

With vacation packages on offer from just $586, 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.