Upper Matecumbe Key Vacation Packages 2026 from $523

Upper Matecumbe Key flight + hotel vacation packages

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

Silver Spray Motel

Hollywood Beach

Save 100% on your flight

$523

per person

May 13 - May 20

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This aparthotel features free WiFi in public areas, laundry facilities, and self parking. Enjoy the 5 outdoor pools and free continental breakfast each morning. A terrace, a picnic area, and concierge services are also on offer.

Creekside Inn

$819

per person

May 15 - May 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

Casablanca Miami Beach

North Beach

$1,870

per person

May 21 - May 24

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.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

Save 100% on your flight

$7,352

per person

May 22 - May 25

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.

Park Central South Beach

South Beach

Save 100% on your flight

$962

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This historic resort features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Unwind with a drink at the bar/lounge and enjoy perks like free continental breakfast and free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.

Top Upper Matecumbe Key hotels deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$371 nightly

$418 total

Apr 12 - Apr 13

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

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$293 nightly

$330 total

Apr 12 - Apr 13

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

80001 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$307 nightly

$346 total

Mar 22 - Mar 23

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

82100 Overseas Highway Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$372 nightly

$419 total

Apr 12 - Apr 13

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

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$322 nightly

$363 total

Mar 22 - Mar 23

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

$235 nightly

$265 total

Apr 12 - Apr 13

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.

History of Diving Museum

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 $523, 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.