Lower Matecumbe Key Vacation Packages 2026 from $415

Lower Matecumbe Key flight + hotel vacation packages

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

The Local House

South Beach

Save 100% on your flight

$415

per person

Aug 15 - Aug 19

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. A poolside bar, a coffee shop, and a terrace are also provided.

The W - Bayshore Unit 1003

East Fort Lauderdale

$718

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,442

per person

Aug 5 - Aug 9

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

MirabileCondoDwntown MIA Brickell w PRKG

Downtown Miami

Save 100% on your flight

$564

per person

Jul 24 - Jul 26

found 19 hours ago

Roundtrip flight included

Boston (BOS) 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.

Pelican Hotel

South Beach

Save 100% on your flight

$571

per person

Aug 21 - Aug 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. 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. Valet parking, a business center, and limo/town car service are also offered.

Top Lower Matecumbe Key hotels deals

Matecumbe Resort

76261 Overseas Hwy Islamorada FL

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A private beach and an outdoor pool are featured at this smoke-free resort. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a picnic area, and laundry facilities are also on offer.

On private beach

Pool

Caloosa Cove Resort by CoolVacay

73801 Overseas Hwy Islamorada FL

$298 nightly

$335 total

Jun 5 - Jun 6

Total with taxes and fees

A marina and a restaurant are featured at this smoke-free condo. Enjoy the outdoor pool and perks like free self parking and free WiFi. A picnic area and barbecue grills are also provided.

Pool

Kitchen

Next available - August 2026 - Oceanfront - Heated Pool - Dock

Islamorada FL

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This vacation home features an outdoor pool and a rooftop terrace. WiFi in public areas is free. A garden, laundry facilities, and barbecue grills are also on offer.

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$264 nightly

$297 total

Jun 3 - Jun 4

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.

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$240 nightly

$270 total

Jun 8 - Jun 9

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton

97000 Overseas Hwy Key Largo FL

$302 nightly

$340 total

Jun 16 - Jun 17

Total with taxes and fees

A private beach, 2 restaurants, and 2 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the arcade/game room and complimentary bicycles.

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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

Anne's Beach

If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.

Robbie’s of Islamorada

Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.

Sunset Drive Beach

Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?

Frequently asked questions

How much are vacation packages to Lower Matecumbe Key?

Travelocity offers flight and hotel packages starting from just $415. With such amazing bargains, you'll be saying hello to Lower Matecumbe Key before you know it.

Where can I get the best vacation package deals for Lower Matecumbe Key?

You can pick up unbeatable Lower Matecumbe Key package deals with Travelocity. Pick from as many as 400 air carriers and 1,000,000 properties worldwide and turn those travel dreams into a reality.

Why should I book my Lower Matecumbe Key vacation bundle with Travelocity?

Nothing tops the satisfaction of knowing you've just bagged the best deal around — that's our Price Match Guarantee. Add to that our incredibly broad range of destinations and 24/7 team of customer service professionals and you've got the blueprint for an unforgettable vacation.

Can I save money on my Lower Matecumbe Key car rental if I bundle it with hotels and flights?

Combining your bookings into a Lower Matecumbe Key vacation package will leave you with some serious savings. Book a car and flight; a flight, car and hotel; or a hotel and car. You won't find a better way to explore the greater Lower Matecumbe Key area than with your own rental car. You can also add experiences and activities to your Travelocity package.

What is there to do in Lower Matecumbe Key?

A vibrant and lively destination, Lower Matecumbe Key boasts some excellent attractions. Anne's Beach and Sunset Drive Beach are a couple of the local highlights.