Lower Matecumbe Key Vacation Packages 2025/2026 from $593

Name: Chesapeake Beach Resort
Price range: $201 total

Lower Matecumbe Key flight + hotel vacation packages

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

Iberostar Waves Miami Beach

South Beach

$593

per person

Jan 21 - Jan 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A restaurant and an outdoor pool are featured at this hotel. WiFi in public areas is free. A coffee shop, a garden, and dry cleaning are also on offer.

Iberostar Waves Berkeley Shore

South Beach

$1,036

per person

Feb 12 - Feb 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. There's a rooftop terrace on site, and a 24-hour front desk and a terrace are also provided.

The Shelborne By Proper, a Member of Design Hotels

South Beach

$930

per person

Jan 21 - Jan 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Cavalier Hotel South Beach

South Beach

$1,004

per person

Feb 12 - Feb 17

found 1 day ago

Roundtrip flight included

Boston (BOS) 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

$7,321

per person

Jan 26 - Jan 30

found 1 day ago

Roundtrip 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.

Top Lower Matecumbe Key hotels deals

Matecumbe Resort

76261 Overseas Hwy Islamorada FL

Get rates

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

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$201 total

Nov 30 - Dec 1

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

$298 nightly

$336 total

Dec 1 - Dec 2

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

Lime Tree Bay Resort

68500 Overseas Hwy Long Key FL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$201 total

Dec 3 - Dec 4

Total with taxes and fees

This resort features a private beach, 3 outdoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the outdoor tennis court and perks like free self parking.

On private beach

Pool

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$205 nightly

$231 total

Nov 30 - Dec 1

Total with taxes and fees

A private beach and a restaurant are 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 outdoor pool and visit the 3 bars/lounges and poolside bar for drinks.

On private beach

Pool

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

97000 Overseas Hwy Key Largo FL

Free Cancellation

Reserve now, pay when you stay

$319 nightly

$359 total

Dec 2 - Dec 3

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.

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

Anne's Beach

3.5/5(139 reviews)

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 $593. 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.