Lower Matecumbe Key Vacation Packages 2025/2026 from $477

Lower Matecumbe Key flight + hotel vacation packages

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

Casa Boutique Hotel

South Beach

$477

per person

Nov 11 - Nov 18

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 coffee shop, and dry cleaning are also offered.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,372

per person

Nov 10 - Nov 14

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.

Cavalier Hotel South Beach

South Beach

$491

per person

Nov 12 - Nov 18

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.

President Villa

South Beach

Save 100% on your flight

$508

per person

Nov 11 - Nov 18

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 free full breakfast each morning. Valet parking, a terrace, and luggage storage are also offered.

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

$557

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This luxury hotel features a private beach, a full-service spa, and 2 restaurants. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.

Top Lower Matecumbe Key hotels deals

Matecumbe Resort

76261 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$141 total

Sep 14 - Sep 15

Total with taxes and fees

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

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

Get rates

A water park and an outdoor pool are featured at this smoke-free vacation home. Enjoy the a rooftop terrace and perks like free WiFi. A garden, laundry facilities, and barbecue grills are also on offer.

Pool

Kitchen

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$169 total

Sep 18 - Sep 19

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, Marker 82, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$176 nightly

$199 total

Sep 17 - Sep 18

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

Hawks Cay Resort

61 Hawks Cay Blvd, Marathon, FL

Free Cancellation

Reserve now, pay when you stay

$300 nightly

$337 total

Sep 14 - Sep 15

Total with taxes and fees

This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.

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

$288 nightly

$324 total

Sep 8 - Sep 9

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

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 $477. 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.