Upper Matecumbe Key Vacation Packages 2025/2026 from $279

Upper Matecumbe Key flight + hotel vacation packages

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

Henrosa Hotel

South Beach

$279

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

This hotel features free WiFi in public areas, concierge services, and valet parking. A terrace, a garden, and luggage storage are also on offer.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$5,248

per person

Nov 5 - Nov 8

found 12 hours ago

Roundtrip flight included

Hartford (BDL) 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.

President Villa

South Beach

$532

per person

Nov 4 - Nov 11

found 8 hours ago

Roundtrip flight included

Dallas (DFW) 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.

ABAE Hotel by Eskape Collection

South Beach

Save 100% on your flight

$525

per person

Nov 4 - Nov 11

found 8 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

A restaurant and an outdoor pool are featured at this hotel. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$835

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Key West (EYW)

This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.

Top Upper Matecumbe Key hotels deals

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$169 total

Sep 7 - Sep 8

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

$187 nightly

$211 total

Sep 7 - Sep 8

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

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$210 nightly

$237 total

Sep 7 - Sep 8

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

$226 nightly

$255 total

Sep 21 - Sep 22

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

$178 nightly

$201 total

Sep 16 - Sep 17

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 terrace 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

$141 nightly

$158 total

Oct 5 - Oct 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.

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

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.

Hurricane Monument

4/5(66 reviews)

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

Frequently asked questions

How much are vacation packages to Upper Matecumbe Key?

With vacation packages on offer from just $279, 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.