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The Best of Miami and the Florida Keys (Self Drive)

8 to 12+ Nights from $1,526*
* Sample price: priced within the past 7 days for a 12/8/2025 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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Add Outbound & Return Flights

This 8 night sample itinerary includes:

  • Flight into and out of Miami
  • Rental Car for 9 days
  • Hotel for 4 nights in Miami
  • Hotel for 2 nights in Key West
  • Hotel for 1 night in Islamorada
  • Hotel for 1 night in Key Largo

    Sample of Included Tours:
  • Miami City Tour plus Cruise
  • Miami Art Deco Walking Tour
  • Little Havana and Food Tour
  • Sunset Cruise from Key West
  • Key West Tour

    Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
  • Driving Time
    Miami – Key West: 4 hr. approx.
    Key West – Islamorada: 1 hr. 50 min. approx.
    Islamorada – Key Largo: 30 min. approx.
    Key Largo – Miami: 1hr 19 min approx.

Miami and the Florida Keys belong together!. The Keys provide a leisurely retreat from the hustle and bustle of Miami (beauty beaches, such as Miami Beach and South Beach, great diving sites as well as its active nightlife). With this vacation package you can enjoy the food, the blend of cultures, the vivid street arts scene and a Key West Sunset Cruise... Of course, we encourage you take on each day as a new adventure, but we won't blame you for claiming a few days rest at the end in beautiful Islamorada and Key Largo.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Flexible Itinerary

  • Miami, FL

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  • Key West, FL

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  • Islamorada, FL

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  • Key Largo, FL

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USA

Customer Reviews

Trip Summary

  • Miami, FL
    Miami, FL

    Miami is the largest city in South Florida and one of the largest cultural, financial, and entertainment epicenters in the United States. Known for its eclectic energy, great nightlife, art galleries and museums, delicious cuisine, and a lively Latin and Caribbean community with particularly noteworthy Cuban and Haitian enclaves, Miami is a multitude of experiences rolled into one big magic city.

    Explore the Vizcaya Museum and Gardens, Bayside Marketplace, Miami Seaquarium, Jungle Island, Art Deco Historic District, PortMiami, Lincoln Road, Bayfront Park, Perez Art Museum, AmericanAirlines Arena, Venetian Pool, Lummus Park, Wynwood Art District, Freedom Tower, Calle Ocho Historic District, Key Biscayne, and so much more!

  • Key West, FL
    Key West, FL

    At the end of the 113-mile Overseas Highway in the Florida Keys is the vibrant town of Key West, the southernmost point in the continental United States. The `Conch Republic`, just 90 miles from Cuba, has a flair and attitude all its own, which you can see out on Duval Street and Mallory Square, places to see and be seen. Grab a cold drink and enjoy the relaxing and welcoming tropical atmosphere only Key West knows how to provide.

    Visit and discover the Ernest Hemingway House and Museum, Southernmost Point Marker, Mallory Square, Duval Street, Fort Zachary Taylor, Smathers Beach, Truman Little White House, Key West Lighthouse, Key West Aquarium, Key West Butterfly and Nature Conservatory, and so much more!

  • Islamorada, FL
    Islamorada, FL

    Located between Miami and Key West on six islands, Islamorada is a fishing paradise. Once here, you will instantly feel the charming small-town island vibes that this little strip of atolls possesses. Furthermore, the Theater of the Sea is a family-owned attraction in Islamorada that has continued to welcome visitors since it opened in 1946. A two hour drive away from the Intracoastal Highway, the islands are a treasure trove of scenic views, water sports, and tons of other attractions.

    Explore the Robbies of Islamorada, Theater of the Sea, Anne`s Beach, Windley Key Fossil Reef Geological State Park, Founders Park, History of Diving Museum and much more.

  • Key Largo, FL
    Key Largo, FL

    Key Largo is the longest of the Florida Keys, stretching for 30 miles, but is only about half a mile wide in most spots. It is the starting point of the 113-mile Overseas Highway, which links the mainland with the rest of the Florida Keys. It is home to the world`s second-largest artificial reef, and is well-known as a scuba diving, yachting, fishing, and swimming destination, not to mention its nature conservatories and gorgeous beaches. Key Largo is home to the world`s second largest artificial reef, the 510 foot USS Spiegel Grove, the John Pennekamp Coral Reef State Park, and the famous Christ of the Abyss underwater statue.

    Explore the Dagny Johnson Key Largo Hammock Botanical State Park, Overseas Heritage Trail, John Pennekamp Coral Reef State Park, Carysfort Reef and Lighthouse, Cannon Beach, Far Beach, Largo Sound, Florida Keys National Marine Sanctuary, and so much more!

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