Monroe County Vacations & Trips from $471

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Your Monroe County Vacation

Choose a vacation package to Monroe County and make travel planning easy. With the logistics organized before you depart, you can focus on enjoying every moment in this wonderful destination. Begin your trip to Monroe County with some time exploring Key West visiting popular sights like Smathers Beach and Mallory Square. Key Largo is another city that draws travelers from far and wide. John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill are two of the top places to see in this destination. When it's time to stop daydreaming and start doing, Expedia will help turn your Monroe County vacation into reality.

Top destinations in Monroe County

South Beach featuring tropical scenes, general coastal views and a beach
FlightsFlightsHotelsHotels

Key West

Key West

The Latest Monroe County Vacation Packages

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

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Price was $929, price is now $471 per person
$471
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (154 reviews)
Good stay at Flow Hotel

Reviewed on Sep 12, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $33,347, price is now $15,480 per person
$15,480
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Sunset Cove Beach Resort

Sunset Cove Beach Resort

2.5 out of 5
Price was $1,398, price is now $707 per person
$707
per person
Dec 2 - Dec 9
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (1,007 reviews)
Amazing place. Will definitely stay again. Super friendly staff, nice guests, everything was perfect.

Reviewed on Sep 1, 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,759, price is now $912 per person
$912
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (781 reviews)
Great location and friendly staff.

Reviewed on Sep 13, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was $2,267, price is now $1,211 per person
$1,211
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,295 reviews)
We loved everything. The spacious rooms the decor the staff the spa everything.

Reviewed on Sep 13, 2025

Best Places to Vacation in Monroe County

1. Book your ideal Key West with a vacation package

Key West, Florida is the perfect destination for a family vacation. With its stunning sunsets, beautiful beaches, and lively atmosphere, there is something for everyone to enjoy. Take a stroll along the iconic Duval Street where you can find a variety of shops, restaurants, and bars. For those looking for adventure, there are plenty of water activities such as boating and snorkeling to partake in. Key West is also known for its vibrant nightlife, with live music and dancing available at many venues. Don't miss out on the chance to experience the lively festivals and entertainment that Key West has to offer.

  • The peak season is from January to March
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Key West

2. Experience Marathon with a travel package

Marathon, Florida is a perfect destination for outdoor enthusiasts. With its beautiful beaches, marinas, and stunning sunsets, it offers a laid-back and relaxing atmosphere. You can enjoy activities like running, snorkeling, and birdwatching in the area. Don't miss the opportunity to go fishing and spot dolphins in the crystal-clear waters. And of course, indulge in delicious seafood at the local restaurants. Marathon truly has something for everyone, whether you're looking for adventure or just want to unwind and enjoy the natural beauty of the sea.

  • The peak season is from February to April
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Marathon

3. Enjoy Key Largo with a travel package

Key Largo is a fantastic destination for outdoor enthusiasts seeking a vacation filled with sun, sea, and adventure. The local atmosphere here is perfect for those who love dolphins, stunning sunsets, boating, snorkeling, and exploring vibrant coral reefs. With a marina and plenty of opportunities for swimming and relaxing, Key Largo offers a peaceful and rejuvenating experience. Don't miss out on the exciting excursions and delicious seafood that this charming town has to offer. Whether you're into destination activities, tours, or sightseeing, Key Largo has something for everyone.

  • The peak season is from October to December
  • The off-peak season is from April to June
  • Travelers tend to stay 3 days in Key Largo

4. Find your perfect Islamorada vacation

Islamorada, located in Florida, offers a vibrant atmosphere perfect for outdoor vacations. With its beautiful beaches and crystal-clear waters, it's a haven for fishing, diving, and snorkeling enthusiasts. The stunning sunsets create a relaxing and romantic ambiance, while the local seafood scene is a must-try for food lovers. For entertainment, there are various activities to choose from, including opera performances and theater shows. Whether you want to explore the sea or simply unwind on the beach, Islamorada provides a unique and unforgettable experience for every traveler.

  • The peak season is from February to April
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Islamorada

6. Escape to Tavernier with a vacation package

Tavernier, located in Florida, offers a perfect outdoor vacation experience for travelers. With its beautiful beaches, crystal-clear sea, and abundance of fish, it is a paradise for beach lovers, fishing enthusiasts, and families looking for a relaxing getaway. The town also boasts various dining options, making it ideal for those seeking a gastronomic adventure. For the adventurous, diving in Tavernier's vibrant underwater world is a must. The marina and boating facilities cater to those who enjoy spending time on the water. With its diverse range of activities, Tavernier promises a memorable vacation for all.

  • The peak season is from March to May
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Tavernier

5. Explore Summerland Key with a vacation package

If you're looking for an outdoor vacation, Summerland Key in Florida is the perfect destination. With its stunning beaches, crystal-clear waters, and vibrant marine life, there's plenty to explore and enjoy. Whether you're into snorkeling, fishing, or simply relaxing on the beach, Summerland Key has it all. You can also visit nearby attractions such as the Bahia Honda State Park, where you can hike nature trails and spot wildlife. With its laid-back atmosphere and beautiful natural surroundings, Summerland Key offers a truly unforgettable outdoor vacation experience.

  • The peak season is from July to September
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Summerland Key

Monroe County Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$201 nightly
The price is $226 total per night from Sep 21 to Sep 22
$226 total
Sep 21 - Sep 22
Total with taxes and fees
8.8/10 Excellent! (1,714 reviews)
"The staff. the staff was helpful and kind. my room was clean,it was an amazing stay"

Reviewed on Sep 8, 2025

Oceans Edge Key West Resort, Hotel & Marina
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $223 total per night from Sep 14 to Sep 15
$223 total
Sep 14 - Sep 15
Total with taxes and fees
8.4/10 Very Good! (1,519 reviews)
"The check in was easy and the front desk staff communicates via text and email if there are issues. They offer a free ride downtown at the top of the hour. This saved us $12 each way if we had to get an Uber. The restaurant is very good! The breakfast is mainly baked goods all made in house. Again ..."

Reviewed on Sep 8, 2025

Beachside Resort & Residences
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $264 total per night from Sep 27 to Sep 28
$264 total
Sep 27 - Sep 28
Total with taxes and fees
8.6/10 Excellent! (1,783 reviews)
"Walkable to the beach. Shuttle to and from downtown with airport shuttle."

Reviewed on Sep 9, 2025

Margaritaville Beach House Key West
See all 8,354 properties in Monroe County
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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Kid Friendly Vacations

Frequently asked questions

How much does a Monroe County vacation package cost?
Our Monroe County packages, which start from just $471, are an easy way to save. Pick your favorite hotels, flights and rental car to create a custom-built trip.
How do I get a cheap travel package to Monroe County?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Pick the combination that suits your style and see your savings grow. We know a package deal is never one-size-fits-all. That's why we offer more than 550 air carriers and 1,000,000 properties globally, which lets you customize your Monroe County getaway.
How far in advance should I book my Monroe County vacation?
To score discount prices, book nice and early. Airlines typically advertise flights, along with some of the lowest fares, up to a year prior to departure. Hotels, car rental and activities should also be booked early to avoid disappointment. If you were hoping for a last-minute getaway to Monroe County, there are always lots of great bargains to be had on Expedia. Book something in today!
What does an Expedia Monroe County travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to build your perfect Monroe County travel package. Once you've made your booking, you can add on the fun stuff like tours and activities. Remember — the more you bundle, the bigger the savings!
What should I know before booking a Monroe County travel package?
An Expedia travel package can be customized for your budget and is an easy way to stretch your hard-earned dollars. How little or much you include is your call. Rental cars, hotels and flights — mix and match whatever combination suits your plans.
Can I choose my airline with a Monroe County Expedia vacation package?
You sure can. Expedia has access to more than 550 airline partners throughout the world, so fly with the carrier that fits your travel needs.
Does Expedia offer Book Now, Pay Later Monroe County vacation packages?
If the reason for your travel has cropped up unexpectedly, Expedia can help to reduce any financial stress. Working in partnership with online lender Affirm, we provide a Book Now, Pay Later option for all vacation packages. It's easy to set up a payment schedule for your travel that works for you.
If I'm not able to travel, can I cancel my Monroe County vacation package?
Because we know life is full of surprises, the answer is yes. To learn more, visit our Customer Service Portal. But generally speaking, if you've booked your Monroe County vacation package in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.
Explore a world of travel with Expedia

Explore a world of travel with Expedia

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.