Monroe County Vacations & Trips from $463

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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

A beach with palm trees, people sunbathing, and a resort in the background.

Key West

Key West
A beachside restaurant with white tables and chairs, palm trees, and a view of the sea.

Key Largo

Key Largo
A beach with palm trees and white lounge chairs under a clear blue sky.

Islamorada

Islamorada
A beach with clear water, palm trees, and people relaxing on the sand.

Marathon

Marathon
A sunset over a beach with a wooden pier and a small structure on it.

Tavernier

Tavernier
A calm river with boats, lush greenery, and a clear blue sky.

Big Pine Key

Big Pine Key
A coastal road with a beach on one side and a marina with boats on the other.

Summerland Key

Summerland Key
An aerial view of a coastal town with a marina, beachfront properties, and a clear blue sea.

Key Colony Beach

Key Colony Beach
A pier with a boat rental sign, a colorful building, and a calm sea.

Long Key

Long Key

The Latest Monroe County Vacation Packages

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

President Hotel

South Beach
Save 100% on your flight
$463
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (2,655 reviews)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
$6,266
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Luxuri Suites

Luxuri Suites

South Beach
Save 100% on your flight
$496
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
6.8/10 (57 reviews)
Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work.

Reviewed on Jul 9, 2026

Pantera Rosa

Pantera Rosa

South Beach
Save 100% on your flight
$898
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (74 reviews)
The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels.

Reviewed on Jun 26, 2026

Amrit Ocean Resort and Residences - Singer Island

Amrit Ocean Resort and Residences - Singer Island

$1,713
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Lauderdale (FLL)
8.8/10 Excellent! (346 reviews)
If you’re looking for a luxurious, relaxing stay, the Amrit is it. This is such a beautiful property! From the staff, to the spa and amenities - I thoroughly enjoyed my stay and will be coming back. I would also highly recommend the Indian restaurant Ayre. A 3-course meal for $75.00 is unbeatable for such great food and amazing wait staff. I have no complaints, I just wish I stayed longer.

Reviewed on Aug 12, 2026

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

Find the Best Monroe County Vacation Packages

Monroe County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Top Sights
Smathers Beach, Dry Tortugas National Park and Sombrero Beach

Monroe County Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$203 nightly
$228 total
Sep 1 - Sep 2
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$192 nightly
$216 total
Aug 16 - Aug 17
Total with taxes and fees
8.6/10 Excellent! (2,430 reviews)
"The room was ok. Hot shower comfy bed. Says it is on the beach not what I expected at all. Swam at other better beaches"

Reviewed on Aug 13, 2026

Beachside Resort & Residences
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$214 nightly
$241 total
Aug 17 - Aug 18
Total with taxes and fees
9.2/10 Wonderful! (1,380 reviews)
"Excellent all around."

Reviewed on Aug 13, 2026

Cheeca Lodge & Spa
See all 8,289 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.

Frequently asked questions

How much does a Monroe County vacation package cost?
Our Monroe County packages, which start from just $463, 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.

Stay near popular Monroe County attractions

A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)
Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.
See properties
A beach with a pier extending into the ocean during sunset.

Florida Keys Beaches

8.4/10 (858 reviews)
Nothing says vacation like spending a carefree day at Florida Keys Beaches, a popular beach in Long Beach Estates.
See properties
A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

Mallory Square

9.2/10 (15,939 reviews)
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
See properties
A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
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A sailboat named 'Soundwave' docked at a calm harbor with clear blue water, surrounded by a sandy beach and lush greenery.

Sombrero Beach

9.0/10 (2,464 reviews)
Play beach games; go swimming, kayaking or snorkeling; and lounge in the sun at one of Marathon’s most visited beaches.
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A beach with white sand, palm trees, and a building in the background.

Smathers Beach

8.4/10 (8,320 reviews)
Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.
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A brick corridor with arched ceilings and benches.

Fort Zachary Taylor Historic State Park

9.0/10 (4,544 reviews)
The displays of old weapons and interpretive panels in a fort at the heart of the southernmost state park in the continental U.S. provide information about the Civil War.
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What to do in Monroe County

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$69
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Monroe County
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Other vacations you might like

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