Monroe County Vacation Packages 2026 from $382

Search vacation packages deals in Monroe County's top destinations

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

Key West

Vacations

Monroe County flight + hotel vacation packages

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

Eden Roc Miami Beach

Mid Beach

$382

per person

Aug 6 - Aug 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

A full-service spa, 2 restaurants, and 3 outdoor pools are all featured at this smoke-free resort. Enjoy the gym and unwind at the bar/lounge and poolside bar.

Nobu Hotel Miami Beach

Mid Beach

$428

per person

Aug 6 - Aug 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

A full-service spa, 2 restaurants, and 4 outdoor pools are all featured at this smoke-free resort. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the gym, poolside bar, and concierge services.

Casablanca Miami Beach

North Beach

$626

per person

Aug 23 - Aug 26

found 4 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.

The 27 Wynwood

Wynwood Art District

Save 100% on your flight

$456

per person

Sep 3 - Sep 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the gym, poolside bar, and concierge services.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$4,609

per person

Aug 2 - Aug 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This aparthotel 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.

Top Monroe County hotels deals

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$202 nightly

$227 total

Jul 6 - Jul 7

Total with taxes and fees

This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.

On private beach

Pool

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$175 nightly

$197 total

Jul 6 - Jul 7

Total with taxes and fees

This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.

Pool

Hot Tub

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$269 total

Jul 14 - Jul 15

Total with taxes and fees

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Hilton Garden Inn Key West / The Keys Collection

3850 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$168 total

Jul 14 - Jul 15

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like a free area shuttle.

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL

Free Cancellation

Reserve now, pay when you stay

$236 nightly

$264 total

Jul 12 - Jul 13

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. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with kayaking.

On private beach

Pool

Pier House Resort & Spa

1 Duval St Key West FL

Free Cancellation

Reserve now, pay when you stay

$376 nightly

$423 total

Jul 8 - Jul 9

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.

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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.

Stay near popular Monroe County attractions

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

Photos of local treasures

Browse Monroe County vacation photos for more inspiration

A waterfront promenade with multi-story buildings, palm trees, and a clear blue sky.

An aerial view of a coastal city with a marina, clear blue waters, and a mix of residential and commercial buildings.

A bridge connecting two landmasses over turquoise waters, surrounded by clear skies and a sunset.

A calm waterfront with a boat docked, palm trees, and a white fence.

An aerial view of a coastal area with a marina, tennis courts, a baseball field, and surrounding greenery.

Frequently asked questions

How much are vacation packages to Monroe County?

Your vacation dreams can come true in Monroe County from an impressive $382. Packages include flights and hotels, so organizing everything should be nice and easy. The only thing you'll have to focus on is having an incredible time.

Where can I get the best vacation package deals for Monroe County?

There's no need to look any further than Travelocity. With as many as 400 partner airlines and 1,000,000 properties across the globe, it's easy to put together a Monroe County package deal that ticks all your boxes.

Why should I purchase my Monroe County vacation bundle with Travelocity?

Fantastic savings, an abundance of enticing destinations and a team of customer service experts available 24/7 — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always score the best possible deal with Travelocity.

Can I save on my Monroe County car rental if I combine it with a hotel or flight?

Combining your bookings into a Monroe County vacation package will save you a handsome sum. Book a flight and car; a car, flight and hotel; or a car and hotel. There's no better way to explore the greater Monroe County area than with your own set of wheels. You can also add tours and experiences to your Travelocity package.

What is there to do in Monroe County?

A diverse and exciting destination, Monroe County is home to some wonderful tourist attractions. Sombrero Beach and Jimmy Johnson's Big Chill are among the most renowned here.

Where to stay in Monroe County: Best areas for travelers

Key West: There's nothing better than staying in the middle of all the action, especially when you have fabulous attractions like Ernest Hemingway Home and Museum within a short distance. After a long day of sightseeing, flop into bed at the Pegasus International Hotel, the Poolside Townhouse With 1 Bedroom, 1 Bath With Kitchen and Pullout Sofa or the Crowne Plaza Key West-La Concha.
Key Largo: If you're planning a visit to this great destination, you'll find there's so much to discover here. Wander around exciting sights like John Pennekamp Coral Reef State Park, Jimmy Johnson's Big Chill and Dolphins Plus Bayside. When you're ready to call it a day, rest your head at the Bayside Inn Key Largo, the Florida Keys Getaway! Cozy Unit for 4, Pool or the Couple\'s Getaway! King Unit, Pool, Free Parking. Spend a few nights here so you have enough time to also see Key Largo Hammocks State Botanical Site, Dolphin Cove and Key Largo Undersea Park.
Marathon: There's nothing quite like exploring someplace completely new, especially when you've got renowned attractions such as Sombrero Beach to look forward to. You can make your vacation even better by locking in one of the top-rated hotels nearby, such as the Sea Dell Motel, the Blackfin Resort and Marina or the Skipjack #203 ~ 1 bed 1 Bath Updated Condo.
Islamorada: With plenty of exciting things to see and do here, you'll have earned a solid night's sleep by the time the sun goes down. The This is Paradise! Beautiful 2 Acre Oceanfront Beach, A Must See. 3/2 Sleeps 6, the Chesapeake Beach Resort or the Ocean House are some of the best places to kick back after exploring Theater of the Sea and Founders Park. Don't forget to make your way to Anne's Beach, Florida Keys Flats Fishing, Bud n' Mary's Dive Center and Florida Keys Dive Center too.
Tavernier: For a hotel that feels like a home away from home, look up the Coconut Palm Inn. The Creekside Inn Islamorada and the Vrbo Property are other options that make superb bases for exploring. Kick off the sightseeing here at Florida Keys Flats Fishing and Laura Quinn Wild Bird Sanctuary. Florida Keys Dive Center is also worth penciling into your itinerary.