Monroe County Vacation Packages 2026 from $564

Search vacation packages deals in Monroe County's top destinations

Key West

Vacations

Monroe County flight + hotel vacation packages

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

The W - Bayshore Unit 1003

East Fort Lauderdale

$564

per person

Jun 14 - Jun 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and valet parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

3BR Pool House Sleeps 8

Driftwood

$855

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

An outdoor pool, free self parking, and barbecue grills are featured at this vacation home. WiFi in public areas is free. A garden is also provided.

Family Pool Home by Hollywood Beach

Hollywood Hills

$794

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.

Brickell Bay 3505

Brickell

$651

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Brickell Bay 3304

Brickell

$628

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Monroe County hotels deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$195 nightly

$219 total

Jun 1 - Jun 2

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

Waterside Suites & Marina

201 Ocean Drive Key Largo FL

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$164 total

May 27 - May 28

Total with taxes and fees

A marina and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A terrace, a picnic area, and luggage storage are also on offer.

Pool

Pet friendly

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$268 nightly

$302 total

May 26 - May 27

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. 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. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.

Pool

Pet friendly

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$236 nightly

$266 total

May 11 - May 12

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

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$312 nightly

$352 total

May 25 - May 26

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.

Pool

Spa

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$373 nightly

$420 total

May 13 - May 14

Total with taxes and fees

A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.

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.

Photos of local treasures

Browse Monroe County vacation photos for more inspiration

Tropical landscape with palm trees reflected in a canal at sunrise, in Key West, Florida.

Tropical landscape panorama at sunrise, in Key West, Florida.

Tropical sandy beach in Key West, Florida with unidentifiable tourists enjoying the sunny warm weather.

Aerial view, Everglades Natuional Park, FLORIDA, USA, AMERICA

Frequently asked questions

How much are vacation packages to Monroe County?

Your vacation dreams can come true in Monroe County from an impressive $564. 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.