Monroe County Vacation Packages 2026 from $426

Search vacation packages deals in Monroe County's top destinations

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

Key West

Vacations

Monroe County flight + hotel vacation packages

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

Creekside Inn

$426

per person

Feb 16 - Feb 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

Bay Breeze Premium Apartments By Eskape Collection

$473

per person

Mar 8 - Mar 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This aparthotel features an outdoor pool and a rooftop terrace. WiFi in public areas is free. Self parking, a garden, and luggage storage are also offered.

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,070

per person

Feb 5 - Feb 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Cavalier Hotel South Beach

South Beach

$439

per person

Feb 9 - Feb 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,148

per person

Feb 14 - Feb 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This condo resort 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

$300 nightly

$337 total

Jan 4 - Jan 5, 2026

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

$283 nightly

$318 total

Jan 8 - Jan 9, 2026

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 an arcade/game room, 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

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$299 nightly

$336 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

Pool

Pet friendly

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$269 nightly

$303 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free beach shuttle.

Pool

Free airport shuttle

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$360 nightly

$405 total

Jan 13 - Jan 14, 2026

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 for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Pool

Spa

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$365 nightly

$411 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

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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

Key Largo showing mangroves and a river or creek

Key West featuring a marina, a coastal town and general coastal views

Marathon showing boating, a house and general coastal views

Big Pine Key featuring a river or creek, a bay or harbor and general coastal views

Frequently asked questions

How much are vacation packages to Monroe County?

Your vacation dreams can come true in Monroe County from an impressive $426. 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.