Monroe County Vacation Packages 2026 from $727

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.

Avi Lux Stay

East Fort Lauderdale

$727

per person

Jan 27 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8 hot tubs, an outdoor pool, and a gym are all featured at this smoke-free aparthotel. WiFi in public areas is free. Valet parking, a 24-hour business center, and luggage storage are also offered.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$15,620

per person

Jan 3 - Jan 7

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Miami Vacation Rentals Downtown with Pool

Downtown Miami

$1,198

per person

Feb 1 - Feb 6

found 1 hour ago

Roundtrip flight included

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

This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A poolside bar, a coffee shop, and a terrace are also provided.

The Crosby Balcony 1BR by Palermo Home

Downtown Miami

$1,078

per person

Jan 16 - Jan 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

An outdoor pool is featured at this apartment, along with free WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

The Crosby Worldcenter 2BR Palermo Home

Downtown Miami

$1,113

per person

Jan 16 - Jan 21

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

Valet parking is available and the apartment's front desk is staffed around-the-clock. Enjoy the 2 outdoor pools and perks like free WiFi.

Top Monroe County hotels deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$238 nightly

$268 total

Nov 16 - Nov 17

Total with taxes and fees

This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a playground, and families will appreciate the onsite laundry facilities.

On private beach

Pool

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$285 nightly

$321 total

Nov 18 - Nov 19

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, poolside bar, and concierge services.

Pool

Hot Tub

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$171 nightly

$192 total

Nov 29 - Nov 30

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

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$166 nightly

$187 total

Nov 16 - Nov 17

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

Pet friendly

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Get rates

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

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$230 nightly

$259 total

Dec 13 - Dec 14

Total with taxes and fees

This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.

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.

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)

With a visit to Duval Street, a favorite shopping spot in Key West, you can search for that perfect souvenir. Wander the seaside or discover the area's beautiful sunsets.

See properties

Photos of local treasures

Browse Monroe County vacation photos for more inspiration

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

A beach with clear turquoise water, a sandy shore, palm trees, and a steel bridge over the water.

A coastal fort with a clear view of the turquoise sea and a paved walkway leading to the water.

A bridge over clear blue water with vehicles on it.

A long bridge over calm, clear blue water with a clear sky.

Frequently asked questions

How much are vacation packages to Monroe County?

Your vacation dreams can come true in Monroe County from an impressive $727. 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.