Deals on vacations and trips to Monroe County
Save when you book Monroe County, FL package deals
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 Retreat Collection at 1 Hotel & Homes South Beach
South Beach
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
EAST Miami Residences
Downtown Miami
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
This luxury hotel features 2 restaurants, 4 outdoor pools, and a 24-hour gym. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and concierge services.
Top Monroe County hotels deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$187 nightly
The price is $210 total per night
$210 total
Aug 26 - Aug 27
Total includes 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
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$166 nightly
The price is $187 total per night
$187 total
Aug 24 - Aug 25
Total includes 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
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$128 nightly
The price is $144 total per night
$144 total
Aug 25 - Aug 26
Total includes taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.
Pool
Pet friendly
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $190 total per night
$190 total
Sep 17 - Sep 18
Total includes taxes and fees
This eco-certified 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 onsite laundry facilities. 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
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$235 nightly
The price is $264 total per night
$264 total
Sep 1 - Sep 2
Total includes 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
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$209 nightly
The price is $236 total per night
$236 total
Aug 20 - Aug 21
Total includes 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
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
Frequently asked questions
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.
- Popular vacation destinations in Monroe County
- Vacations and getaways similar to Monroe County
- All inclusive vacations