Deals on vacations and trips to Monroe County
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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.
Riverside Hotel
East Fort Lauderdale
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A poolside bar, a 24-hour front desk, and a coffee shop are also provided.
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
EAST Miami
Downtown Miami
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
This smoke-free 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. You'll appreciate the a rooftop terrace, poolside bar, and snack bar/deli.
Top Monroe County hotels deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$184 nightly
The price is $207 total per night
$207 total
Aug 18 - Aug 19
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
$196 nightly
The price is $221 total per night
$221 total
Sep 16 - Sep 17
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
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 16 - Sep 17
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
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$189 nightly
The price is $212 total per night
$212 total
Aug 18 - Aug 19
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
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Free Cancellation
$237 nightly
The price is $266 total per night
$266 total
Sep 1 - Sep 2
Total includes 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
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
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.
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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.
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