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 Shelborne By Proper
South Beach
per person
Sep 3 - Sep 7
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.
Amrit Ocean Resort and Residences - Singer Island
per person
Sep 12 - Sep 19
just found
Roundtrip flight included
Boston (BOS) to Fort Lauderdale (FLL)
This smoke-free hotel features a full-service spa, 2 outdoor pools, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. With 2 coffee shops/cafes, bar/lounge, and beach bar, there are plenty of spots to dine and unwind.
Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
Save 100% on your flight
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This luxury hotel features a private beach, a full-service spa, and 2 restaurants. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.
Top Monroe County hotels deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
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
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Free Cancellation
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
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
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
Hawks Cay Resort
61 Hawks Cay Blvd, Marathon, FL
Free Cancellation
Reserve now, pay when you stay
This traditional hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area.
On private beach
Pool
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
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
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
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
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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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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