Deals on vacations and trips to Monroe County

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

Key West

Vacations
Key West

Top Monroe County hotels deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Free Cancellation
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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

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Free Cancellation
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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

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Free Cancellation
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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

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd, Marathon, FL
Free Cancellation
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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

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Free Cancellation
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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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
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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
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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

Monroe County
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 . 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.