Book Exclusive Monroe County Vacation Packages

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Search vacation packages deals in Monroe County's top destinations

A beach with palm trees, people sunbathing, and a resort in the background.

Key West

Vacations
Key West

Monroe County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Shore View Hotel

Shore View Hotel

3 out of 5
Hollywood Beach
Save 100% on your flight
Price was CA $2,692, price is now CA $1,603 per person
CA $1,603
per person
Nov 21 - Nov 28
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
Book a stay at this beach aparthotel in Hollywood. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Hollywood Beach and Aventura Mall are located nearby.
Private Oasis at Arya

Private Oasis at Arya

3.5 out of 5
Coconut Grove
Save 100% on your flight
Price was CA $3,180, price is now CA $1,665 per person
CA $1,665
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
Book a stay at this business-friendly aparthotel in Miami. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Brickell City Centre and Bayside Marketplace are located nearby.
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
Price was CA $3,362, price is now CA $1,981 per person
CA $1,981
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Miami Beach Boardwalk and Lincoln Road Mall are located nearby.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was CA $6,788, price is now CA $4,015 per person
CA $4,015
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
Book a stay at this luxury hotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was CA $3,137, price is now CA $1,931 per person
CA $1,931
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free WiFi, beach cabanas (surcharge), and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

Top Monroe County hotels deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free cancellation
Reserve now, pay when you stay
The price is CA $241 per night
CA $241
CA $375 total
Oct 19 - Oct 20
includes taxes & fees
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Florida Keys Brewing Co. and Lorelei Restaurant & Cabana Bar are located nearby.
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
The price is CA $198 per night
CA $198
CA $303 total
Oct 18 - Oct 19
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions History of Diving Museum and Windley Key Fossil Reef Geological State Park are located nearby.
On private beach
Pool
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Free cancellation
Reserve now, pay when you stay
The price is CA $298 per night
CA $298
CA $425 total
Oct 6 - Oct 7
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Pool
Hot tub
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free cancellation
Reserve now, pay when you stay
The price is CA $168 per night
CA $168
CA $270 total
Oct 6 - Oct 7
includes taxes & fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Pool
Hot tub
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Free cancellation
Reserve now, pay when you stay
The price is CA $124 per night
CA $124
CA $276 total
Oct 6 - Oct 7
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
On private beach
Pool
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Free cancellation
Reserve now, pay when you stay
The price is CA $182 per night
CA $182
CA $295 total
Nov 3 - Nov 4
includes taxes & fees
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Pool
Hot tub
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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.
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Photos of local treasures

Browse Monroe County vacation photos for more inspiration

A waterfront promenade with multi-story buildings, palm trees, and a clear blue sky.
An aerial view of a coastal city with a marina, clear blue waters, and a mix of residential and commercial buildings.
A bridge connecting two landmasses over turquoise waters, surrounded by clear skies and a sunset.
A calm waterfront with a boat docked, palm trees, and a white fence.
An aerial view of a coastal area with a marina, tennis courts, a baseball field, and surrounding greenery.

Frequently asked questions

How much are vacation packages to Monroe County?
Your vacation dreams can come true in Monroe County from an impressive CA $1,603. 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.