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.
Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
South Beach
Price was CA $1,316, price is now CA $705 per person
CA $705
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
Stay at this guesthouse in Miami Beach. Enjoy free WiFi, a garden, and a picnic area. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $16,647, price is now CA $8,602 per person
CA $8,602
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
Book a stay at this luxury aparthotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Price was CA $1,378, price is now CA $794 per person
CA $794
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
Stay at this aparthotel in Bay Harbor Islands. Enjoy free WiFi, private pools, and a rooftop terrace. Popular attractions Miami Beach Boardwalk and Aventura Mall are located nearby.
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was CA $2,592, price is now CA $1,504 per person
CA $1,504
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) 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.
The Local House

The Local House

3.5 out of 5
South Beach
Price was CA $2,073, price is now CA $1,213 per person
CA $1,213
per person
Oct 28 - Nov 2
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
Book a stay at this boutique hotel in Miami Beach. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.

Top Monroe County hotels deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free cancellation
Reserve now, pay when you stay
The price is CA $191 per night
CA $191
CA $315 total
Sep 1 - Sep 2
includes taxes & fees
Book a stay at this spa hotel in Key West. 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 Duval Street and South Beach are located nearby.
Pool
Spa
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 $205 per night
CA $205
CA $332 total
Sep 2 - Sep 3
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.
On private beach
Pool
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard Marathon FL
Free cancellation
Reserve now, pay when you stay
The price is CA $309 per night
CA $309
CA $431 total
Aug 25 - Aug 26
includes taxes & fees
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sombrero Beach and Vaca Key are located nearby.
Pool
Spa
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $211 total
Aug 23 - Aug 24
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
On private beach
Pool
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd Marathon FL
Free cancellation
Reserve now, pay when you stay
The price is CA $256 per night
CA $256
CA $394 total
Sep 21 - Sep 22
includes taxes & fees
Book a stay at this luxury hotel in Marathon. 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 Little Conch Key and Walkers Island 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 $199 per night
CA $199
CA $311 total
Sep 7 - Sep 8
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.
See properties

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 $705. 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.