Book Exclusive Monroe County Vacation Packages

Choose one or more items to build your trip:

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.
Liberty Park Hotel South Beach

Liberty Park Hotel South Beach

4 out of 5
South Beach
Price was CA $774, price is now CA $485 per person
CA $485
per person
Aug 9 - Aug 14
found 14 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). 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.
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 $19,250, price is now CA $10,384 per person
CA $10,384
per person
Sep 5 - Sep 9
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) 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.
Luxuri Suites

Luxuri Suites

3 out of 5
South Beach
Price was CA $1,362, price is now CA $807 per person
CA $807
per person
Sep 7 - Sep 13
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free WiFi, Netflix, and satellite TV channels. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.
Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Price was CA $2,033, price is now CA $1,239 per person
CA $1,239
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
Book a stay at this luxury resort in Miami Beach. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Miami Beach Boardwalk and Lincoln Road Mall are located nearby.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was CA $2,795, price is now CA $1,773 per person
CA $1,773
per person
Aug 13 - Aug 17
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Southernmost Point and Duval Street are located nearby.

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
Reserve now, pay when you stay
The price is CA $156 per night
CA $156
CA $311 total
Jul 7 - Jul 8
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 Southernmost Point are located nearby.
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
Reserve now, pay when you stay
The price is CA $178 per night
CA $178
CA $280 total
Jul 7 - Jul 8
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 Southernmost Point are located nearby.
Pool
Hot tub
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 $237 per night
CA $237
CA $371 total
Jul 14 - Jul 15
includes taxes & fees
Book a stay at this beach 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 Southernmost Point and Duval Street are located nearby.
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
Reserve now, pay when you stay
The price is CA $175 per night
CA $175
CA $237 total
Jul 14 - Jul 15
includes taxes & fees
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Southernmost Point and Duval Street are located nearby.
Pool
Hot tub
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 $236 per night
CA $236
CA $375 total
Jul 13 - Jul 14
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
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 $237 per night
CA $237
CA $371 total
Jul 7 - Jul 8
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
Don't see what you're looking for?
See all available properties in Monroe County
View all properties
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 beach with a pier extending into the ocean during sunset.

Florida Keys Beaches

8.4/10 (858 reviews)
Nothing says vacation like spending a carefree day at Florida Keys Beaches, a popular beach in Long Beach Estates.
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 $485. 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.