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.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Save 100% on your flight
Price was CA $2,421, price is now CA $1,488 per person
CA $1,488
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall 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 $24,105, price is now CA $12,167 per person
CA $12,167
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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.
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was CA $2,878, price is now CA $1,776 per person
CA $1,776
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
Book a stay at this luxury hotel in Fort Lauderdale. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fort Lauderdale Beach and Las Olas Beach 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 $8,996, price is now CA $5,656 per person
CA $5,656
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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.
Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
Downtown Miami
Save 100% on your flight
Price was CA $4,302, price is now CA $2,738 per person
CA $2,738
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
Book a stay at this luxury hotel in Miami. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Brickell City Centre and Bayfront Park 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 $238 per night
CA $238
CA $372 total
Oct 22 - Oct 23
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
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
The price is CA $297 per night
CA $297
CA $424 total
Oct 12 - Oct 13
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 $178 per night
CA $178
CA $280 total
Oct 11 - Oct 12
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
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 $181 per night
CA $181
CA $294 total
Oct 25 - Oct 26
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
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 $152 per night
CA $152
CA $308 total
Oct 11 - Oct 12
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
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Free cancellation
Reserve now, pay when you stay
The price is CA $155 per night
CA $155
CA $215 total
Oct 27 - Oct 28
includes taxes & fees
Stay at this hotel in Key Largo. Enjoy free WiFi, a marina, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park are located nearby.
Pool
Pet-friendly
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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 $1,488. 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.