Havana Vacations from $478

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The Latest Havana vacation packages

Price found within the past 48 hours. Click for updated prices.
Rodeway Inn

Rodeway Inn

2.5 out of 5
Price was $542, price is now $478 per person
$478
per person
Feb 10 - Feb 15
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tallahassee (TLH)
6/10 (68 reviews)
Room very clean. Bed super comfortable. Friendly staff. Next to Walmart, dining, shops, food all within walking distance. Great rates

Reviewed on Nov 8, 2025

La Familia Stay Inn

La Familia Stay Inn

2 out of 5
Price was $1,642, price is now $1,306 per person
$1,306
per person
Feb 10 - Feb 15
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tallahassee (TLH)
5.4/10 (20 reviews)
Room was clean and staff was super nice. Really enjoyed my stay.

Reviewed on Dec 16, 2025

Staybridge Suites Tallahassee by IHG

Staybridge Suites Tallahassee by IHG

3 out of 5
Price was $1,009, price is now $828 per person
$828
per person
Feb 10 - Feb 15
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tallahassee (TLH)
9/10 Wonderful! (1,002 reviews)
Staff was very courteous however, housekeeping could've step up a bit more. I didnt enjoy the breakfast, it's was better to cook or purchase breakfast of property.....

Reviewed on Dec 29, 2025

Quality Inn Quincy - Tallahassee West

Quality Inn Quincy - Tallahassee West

2.5 out of 5
Price was $745, price is now $643 per person
$643
per person
Feb 10 - Feb 15
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tallahassee (TLH)
7.6/10 Good! (485 reviews)
Staff very nice. Bed very good. Quiet location. Breakfast up to expectations. Beyond that, not worth it cost. An old place and shows it.

Reviewed on Dec 13, 2025

Commodore Bed and Breakfast

Commodore Bed and Breakfast

2 out of 5
Price was $816, price is now $716 per person
$716
per person
Feb 10 - Feb 15
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tallahassee (TLH)
9.4/10 Exceptional! (11 reviews)
We had to book last minute to attend a funeral, they were incredibly accommodating! We enjoyed our stay and would definitely come again! Breakfast was homemade and the quiche was a crowd fave, so yummy!

Reviewed on Oct 22, 2025

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Discover the most popular places to visit in Havana

Florida Highway Patrol Training Academy

5/5(1 review)

Take a campus tour or just explore the area of Florida Highway Patrol Training Academy, during your travels in Havana. While in this family-friendly area, you can savor the top-notch restaurants.

Florida Highway Patrol Training Academy

Pat Thomas Law Enforcement Academy

4/5(6 reviews)

Take a campus tour or just explore the area of Pat Thomas Law Enforcement Academy, during your travels in Havana. While in this family-friendly area, you can savor the top-notch restaurants.

Pat Thomas Law Enforcement Academy

Havana Hotel Deals

All the best amenities in a convenient, yet private, home for large groups

All the best amenities in a convenient, yet private, home for large groups

Havana FL
$490 nightly
The price is $531 total per night from Jan 1 to Jan 2
$531 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
10/10 Exceptional! (9 reviews)
This home is adorable. It was a good size inside and the outdoor space amazing! Lydia had a welcome tray of s’mores to welcome us. She was very responsive and checked in on us to make sure we had everything we needed. A

Reviewed on Nov 25, 2025

All the best amenities in a convenient, yet private, home for large groups
DoubleTree by Hilton Hotel Tallahassee

DoubleTree by Hilton Hotel Tallahassee

4 out of 5
101 S Adams St Tallahassee FL
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $92 total per night from Jan 2 to Jan 3
$92 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
7.4/10 Good! (1,006 reviews)
Did not eat breakfast at the hotel. Parking is located in the parking garage for a healthy fee. Free parking on the streets on the weekends. The overall the room was comfortable and clean.

Reviewed on Dec 29, 2025

DoubleTree by Hilton Hotel Tallahassee
Four Points by Sheraton Tallahassee Downtown

Four Points by Sheraton Tallahassee Downtown

3 out of 5
316 W Tennessee St Tallahassee FL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $110 total per night from Jan 1 to Jan 2
$110 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.4/10 Very Good! (1,067 reviews)
Excellent room. Friendly staff.

Reviewed on Dec 29, 2025

Four Points by Sheraton Tallahassee Downtown
See all 802 properties in Havana
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.

Find the Best Havana Vacation Packages

Havana Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tallahassee Intl. Airport (TLH)
Population
1,700
Max Temp Winter
65ºF
Max Temp Summer
90ºF

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Frequently asked questions

How much does a Havana vacation package cost?
You'll find cheap prices from $478 on Expedia for your Havana break. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Havana costs.
What are the cheapest months to go to Havana?
If you'd like to book a cheap Havana vacation package, consider visiting in July, September and October. You'll typically find lower prices on airfares and hotels during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Havana?
The ideal duration of your Havana vacation depends on what you'd like to see. Usually, a few days to a week will give you time to tick off all the leading sights and explore some hidden gems along the way.
How to find the best Havana package deals?
Use Expedia's filters to help you find some tempting Havana package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Havana package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Havana vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Havana vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Havana?
If you're considering an impromptu Havana vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Havana vacation packages?
Jet off on your perfect trip to Havana with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stay on budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.