Saint Leo Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Saint Leo Vacation

With all the details organized before you go, our Saint Leo vacation packages mean you can focus more on letting the good times roll. Whether you're staying in the neighborhood of Lake Jovita, which is great for golfing, or another area, this city offers an array of discoveries. Ready to venture out and explore? Saint Leo University, Lake Jovita Golf and Country Club and Dade City Atlantic Coast Line Railroad Depot are among the top places to visit during your trip to Saint Leo. Whoever you're heading away with and whatever the size of your budget, your dream Saint Leo vacation is only clicks away with Expedia.

Top Saint Leo Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,523, price is now CA $859 per person
CA $859
per person
Jan 1 - Jan 8
found 9 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very good! (2,105 reviews)
Muy bueno. Recomendable para el fin de semana o pasarla bien

Reviewed on Oct 31, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was CA $3,309, price is now CA $1,717 per person
CA $1,717
per person
Jan 1 - Jan 8
found 23 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,229, price is now CA $1,266 per person
CA $1,266
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
8.6/10 Excellent! (572 reviews)
Great family stay

Reviewed on Oct 31, 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was CA $2,286, price is now CA $1,304 per person
CA $1,304
per person
Jan 1 - Jan 8
found 9 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.6/10 Exceptional! (1,234 reviews)

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was CA $2,640, price is now CA $1,510 per person
CA $1,510
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)
Everything about the resort is great! I highly recommend to people considering a stay there.

Reviewed on Oct 31, 2026

Ready to book your vacation to Saint Leo?

 

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Saint Leo Hotel Deals

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
5700 Saddlebrook Way Wesley Chapel FL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 29 to Nov 30
CA $162
CA $225 total
Nov 29 - Nov 30
includes taxes & fees
Saddlebrook Resort
Hyatt Place Tampa/Wesley Chapel

Hyatt Place Tampa/Wesley Chapel

3 out of 5
26000 Sierra Center Boulevard Lutz FL
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Nov 11 to Nov 12
CA $154
CA $172 total
Nov 11 - Nov 12
includes taxes & fees
Hyatt Place Tampa/Wesley Chapel
SpringHill Suites by Marriott Tampa North/I 75 Tampa Palms

SpringHill Suites by Marriott Tampa North/I 75 Tampa Palms

3 out of 5
5396 Primrose Lake Cir Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Nov 15 to Nov 16
CA $135
CA $154 total
Nov 15 - Nov 16
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"The property was well maintained Staff is friendly courteous and professional. Room was clean bed was comfortable the set up of space was very accommodating. I always enjoy my stay it is close to all my events I participate in. Truly 5 star service Thank You"

Reviewed on Oct 31, 2026

SpringHill Suites by Marriott Tampa North/I 75 Tampa Palms
See all 692 properties in Saint Leo
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Saint Leo vacation package cost?
Offering excellent value package deals from CA $859 on Expedia, you'll be surprised at how little a vacation to Saint Leo costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Saint Leo?
You can generally find reduced prices and better availability in January, February and September. Take a look at our cheap Saint Leo vacation packages and you could land some excellent off-season deals.
How many days is enough for Saint Leo?
Generally, a few days is ideal for a Saint Leo vacation. With a carefully crafted itinerary, you can go to all the main sights like The HiBrow Gallery, as well as explore some hidden treasures along the way.
How to find the best Saint Leo package deals?
Use Expedia's filters to help you find some of the best Saint Leo 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 search for Saint Leo package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Saint Leo vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Saint Leo vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Saint Leo?
Score incredible discounts by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Saint Leo adventure.
How to plan a trip to Saint Leo?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred season and the activities on offer will also help you decide when to escape to Saint Leo.
  2. Budget wisely: As well as the cost of your accommodations, you should factor in other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Saint Leo.
  3. Decide how long to go away for: Now that you're more familiar with Saint Leo, you can work out the ideal length of your vacation. Put together a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your airfare and accommodations: Once you've settled on your travel dates and duration, book the ideal Saint Leo vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.