Skip to main content
A building with a corner featuring arched windows and a triangular pediment against a clear blue sky.
Photo by Holly Smith
Open Photo by Holly Smith

Saint Leo Vacations from $286

Book a Hotel + Flight or Car together to unlock savings

The Latest Saint Leo Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • In-room safe, laptop workspace, blackout drapes, iron/ironing board
    Sep 15 - Sep 18

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    3 nights
    3.0 star property
    8.4/10 - Very Good (5,285 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $529
    $286
    per traveler
    found 1 day ago
    Palazzo Lakeside Hotel
  • Terrace/patio
    Oct 29 - Nov 1

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,303 reviews)
    "Very nice hotel and location was great. The staff was very helpful."
    Reviewed August 4, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $756
    $389
    per traveler
    found 2 hours ago
    Westgate Palace Hotel / Universal / I-Drive
  • Aerial view
    Oct 21 - Oct 25

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    4 nights
    4.0 star property
    8.2/10 - Very Good (2,031 reviews)
    "No cleaning service for a 6 day stay."
    Reviewed August 4, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $552
    $296
    per traveler
    found 7 hours ago
    Westgate Vacation Villas Resort
  • Restaurant
    Oct 21 - Oct 25

    Westgate Towers Resort + Flight

    Kissimmee
    4 nights
    3.5 star property
    8.6/10 - Excellent (1,002 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $546
    $296
    per traveler
    found 7 hours ago
    Westgate Towers Resort
  • Exterior
    Sep 14 - Sep 19

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    5 nights
    3.0 star property
    9.2/10 - Wonderful (568 reviews)
    "Will stay there again. Very convenient location near everything one might need while on vacation. Cottage was very clean and well equipped. Staff was very friendly and helpful."
    Reviewed August 3, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - SRQ • 1 stop SRQ - BOS • 1 stop
    Save 100% on your flight
    $1,863
    $1,071
    per traveler
    found 1 day ago
    Cedar Cove Resort and Cottages

Saint Leo Hotel Deals

Lobby sitting area

Hyatt Place Tampa/Wesley Chapel

Hyatt Place Tampa/Wesley Chapel
3.0 star property
12.5 mi from Saint Leo
9.2 out of 10, Wonderful, (1,084 reviews)
"Hotel was great, rooms were clean and also cleaned every day. The staff were very friendly. Only suggestions I have is to put mats on the gym floor. Very hard to do floor exercises on hardwood. Other then that, wonderful place"
$110 nightly
The price is $123
Aug 12 - Aug 13
Total with taxes and fees
Hyatt Place Tampa/Wesley Chapel
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.
See all properties in Saint Leo

Frequently Asked Questions

How much does a Saint Leo vacation package cost?

Offering great value package deals from $286 on Expedia, you'll be thrilled with how little a vacation to Saint Leo costs! Our packages make travel planning easier and your savings go further.

What are the cheapest months to go to Saint Leo?

May, July and August are great times to look for cheap Saint Leo vacation packages. Opting to travel in quieter periods means you'll typically find better prices on hotels and flights.

How many days is enough for Saint Leo?

With a well-planned itinerary, you can easily visit the most popular Saint Leo sights in a handful of days. But if you'd like to discover lesser-known spots or go on day tours, consider booking your Saint Leo vacation for longer.

How to find the best Saint Leo package deals?

Start your search for a Saint Leo package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Saint Leo package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Saint Leo escape underway.

Is it cheaper to book a Saint Leo vacation as a package?

An Expedia vacation package could land you considerable savings when compared to booking flights and hotels separately. Better still, you can personalize your Saint Leo trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.

When to book a vacation package to Saint Leo?

If you're planning an impromptu Saint Leo trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking ahead.

Does Expedia offer Book Now, Pay Later Saint Leo vacation packages?

Your Saint Leo trip is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to allow you extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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