Naples Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

Naples Hotel Deals

Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $68 total per night from Jul 12 to Jul 13
$68 total
Jul 12 - Jul 13
Total with taxes and fees
8.4/10 Very Good! (816 reviews)
"Great, helpful staff. Was clean but had large stain on carpet in our room."

Reviewed on Jul 8, 2026

Best Western Jacksonville Inn
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $93 total per night from Jul 26 to Jul 27
$93 total
Jul 26 - Jul 27
Total with taxes and fees
8.8/10 Excellent! (529 reviews)
"Clean rooms and friendly staff."

Reviewed on Jun 26, 2026

Hampton Inn Jacksonville
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
$85 nightly
The price is $93 total per night from Jul 12 to Jul 13
$93 total
Jul 12 - Jul 13
Total with taxes and fees
9.2/10 Wonderful! (365 reviews)
"A must stop for any history lover. Beautiful building! AC was sufficient, parking was easy even though the hotel is on a main road. Our room was in the middle of the building so we didn’t hear much road noise. And yes it’s on a main road, but this is a small town so the traffic isn’t anything major. ..."

Reviewed on Jul 7, 2026

William Watson Hotel
See all 51 properties in Naples
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 Naples Vacation Packages

Naples Essential Information

Language
English
Currency
U.S dollars

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Naples vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Naples costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Naples?
December, January and February are the best times to look for cheap Naples vacation packages. Traveling in less busy periods means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Naples?
With a well-planned schedule, you can easily hit the most popular Naples attractions in a handful of days. But if you want to discover lesser-known spots or go on day trips, think about booking your Naples vacation for longer.
How to find the best Naples package deals?
Use Expedia's filter tool to help you find some of the best Naples package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Naples package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Naples vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays separately. Better still, you can personalize your Naples getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Naples?
If you've got your Naples vacation dates confirmed, book early to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Naples vacation packages?
Your Naples trip should be an escape from your daily routine, not a source of money worries. So to give you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.