Naples Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 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

Find the Best Naples Vacation Packages

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
The price is AEDĀ 275 per night from Nov 15 to Nov 16
AEDĀ 275
AEDĀ 314 total
15 Nov - 16 Nov
includes taxes & fees
Best Western Jacksonville Inn
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
The price is AEDĀ 312 per night from Nov 13 to Nov 14
AEDĀ 312
AEDĀ 343 total
13 Nov - 14 Nov
includes taxes & fees
9.4/10 Exceptional! (385 reviews)
"We had a wonderful little stay in Pittsfield!"

Reviewed on 12 November 2026

William Watson Hotel
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is AEDĀ 309 per night from Nov 22 to Nov 23
AEDĀ 309
AEDĀ 352 total
22 Nov - 23 Nov
includes taxes & fees
8.8/10 Excellent! (542 reviews)
"The hotel had been recently renovated & was very nice! Lots of choices for breakfast with different options every day & the staff was very friendly. Definitely recommend staying here."

Reviewed on 9 November 2026

Hampton Inn Jacksonville
See all 52 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.

Frequently asked questions

How much does a Naples vacation package cost?
You'll find cheap prices on Expedia for your Naples getaway. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Naples costs.
What are the cheapest months to go to Naples?
You can typically find reduced prices and better availability in January, February and November. Take a look at our cheap Naples vacation packages and you could get some great off-season deals.
How to find the best Naples package deals?
Bagging a cheap Naples package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add some filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most affordable Naples package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Naples vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Naples vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Naples?
If you have your Naples vacation dates confirmed, book as early as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Naples?

  1. Pick your travel dates: The things you want to do in Naples and your preferred season will help you decide when to go.
  2. Set your budget: Consider costs like transportation, flights and meals when calculating how much to set aside for your trip to Naples. Then, select a property that works with your budget, whether that's a low-cost stay or a deluxe retreat.
  3. Decide how long to go for: Now that you're up to speed on Naples, you can figure out the right length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your airfare and accommodations: After you've settled on your trip dates and duration, book the perfect Naples vacation package for you.