Ole Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Ole
Price found within the past 48 hours. Click for updated prices.
Where to stay in Ole
Find the best Ole areas and neighborhoods for the activities you enjoy most. Learn more about Ole
Central Naples
If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing.
East Naples
Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.
Old Naples
3 out of top 10 points of interest in this area
The stunning beaches and popular shops are just a few highlights of Old Naples. Make a stop by Fifth Avenue South or Naples Beach while you're exploring the area.
Naples Park
Located in North Naples, Naples Park is bounded by U.S. Route 41 and offers easy access to Vanderbilt Lagoon. Enjoy shopping at the nearby outdoor mall, The Mercato, for a delightful experience.
Vanderbilt Beach
1 out of top 10 points of interest in this area
While visiting Vanderbilt Beach, you might make a stop by sights like Vanderbilt Beach and Delnor-Wiggins Pass State Park.
Ole Hotel Deals
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
CA $291
CA $402 total
Oct 18 - Oct 19
includes taxes & fees
Fairways Inn of Naples
103 Palm River Blvd Naples FL
Fully refundableReserve now, pay when you stay
CA $103
CA $114 total
Oct 13 - Oct 14
includes taxes & fees
9.4/10 Exceptional! (1,342 reviews)
"Great place"
Reviewed on Oct 7, 2026
Compass by Margaritaville Hotel Naples
4805 Tamiami Trl N Naples FL
Fully refundableReserve now, pay when you stay
CA $135
CA $185 total
Oct 14 - Oct 15
includes taxes & fees
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 an Ole vacation package cost?
From as little as CA $1,219. Yes, you read that right. Our Ole packages are the best way to stretch your budget further. Bundle your favorite flights, hotels and rental car and get out and see this vibrant destination.
How do I get a cheap travel package to Ole?
Bundling your flight and hotel with Expedia won't just save valuable time — it'll save you a tidy sum too. An Ole vacation package makes it easy to create your perfect trip. With more than 550 airlines around the world to pick from, finding flights that suit your schedule will be no sweat. In addition to that, we have over 1,000,000 properties globally to select from. Talk about choice! No matter who you are, Expedia brings the world within your reach.
Where should I stay in Ole?
A getaway to Ole wouldn't be complete without paying a visit to Eagle Lakes Community Park. Why not choose a hotel within walking distance of this much-loved tourist attraction?
What are the top hotels in Ole?
Get your escape off to a great start by staying at Beautiful Pool View Condo. It's one of most popular properties in Ole. Another top option is Quiet Lely Resort Condo With Pool.
How far in advance should I book my Ole vacation?
It can be difficult to know when is the ideal time to book your vacation to Ole. But usually the earlier you book, the cheaper the prices. Sometimes, you can reserve your flights and hotels up to 12 months prior to departure. If you're hoping for a last-minute getaway, no need to worry! There are fabulous deals posted on Expedia all the time.
What does an Expedia Ole travel package include?
Car rentals, hotels and flights — we connect you to all the best deals. All you have to do is figure out your favorite combination. Once you've made your booking, you can add on the exciting stuff like tours and experiences. Our travel packages make it easy to create an unforgettable Ole trip.
What should I know before booking an Ole travel package?
Booking all the parts of your getaway together is one of the best ways to save. Bundle your flights, car rentals and hotels into one package. But you're not limited to hotels. Expedia features all kinds of properties, including vacation rentals like mountain cabins and spacious residences. The list goes on!
Can I choose my airline with an Ole Expedia vacation package?
You can, and with more than 550 airlines to select from all over the world, you have plenty of choice. Browse the available options and see which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Ole vacation package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Ole vacation package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal for further details.
Things to do
Gulf of Mexico Sunset Cruise from Naples
CA $103
per adult
88% of travellers recommend
Beach Island Shelling Cruise to Keewaydin Island Tour
CA $78
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.