Oakes Estates Vacation Packages
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Top Holiday Package Deals in Oakes Estates
Price found within the past 48 hours. Click for updated prices.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
CA $1,559
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (135 reviews)
We scheduled our stay for my wife's 60th birthday party. We had spoken to the hotel staff about how we were looking forward to celebrating by the rooftop pool..
THE ROOFTOP POOL WAS CLOSED THE ENTIRE TIME WE WERE THERE FOR A PRIVATE COMPANY PARTY.
EXTREMELY DISAPPOINTED!!
Reviewed on Oct 25, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
CA $5,136
per person
Dec 28 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
Very helpful staff, great Gulf side room. Undergoing some renovation so only one elevator working but didn’t create too much of a problem. Great location, nice people.
Reviewed on Oct 25, 2026
Where to stay in Oakes Estates
Find the best Oakes Estates areas and neighborhoods for the activities you enjoy most. Learn more about Oakes Estates
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.
Central Naples
1 out of top 10 points of interest in this area
If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing.
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.
Oakes Estates Hotel Deals
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
CA $237
CA $334 total
Oct 27 - Oct 28
includes taxes & fees
Fairways Inn of Naples
103 Palm River Blvd Naples FL
Fully refundableReserve now, pay when you stay
CA $118
CA $131 total
Oct 27 - Oct 28
includes taxes & fees
9.4/10 Exceptional! (1,348 reviews)
"Naturaleza"
Reviewed on Oct 24, 2026
Compass by Margaritaville Hotel Naples
4805 Tamiami Trl N Naples FL
Fully refundableReserve now, pay when you stay
CA $133
CA $182 total
Oct 30 - Oct 31
includes taxes & fees
9.6/10 Exceptional! (1,906 reviews)
"All perfect enjoy"
Reviewed on Oct 26, 2026
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 Oakes Estates vacation package cost?
Discover the best of Oakes Estates from just CA $291. We offer a great selection of hotels, flights and rental cars to suit every style and budget. Score even more discounts when you add some sightseeing activities to your vacation package.
How do I get a cheap travel package to Oakes Estates?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got it all. Select a combination that best fits you and see your savings grow. Of course, a package deal is never a one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 hotels globally, which lets you customize your Oakes Estates adventure.
Where should I stay in Oakes Estates?
Most who travel to Oakes Estates put both Naples Pier and Barefoot Beach on their bucket lists. Why not choose a hotel within walking distance of these top attractions?
What are the top hotels in Oakes Estates?
If this will be your first time in Oakes Estates, secure a room at Newly Built Modern North Naples Villa On 3 Acres or Private Studio On 3 Acre Property In Paradise. Both hotels offer comfortable beds and are favorites among many savvy travelers.
How far in advance should I book my Oakes Estates vacation?
Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to 12 months prior to departure dates. This is usually the cheapest time to book. If circumstances have left you booking late, great deals to Oakes Estates are still known to appear just weeks before departure.
What does an Expedia Oakes Estates travel package include?
Flights, hotels and car rentals — we bring you the very best deals. All you'll have to do is pick your favorite combination. After you've made your booking, you can add on the fun stuff like experiences and tours. Our travel packages make it simple to craft an exciting Oakes Estates vacation.
What should I know before booking an Oakes Estates travel package?
You'll pick up impressive savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything together makes trip planning easier. So why waste your time or money? Whether you're organizing an upscale romantic escape or a budget family adventure, have a look at our package deals today.
Can I choose my airline with an Oakes Estates Expedia vacation package?
You can, and with more than 550 airlines to choose from worldwide, you've got lots of choice. Have a look through the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Oakes Estates vacation package?
If your travel plans in Oakes Estates have been upended, it's good to know that you can amend or cancel your booking. If you made your booking in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. To learn more, check our Customer Service Portal.
Things to do
Gulf of Mexico Sunset Cruise from Naples
CA $89
per adult
88% of travellers recommend
Beach Island Shelling Cruise to Keewaydin Island Tour
CA $84
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.