Ole Holidays from £948
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- Rest easyPackages with flights are ATOL protected
Your Ole Holiday
Our Ole holiday packages are a fast and practical way to plan and reserve your next retreat. Experience the magic of this unique neighbourhood without the pressure of having to organise everything yourself. Kick off your trip to Ole by visiting nearby attractions such as Flamingo Island Course - Lely Resort, TPC Treviso Bay and Mustang Course - Lely Resort. Stop dreaming and start doing. When you're ready to lock in your next holiday to Ole, Expedia is here to help.
Price found within the past 48 hours. Click for updated prices.
Casa Ybel Resort
Mid Island
£1,113
per person
26 Oct - 2 Nov
found 6 hours ago
Return flight included
London (LGW) to Fort Myers (RSW)
8.8/10 Excellent! (412 reviews)
The property is super convenient the beaches across the street a volleyball pool and then a huge lighted pool. The rooms were very clean older but clean and very comfortable. Mine felt like a little apartment tiki bar downstairs is great. The food is good. The drinks were good. They do play music until about midnight so if you don’t like music till that time, this isn’t the place for you lol. We will definitely stay here again.
Reviewed on 30 Aug 2026
Resort Harbour Properties
Punta Rassa
£1,136
per person
27 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9.6/10 Exceptional! (372 reviews)
The property was clean and absolutely gorgeous. The pictures honestly didn't do it justice. The hospitality was great! The communication was top notch, but they weren't too much at all. Great privacy! Beach was steps away from the elevator. The location was wonderful! It was secluded but everything we needed was very close by. Sanibel Island was a 10 minute drive at most! We are only going to stay at this property in the future.
Reviewed on 11 Aug 2026
Windward Passage Resort
£1,031
per person
27 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Fort Myers (RSW)
8.6/10 Excellent! (9 reviews)
Staff was very friendly. The ocean view was amazing. Our unit was well maintained and very clean. Would love to stay here again!
Reviewed on 3 Sept 2026
Where to stay in Ole
Find the best Ole areas and neighborhoods for the activities you enjoy most. Learn more about Ole
Central Naples
1 out of top 10 points of interest in this area
While visiting Central Naples, you might make a stop by sights like Naples Zoo at Caribbean Gardens and Naples Grande Golf Club.
East Naples
Beaches, shopping and restaurants are some highlights of East Naples. Make a stop by Fifth Avenue South or Naples Botanical Garden while you're exploring.
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
Beaches, spas and parks are some highlights of Naples Park. You might stop by Mercato or Vanderbilt Beach while you're in the area.
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.
Top hotels in Ole
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
£202
15 Sept - 16 Sept
includes taxes & fees
9/10 Wonderful! (2,004 reviews)
"Great"
Reviewed on 3 Sept 2026
The Perry Hotel Naples
12155 Tamiami Trail N Naples FL
Fully refundableReserve now, pay when you stay
£125
8 Sept - 9 Sept
includes taxes & fees
La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S Naples FL
Fully refundableReserve now, pay when you stay
£57
20 Sept - 21 Sept
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 travel package cost?
Get ready to book, because a getaway to Ole starts from an enticing £948. When you combine your flights, hotels and car rentals into a package, you'll enjoy the best bargains.
If I'm not able to travel, can I cancel my Ole travel package?
Whether it's your hotel or flight, you can cancel or amend it. Locked in your Ole travel package in the last 24 hours? You may be able to make changes at no cost. For bookings older than that, you may incur a charge from your hotel, airline or car rental company. For more details, visit our Customer Service Portal. We'll help you every step of the way.
How do I get a cheap travel package to Ole?
Bundling your hotel and flight with Expedia won't just save precious time — it'll save you a tidy sum too. An Ole travel package makes it simple to arrange your dream adventure. With more than 550 airlines throughout the world to pick from, finding convenient flights that suit your schedule won't be a challenge. Not only that, we've got over 1,000,000 properties globally to select from. Now that's what you call choice. Whatever your budget, Expedia brings the world within your reach.
Does Expedia offer Book Now, Pay Later Ole holidays?
Expedia has joined forces with online lender Klarna to make booking your next getaway a little easier on the wallet. Paying by instalment means you can spread the costs of your next adventure, leaving you with more money to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits into your budget. Take a look at these flexible payment options:
- Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying bite-sized amounts each month works for you, choose this option at checkout.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your holiday across multiple transactions.
- Low deposit holidays: Clicking on the "book now" button is easier with this payment option. Just put down a small deposit on your escape and then start working on your travel plans.
Where should I stay in Ole?
Visitors come from all over the world to experience Barefoot Beach and Naples Pier in Ole. Stay within walking distance of these wonderful attractions to make sightseeing easy.
What are the top hotels in Ole?
Naples Grande Beach Resort and Hampton Inn - Naples - I-75 are two of the most popular properties in Ole. Why not look up the amenities and rates at each and then make a decision?
How far in advance should I book my Ole holiday?
Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers display prices up to a year in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Ole sometimes become available in the weeks leading up to departure.
What does an Expedia Ole travel package include?
With Expedia, you can choose a combination of car rentals, hotels and flights to create your ideal Ole travel package. Once you've made your booking, you can add on fun stuff like tours and activities. Remember — the more you bundle, the more you stand to save!
What should I know before booking an Ole travel package?
An Expedia travel package can be tailored to your budget and is an easy way to make your budget go further. How little or much you include is your call. Rental cars, hotels and flights — come up with a combination that suits your style.
Can I choose my airline with an Ole Expedia travel package?
Yes, and with more than 550 airlines to choose from throughout the world, it's all about choice. Have a look through the available options and see which airline best fits your budget and needs.
Things to do
Everglades National Park: Pontoon Boat Tour & Boardwalk
£44
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.