Ole Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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
Price found within the past 48 hours. Click for updated prices.
  • 3 outdoor pools, cabanas (surcharge), pool umbrellas
    Aug 12 - Aug 20

    Hyatt Vacation Club at Coconut Cove, Bonita Springs + Flight

    Bonita Springs
    8 nights
    4.0 star property
    9.0/10 - Wonderful (886 reviews)
    "Xx"
    Reviewed May 26, 2026
    Roundtrip • Montreal (YUL) - Miami (MIA)
    YUL - MIA • Nonstop MIA - YUL • Nonstop
    CA $2,058
    CA $1,350
    per traveller
    found 18 hours ago
    Hyatt Vacation Club at Coconut Cove, Bonita Springs
  • View from room
    Jul 18 - Jul 25

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    7 nights
    4.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Enjoyed the bar/food access on the beach; plenty of chairs/umbrellas/towels (which were all included); all the men were quick to help you set-up your preferred location on the Beach. Food was great (with healthy options) and room service was quick. Snack and drink options provided in rooms were also a big plus."
    Reviewed May 26, 2026
    Roundtrip • Detroit (DTW) - Fort Myers (RSW)
    DTW - RSW • 1 stop RSW - DTW • 1 stop
    CA $3,683
    CA $2,036
    per traveller
    found 19 hours ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • 2 outdoor pools, cabanas (surcharge), pool umbrellas
    Aug 10 - Aug 21

    The Perry Hotel Naples + Flight

    Naples
    11 nights
    4.5 star property
    9.6/10 - Exceptional (827 reviews)
    "I come back again"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YYZ) - Miami (MIA)
    YYZ - MIA • Nonstop MIA - YYZ • Nonstop
    CA $2,282
    CA $1,371
    per traveller
    found 1 day ago
    The Perry Hotel Naples
  • 2 outdoor pools
    Aug 8 - Aug 15

    The Lighthouse Resort Inn & Suites + Flight

    Fort Myers Beach
    7 nights
    3.0 star property
    8.6/10 - Excellent (1,669 reviews)
    "The bathroom was poorly maintained, the sink was clogged, and the noise was very annoying. The terrace was right above the tiki bar, and the breakfast service included items different from what I ordered. They gave room keys to other people who entered while we were resting, which was a big mistake."
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • 1 stop RSW - YYZ • 1 stop
    CA $2,143
    CA $1,401
    per traveller
    found 1 day ago
    The Lighthouse Resort Inn & Suites
  • Exterior
    Jul 18 - Jul 25

    Shell Island Beach Club + Flight

    East End
    7 nights
    4.0 star property
    9.6/10 - Exceptional (23 reviews)
    "Very clean. Excellent location, close to beach, walkable to restaurants."
    Reviewed December 21, 2025
    Roundtrip • Detroit (DTW) - Fort Myers (RSW)
    DTW - RSW • 1 stop RSW - DTW • 1 stop
    CA $2,999
    CA $2,019
    per traveller
    found 19 hours ago
    Shell Island Beach Club

Where to stay in Ole

Find the best Ole areas and neighborhoods for the activities you enjoy most. Learn more about Ole
East Naples

East Naples

4/5(11 area reviews)

Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Gulf Shores Marina or Fifth Avenue South while you're exploring the area.

Find hotels in East Naples

Ole Hotel Deals

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
The price is CA $351 per night from Jun 14 to Jun 15
CA $351
CA $466 total
Jun 14 - Jun 15
includes taxes & fees
9/10 Wonderful! (1,790 reviews)
"Excellent"

Reviewed on May 27, 2026

Hilton Marco Island Beach Resort and Spa
Fairways Inn of Naples

Fairways Inn of Naples

3 out of 5
103 Palm River Blvd Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Jun 7 to Jun 8
CA $111
CA $123 total
Jun 7 - Jun 8
includes taxes & fees
9.4/10 Exceptional! (1,307 reviews)
"Súper bueno todo 100%"

Reviewed on May 26, 2026

Fairways Inn of Naples
Great Wolf Lodge Naples

Great Wolf Lodge Naples

3 out of 5
3900 City Gate Blvd N. Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $275 per night from Jun 10 to Jun 11
CA $275
CA $305 total
Jun 10 - Jun 11
includes taxes & fees
9.4/10 Exceptional! (843 reviews)
"Good"

Reviewed on May 26, 2026

Great Wolf Lodge Naples
See all 9,759 properties in Ole
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Ole vacation package cost?
From as little as . 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.

Discover the most popular places to visit in Ole

Fifth Avenue South

Fifth Avenue South

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Fifth Avenue South
Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA

Naples Beach

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

Naples Beach
Naples Pier

Naples Pier

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

Naples Pier

Things to do

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

CA $73
per adult
94% of travellers recommend
Naples Sightseeing Boat Tour
Naples Florida: Downtown Electric Trike Tour

Naples Florida: Downtown Electric Trike Tour - Family Fun

CA $96
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Trike Tour - Family Fun
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

CA $100
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
See all activities in Naples
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.