Ole Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Ole

Price found within the past 48 hours. Click for updated prices.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was CA $2,203, price is now CA $1,213 per person
CA $1,213
per person
Apr 20 - Apr 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Great view and staff

Reviewed on Feb 6, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $2,242, price is now CA $1,241 per person
CA $1,241
per person
May 2 - May 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
everyone was great room was amazing

Reviewed on Feb 11, 2026

Edison Beach House

Edison Beach House

3.5 out of 5
Price was CA $2,593, price is now CA $1,455 per person
CA $1,455
per person
Apr 4 - Apr 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,554 reviews)
Location and suite amenities were perfect

Reviewed on Feb 11, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $2,531, price is now CA $1,477 per person
CA $1,477
per person
May 7 - May 11
found 22 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,000 reviews)
The best part is that this hotel is right on the beach. We only stayed two nights because this hotel is very expensive, and the restaurant is very expensive.

Reviewed on Feb 1, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was CA $3,573, price is now CA $2,118 per person
CA $2,118
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
The 2 room condo was huge& had everything you could ask for. The surroundings were beautiful.

Reviewed on Jan 30, 2026

Where to stay in Ole

Find the best Ole areas and neighborhoods for the activities you enjoy most. Learn more about Ole
Six beautiful cultivated gardens, 2.5 miles of hiking trails and a restored nature preserve

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

Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
480 S Collier Blvd Marco Island FL
The price is CA $513 per night from Mar 4 to Mar 5
CA $513
CA $607 total
Mar 4 - Mar 5
includes taxes & fees
8.6/10 Excellent! (1,199 reviews)
Great room with an outstanding oven view. It would be great for families.

Reviewed on Feb 4, 2026

Marco Beach Ocean Suites
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
1221 5th Ave S Naples FL
The price is CA $402 per night from Mar 9 to Mar 10
CA $402
CA $446 total
Mar 9 - Mar 10
includes taxes & fees
8.6/10 Excellent! (1,712 reviews)
The staff was very friendly and efficient. The room was very clean and spacious, The hotel is older, yet going through renovation. The location and harbor view is great. Priced right.

Reviewed on Feb 10, 2026

Bayfront Inn Fifth Avenue
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $581 per night from Mar 12 to Mar 13
CA $581
CA $712 total
Mar 12 - Mar 13
includes taxes & fees
8.8/10 Excellent! (2,028 reviews)
Th staff is fast, friendly, and efficient. The rooms are very da

Reviewed on Jan 30, 2026

Naples Grande Beach Resort
See all 10,031 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 CA $1,213. 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

Vanderbilt beach in Naples, Florida

Vanderbilt Beach

4.5/5(26 reviews)

If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples.

Vanderbilt Beach
5th Avenue Shopping District which includes markets, street scenes and a city

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

4.5/5(102 reviews)

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

Things to do

SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

CA $90
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Sunset Tour in Naples Bay on a New Godfrey- All included

Naples Sunset Cruise - Complimentary Charcuterie and wine

CA $150
per adult
100% of travellers recommend
Naples Sunset Cruise - Complimentary Charcuterie and wine
Wild Dolphin Boat Tour

Best of Marco Dolphin Tour

CA $136
per adult
Best of Marco Dolphin Tour
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.