Title: Ole Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $793 Expedia.ca

[Hotels in Ole](https://expedia.ca/Ole-Naples-Hotels.0-n553248635976468752-0.Travel-Guide-Filter-Hotels)[Flights to Naples](https://expedia.ca/Cheap-Flights-To-Naples.d602724.Travel-Guide-Flights)[Things to do in Naples](https://expedia.ca/Things-To-Do-In-Naples.d602724.Travel-Guide-Activities)[Ole Car Rentals](https://expedia.ca/Car-Rentals-In-Ole.d553248635976468752.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635976468752/5705a90b-e052-44ed-bfca-ddd569917347.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Ole Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 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

## Top Holiday Package Deals in Ole

Price found within the past 48 hours. Click for updated prices.

![The Perry Hotel Naples](https://images.trvl-media.com/lodging/103000000/102390000/102386400/102386398/0ad2742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Perry Hotel Naples

CA $793

per person

May 15 - May 18

found 4 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Fort Myers (RSW)

9.6/10 Exceptional! (725 reviews)

This hotel is a refreshing experience for a traveler.

Reviewed on Apr 1, 2026

![LaPlaya Beach & Golf Resort - A Noble House Resort](https://images.trvl-media.com/lodging/1000000/30000/25200/25199/d2442103_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

CA $1,938

per person

May 22 - May 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

9/10 Wonderful! (1,002 reviews)

Great location. The rooms have amazing views. The hotel is a little bit dated and the service is a little slow, although the staff is very nice.

Reviewed on Apr 2, 2026

![Matanzas Inn Bayside Resort and Marina](https://images.trvl-media.com/lodging/3000000/2670000/2665100/2665085/78d7ce83_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Matanzas Inn Bayside Resort and Marina

CA $995

per person

Jun 22 - Jun 29

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

9.4/10 Exceptional! (1,021 reviews)

Great location for the Key West Express.

Reviewed on Apr 3, 2026

![Poolside 2BR/2.5BA Near Downtown Fort Myers](https://images.trvl-media.com/lodging/125000000/124370000/124368300/124368241/w1284h951x0y0-f1e7dda1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Poolside 2BR/2.5BA Near Downtown Fort Myers

CA $1,083

per person

Jun 22 - Jun 29

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

No reviews

![Marriott Sanibel Harbour Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/3100/3079/0ef86cd3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Marriott Sanibel Harbour Resort & Spa

Punta Rassa

CA $1,236

per person

Jun 6 - Jun 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Fort Myers (RSW)

8.4/10 Very Good! (1,013 reviews)

Clean room, friendly staff, good food, great view of sunset

Reviewed on Mar 30, 2026

## Where to stay in Ole

Find the best Ole areas and neighborhoods for the activities you enjoy most. [Learn more about Ole](https://expedia.ca/Naples-Ole.dx553248635976468752)

![East Naples](https://images.trvl-media.com/place/6177501/5f861be1-5382-48a5-99ea-10946f7b2f07.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### East Naples

4/5(11 area reviews)

 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. 

[Find hotel + flight trips in East Naples](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Naples&DestID=6177511&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![walking down the bridge of Baker park in Naples Florida in southwest Florida public park ](https://images.trvl-media.com/place/553248635975749203/5fdacfb7-94ce-4350-9d5b-8788aaea5743.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in Central Naples](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Central%20Naples&DestID=553248635975749203&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![old city dock  in tropical Naples Florida; Shutterstock ID 155142134](https://images.trvl-media.com/place/6337317/773e6b3f-e6bb-40d2-8271-236a37a0dcaa.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Old Naples

3 out of top 10 points of interest in this area

5/5(25 area reviews)

 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. 

[Find hotel + flight trips in Old Naples](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Old%20Naples&DestID=6337317&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Delnor Wiggins State Park - Panoramic aerial view](https://images.trvl-media.com/place/6177550/10d8a15d-ce96-43ef-bf31-e37eb5973c97.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in Naples Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Naples%20Park&DestID=6177550&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Vanderbilt Beach](https://images.trvl-media.com/place/6065875/2d1b283b-31ba-4ddc-adeb-36fe90f32f9d.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Vanderbilt Beach

1 out of top 10 points of interest in this area

4.5/5(4 area reviews)

 While visiting Vanderbilt Beach, you might make a stop by sights like Vanderbilt Beach and Delnor-Wiggins Pass State Park. 

[Find hotel + flight trips in Vanderbilt Beach](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Vanderbilt%20Beach&DestID=553248635977184221&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Ole Hotel Deals

![Hilton Marco Island Beach Resort and Spa](https://images.trvl-media.com/lodging/1000000/20000/17600/17575/65dd4041_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL

Fully refundableReserve now, pay when you stay

CA $405

CA $527 total

May 4 - May 5

includes taxes & fees

9/10 Wonderful! (1,737 reviews)

Rooms and bathroom didn’t feel clean. Strong smell in our room. Eddie the bellman was great.

Reviewed on Apr 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=04%2F05%2F2026&endDate=05%2F05%2F2026&selected=17575&PinnedHotelID=17575&HadPinnedHotel=true&regionId=553248635976468752)

![Great Wolf Lodge Naples](https://images.trvl-media.com/lodging/113000000/112020000/112014600/112014521/c6e60574_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL

Fully refundableReserve now, pay when you stay

CA $222

CA $246 total

May 3 - May 4

includes taxes & fees

9.4/10 Exceptional! (634 reviews)

Nice getaway for a family.

Reviewed on Apr 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=03%2F05%2F2026&endDate=04%2F05%2F2026&selected=112014521&PinnedHotelID=112014521&HadPinnedHotel=true&regionId=553248635976468752)

![La Quinta Inn & Suites by Wyndham Naples Downtown](https://images.trvl-media.com/lodging/1000000/30000/24700/24612/3a0774b2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL

Fully refundableReserve now, pay when you stay

CA $143

CA $159 total

May 3 - May 4

includes taxes & fees

8.2/10 Very Good! (1,889 reviews)

Good location, easy parking, clean, good value for money

Reviewed on Apr 4, 2026

[](https://expedia.ca/Hotel-Search?startDate=03%2F05%2F2026&endDate=04%2F05%2F2026&selected=24612&PinnedHotelID=24612&HadPinnedHotel=true&regionId=553248635976468752)

[See all 9,933 properties in Ole](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&regionId=553248635976468752)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does an Ole vacation package cost?

### How do I get a cheap travel package to Ole?

### Where should I stay in Ole?

### What are the top hotels in Ole?

### How far in advance should I book my Ole vacation?

### What does an Expedia Ole travel package include?

### What should I know before booking an Ole travel package?

### Can I choose my airline with an Ole Expedia vacation package?

### If I'm not able to travel, can I cancel my Ole vacation package?

### Discover the most popular places to visit in Ole

![Fifth Avenue South](https://images.trvl-media.com/place/6337227/652d7a23-0ecb-418a-b7cc-95f00eef6cc8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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.

[](https://expedia.ca/Fifth-Avenue-South-Old-Naples.d6337227.Vacation-Attraction)

![Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA](https://images.trvl-media.com/place/553248621565061337/c3e350a9-2166-42a1-bc09-fe8d70fa80a9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.ca/Naples-Beach-West-Naples.d553248621565061337.Vacation-Attraction)

![Vanderbilt beach in Naples, Florida](https://images.trvl-media.com/place/553248621532652404/2e032eea-d142-4ae9-80c9-a10de88f17a7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.ca/Vanderbilt-Beach-Vanderbilt-Beach.d553248621532652404.Vacation-Attraction)

### Things to do

![Naples Sightseeing Boat Tour](https://mediaim.expedia.com/localexpert/1343716/ac14e815-1432-4873-b606-0821d4890ff8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Naples Sightseeing Boat Tour

CA $90

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/naples-sightseeing-boat-tour.a1343716.activity-details)

![Naples Florida: Downtown Electric Trike Tour](https://mediaim.expedia.com/localexpert/47891159/6efb2442-2dc7-4d4b-aa54-fffa02778569.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Naples Florida: Downtown Electric Trike Tour - Family Fun

CA $96

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/naples-florida-downtown-electric-trike-tour-family-fun.a47891159.activity-details)

![Gulf of Mexico Sunset Cruise from Naples](https://mediaim.expedia.com/localexpert/1344546/f630ba30-182b-40d9-a356-41d6167ac3b3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Gulf of Mexico Sunset Cruise from Naples

CA $101

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/gulf-of-mexico-sunset-cruise-from-naples.a1344546.activity-details)

[See all activities in Naples](https://expedia.ca/things-to-do/search?rid=553248635976468752)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.