Title:  Wing South Vacation Packages & Trips 2025 from $289 | Expedia.ca

  

[Hotels in Wing South](https://expedia.ca/Wing-South-Naples-Hotels.0-n553248635976481348-0.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)[Wing South Car Rentals](https://expedia.ca/Car-Rentals-In-Wing-South.d553248635976481348.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Wing South 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 Wing South

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

![Hilton Garden Inn Ft Myers](https://images.trvl-media.com/lodging/1000000/850000/848800/848740/d8bd559a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Garden Inn Ft Myers

Villas

CA $570

per person

Dec 4 - Dec 11

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

8.6/10 Excellent! (1,011 reviews)

The man that was working the night we checked in is very rude. We had two interactions with him and both were awful.

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-11/?FromAirport=DTW&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=848740&paandie=true&dealMarker=QmXusEQ-G1l6bNsDcuwL0eTzXjskNe0SBi4eqLUzbYZcLQmYYT2MEzsa8i4x4OmA)

![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 $1,469

per person

Dec 4 - Dec 11

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

8.8/10 Excellent! (1,002 reviews)

Our experience at La Playa was exceptional, everything was what we wanted and expected it to be

Reviewed on Sep 29, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-11/?FromAirport=DTW&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25199&paandie=true&dealMarker=snyYlfDcl_3Va8lTUe7YHzP5hTj9MTMP4Pc8BJxtmm0UDX9NmWiTzsH4uSoklaQ7)

![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 $933

per person

Dec 4 - Dec 11

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

9.6/10 Exceptional! (417 reviews)

Great all around 10/10 ; tigress restaurant is worth checking out as well

Reviewed on Sep 28, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-11/?FromAirport=DTW&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=102386398&paandie=true&dealMarker=YWiWtCm_b0sHuiTPqDk47yUPGmeX3BdFRRP3DzdeSa7tiQ6eNeRBYjWZNxpACgku)

![Matanzas Inn Bayside Resort and Marina](https://images.trvl-media.com/lodging/3000000/2670000/2665100/2665085/fc463bf9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Matanzas Inn Bayside Resort and Marina

CA $1,302

per person

Dec 21 - Dec 27

found 21 hours ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

9.2/10 Wonderful! (1,002 reviews)

I stayed one night for a girl's beach trip and Islandhopper Songwriter Festival. The location was perfect! Walking distance to everything we wanted to see and do. Restaurant and bar on property were great. Enjoyed a sunrise over the marina in the morning, a short walk from our room.

Reviewed on Sep 29, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-27/?FromAirport=DTW&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2665085&paandie=true&dealMarker=AeCmqHC8XsuyHJkuxS36-wi9QqhSyk0AtwB-yHe3bzhIZFcZsOd0axM8h8LC7fAD)

![Edison Beach House](https://images.trvl-media.com/lodging/12000000/11760000/11753200/11753200/fb0b7d7c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Edison Beach House

CA $1,101

per person

Dec 4 - Dec 11

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

9.4/10 Exceptional! (1,499 reviews)

Very clean rooms and the staff was great! Especially Ms Annie ….. she was wonderful!

Reviewed on Oct 1, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-11/?FromAirport=DTW&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11753200&paandie=true&dealMarker=YWiWtCm_b0sHuiTPqDk47yIWDvGEJSDlaCl7cXFsNRpOGSBBEupwAAtcZILazFxt)

## Where to stay in Wing South

Find the best Wing South areas and neighborhoods for the activities you enjoy most. [Learn more about Wing South](https://expedia.ca/Naples-Wing-South.dx553248635976481348)

![Naples Botanical Garden which includes a pond and a garden](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/64000/64052-Naples-Botanical-Garden.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)

![Naples Zoo at Caribbean Gardens featuring wild flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/242000/242067-Naples-Zoo-At-Caribbean-Gardens.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 Grande Golf Club and Naples Zoo at Caribbean Gardens 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)

![South Florida showing a bay or harbour, a marina and a coastal town](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/196000/196422-South-Florida.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)

![Default Image](https://mediaim.expedia.com/destination/1/ef59193709d049c8c036a66a0396fdc9.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)

![The Baker Museum showing modern architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/64000/64135-Naples-Museum-Of-Art.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Pelican Bay

4.5/5(8 area reviews)

The beaches and abundant dining options are top of the list for many visitors to Pelican Bay. A stop by Pelican Bay North Beach or Artis-Naples might round out your trip.

[Find hotel + flight trips in Pelican Bay](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Pelican%20Bay&DestID=6177555&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Wing South Hotel Deals

![Naples Grande Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/15900/15898/65da812e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Naples Grande Beach Resort

475 Seagate Drive, Naples, FL

Fully refundableReserve now, pay when you stay

CA $271

CA $371 total

Oct 13 - Oct 14

includes taxes & fees

9/10 Wonderful! (1,825 reviews)

"Wonderful staff and fast elevators!! Clean facilities and room service was phenomenal"

Reviewed on Sep 30, 2025

[](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=15898&PinnedHotelID=15898&HadPinnedHotel=true&regionId=553248635976481348)

![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 $274

CA $367 total

Oct 6 - Oct 7

includes taxes & fees

8.8/10 Excellent! (1,586 reviews)

"Nice view to the beach"

Reviewed on Sep 30, 2025

[](https://expedia.ca/Hotel-Search?startDate=06%2F10%2F2025&endDate=07%2F10%2F2025&selected=17575&PinnedHotelID=17575&HadPinnedHotel=true&regionId=553248635976481348)

![Hyatt House Naples/5th Avenue](https://images.trvl-media.com/lodging/13000000/12810000/12805400/12805323/b4e7afd1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hyatt House Naples/5th Avenue

1345 5th Avenue South, Naples, FL

Fully refundableReserve now, pay when you stay

CA $236

CA $262 total

Oct 26 - Oct 27

includes taxes & fees

9/10 Wonderful! (1,477 reviews)

"Excellent value, especially for Naples. We came here for a two nights stay for my birthday and were pleased with staff and the value, for such a great location at such a quality hotel. We arrived late and went looking for food elsewhere only to find out most places were closed at 9 PM. We were thrilled ..."

Reviewed on Sep 30, 2025

[](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=12805323&PinnedHotelID=12805323&HadPinnedHotel=true&regionId=553248635976481348)

[See all 10,769 properties in Wing South](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F10%2F2025&endDate=05%2F10%2F2025&regionId=553248635976481348)

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 a Wing South vacation package cost?

> We make it easy for everyone to travel, with Wing South packages starting from just CA $570. You'll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate escape, why not add some experiences and tours to your travel itinerary?

### How do I get a cheap travel package to Wing South?

> Browse and book everything in the one place with our Wing South vacation packages. You'll find bargains on hotels, flights and more that'll keep your travel budget happy and your spirit of adventure alive. And, with more than 550 air carriers and 1,000,000 hotels around the globe to pick from, you'll have endless opportunities to mix and match as you please.

### Where should I stay in Wing South?

> There's loads to explore in Wing South, so stay close to its attractions and maximize your time sightseeing. Mustang Golf Course is one spot to put on your to-do list.

### How far in advance should I book my Wing South vacation?

> While not all airlines advertise ticket prices early, it's usually possible to compare international airfares on Expedia up to a year in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you might still get lucky. Discounted prices occasionally emerge just weeks before departure.

### What does an Expedia Wing South travel package include?

> That mostly depends on you. You can choose from a range of Wing South bundles, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your Wing South escape looks like, you're sure to save!

### What should I know before booking a Wing South travel package?

> You'll enjoy impressive savings when you bundle your flights, hotels and rental cars into a travel package. Not just that, booking everything together just makes things easier. So why waste money or time? Whether you're putting together a ritzy city getaway or an affordable family break, take a look at our vacation packages today.

### Can I choose my airline with a Wing South Expedia vacation package?

> With a vacation package, you're in control. Whether you'd prefer to fly to Wing South in economy or first class, simply select from the available airline options. Expedia has access to more than 550 partner airlines throughout the world.

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

> Yes, it's possible to cancel your Wing South booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Head to our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) for more information.

### Discover the most popular places to visit in Wing South

![Naples Beach](https://mediaim.expedia.com/destination/1/6b7a9cc1903ff9d66022b1c3a4cf0938.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)

![5th Avenue Shopping District which includes markets, street scenes and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63814-5th-Avenue-Shopping-District.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)

![Naples Pier featuring landscape views and a beach as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63640-Naples.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Naples Pier

4.5/5(74 reviews)

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.

[](https://expedia.ca/Naples-Pier-Old-Naples.d6068669.Vacation-Attraction)

### Things to do

![Naples Florida Electric Trike Tour - Fun For The Entire Family!](https://mediaim.expedia.com/localexpert/47155840/dc0455f9-3889-4c9d-b337-46937897f517.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Naples Florida Electric Trike Tour - Fun For The Entire Family!

CA $94

per adult

[](https://expedia.ca/things-to-do/naples-florida-electric-trike-tour-fun-for-the-entire-family.a47155840.activity-details)

![Naples Florida: Downtown Electric Trike Tour - Family Fun](https://mediaim.expedia.com/localexpert/47891159/3acb618e-8eee-4ed7-babd-9dd3f4674f53.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

CA $77

per adult

**100%** of travellers recommend

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

![Kissimmee: 1-Hour Airboat Everglades Adventure Tour](https://mediaim.expedia.com/localexpert/4847898/82c8eb5f-7741-45ea-ac7a-16078276b020.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Kissimmee: Everglades Airboat Adventure Tour

CA $97

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/kissimmee-everglades-airboat-adventure-tour.a4847898.activity-details)

[See all activities in Naples](https://expedia.ca/things-to-do/search?rid=553248635976481348)

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