Title: Pine Woods Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,281 Expedia.ca

[Hotels in Pine Woods](https://expedia.ca/Pine-Woods-Naples-Hotels.0-n553248635976481489-0.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)[Pine Woods Car Rentals](https://expedia.ca/Car-Rentals-In-Pine-Woods.d553248635976481489.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)

# Pine Woods 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 Pine Woods

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

![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 $1,281

per person

Apr 28 - May 5

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

9.4/10 Exceptional! (1,021 reviews)

Penny was very cheerful,helpful and accommodating.

Reviewed on Mar 10, 2026

![Windward Passage Resort](https://images.trvl-media.com/lodging/123000000/122910000/122905200/122905151/23bcb5a8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Windward Passage Resort

CA $3,493

per person

Apr 28 - May 5

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

No reviews

![Tween Waters Island Resort & Spa](https://images.trvl-media.com/lodging/1000000/180000/170800/170769/a5c54d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tween Waters Island Resort & Spa

CA $1,702

per person

May 9 - May 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

8.6/10 Excellent! (1,008 reviews)

Views and location were great

Reviewed on Mar 17, 2026

![Shell Island Beach Club](https://images.trvl-media.com/lodging/112000000/111490000/111488300/111488225/9e849186_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Shell Island Beach Club

East End

CA $2,240

per person

May 9 - May 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

9.6/10 Exceptional! (23 reviews)

Beautiful view and beautiful beach!

Reviewed on Aug 2, 2025

## Where to stay in Pine Woods

Find the best Pine Woods areas and neighborhoods for the activities you enjoy most. [Learn more about Pine Woods](https://expedia.ca/Naples-Pine-Woods.dx553248635976481489)

![Six beautiful cultivated gardens, 2.5 miles of hiking trails and a restored nature preserve](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)

![paddle boarding at Baker park in Naples Florida south west Florida public park ](https://images.trvl-media.com/place/553248635975749203/2ad7f7a2-06e4-4c5f-b637-209e07bf70ab.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)

![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 Historical Society's Historic Palm Cottage 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)

![Naples Pier and beach in florida USA sunny day; Shutterstock ID 446686663; purchase_order: SP-1269 HA 2018 Batch 1; Order: ; client: ; other:](https://images.trvl-media.com/place/6177550/152a5c2a-26db-4722-a5ab-87f5c84d4dac.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)

![Delnor-Wiggins Pass State Park showing a river or creek](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)

## Pine Woods Hotel Deals

![Compass by Margaritaville Hotel Naples](https://images.trvl-media.com/lodging/1000000/550000/543700/543614/03101902_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Compass by Margaritaville Hotel Naples

4805 Tamiami Trl N Naples FL

Fully refundableReserve now, pay when you stay

CA $258

CA $321 total

Apr 1 - Apr 2

includes taxes & fees

9.6/10 Exceptional! (1,337 reviews)

Pool space was good. Everything was nice but there was a great big bug I. Our bathroom that scared me.

Reviewed on Mar 17, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=543614&PinnedHotelID=543614&HadPinnedHotel=true&regionId=553248635976481489)

![Naples Grande Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/15900/15898/018506a5_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Naples Grande Beach Resort

475 Seagate Drive Naples FL

Fully refundable

CA $563

CA $694 total

Mar 27 - Mar 28

includes taxes & fees

9/10 Wonderful! (2,030 reviews)

I had a wonderful trip with my family. Everyone was very nice and the resort was perfect for our getaway. I will be sure to come back.

Reviewed on Mar 17, 2026

[](https://expedia.ca/Hotel-Search?startDate=27%2F03%2F2026&endDate=28%2F03%2F2026&selected=15898&PinnedHotelID=15898&HadPinnedHotel=true&regionId=553248635976481489)

![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 $218

CA $242 total

Apr 9 - Apr 10

includes taxes & fees

9.4/10 Exceptional! (566 reviews)

A lot of entrainment for kids! Buffet was definitely dirty and not worth 100 bucks but overall park it’s good for kids and place it’s good for a day!

Reviewed on Mar 17, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=112014521&PinnedHotelID=112014521&HadPinnedHotel=true&regionId=553248635976481489)

[See all 11,611 properties in Pine Woods](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F03%2F2026&endDate=20%2F03%2F2026&regionId=553248635976481489)

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 Pine Woods vacation package cost?

### How do I get a cheap travel package to Pine Woods?

### Where should I stay in Pine Woods?

### How far in advance should I book my Pine Woods vacation?

### What does an Expedia Pine Woods travel package include?

### What should I know before booking a Pine Woods travel package?

### Can I choose my airline with a Pine Woods Expedia vacation package?

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

### Discover the most popular places to visit in Pine Woods

![5th Avenue Shopping District which includes markets, street scenes and a city](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

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

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

![SEAS The Day with Pure Florida](https://mediaim.expedia.com/localexpert/1343716/f21f40c9-c549-4450-bd62-ddee3f6b0cb6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Naples Sightseeing Boat Tour

CA $90

per adult

**98%** of travellers recommend

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

![Gulf of Mexico Sunset Cruise from Naples](https://mediaim.expedia.com/localexpert/1344546/aa34e981-022c-4ba8-903b-b596812d1864.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Gulf of Mexico Sunset Cruise from Naples

CA $94

per adult

**88%** of travellers recommend

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

![Wild Dolphin Boat Tour](https://mediaim.expedia.com/localexpert/48093797/4cb49939-0fd0-4f3f-a989-1bc6a78b37f8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Best of Marco Dolphin Tour

CA $137

per adult

[](https://expedia.ca/things-to-do/best-of-marco-dolphin-tour.a48093797.activity-details)

[See all activities in Naples](https://expedia.ca/things-to-do/search?rid=553248635976481489)

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