Pine Woods Vacation Packages

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Top Holiday Package Deals in Pine Woods

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

Edison Beach House

3.5 out of 5
Price was CA $1,010, price is now CA $604 per person
CA $604
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (1,490 reviews)
First stay at Edison beach house having stayed numerous times at FMB. Lift out of order and on the 5th floor but the balcony view over the beach and sunsets were awesome. Carpet tired in places and air con very noisy otherwise only complaint was the smoking from other guests throughout out stay.

Reviewed on Sep. 4, 2025

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 $4,007, price is now CA $1,784 per person
CA $1,784
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
The overall experience at the hotel was excellent.

Reviewed on Sep. 2, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $2,577, price is now CA $1,363 per person
CA $1,363
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
Location, service and amenities are excellent

Reviewed on Aug. 31, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was CA $1,262, price is now CA $734 per person
CA $734
per person
Oct 20 - Oct 27
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
Kind and helpful staff

Reviewed on Sep. 4, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,969, price is now CA $1,175 per person
CA $1,175
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (406 reviews)
“My stay at this hotel exceeded my expectations. The room was spotless, the staff were attentive and welcoming, and the amenities made my stay very comfortable. I would definitely recommend it to others.”

Reviewed on Sep. 3, 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
Naples Botanical Garden which includes a pond and a garden

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 hotels in East Naples

Pine Woods Hotel Deals

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 $242 per night from Sep 7 to Sep 8
CA $242
CA $337 total
Sep 7 - Sep 8
includes taxes & fees
Naples Grande Beach Resort
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South, Naples, FL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Sep 15 to Sep 16
CA $164
CA $182 total
Sep 15 - Sep 16
includes taxes & fees
Hyatt House Naples/5th Avenue
Hilton Naples

Hilton Naples

4 out of 5
5111 Tamiami Trl N, Naples, FL
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Sep 14 to Sep 15
CA $181
CA $201 total
Sep 14 - Sep 15
includes taxes & fees
Hilton Naples
See all 11,136 properties in Pine Woods
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 a Pine Woods vacation package cost?
We make it easy for everyone to travel, with Pine Woods packages starting from as little as CA $604. You'll have the flexibility to bundle your favorite airlines, hotels and car rental. For the ultimate escape, why not add a few tours and activities to your travel itinerary?
How do I get a cheap travel package to Pine Woods?
You'll save loads of cash if you bundle your flights, hotels and car rentals into a Pine Woods travel package. Sometimes cheap means fewer options. But not with Expedia. We offer more than 550 air carriers and 1,000,000 properties all over the world, so you'll always have plenty of variety to choose from. Want to save even more? Add some interesting activities to your package deal to unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Pine Woods?
A visit to Pine Woods isn't complete until you've seen Naples Pier and Barefoot Beach. Book a room nearby for quick access to these fantastic tourist attractions.
How far in advance should I book my Pine Woods vacation?
It's tricky picking the ideal time for airfares, but we usually say the earlier, the better. Plenty of international flights on Expedia become available up to a year in advance. If you're booking last minute, fear not. Discounted prices occasionally appear within a few weeks of departure dates.
What does an Expedia Pine Woods travel package include?
Flights, hotels and a reliable car for all your fun road trip adventures. Simply select your favorite bundle and get access to incredible deals. Once you've made your booking, add on a couple of tours and experiences and watch your savings pile up. When it comes to creating your Pine Woods trip, the choice is all yours!
What should I know before booking a Pine Woods travel package?
You can save big by combining your hotels, flights and rental cars. Once you've made your booking, you can add on sightseeing tours or experiences. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Pine Woods Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to pick from around the globe. With all that choice at your fingertips, finding the right carrier to fly you to Pine Woods will be a snap.
If I'm not able to travel, can I cancel my Pine Woods vacation package?
Don't stress if you're rethinking your Pine Woods vacation package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that life can sometimes throw you a curveball, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.

Discover the most popular places to visit in Pine Woods

Naples Beach

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
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
Naples Pier featuring landscape views and a beach as well as a large group of people

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

SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

CA $88
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Cute Manatee

Manatee Sightseeing and Wildlife Boat Tour

CA $96
per adult
90% of travellers recommend
Manatee Sightseeing and Wildlife Boat Tour
Naples Florida: Downtown Electric Moped Tour

Naples Florida: Downtown Electric Moped Tour

CA $82
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Moped 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.