Pine Island Vacation Packages

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

When adventure calls, answer it with a customized vacation package to Pine Island. Wherever your travels take you and whatever you have planned, prepare to experience a destination that'll make you feel alive. A trip to Pine Island offers so much to see and do. Not sure where to kick off your itinerary? Saint James City is a popular place to stay here. Quit dreaming and get packing, because your Pine Island vacation is just a few clicks away with Expedia.

Top Pine Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
per person
Aug 30 - Sep 6
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,169 reviews)
nice I didn't like the resort fee's, parking fee's. Very expensive to eat and drink at the pool .

Reviewed on Jul. 29, 2025

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Pine Island Hotel Deals

Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Aug 2 to Aug 3
CA $173
CA $254 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (1,263 reviews)
Amazing place
"Great customer service. Comfortable location."

Reviewed on Jul. 28, 2025

Sunseeker Resort Charlotte Harbor
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Aug 6 to Aug 7
CA $193
CA $277 total
Aug 6 - Aug 7
includes taxes & fees
8.4/10 Very Good! (1,037 reviews)
"Nice facility, in spite of the rebuilding and renovation. Would definitely return."

Reviewed on Jul. 27, 2025

Lani Kai Beachfront Resort
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr, Sanibel, FL
Fully refundableReserve now, pay when you stay
The price is CA $281 per night from Aug 10 to Aug 11
CA $281
CA $348 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,250 reviews)
"The property was nice and clean. We like having a restaurant and snack bar, very convenient. The bed was very comfortable, and the room was clean. We enjoyed our stay!"

Reviewed on Jul. 29, 2025

Sanibel Island Beach Resort
See all 17,008 properties in Pine Island
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

What to do in Pine Island

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

CA $100
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
See all activities in Pine Island

Frequently asked questions

How much does a Pine Island vacation package cost?
Starting from only CA $1,107, a vacation package is your ticket to affordable travel. Custom make your Pine Island trip by picking from our huge range of airfares, hotels and rental cars.
How do I get a cheap travel package to Pine Island?
Browse and lock in everything in the one place with our Pine Island vacation packages. You'll discover bargains on flights, hotels, tours and more that'll keep your bank account happy and adventurous side satisfied. And, with more than 550 partner airlines and 1,000,000 hotel options worldwide to pick from, there are endless opportunities to mix and match your own way.
What are the top hotels in Pine Island?
For hotels in Saint James City with comfy beds and friendly service, check out Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park and Best Western Fort Myers Inn & Suites. If you're stopping by Bokeelia as well, you can look forward to a solid night's sleep at Trianon Bonita Bay or Sanibel Island Beach Resort.
How far in advance should I book my Pine Island vacation?
While prices change from time to time, we generally suggest booking your flight as early as possible. Many international fares are available on Expedia up to 12 months in advance. If you're booking late, you might still be in luck. Discount prices to Pine Island occasionally appear just weeks before departure.
What does an Expedia Pine Island travel package include?
Packages include flights, rental cars and hotels, but you can combine any of them to create your dream Pine Island vacation. You can also add on experiences and activities once you've made your booking. You're in control! When you bundle your bookings with Expedia, you'll enjoy discounts you won't find elsewhere.
What should I know before booking a Pine Island travel package?
Bundling your bookings into a Pine Island vacation package is the most convenient way to organize your trip. Not only that, you'll save big just for combining your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Pine Island Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Just choose the airline you want and create your ideal Pine Island vacation.
If I'm not able to travel, can I cancel my Pine Island vacation package?
We totally understand that life sometimes gets in the way of your plans. If you've locked in a Pine Island vacation package and have to change or cancel it, we can help. We suggest looking up our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to change your itinerary for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a fee.

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