Pineland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $775 when you book a flight and hotel together*
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Your Pineland Vacation

Say bye-bye to the worries of planning and hello to a Pineland vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with North Captiva, which is good for watersports, cycling and coastal beaches. Ready to venture out and explore? Calusa Heritage Trail, Randell Research Center and Useppa Museum are just three of the best places to visit during your trip to Pineland. No matter your travel plans or the size of your budget, putting together a tailored Pineland vacation is a piece of cake with Expedia.

Top Pineland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
per person
Jul. 7 - Jul. 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Punta Gorda Airport (PGD)
9.8/10 Exceptional! (548 reviews)
Beautiful clean and very spacious. It is definitely home away from home even if it is just a short get away. The space is truly unique and we had an unforgettable experience ^.^

Reviewed on May 31, 2024

Off the Charts Inn & Out Island Resort

Off the Charts Inn & Out Island Resort

2.5 out of 5
per person
Aug. 18 - Aug. 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Punta Gorda Airport (PGD)
9.6/10 Exceptional! (126 reviews)
This place was clean and the location on the island was good because walking distance to bars and boat ramp. Just know there is nobody from the hotel on site except when we checked in on Friday. We really didn't need anyone and I believe there was a contact phone number if we did. The place was clean and roomy. It would of been nice if my AC would of went lower or at least a fan in the room over bed as I like it cold at night but I will be coming back with wifey next time as this was a guys trip.

Reviewed on May 28, 2024

Pineland Hotel Deals

Margaritaville Beach Resort Fort Myers
Margaritaville Beach Resort Fort Myers
4 out of 5
251 Crescent Street, Fort Myers Beach, FL
The price is CA $395 per night from Jun. 30 to Jul. 1
CA $395
CA $494 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (316 reviews)
"Ok"

Reviewed on May 28, 2024

Margaritaville Beach Resort Fort Myers
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 $327 per night from Jun. 3 to Jun. 4
CA $327
CA $399 total
includes taxes & fees
Jun 3 - Jun 4
8.4/10 Very Good! (1,021 reviews)
"They are really nice and clean. They're right in front of the beach, They have a restaurant on on their on their site, So if you're hungry ,you can order some food by the Pool have it delivered to you. And The Food WAS AWESOME , EVEN THE FRYS WHICH IS HARD TO DO..😋😋😋😋"

Reviewed on May 29, 2024

Sanibel Island Beach Resort
Dolphin Key Resort
Dolphin Key Resort
3 out of 5
1502 Miramar Street, Cape Coral, FL
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Jul. 1 to Jul. 2
CA $97
CA $109 total
includes taxes & fees
Jul 1 - Jul 2
8.4/10 Very Good! (1,105 reviews)
"I've stayed here twice and both were exceptional! The room was spacious, clean, and well maintained. The staff at the front desk was friendly and helpful. I think her name was Meghan and she went above and beyond. I hope the owners know what a gem they have with her. I travel to Cape Coral often ..."

Reviewed on May 30, 2024

Dolphin Key Resort
See all 11,476 properties in Pineland
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 Pineland vacation package cost?
Tailor make your Pineland vacation package from only CA $1,051. Pick from any combination of flights, hotels and rental cars to put together the trip of your dreams. Don’t forget to add on some activities and experiences!
How do I get a cheap travel package to Pineland?
Our Pineland vacation packages offer plenty of savings for the savvy traveler. For the best deal, simply bundle your hotel, flights and activities into a neat and tidy package. But impressive bargains are only the start of your next epic adventure. When you book with Expedia, you’ll have more than 550 air carriers and 1,000,000 hotels throughout the world to pick from. Whatever your budget, there’s a vacation package with your name on it.
Where should I stay in Pineland?
With interesting attractions such as Calusa Heritage Trail and Randell Research Center in this neighborhood, try to find a hotel situated near either one. Koucky Gardens & Gallery is another sight in Pineland that travelers flock to.
What are the top hotels in Pineland?
If it’s your first visit to Pineland, book a room at Sophisticated Home With Private Pool And Fast Wifi or 2/2 Privacy In Pine Island. Both have good amenities and are top options with many travelers.
How far in advance should I book my Pineland vacation?
It’s hard to pick the best time for airfares, but we usually say the earlier, the better. Most international flights on Expedia become available to compare up to 12 months in advance. If you’re booking late, don’t worry. Bargain prices occasionally appear within a few weeks of departure dates.
What does an Expedia Pineland travel package include?
With Expedia, you can choose a combination of hotels, car rentals and flights to build your ideal Pineland travel package. Once you’ve made your booking, you can add on the fun things like day tours and activities. Remember — the more you bundle, the more discounts you’ll get!
What should I know before booking a Pineland travel package?
Locking in all the parts of your escape together is a great way to save. Combine your car rentals, flights and hotels into one little package. But you’re not restricted to hotels. Expedia has all sorts of properties, including vacation rentals like beachside villas and city apartments. The list is almost endless!
Can I choose my airline with a Pineland Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to select from all over the world. With all that choice, finding the right carrier to whisk you off to Pineland will be easy.
If I'm not able to travel, can I cancel my Pineland vacation package?
If your travel plans in Pineland have changed, it’s good to know that it is possible to cancel your booking. If you made your booking within the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose fees. For more information, visit our Customer Service Portal.

Discover the most popular places to visit in Pineland

Image for Bokeelia Island

Bokeelia Island

Commune with nature and explore the great outdoors at Bokeelia Island during your travels in Bokeelia. Take in the museums while you're in the area.

Bokeelia Island
Image for Calusa Heritage Trail

Calusa Heritage Trail

You can take time to visit Calusa Heritage Trail during your travels to Pineland.

Calusa Heritage Trail
Image for Goodwins Island

Goodwins Island

Commune with nature and explore the great outdoors at Goodwins Island during your travels in Bokeelia. Take in the museums while you're in the area.

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