Pine Island Vacations from $377
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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.
The Latest Pine Island vacation packages
Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Save 100% on your flight
Price was $1,890, price is now $1,133 per person
$1,133
per person
Feb 21 - Feb 28
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.8/10 Exceptional! (1,027 reviews)
Everything was wonderful! The views were stunning!
Reviewed on Nov 30, 2025
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Save 100% on your flight
Price was $717, price is now $484 per person
$484
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,612 reviews)
Everything is great Everything!!
Reviewed on Dec 7, 2025
Wyvern Hotel, an Ascend Collection Hotel
Downtown Punta Gorda
Save 100% on your flight
Price was $1,501, price is now $1,021 per person
$1,021
per person
Feb 21 - Feb 28
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9/10 Wonderful! (1,003 reviews)
Beautiful room! Had a lovely stay I highly recommend the Wyvern.
Reviewed on Dec 2, 2025
Off the Charts Inn & Out Island Resort
Price was $858, price is now $760 per person
$760
per person
Feb 28 - Mar 4
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.6/10 Exceptional! (144 reviews)
Hotel was clean and located in a nice area. First time my wife and I had visited this area. This is a no conract hotel and we had no issues with that all. Would stay here again.
Reviewed on Jun 7, 2025
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See all available trips from Columbus to Pine Island
View all tripsDiscover the most popular places to visit in Pine 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.
Koucky Gardens & Gallery
You can spend time exploring the galleries in Koucky Gardens & Gallery in Pine Island Center. Wander the beautiful beaches and marina in this family-friendly area.
Useppa Museum
You can spend time studying the exhibits at Useppa Museum in Bokeelia. Amble around the area's marina, or seek out its fishing spots.
What to do in Pine Island
Clear Kayak Tours in Weeki Wachee
$79
per adult
100% of travellers recommend
Pine Island Hotel Deals
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $204 total per night from Jan 2 to Jan 3
$204 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,650 reviews)
Yes
Reviewed on Dec 2, 2025
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$212 nightly
The price is $237 total per night from Dec 14 to Dec 15
$237 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (1,685 reviews)
Great place. Great entertainment
Reviewed on Dec 2, 2025
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $172 total per night from Dec 9 to Dec 10
$172 total
Dec 9 - Dec 10
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Clean rooms, friendly staff, so much to do there and nearby
Reviewed on Dec 3, 2025
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.
Find the Best Pine Island Vacation Packages
Pine Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Southwest Florida Intl. Airport (RSW) |
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- Museum of the Islands
- Lovegrove Gallery & Gardens
- Matlacha Vacations
- Koucky Gardens & Gallery
- Visit Matlacha
- Griffen American Center for Haitian Art
- Calusa Heritage Trail
- Royal Tee Golf Club
- Alison Hagerup Beach Park
- Visit Pelican
- Captiva Vacations
- Captiva Island Vacations
- Visit Saint James City
- McCarthy's Marina
- Jensen’s Marina
- Jungle Drums
- Saint James City Vacations
- Visit North Captiva
- Captiva Chapel By the Sea
- Palmetto-Pine Country Club
- Visit Captiva Island
- Visit Captiva
- Car rentals near Pine Island Center
- Car rentals near Flamingo Bay
- Car rentals near Matlacha
- Car rentals near Matlacha Isles-Matlacha Shores
- Car rentals near Alden Pines
- Car rentals near Alison Hagerup Beach Park
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- Van Car Rentals in Captiva Island
- Dollar Rental Cars in Captiva Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.