Pine Island Vacations from $382
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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.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Price was $1,145, price is now $865 per person
$865
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,993 reviews)
The property is beautiful! Both pools are nice and relaxing. The big pool has plenty of seating with wait staff coming around to take your order. Every staff member we spoke with were so nice and welcoming. They also have a lot of food options right on the property. Our room was very spacious and clean. I highly recommend this property.
Reviewed on Mar 9, 2026
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Discover 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.
Calusa Heritage Trail
You can take time to visit Calusa Heritage Trail during your travels to Pineland.
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
$210 nightly
The price is $235 total per night from Apr 6 to Apr 7
$235 total
Apr 6 - Apr 7
Total with taxes and fees
9.2/10 Wonderful! (2,050 reviews)
The property is beautiful! Both pools are nice and relaxing. The big pool has plenty of seating with wait staff coming around to take your order. Every staff member we spoke with were so nice and welcoming. They also have a lot of food options right on the property. Our room was very spacious and ...
Reviewed on Mar 9, 2026
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E Cape Coral FL
Fully refundable
$101 nightly
The price is $113 total per night from Apr 5 to Apr 6
$113 total
Apr 5 - Apr 6
Total with taxes and fees
9.2/10 Wonderful! (1,286 reviews)
Super clean hotel and property. Comfortable beds. Buffet breakfast was fresh and plentiful .Fresh ground coffee was a plus!
Reviewed on Mar 7, 2026
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$410 nightly
The price is $458 total per night from Apr 7 to Apr 8
$458 total
Apr 7 - Apr 8
Total with taxes and fees
9/10 Wonderful! (1,929 reviews)
Great resort, nice clean rooms, staff is very friendly and the pool and food are excellent.
Reviewed on Mar 8, 2026
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
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- Visit Saint James City
- Mccarthy's Marina
- Jensen’s Marina
- Jungle Drums
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- Visit North Captiva
- Captiva Chapel By the Sea
- Palmetto-Pine Country Club
- Visit Captiva Island
- Visit Captiva
- Car rentals near Pine Island Center
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- Car rentals near Matlacha
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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.
