Pine Island Vacation Packages 2026

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.

Stay near popular Pine Island attractions

Goodwins Island

This pristine, uninhabited island near Bokeelia offers a glimpse into Florida's untouched coastal ecosystems. Explore by private boat for excellent birdwatching opportunities in the serene Pine Island Sound.

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Koucky Gardens & Gallery

This artisan studio showcases handcrafted pottery and woodwork in a tropical garden setting. Visit during the monthly Potters' Guild Show to watch live demonstrations and meet local artists.

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Useppa Museum

This intimate island museum chronicles Useppa's evolution from Native American settlement to exclusive retreat. Explore artifacts spanning 10,000 years and discover the island's fascinating WWII history.

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Museum of the Islands

Step into Pine Island's past at MOTI, housed in the island's first public library. Marvel at local artifacts and the unique manatee skeleton with heart-shaped spine bones.

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Phillips Community Park

Phillips Community Park in Bokeelia, Florida offers lighted tennis courts, baseball fields, and a swimming pool. Enjoy family picnics under the pavilion or let children play in this relaxed recreational space.

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Calusa Heritage Trail

10.0/10 (1 review)

Walk ancient Calusa shell mounds and canals on this archaeological trail. Climb to observation platforms for panoramic views of this 1,500-year-old indigenous civilization's remarkable engineering remains.

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What to do in Pine Island

Clear Kayak Tours in Weeki Wachee

$79

per adult

100% of travellers recommend

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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

$208 nightly

$233 total

Oct 1 - Oct 2

Total with taxes and fees

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$200 nightly

$223 total

Oct 6 - Oct 7

Total with taxes and fees

Baymont by Wyndham Fort Myers Central

4850 S Cleveland Ave Fort Myers FL

Fully refundableReserve now, pay when you stay

$45 nightly

$50 total

Sep 17 - Sep 18

Total with taxes and fees

See all 19,037 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.