Pine Island Vacation Packages 2026

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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.

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

Baymont by Wyndham Fort Myers Central

4850 S Cleveland Ave Fort Myers FL

Fully refundableReserve now, pay when you stay

$53 nightly

$59 total

Sep 24 - Sep 25

Total with taxes and fees

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$195 nightly

$218 total

Oct 1 - Oct 2

Total with taxes and fees

9/10 Wonderful! (2,580 reviews)

"We had to request a room change. Not sure what was going on this weekend, but teenagers being loud, running up and down the halls, sitting on the floors of the hallways, and being loud in the rooms til past midnight. First time I have ever called security to keep the noise down. We were moved across ..."

Reviewed on Sep 22, 2026

See all 19,042 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.