Pine Island Vacation Rentals

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Make Pine Island your next getaway—choose from 6 great vacation rentals

Spending time in one of our Pine Island vacation rentals is a great way to experience this lovely island on Florida's southwest Gulf Coast. Home to year-round warm temperatures and unbridled coastal wilderness, this island attracts vacationers of all ages seeking fun and relaxation in Florida’s abundant sunshine.

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House rentals

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Townhouses

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Pine Island vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Oh What A View
4 Bed | 3 Bath | Sleeps 12

Oh What A View - Saint James City, FL

$799 avg / night
Eagles Nest
3 Bed | 3 Bath | Sleeps 6

Eagles Nest - Bokeelia, FL

$298 avg / night
Casa Pineland
3 Bed | 2 Bath | Sleeps 6

Casa Pineland - Bokeelia, FL

$273 avg / night
Bocilla Breeze
2 Bed | 3 Bath | Sleeps 9

Bocilla Breeze - Bokeelia, FL

$422 avg / night
Mermaid Haven at Bocilla
2 Bed | 2.5 Bath | Sleeps 6

Mermaid Haven at Bocilla - Bokeelia, FL

$245 avg / night

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Recent Pine Island vacation rental reviews

Nate W. | Oct 2022
The view and amenities were great!!! Lots to do at the house.
Darla E. | Sep 2022
It was great location, just needed more time there. The house has so much to offer, very relaxing, too. Peaceful and beautiful, many amenities. Was fun watching the dolphins, manatees, geckos, iguanas and lots of good restaurants close by.
3555 San Carlos J LLC -. | Sep 2022
Pine Island Frequently Asked Questions

Yes. 6 of our Pine Island vacation rentals have internet access, so you can stay connected throughout your trip.

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Some of the most popular amenities in our Pine Island vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Pine Island team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Pine Island, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning


Comprised of four towns–Pine Island Center, St. James City, Bokeelia, and Pineland – Pine Island offers a small-town atmosphere and a laid-back destination that's only 20 miles west of Fort Myers. With miles of wild mangrove coastline, it's also home to some of the world's best sport-fishing, as well as open water kayaking and canoeing on Pine Island Sound.

Things to Do on Pine Island, FL

Bordered by the barrier islands of Sanibel to the south, Captiva to the southwest, and North Captiva to the west, Pine Island is a lesser-visited island that in its neighbors, but still offers plenty of activities that will appeal both to the casual vacationer and the thrill-seeking sportsman. Whichever category you fit into, our Pine Island vacation rentals will give you front-door access to all the action on Florida's Gulf Coast!

Head out in the morning with an experienced fishing guide from Anglers Advantage Guide Service or any of other fishing charters on the island, to reel in trophy-size tarpon, snook, redfish, barracuda, and many more gulf species.

Continue your exploration of the unique island waterways aboard a tour boat to Useppa Island, which is a boat ride away from the north end of Pine Island. There you'll find a variety of interesting shops, eclectic restaurants, and unspoiled natural areas. Bring the kids for a fun history of the island tour at the Barbara Sumwalt Useppa Island Historical Museum where they'll view many fascinating exhibits, learn about the island's ancient inhabitants, and much more.

Wind down your day with some shopping and sightseeing among Bokeelia's many art galleries such as the Mel Meo Studio, Mullethead Outpost, and Crossed Palms Gallery.

Day Trips from Pine Island, FL

Though Pine Island has enough great fishing, dining, shopping, and sightseeing to keep you busy for the entirety of your vacation, many great city amenities are within an easy 20-mile drive to Fort Myers. Visit the Fort Myers River District for attractions such as eclectic restaurants, upscale nightclubs, historic home tours, museums, performing arts theaters, and much more. Sanibel Island, with its beautiful sugar-sand beaches, is also a worthy day trip at only 30 miles away.

Whether you've come for water-themed action or low-key relaxation, our Pine Island vacation rentals are a sure bet for fun in the sun, sand, and surf of Southwest Florida!

Photo credit: forestpath via Shutterstock