Pine Island Vacation Rentals

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Make Pine Island your next getaway—choose from 7 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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Pine Island vacation rentals for every getaway

Dog-friendly Hot tub Internet
Oh What A View 3D Tour
4 Bedroom | 3 Bath | Sleeps 12

Oh What A View - Saint James City, FL

From $298
Il Nido 3D Tour
3 Bedroom | 2 Bath | Sleeps 6

Il Nido - Bokeelia, FL

From $136
Eagles Nest 3D Tour
3 Bedroom | 3 Bath | Sleeps 6

Eagles Nest - Bokeelia, FL

From $151
Flamingo Bungalow 3D Tour
2 Bedroom | 2 Bath | Sleeps 8

Flamingo Bungalow - Bokeelia, FL

From $115
Mermaid Haven at Bocilla 3D Tour
2 Bedroom | 2.5 Bath | Sleeps 6

Mermaid Haven at Bocilla - Bokeelia, FL

From $123

View 2 more homes

Recent Pine Island vacation rental reviews

Kelly M. | May 2022
We’ve stayed at this location for the past 3 years and love it every year!
Scott C. | May 2022
Great view of the bay and marina, dolphins would swim close every day. Walk to the pools or ply tennis at the courts. Bike down to Captain Cons who has the BEST pie in Florida, hands down. No contest. Trust me. Take a bike to the little streets lining the channels of water. The townhome was comfortable and clean. It had all that we needed. It could use a few more linens and pillows (maybe upgrade or update the sheets as ours were a little scratchy/piled from use). Pans were fine but may need some replacing soon. I appreciated the fishing rods since we fished off the docks a lot with our kids and could buy bait at the marina right at the place. A couple beach chairs were handy for Cayo Costa beach - GO, it’s amazing!! We even left a beach umbrella if you need it! Pool toys and some beach toys were also handy for our kids. Super friendly and laid back, well kept property. We’ll definitely visit again.
Chelsey H. | Apr 2022

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