Pine Island Vacation Rentals

Compare 8 vacation rentals.
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Make Pine Island your next getaway

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.

Top Pine Island property types

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House rentals

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Condo rentals

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Townhouses

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Popular amenities for Pine Island vacation rentals

Popular
Dog-friendly Hot tub Internet
Four Winds North 502
2 Bedroom | 2 Bath | Sleeps 6

Four Winds North 502 - Bokeelia, FL

$164 avg / night
(excludes fees and taxes)
Coastal Escape
4 Bedroom | 3 Bath | Sleeps 10

Coastal Escape - Saint James City, FL

$429 avg / night
(excludes fees and taxes)
4.9 (10)
Bowline Oasis
3 Bedroom | 2 Bath | Sleeps 8

Bowline Oasis - Bokeelia, FL

$307 avg / night
(excludes fees and taxes)
4.25 (4)
Rock N' Reel Retreat
3 Bedroom | 1.5 Bath | Sleeps 6

Rock N' Reel Retreat - Saint James City, FL

$259 avg / night
(excludes fees and taxes)
4.0 (2)
Lavender Life
3 Bedroom | 2 Bath | Sleeps 6

Lavender Life - Saint James City, FL

$242 avg / night
(excludes fees and taxes)
5.0 (10)

View 3 more homes

Recent Pine Island guest reviews

The home that we rented was beautifully appointed and prepared for our arrival. We really appreciated the attention to details, cleanliness, and amenities provided. We are quite likely to repeat our rental at this home for years to come.
Taylor T. | Oct 2025
We loved the location and spaciousness of this home. Furnishings were above average and the pool and spa area are great. Overall great experience.
Ian L. | Jul 2025
We very much enjoyed the quietness of the area in the quaint town at the lower end of the island. The house was lovely and has a nice layout; everything was so clean and organized. The inside of the house has been mostly updated and was done really well. There are some updates that still need to be done outside like new deck boards all around. Many of the boards are loose and have come undone from the fasteners and we had one board break creating a hole in the deck. You can tell the homeowners are working towards the updates as they had some landscaping done while we were there. Unfortunately these are the 2 reasons we are not giving it 5 stars; there was no notice of the major landscaping work going to happen for 3 of the days during our stay and the broken board didn’t get fixed until after we left. We reported it immediately to the management company when it happened and had to deal with it for several days. My sister and niece were able to enjoy having their own space by staying in the lower level with all the amenities you have on the main floor. The pool was amazing and we were able to enjoy playing in it day and night. We enjoyed fishing in the channel and got to watch manatees swimming by every day throughout the day! The island itself is amazing and the locals are great, friendly, and (unlike so many other places) they love having out of town visitors. We enjoyed lunch at the Waterfront Restaurant & Marina and drinks at Phuzzy’s. The guys at the local bait shop were very helpful and gave us hints on fishing the channels. Despite the heat we took advantage of a kayaking tour around the bridge connecting the island and mangrove trees which was only 10 mins away from the house. The nearest beach is almost an hour away along with most anything else you want to do. We knew this when we booked and already had the expectation but the reality hit while driving back to the house from the beach. Driving for an hour with salt on your skin is not ideal!
Kenneth K. | Jun 2025
Pine Island vacation rental FAQ

Yes. 8 of our Pine Island vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Pine Island, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
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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