Discover a selection of 7,000 vacation rentals in Pine Island, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $75 per night, and houses and cottages are popular options for a stay in Pine Island. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Pine Island
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Destination guide

Explore the waterfront setting in Pine Island

The island views and surrounding scenery provide a peaceful ambiance to your vacation home in Pine Island. This relaxing city is known for its fishing, boating and biking. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Things to do

Sightseeing in and around Pine Island

Are you searching for attractions to visit in the city? Venture out of your vacation home and experience everything that makes Pine Island a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Sun Splash Family Waterpark (8.8 mi / 14.2 km)
  • Sun Splash Water Park (8.8 mi / 14.2 km)
  • Jungle Golf Ft. Myers (12.9 mi / 20.7 km)
  • Fort Myers Country Club (14.4 mi / 23.1 km)
  • Legends Golf and Country Club (19.1 mi / 30.8 km)
  • Hunters Run Executive Golf Course (9.4 mi / 15.1 km)
Natural features

Exploring the natural features in Pine Island

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Pine Island. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • North Captiva Island Beach (6.3 mi / 10.2 km)
  • Useppa Island (7.8 mi / 12.5 km)
  • Captiva Beach (7.9 mi / 12.8 km)
  • Cabbage Key (8.1 mi / 13.1 km)
  • Cayo Costa Beaches (8.3 mi / 13.4 km)
  • Turner Beach (9 mi / 14.4 km)

What are the top vacation rentals in Pine Island?

Elegant condos, unique treehouses and quaint cottages — everyone's dream getaway is different. Whatever your tastes, you're sure to find something you love among these top vacation rentals in Pine Island:

  • "New Modern St James City Home W": If you're searching for a comfy space in Saint James City, this escape won't disappoint. It comes with 3 bedrooms and a host of amenities including a barbecue grill and a washing machine.
  • "Quiet And Cozy Island Retreat. Beautifully Remodeled": Stay a week or so at this escape in Pine Island Center and make use of a microwave oven, lowered locks and more. It has 2 bedrooms to accommodate the ones you love.

For even more great options, use the search bar at the top of the page to find the perfect Pine Island vacation rental for you.

What are the best tiny house vacation rentals in Pine Island?

You need only set foot in one of our tiny house vacation rentals in Pine Island to figure out that amazing things really do come in tiny packages. Expertly designed to maximize every square inch of space, these pocket-sized digs promise a big vacation experience:

  • Experience a simpler way of life at "New Tiny House - Introductory Price Minutes From Sanibel And Fort Myers Beach". Amenities at this retreat in Iona include a free nearby fitness center, air conditioning and more.
  • "Hobbit House, Tiny Home" in Jacarandas is another top-rated pick. A pool and internet services will make your getaway here even more comfortable.

What are the top-rated vacation rentals for weekend getaways in Pine Island?

If you're eager for an escape from the rat race, Vrbo's got the perfect antidote. Return home on cloud nine after a weekend getaway in Pine Island at one of these vacation rentals:

  • "Quaint Waterfront Cottage Near Beaches And Fishing": A couple of days away at this Flamingo Bay stay will have you feeling like your old self again. Amenities here include a pool and a washing machine. When you're ready to explore, Causeway Islands Park An and Estero Bay Preserve State Park are some of the nearby natural attractions.
  • "Direct Gulf Access Island Retreat": An equally appealing stay, this escape in Pine Island Center comes with a bicycle, a kitchen and more. Calusa Heritage Trail and Cayo Costa Beaches are nearby when you need to get your fix of nature.

Can I find studio apartments for rent in Pine Island?

Generally well located and with a price tag that won't break the bank, studio apartments offer privacy and style with the comforts of home. Book one of these studio apartments for rent in Pine Island and use it as a base to discover the sights around you:

  • "Toby's View Apt #2, Incredible Matlacha Views And Fishing From Your Yard" in Matlacha puts you within easy reach of some of the area's best cultural attractions, including BIG Arts Center and Sidney & Berne Davis Art Center. A barbecue grill and nearby ecotour services are a couple of the amenities you'll have at hand here.
  • "Matlacha Cutie Canal Home" in Matlacha is another fabulous option that offers a TV and coffee and tea making facilities. Jungle Drums and Florida Repertory Theater should be on your to-do list in this area.

Can I find short term rentals in Pine Island?

Short-term rentals come in all shapes, sizes and budgets in Pine Island. Whether you're organizing a mini break with the family or a few nights with your partner, Vrbo will help you find the ideal retreat. Check out these tempting options:

  • Located close to the center of Flamingo Bay, "Quaint Waterfront Cottage Near Beaches And Fishing" is suited to a short stay. Use it as a base to explore nearby attractions, such as Captiva Chapel By the Sea and Jensen’s Marina.
  • "Direct Gulf Access Island Retreat" is another wonderful choice. Spend several days at this property in Pine Island Center and plan an outing to Native Attitude Fishing Charters and Lovegrove Gallery & Gardens, which are within close reach.

What are the best houses for rent with a pool in Pine Island?

There's no shortage of houses with a pool in Pine Island, so toss your swimsuit into your bag and get set to spend your days having fun in the water. Here are some top-rated options to tempt you:

  • Kids, parents, uncles, aunts — everyone will love relaxing by the pool at "Charming Waterfront House In Artsy". Treat the whole family on a break at this Matlacha rental house which also features a dishwasher and a TV.
  • Jump out of bed and enjoy an early morning dip at "Beautiful And Laid Back Pool House" in Saint James City. Childrens activities and a porch are other amenities at this exceptional option.

What are the best large family vacation rentals in Pine Island?

There's nothing like a vacation to bring a family together, but first, you need to find a space where the magic can happen. These family vacation rentals in Pine Island come with tons of room to reconnect with your loved ones:

  • "Tropical Matlacha Escape With Dock And Canal Views" in Matlacha will make your family get-together one you won't forget. It has 3 bedrooms sleeping up to 8 guests and loads of amenities, including a kitchen and a microwave oven.
  • Alternatively, treat the gang to a break at "Spacious Home With Hot Tub, Dock And Boat Lift. Xtra Parking. Walk To Restaurants". This Matlacha property has 3 bedrooms and can accommodate up to 10 guests. Make use of childrens activities and a travel crib during your stay here.

Are there one-bedroom vacation rentals in Pine Island?

If you're traveling by yourself or with your partner and don't need much space, a single-bedroom vacation rental will be just the ticket. Enjoy a fantastic break with all of the home comforts at one of these properties in Pine Island:

  • Bunk down for a few nights or more at "House Igor - 85691 - K1 - - Novi Vinodolski - Crikvenica" and discover the best bits of Novi Vinodolski. This one-bedroom retreat has a garden, a nearby waterfront and other amenities to make your stay comfortable.
  • Or, unpack your luggage and spend your vacay at "Nature Lovers Paradise - Lovers Key Resort". A nearby waterfront and a beach view are just a couple of the many conveniences you'll have at hand at this property in Fort Myers Beach.

Can I find two-bedroom vacation rentals in Pine Island?

From cozy cottages to luxurious condos, we've got two-bedroom vacation rentals to suit all budgets and styles. Here are some of our top picks in Pine Island:

  • Invite some pals to share in the great times at "Quiet And Cozy Island Retreat. Beautifully Remodeled". As well as two bedrooms, this Pine Island Center retreat has everything you need for a comfortable stay, including a garden and a kitchen.
  • Another excellent property is "Quaint Waterfront Cottage Near Beaches And Fishing" in Flamingo Bay. It comes with a swimming pool, high-speed internet services and many other great extras.

What are the best three-bedroom vacation rentals in Pine Island?

It feels great to have a big family or friend group — until you have to look for a vacation property that'll take you all in. Luckily, Vrbo has a selection of three-bedroom properties in Pine Island ready to welcome your gang:

  • Located in Saint James City, "New Modern St James City Home W" will get the stamp of approval from your travel companions. Along with room to stretch out, it comes with a great range of amenities, such as a kitchen and a barbecue grill.
  • Invite your family to "Beautiful Waterfront Key West Style Home With A Pool" and spend quality time together. This three-bedroom vacation rental in Pine Island Center has plenty to offer, including a nearby waterfront and a swimming pool.