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Pine Island, FL

Pine Island vacation rentals

We found 7,793 vacation rentals — enter your dates for availability

Discover a selection of 8,000 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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Find spaces that suit your style

Houses

View 4,301 Houses

Cottages

View 106 Cottages

Villas

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Condos/Apartments

View 3,287 Condos/Apartments

Cabins

View 108 Cabins

Bungalows

View 106 Bungalows

Townhouses

View 115 Townhouses

Resorts

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Studios

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Caravans

View 44 Caravans

Hotels

View 91 Hotels

Find the best place to stay — Pine Island

Canal Life On Matlacha!

Sleeps 8 · 4 Bedrooms · 3 Bathrooms
$200 avg/night
(66)

Spacious three bed, three bath home with heated pool on a quiet canal

Sleeps 4 · 3 Bedrooms · 3 Bathrooms
$133 avg/night
(14)

Waterfront With Direct Gulf Access, Natural Paradis

Sleeps 4 · 1 Bedroom · 1 Bathroom
$75 avg/night
(52)

Beautiful, Spacious House With In Ground Pool In A Tropical Setting!

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$121 avg/night
(56)

Island Oasis with pool.

Sleeps 5 · 3 Bedrooms · 2 Bathrooms
$179 avg/night
(12)

Incredible Matlacha Fishing and Outstanding Views

Sleeps 3 · 1 Bedroom · 1 Bathroom
$144 avg/night
(53)

Search 7,793 vacation rentals

Top rated rentals — Pine Island
Stayed Jun 2021

Excellent Fathers Day Getaway

We had an AMAZING time. We have stayed at numerous rentals in the past in locations all over and this was one of the best in cleanliness, deep water fishing and proximity to walking to a few restaurants and bait shops. Anything else was just a couple...

Theresa H.
Theresa H.

Ocala, FL

Stayed Jun 2021

Island Getaway

Fantastic location for relaxation and fishing. Never been to Matlacha before but will plan to return. The house is vary spacious and well appointed. The bikes were great could use a little general maintenance though and the Kayaks were awesome. We di...

Steve y.
Steve y.
Stayed Jun 2021

Amazing Home!

The moment we stepped in, we felt right at home! The house was exceptionally clean. The kitchen is stocked with everything you could possibly need. We used the beach chairs and umbrella that are available during our trips to the beach. There are plen...

Alitza R.
Alitza R.
Stayed Jun 2021

Great vacation place!

Wonderful home to stay in that is airy, clean, functional and a fun place to hang out. The host welcomed us with snacks and the kitchen was well stocked with dishes, cookware, spices, etc. we had a convenient place to dock our rental boat and we were...

Susan W.
Susan W.
Stayed Jun 2021

Thank you for sharing your lovely cottage with us!

We had a relaxing stay at this wonderful cottage. Marybeth went out of her way to make us feel welcome. The cottage is beautifully decorated and has all the amenities you need for a fun getaway. We visited Naples, Sanibel and enjoyed the quirky, fun ...

Camille W.
Camille W.

Moorestown, NJ

Stayed May 2021

Amazing Vacation - Just Perfect

My friend and I stayed for a week and the property was perfect for us. The property was exactly as described although I was surprised that the living room is the back room (through the bedroom from the kitchen/dining area.) There is not a door separa...

Sharron L.
Sharron L.
Stayed May 2021

Great house!

This was our second year in a row that we have stayed here. Perfect dock for our 24' boat. So nice to have the lift! We enjoyed sitting outside by the pool each night. With the quite neighborhood and comfortable beds we slept well! Can't wait to stay...

Julie R.
Julie R.
Stayed May 2021

Old Florida Paradise

Beautiful property and cool surrounding area. St. James City has a great Old Florida vibe. The Cabana was super clean and perfect for two people. The landscaping was amazing. Liz and Parker are great hosts and there if you’re need them for anything. ...

Rick J.
Rick J.
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How many vacation rentals are available around Pine Island, US?

Our 2021 property listings offer a large selection of 7,793 vacation rentals around Pine Island. From 4,301 house rentals to 106 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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