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Vacation Rentals in Pine Island, Florida

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about Pine Island

Pine Island, Florida Vacation Rentals and Tourism

Stop putting off writing that novel and consider Pine Island vacation rentals the next time you’re planning a trip to Florida. Find out why they call it Florida’s “Creative Coast” and check into a Pine Island condo or apartment. Discover why so many artists, writers and musicians choose to spend time here. Pine Island holds on to its rural roots and resists development, a far cry from the concrete cities found on several Florida islands.

 When you stay in a Pine Island condo or apartment, you can enjoy comfortable luxuries you won’t find at a commercial hotel. From simple things like soft, high thread count sheets and linens to more extravagant details like indoor hot tubs or home movie theater systems, rentals in Pine Island offer amenities to make you feel at home.

There’s much to do in Pine Island if you can tear yourself away from your magnum opus long enough to explore the area. Find inspiration at a local art gallery or let off some steam at the Bokeelia golf course, among tropical fruit and palm trees. Make plans to visit during July during the famous annual Mangomania festival. Book your Pine Island rental today!

Pine Island Vacation Rental Deals

You deserve to treat yourself to a vacation to Pine Island, but you also deserve to pay low prices that won't just stress you out. You'll be able to find great deals on a place to stay with affordable Pine Island vacation rentals. Choose from a variety of budget-friendly Pine Island condos, cabins, or town homes that will fit your vacation needs. Decide to go to Pine Island last minute?  No problem; you can find discount Pine Island vacation rentals at affordable prices for last-minute booking.  Because Pine Island vacation rentals can accommodate your groupyou’re your wallet, no matter how large or small, we are confident you will find a great deal and a perfect spot to stay with us for you next Pine Island vacation.

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

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Weekly rate:

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$2,000
$4,000+

Bedrooms: Min 0, Max 5

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Nellie's Nest
Pine Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $135 /nt
    $900 /wk
    $2,700 /mth
 
 
 
 
 

29 reviews write a review

Matlacha Cottage 1
Pine Island Cottage Rental Picture
  • bedrooms 1
  • community
  • rental type Cottage
  • sleeps 3
  • baths 1
  • rates (USD) $400 - $550 /wk
    $1,200 - $1,650 /mth
 
 
 
 
 

1 reviews write a review

Shell House with its own boat ramp & lift
Pine Island House Rental Picture
  • bedrooms 2
  • community Bokeelia
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $100 - $160 /nt
 
 
 
 
 

11 reviews write a review

Lemon Ambiance
Pine Island House Rental Picture
  • bedrooms 4
  • community Civic association
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1 /nt
    $1,500 /wk
    $2,600 /mth
 
 
 
 
 

2 reviews write a review

Blue Winds Condo at Four Winds Marina
Pine Island Condo Rental Picture
  • bedrooms 2
  • community Four Winds Condos
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $99 - $167 /nt
    $650 - $1,014 /wk
    $2,400 - $3,200 /mth
 
 
 
 
 

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Seagull Bay
Pine Island Townhome Rental Picture
  • bedrooms 3
  • community Seagull Bay
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $2,000 - $3,500 /mth
 
 
 
 
 

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Seascape Waterfront Fun
Pine Island House Rental Picture
  • bedrooms 4
  • community neighborhood
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $900 - $3,200 /wk
 
 
 
 
 

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Prettiest Sunset View Pine Island, Waterfront Home on Water
Pine Island House Rental Picture
  • bedrooms 2
  • community Pineland
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $150 - $200 /nt
    $800 - $1,200 /wk
    $3,000 - $4,000 /mth
 
 
 
 
 

5 reviews write a review

Waterfront Townhouse - Beautiful End Unit with Boat Slip!
Pine Island Townhome Rental Picture
  • bedrooms 2
  • community Bocilla Island Club
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $142 /nt
    $800 - $1,000 /wk
    $2,100 - $2,900 /mth
 
 
 
 
 

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Paradise Nest
Pine Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $1,600 - $1,900 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

1 reviews write a review

Island Dreams
Pine Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $135 /nt
    $900 - $1,000 /wk
    $3,600 - $3,800 /mth
 
 
 
 
 

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Matlacha Bungalo
Pine Island House Rental Picture
  • bedrooms 2
  • community Matlacha
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $1,000 - $1,400 /wk
    $3,000 - $3,800 /mth
 
 
 
 
 

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St. James City Waterfront Home with direct Gulf Access
Pine Island House Rental Picture
  • bedrooms 4
  • community Bayview Acres
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,000 /wk
 
 
 
 
 

1 reviews write a review

Matlacha Cottage 2
Pine Island Cottage Rental Picture
  • bedrooms 1
  • community
  • rental type Cottage
  • sleeps 3
  • baths 1
  • rates (USD) $450 - $600 /wk
    $1,350 - $1,800 /mth
 
 
 
 
 

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Waterfront Townhome & Dock, Gorgeous View
Pine Island Townhome Rental Picture
  • bedrooms 2
  • community Bocilla Island Club
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $800 - $1,000 /wk
 
 
 
 
 

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Welcome to Pine Island
Pine Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $900 /wk
    $1,800 /mth
 
 
 
 
 

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The Overwater Snook Cottage At Yellowdog Matlacha
Pine Island Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $209 - $239 /nt
    $1,100 - $1,250 /wk
    $2,850 - $3,150 /mth
 
 
 
 
 

2 reviews write a review

Beautiful 4 BR Villa / Best Neighborhood of Sw Cape Coral
Pine Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $990 /wk
    $3,200 /mth
 
 
 
 
 

6 reviews write a review

Luxurious Western Exposure Canal Home near Cape Harbor
Pine Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD)
 
 
 
 
 

26 reviews write a review

BAY IS YOUR BACKYARD
Pine Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $175 /nt
    $1,200 /wk
 
 
 
 
 

4 reviews write a review

WE GOT IT ALL!!!!POOL W SANDY BEACH, DOCK WITH BOAT LIFT, TOTALLY COOL 2/2
Pine Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $175 /nt
    $1,200 /wk
 
 
 
 
 

3 reviews write a review