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

St James City townhouse on canal with dockage
Pine Island Townhome Rental Picture
  • bedrooms 1
  • sleeps 2
  • community
  • baths 1
  • rental type Townhome
  • rates (USD) $1,200 - $2,050 /mth
 
 
 
 
 
Dots Cottage on Goodwins Island
Pine Island Cottage Rental Picture
  • bedrooms 2
  • sleeps 6
  • community
  • baths
  • rental type Cottage
  • rates (USD) $650 - $650 /wk
    $1,800 - $2,500 /mth
 
 
 
 
 
The Shell House Fishing Vacation Home w/ ramp & lift
Pine Island House Rental Picture
  • bedrooms 2
  • sleeps 6
  • community
  • baths 2
  • rental type House
  • rates (USD) $900 - $900 /wk
 
 
 
 
 
Welcome to Paradise!
Pine Island House Rental Picture
  • bedrooms 2
  • sleeps 4
  • community Cherry Estates
  • baths 2
  • rental type House
  • rates (USD) $200 - $200 /nt
    $850 - $850 /wk
    $2,000 - $2,000 /mth
 
 
 
 
 
Luxury At A Great Price!
Pine Island House Rental Picture
  • bedrooms 2
  • sleeps 4
  • community Cherry Estates
  • baths 2
  • rental type House
  • rates (USD) $1,000 - $2,000 /mth
 
 
 
 
 
Nellie's Nest
Pine Island House Rental Picture
  • bedrooms 2
  • sleeps 6
  • community
  • baths 2
  • rental type House
  • rates (USD) $135 - $135 /nt
    $900 - $900 /wk
    $2,700 - $2,700 /mth
 
 
 
 
 
Island Dreams
Pine Island House Rental Picture
  • bedrooms 2
  • sleeps 6
  • community
  • baths 2
  • rental type House
  • rates (USD) $135 - $135 /nt
    $900 - $1,000 /wk
    $3,600 - $3,800 /mth
 
 
 
 
 
Waterfront Townhouse - Boating and Fishing Paradise!
Pine Island Townhome Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Bocilla Island Club
  • baths
  • rental type Townhome
  • rates (USD) $142 - $142 /nt
    $800 - $1,000 /wk
    $2,100 - $2,900 /mth
 
 
 
 
 
"The Driftwood Grande" Waterfront Townhouse Bokeelia
Pine Island Townhome Rental Picture
  • bedrooms 2
  • sleeps 8
  • community Bocilla Island Club
  • baths
  • rental type Townhome
  • rates (USD) $1,100 - $1,300 /wk
 
 
 
 
 
Bokeelia/Blue Crab Key
Pine Island Condo Rental Picture
  • bedrooms 2
  • sleeps 5
  • community Blue Crab Key
  • baths
  • rental type Condo
  • rates (USD) $1,600 - $2,300 /mth
 
 
 
 
 
Waterfront Townhome & Dock, Many Open Dates, Gorgeous View
Pine Island Townhome Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Bocilla Island Club
  • baths
  • rental type Townhome
  • rates (USD) $800 - $1,000 /wk
 
 
 
 
 
Bocilla Island Palms
Pine Island Condo Rental Picture
  • bedrooms 2
  • sleeps 4
  • community Bocilla Island Club
  • baths
  • rental type Condo
  • rates (USD) $2,200 - $2,500 /mth
 
 
 
 
 
Matlacha on the Bay
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 6
  • community
  • baths 2
  • rental type House
  • rates (USD) $600 - $800 /wk
 
 
 
 
 
St. James Waterfront
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 7
  • community
  • baths 2
  • rental type House
  • rates (USD) $1,800 - $2,200 /mth
 
 
 
 
 
Beautiful Waterfront Property on Quiet Island
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 6
  • community
  • baths 2
  • rental type House
  • rates (USD) $200 - $200 /nt
    $1,110 - $1,110 /wk
    $3,250 - $3,550 /mth
 
 
 
 
 
Bokeelia waterfront with beach access
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 6
  • community Seagull Bay
  • baths 2
  • rental type House
  • rates (USD) $500 - $600 /nt
    $425 - $500 /wk
    $425 - $500 /mth
 
 
 
 
 
Sea Scape
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 7
  • community Saint James City
  • baths 2
  • rental type House
  • rates (USD) $1 - $1 /nt
    $900 - $1,500 /wk
    $2,500 - $3,900 /mth
 
 
 
 
 
Paradise Found - Sanibel Island's alternative!
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 6
  • community
  • baths 2
  • rental type House
  • rates (USD) $1,650 - $2,100 /wk
    $4,700 - $5,300 /mth
 
 
 
 
 
Watch the Manatee play
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 6
  • community
  • baths 2
  • rental type House
  • rates (USD) $1,000 - $2,000 /wk
    $3,500 - $5,500 /mth
 
 
 
 
 
Magnificent Pool Home in Tropical Paradise
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 8
  • community
  • baths 2
  • rental type House
  • rates (USD) $850 - $1,000 /wk
    $2,200 - $3,000 /mth
 
 
 
 
 
Bokeelia golfing and fishing vacation house
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 6
  • community
  • baths 2
  • rental type House
  • rates (USD) $700 - $900 /wk
    $2,200 - $3,000 /mth
 
 
 
 
 
Bokeelia / Fishermans Paradise
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 8
  • community
  • baths
  • rental type House
  • rates (USD) $2,000 - $2,800 /mth
 
 
 
 
 
Casa Calusa Matlacha Waterfront Home
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 8
  • community
  • baths 3
  • rental type House
  • rates (USD) $800 - $1,400 /wk
 
 
 
 
 
Paradise Nest
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 6
  • community
  • baths 3
  • rental type House
  • rates (USD) $1,500 - $1,725 /wk
    $4,675 - $4,875 /mth
 
 
 
 
 
St. James City Waterfront Home with direct Gulf Access
Pine Island House Rental Picture
  • bedrooms 3
  • sleeps 8
  • community Bayview Acres
  • baths 3
  • rental type House
  • rates (USD) $1,000 - $1,000 /wk