This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Pine Island Vacation Rentals Show this location only Back to top
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Enjoy Coastal Tropical Hideaway, Harbor Views & Private Pier
2BR+/2.5BA
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Sleeps 6-8
– Bokeelia #374372
Monthly $2,200 - $2,500
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Blue Crab Key Condo
2BR/2.5BA
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Sleeps 4-5
– Bokeelia #76328
$1250 - 2695/month
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Summer/Fall Special $45/nt ($1350/Mo)
3BR/2BA
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Sleeps 5
– Bokeelia #188247
$2310 per month 30 night min stay
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Island Ave Beauty-Heated Pool, Renovated, Great Sunsets,Dock!
2BR+/1.5BA
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Sleeps 4-6
– Matlacha #328252
$900-$2,000/wk - $2,650-$5,200/mo
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Experience the Finest in Coastal Living, Bocillia Island Club
2BR+/2.5BA
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Sleeps 6-8
– Bokeelia #327480
From $105/nt - $630/wk - $2310/mo
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Relax on Island Time at Casa High Tide
3BR/2BA
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Sleeps 6-8
– Matlacha #297719
$800- $2000/wk
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Bocilla Island Club, Water View, 23' Dock - Bokeelia, Florida
2BR+/2.5BA
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Sleeps 6
– Bokeelia #130438
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Magnificent Pool Home in Tropical Paradise
3BR+/2BA
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Sleeps 6-8
– St. James City #251838
$900-$1,250/wk - $2,300-$3,400/mo
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Island Ave Splendor, Renovated, Heated Pool, Dock, Sunsets!
3BR+/2.5BA
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Sleeps 6-8
– Matlacha #333179
$ 1,200-2,400 wk/ $ 3,200-$ 6,200/mo
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Beachfront with Boat Dock &
Amazing Views of Charlotte Harbor
2BR+/2BA
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Sleeps 4-6
– Bokeelia #385296
Dec-April $3,375 May-Nov $1,875 mo
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Waterfront Cottage Minutes to Pine Island Sound
2BR+/1BA
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Sleeps 4-6
– St. James City #177093
From $550/wk
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Waterfront with Great Fishing and Boating
2BR+/2BA
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Sleeps 4-6
– St. James City #55622
$500/wk - $1950/mo
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Clean, Bright , Safe & Friendly!! Great Dockage! Beautiful!!
3BR+/2BA
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Sleeps 6-8
– Bokeelia #51907
From $995/wk & From $3,100/mo
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Beautiful Waterfront Property on Quiet Island
3BR/2BA
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Sleeps 6-7
– St. James City #38916
$1000/wk - $3550/mo
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The Round House
2BR+/3BA
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Sleeps 6
– Bokeelia #144851
From $700/wk - $2200/mo
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Welcome to Paradise
2BR+/2BA
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Sleeps 4-6
– Matlacha #170198
$1505 per week 7 night min stay
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Nellie's Nest - 5 Min to Open Water!
2BR+/2BA
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Sleeps 4-6
– Bokeelia #262069
$135/nt - $900/wk
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Coastal Living at Bocilla Island Club
2BR+/2.5BA
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Sleeps 4-6
– Bokeelia #186073
$800-$1000/wk - $2400-$3000/mo
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Fishermen, Kayakers &Birdwatchers Paradise -Fish in 5 Minutes
3BR/2BA
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Sleeps 6
– Bokeelia #276004
$650/wk - $2500/mo
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Best of Bocillia Island Club: on Water, W/Slip, Great Fishing!
2BR+/2.5BA
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Sleeps 5-6
– Bokeelia #159187
$900- $1200/wk
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2 BR/2.5 BA Condo - Beautiful Secluded Island in Western Florida
2BR/2.5BA
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Sleeps 4-6
– Bokeelia #316072
$750-$1000/wk; $2500-$3500/mo
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Bocilla Island Club Hide Away with a Private Dock!
2BR/2.5BA
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Sleeps 2-4
– Bokeelia #255218
$1700- $2800/mo
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Bocilla Island Club with a Boat Dock!
2BR/2.5BA
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Sleeps 2-4
– Bokeelia #258023
$1800- $2800/mo
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Fishing-Boating-Paddling on the Florida Gulf Coast
2BR/2BA
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Sleeps 4
– Bokeelia #436712
$1500 - $2400monthly, $140 - $150 night
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Island Time Private Vacation Paradise Home!
2BR/2.5BA
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Sleeps 4-6
– Bokeelia #316766
From $800-$950/wk - $2700-$3400/mo
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Waterfront Bungalow with Heated Pool and Large Boat Lift
3BR/2BA
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Sleeps 6
– St. James City #464791
$2500 - $3500/mo. $900/wk. (off season) $
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Great Reviws - Stunning,Tropical Golf, Private Pool - Great Reviews
3BR/2.5BA
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Sleeps 6
– Pineland #144149ha
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Nice Home with Pool on Matlacha Pass
2BR+/2BA
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Sleeps 4-6
– Matlacha #102095
From $89/nt to $129/nt
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Water Views, Sunsets and Fishing - Boat Dock/Ramp
2BR+/2BA
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Sleeps 4-6
– Bokeelia #76992
$875-$950/wk - $2250/$2950/mo
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Waterfront - Outdoor Lovers Paradise
2BR/1BA
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Sleeps 4
– St. James City #106736
$1500- $1900/mo .
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Enjoy the Beautiful Sunsets,Fish and Relax in Delightful Pine Island
2BR/2BA
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Sleeps 4
– Bokeelia #301925
Weekend rate $375 summer, $650 winter
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Pine Island Paradise. Beautiful Condo at Four Winds. Monthly Rentals Only
2BR/2BA
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Sleeps 4
– Bokeelia #403243
FROM $2950.00 MONTHLY
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Chic Redfish Key West Style Cottage at Yellowdog in Matlacha
1BR+/1BA
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Sleeps 4
– Matlacha #391708
from $189 a night
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Sun and Island Breezes Matlacha Waterfront Home W/ Hot Tub, Boatlift
3BR/4BA
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Sleeps 6
– Matlacha #419296
$800.-$1400./wk, $2700./mo - $3400/mo
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Captain Cove Condo
2BR/2BA
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Sleeps 2-4
– Bokeelia #72584
$1400- $2400/mo
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Quaint Matlacha Cottage
3BR/2BA
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Sleeps 6
– Matlacha #473723
$1350 per week 7 night min stay
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Stunning Tarpon Cottage at Yellowdog Matlacha
2BR/1.5BA
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Sleeps 4
– Matlacha #392267
from $219 a night
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Island Avenue Home with Pool, Boatlift & Sunset View!
3BR/3BA
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Sleeps 6
– Matlacha #454705
$805-1015/week or $2700-3600/month
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Four Winds Marina/ Boca Grande Tarpon /55 Inch High Def,3d TV / Condo
2BR+/2BA
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Sleeps 4-6
– Bokeelia #426588
FROM $200/NT TO $ 2950/MO
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Great Condo, Boat Slip, Tennis Courts, 2 Pools,Gated Fishing D
2BR+/2.5BA
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Sleeps 5-7
– Bokeelia #388232
$3,100.00 to $3,500.00 monthly
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Waterfront* Gorgeous Canal Home Opens Onto Matlatcha Pass
3BR/2BA
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Sleeps 6-8
– Bokeelia #457147
$125 per night 6 night min stay
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Captain Cove Condo
2BR/2BA
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Sleeps 2-4
– Bokeelia #232901
$1400 - $2300 MONTHLY
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Matlacha.....
2BR/2BA
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Sleeps 2-6
– Matlacha #395878
2800/1500/Monthly
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Come Savor the Island Life Enjoy All Pine Island Has to Offer
3BR/2BA
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Sleeps 5
– Bokeelia #395478
2100/MONTHLY
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Captain's Harbor Waterfront Condo with Dock, Garage & Pool
2BR+/2BA
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Sleeps 4-6
– Bokeelia #268818
From $1500/mo
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Private Canal Home, Fishing and Kayaking Paradise
2BR/2BA
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Sleeps 5-6
– Bokeelia #462580
$840 per week 7 night min stay
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Waterfront Efficiency Condo with Boat Slip
Studio/1BA
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Sleeps 2-4
– Bokeelia #445288
$560 per week 7 night min stay
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Large Pool Home at End of Canal
3BR/3BA
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Sleeps 6
– St. James City #426885
$3200/mo., $950 wk Jan - March
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Florida Pool Home
2BR+/2BA
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Sleeps 2-4
– St. James City #298533
$725/1700
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Historic Matlacha House on Canal
2BR/1.5BA
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Sleeps 4-5
– Matlacha #448517
$350 per week 6 night min stay
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Prime Waterfront Pool Home
2BR+/3BA
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Sleeps 6
– St. James City #457203
$180 per night 6 night min stay
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Tropical Vacation Pool Rental, Pine Island Florida
1BR+/1.5BA
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Sleeps 2-4
– Bokeelia #437445
1400.00/7 nights
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Manatee Bay - Pool and Canal Home
3BR/3BA
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Sleeps 6
– St. James City #330713
$2200- $3500/mo
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Four Winds Marina Condo
2BR/2BA
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Sleeps 4-6
– Bokeelia #444016
Seasonal $2250 to $2950 a Mth
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The Driftwood Grande, Waterfront Bocilla Island Club, Sleeps 8
2BR+/3BA
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Sleeps 6-8
– Bokeelia #381891
From $125/nt to $1,000/wk
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Wilson House on Pine Island!
2BR+/1BA
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Sleeps 4
– Bokeelia #375124
$80 per night 3 night min stay
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A Peaceful Sunrise Awaits You on Matlacha Bay~Pool, Boatlift
3BR/0BA
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Sleeps 6
– Matlacha #467210
$1190 per week 7 night min stay
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Go Fish House on Beautiful Cove with Dock!
2BR+/2BA
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Sleeps 3-5
– Bokeelia #418195
$1800- $3000/month depending on season.
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Connected by a Bridge - a Lush Barrier Island in the Gulf of Mexico, Florida
4BR/2BA
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Sleeps 8
– Pineland #1023213ha
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3 BR, 2 BA Canal Front Home W/ Dock - Summer Special! $650/Week
3BR/2BA
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Sleeps 5-6
– Bokeelia #446574
$650 per week - Summer Special
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Bocilla Island Club. Wonderful Jug Creek Views. Dock Included!
2BR/2BA
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Sleeps 2-4
– Bokeelia #272506
$1700- $3000/mo
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Captain Cove Beauty Call Now!
2BR/2BA
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Sleeps 4
– Bokeelia #389464
1500- 2500 mthly
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Stilted Island Home
2BR/2BA
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Sleeps 4-6
– Bokeelia #446632
Seasonal $1250 to $2000 a Mth.
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Fishing from the Dock and Tropical Sunsets, Too!
2BR+/3BA
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Sleeps 4-6
– Matlacha #383116
From $1900 to $2500/mo
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Beautiful 2BR/2bath Waterfront on Pine Island - Ideal Fishing
2BR+/2BA
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Sleeps 4-6
– St. James City #370365
From $1400 - $1700/mo plus tax
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Tropical Paradise on the Grounds of Blue Crab Key
2BR/2.5BA
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Sleeps 4-6
– Bokeelia #453205
monthly
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Steps Away from Sand and Bay from This Apartment in Bokeelia, on Pine
1BR/1BA
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Sleeps 2
– Bokeelia #310083ha
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Extraordinary, Massively Built Villa in the New Florida Syle in South West of Cc
3BR/3BA
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Sleeps 6
– Matlacha #520370ha
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Pool Home (Villa) in Southwest Cape Coral with Gulf Access
3BR/1BA
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Sleeps 6
– Matlacha #504950ha
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Waterfront Heated Heated Pool with Dock Kayaks Bicycles Island Living
3BR/2BA
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Sleeps 7
– St. James City #288478ha
$2310 per week 7 night min stay
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Blue Crab Key Luxury Condo on Open Water. Rates Just Discounted
2BR/2.5BA
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Sleeps 4
– Bokeelia #246383ha
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Waterfront Vacation Home with Two Master Suites, Private Pool and Boat Docks.
4BR/3BA
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Sleeps 12
– Bokeelia #373727ha
$250 per night 2 night min stay
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Tropical Island Paradise on Pine Iceland Including Motorboat with Access to the Sea
2BR/2BA
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Sleeps 4
– St. James City #536423ha
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Beautiful/Open Floor Style Pool Home/Boat and Wave Runner Lift
3BR/2BA
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Sleeps 6
– St. James City #358026ha
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The Island Retreat, Your Tropical Island Paradise!
4BR+/3BA
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Sleeps 10
– St. James City #999233ha
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Exclusive Vacation Villa on the Canal in Cape Coral Southwest
3BR/3BA
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Sleeps 6
– Matlacha #2060388ha
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Enjoy Coastal Tropical Hideaway, Harbor Views & Private Pier
2BR+/2.5BA
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Sleeps 6-8
– Bokeelia #374372
Overview of Pine Island Vacation Rentals
Look No Further Than Pine Island Vacation Rentals for Affordability and Comfort
On your Pine Island vacation there will be never be a dull moment as you dolphin-watch and shark-see with the King Fisher Ariel Sightseeing company, kayak the coast, and explore the Wild Child and Matlacha art galleries. If you're in need of lodging, look no further than Pine Island vacation rentals that provide as much comfort to your pocketbook as they do to your tired body after a long day of activities. Conveniently equipped with everything you will need, a vacation rental is Pine Island combines luxury with the feel of home, and comes at a price you can afford.
Pine Island Beach Rentals Give You the Ultimate Florida Vacation
Get the most out of your Florida vacation by staying right on the beach and indulging your senses in the sun, sand and water. Pine Island Beach rentals allow you to reserve vacation lodging in the form of a house, villa or condominium that is ideally located on the shores of some of the most beautiful beaches in the country. Styled with nautical flair and furnished with state-of-the-art appliances, you can enjoy cooking in your Pine Island Beach rental or watching the sunset on your own private outdoor patio. Offering you so much more than a hotel stay, treat yourself to beachfront property that you can customize to fit your needs.
Add a Touch of Perfection with Pine Island Condos
If you desire a dream vacation, Pine Island is the place for you. Full of beauty, water sports, shopping, food and fun, Pine Island will make you feel refreshed and inspired. While there, Pine Island condos give that touch of perfection to your vacation by way of their roomy layouts, private quarters, onsite cooking and laundry facilities, and locations that put you near all the attractions and incredible ocean views.