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Pineland Holiday Apartments

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60 rentals in Pineland.
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Rockstar Beach House North Captiva Island (Accessible by ferry boat only), holiday rental in Pineland
Rockstar Beach House North Captiva Island (Accessible by ferry boat only), holiday rental in Pineland
Rockstar Beach House North Captiva Island (Accessible by ferry boat only), holiday rental in Pineland

Rockstar Beach House North Captiva Island (Accessible by ferry boat only)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW RENTAL*LUXURY HOME*STEPS 2 OCEAN* OVERSIZED POOL*LOCAL OWNERS*LO FEES, holiday rental in Pineland
NEW RENTAL*LUXURY HOME*STEPS 2 OCEAN* OVERSIZED POOL*LOCAL OWNERS*LO FEES, holiday rental in Pineland
NEW RENTAL*LUXURY HOME*STEPS 2 OCEAN* OVERSIZED POOL*LOCAL OWNERS*LO FEES, holiday rental in Pineland

NEW RENTAL*LUXURY HOME*STEPS 2 OCEAN* OVERSIZED POOL*LOCAL OWNERS*LO FEES

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Las Olas, 360* Ocean View,  close to the best Beach on Island!, holiday rental in Pineland
Las Olas, 360* Ocean View,  close to the best Beach on Island!, holiday rental in Pineland
Las Olas, 360* Ocean View,  close to the best Beach on Island!, holiday rental in Pineland

Las Olas, 360* Ocean View, close to the best Beach on Island!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Distancing Opportunity with Uncrowded Beaches, Hiking, Biking, Kayaking, holiday rental in Pineland
Perfect Distancing Opportunity with Uncrowded Beaches, Hiking, Biking, Kayaking, holiday rental in Pineland
Perfect Distancing Opportunity with Uncrowded Beaches, Hiking, Biking, Kayaking, holiday rental in Pineland

Perfect Distancing Opportunity with Uncrowded Beaches, Hiking, Biking, Kayaking

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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1 Minute to Beach, Luxury New pool home, Gulf sunrise and sunset Views, holiday rental in Pineland
1 Minute to Beach, Luxury New pool home, Gulf sunrise and sunset Views, holiday rental in Pineland
1 Minute to Beach, Luxury New pool home, Gulf sunrise and sunset Views, holiday rental in Pineland

1 Minute to Beach, Luxury New pool home, Gulf sunrise and sunset Views

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Tropical paradise awaits at the Blue Tortuga, holiday rental in Pineland
Tropical paradise awaits at the Blue Tortuga, holiday rental in Pineland
Tropical paradise awaits at the Blue Tortuga, holiday rental in Pineland

Tropical paradise awaits at the Blue Tortuga

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bluefin Beach House, holiday rental in Pineland
Bluefin Beach House, holiday rental in Pineland
Bluefin Beach House, holiday rental in Pineland

Bluefin Beach House

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Hidden Treasure - Secluded NEW Home - Pool-Tiki-Basketball- Near Beach- Club Use, holiday rental in Pineland
Hidden Treasure - Secluded NEW Home - Pool-Tiki-Basketball- Near Beach- Club Use, holiday rental in Pineland
Hidden Treasure - Secluded NEW Home - Pool-Tiki-Basketball- Near Beach- Club Use, holiday rental in Pineland

Hidden Treasure - Secluded NEW Home - Pool-Tiki-Basketball- Near Beach- Club Use

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beachfront, Pet Friendly Home, Free Cancellation  - 202, holiday rental in Pineland
Beachfront, Pet Friendly Home, Free Cancellation  - 202, holiday rental in Pineland
Beachfront, Pet Friendly Home, Free Cancellation  - 202, holiday rental in Pineland

Beachfront, Pet Friendly Home, Free Cancellation - 202

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Perfect Placement, Beautiful Ocean Front Home, holiday rental in Pineland
Perfect Placement, Beautiful Ocean Front Home, holiday rental in Pineland
Perfect Placement, Beautiful Ocean Front Home, holiday rental in Pineland

Perfect Placement, Beautiful Ocean Front Home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beach's Edge, One Of A Kind Beachfront Experience, holiday rental in Pineland
Beach's Edge, One Of A Kind Beachfront Experience, holiday rental in Pineland
Beach's Edge, One Of A Kind Beachfront Experience, holiday rental in Pineland

Beach's Edge, One Of A Kind Beachfront Experience

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Island Oasis/Hidden Beach House-Private pool, holiday rental in Pineland
Island Oasis/Hidden Beach House-Private pool, holiday rental in Pineland
Island Oasis/Hidden Beach House-Private pool, holiday rental in Pineland

Island Oasis/Hidden Beach House-Private pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Newly Renovated Island Pool Home, holiday rental in Pineland
Newly Renovated Island Pool Home, holiday rental in Pineland
Newly Renovated Island Pool Home, holiday rental in Pineland

Newly Renovated Island Pool Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Captiva Beach Sunset ~Gulf front, private pool, 5 BR, NCIC & Airstrip Membership, holiday rental in Pineland
Captiva Beach Sunset ~Gulf front, private pool, 5 BR, NCIC & Airstrip Membership, holiday rental in Pineland
Captiva Beach Sunset ~Gulf front, private pool, 5 BR, NCIC & Airstrip Membership, holiday rental in Pineland

Captiva Beach Sunset ~Gulf front, private pool, 5 BR, NCIC & Airstrip Membership

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Serendipity - Pool, 2 Golf Carts, NCIC, location, location, location!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Property with Dock and 2 Minute Walk to the Beach, holiday rental in Pineland
Waterfront Property with Dock and 2 Minute Walk to the Beach, holiday rental in Pineland
Waterfront Property with Dock and 2 Minute Walk to the Beach, holiday rental in Pineland

Waterfront Property with Dock and 2 Minute Walk to the Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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'Sea Urchins' ***** Private Property Beachfront with Beachside Pool & Boat Dock, holiday rental in Pineland
'Sea Urchins' ***** Private Property Beachfront with Beachside Pool & Boat Dock, holiday rental in Pineland
'Sea Urchins' ***** Private Property Beachfront with Beachside Pool & Boat Dock, holiday rental in Pineland

'Sea Urchins' ***** Private Property Beachfront with Beachside Pool & Boat Dock

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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*** LAST MINUTE SPECIAL ON JANUARY 2ND TO 9TH!!! INQUIRE TODAY!!! ***, holiday rental in Pineland
*** LAST MINUTE SPECIAL ON JANUARY 2ND TO 9TH!!! INQUIRE TODAY!!! ***, holiday rental in Pineland
*** LAST MINUTE SPECIAL ON JANUARY 2ND TO 9TH!!! INQUIRE TODAY!!! ***, holiday rental in Pineland

*** LAST MINUTE SPECIAL ON JANUARY 2ND TO 9TH!!! INQUIRE TODAY!!! ***

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Oceanfront Luxury Home with Secluded Private Beach, holiday rental in Pineland
Oceanfront Luxury Home with Secluded Private Beach, holiday rental in Pineland
Oceanfront Luxury Home with Secluded Private Beach, holiday rental in Pineland

Oceanfront Luxury Home with Secluded Private Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Second Star is nestled in palms and just 800' to the beach overlooking the lake!, holiday rental in Pineland
Second Star is nestled in palms and just 800' to the beach overlooking the lake!, holiday rental in Pineland
Second Star is nestled in palms and just 800' to the beach overlooking the lake!, holiday rental in Pineland

Second Star is nestled in palms and just 800' to the beach overlooking the lake!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Paradise Found/ North Captiva / Heated Pool, holiday rental in Pineland
Paradise Found/ North Captiva / Heated Pool, holiday rental in Pineland
Paradise Found/ North Captiva / Heated Pool, holiday rental in Pineland

Paradise Found/ North Captiva / Heated Pool

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home, holiday rental in Pineland
TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home, holiday rental in Pineland
TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home, holiday rental in Pineland

TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront, Pet Friendly Home, Free Cancellation - 201

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Windows on the Water 'W.O.W'  A new ocean front oasis!  Come enjoy the view!, holiday rental in Pineland
Windows on the Water 'W.O.W'  A new ocean front oasis!  Come enjoy the view!, holiday rental in Pineland
Windows on the Water 'W.O.W'  A new ocean front oasis!  Come enjoy the view!, holiday rental in Pineland

Windows on the Water 'W.O.W' A new ocean front oasis! Come enjoy the view!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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FLORIDA AT THE BEACH, NEWLY REMODELED 2021- BEACH -OCEAN VIEW- GOLF CART, holiday rental in Pineland
FLORIDA AT THE BEACH, NEWLY REMODELED 2021- BEACH -OCEAN VIEW- GOLF CART, holiday rental in Pineland
FLORIDA AT THE BEACH, NEWLY REMODELED 2021- BEACH -OCEAN VIEW- GOLF CART, holiday rental in Pineland

FLORIDA AT THE BEACH, NEWLY REMODELED 2021- BEACH -OCEAN VIEW- GOLF CART

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Newly renovated BEACHFRONT home on Gulf in North Captiva, Florida, holiday rental in Pineland
Newly renovated BEACHFRONT home on Gulf in North Captiva, Florida, holiday rental in Pineland
Newly renovated BEACHFRONT home on Gulf in North Captiva, Florida, holiday rental in Pineland

Newly renovated BEACHFRONT home on Gulf in North Captiva, Florida

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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New luxury home, 2 min to beach, 360 water views, club amenities, holiday rental in Pineland
New luxury home, 2 min to beach, 360 water views, club amenities, holiday rental in Pineland
New luxury home, 2 min to beach, 360 water views, club amenities, holiday rental in Pineland

New luxury home, 2 min to beach, 360 water views, club amenities

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
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Perfect Beach, Private Pool and Hot tub.  Best Beach Sunset Views on the Island., holiday rental in Pineland
Perfect Beach, Private Pool and Hot tub.  Best Beach Sunset Views on the Island., holiday rental in Pineland
Perfect Beach, Private Pool and Hot tub.  Best Beach Sunset Views on the Island., holiday rental in Pineland

Perfect Beach, Private Pool and Hot tub. Best Beach Sunset Views on the Island.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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13 Sunset Captiva  2 Bedroom / 2 Bath House, holiday rental in Pineland
13 Sunset Captiva  2 Bedroom / 2 Bath House, holiday rental in Pineland
13 Sunset Captiva  2 Bedroom / 2 Bath House, holiday rental in Pineland

13 Sunset Captiva 2 Bedroom / 2 Bath House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Vitamin SEA 365.  Off the grid Bliss.  Private Beach and Dock, holiday rental in Pineland
Vitamin SEA 365.  Off the grid Bliss.  Private Beach and Dock, holiday rental in Pineland
Vitamin SEA 365.  Off the grid Bliss.  Private Beach and Dock, holiday rental in Pineland

Vitamin SEA 365. Off the grid Bliss. Private Beach and Dock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Under New Management-SMUGGLERS HIDEAWAY-Private Pool-Hot Tub-Club Access-Sleep 7, holiday rental in Pineland
Under New Management-SMUGGLERS HIDEAWAY-Private Pool-Hot Tub-Club Access-Sleep 7, holiday rental in Pineland
Under New Management-SMUGGLERS HIDEAWAY-Private Pool-Hot Tub-Club Access-Sleep 7, holiday rental in Pineland

Under New Management-SMUGGLERS HIDEAWAY-Private Pool-Hot Tub-Club Access-Sleep 7

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Remember When, Old Florida Beach House, holiday rental in Pineland
Remember When, Old Florida Beach House, holiday rental in Pineland
Remember When, Old Florida Beach House, holiday rental in Pineland

Remember When, Old Florida Beach House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SEA LA VIE- BEACHFRONT-Large & Private, sleeps 10+Club Membership, 2 golf carts, holiday rental in Pineland
SEA LA VIE- BEACHFRONT-Large & Private, sleeps 10+Club Membership, 2 golf carts, holiday rental in Pineland
SEA LA VIE- BEACHFRONT-Large & Private, sleeps 10+Club Membership, 2 golf carts, holiday rental in Pineland

SEA LA VIE- BEACHFRONT-Large & Private, sleeps 10+Club Membership, 2 golf carts

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Easy Walk to Beautiful Beach, Sleep 10 In Beds, Watch the Sunset From Your Deck, holiday rental in Pineland
Easy Walk to Beautiful Beach, Sleep 10 In Beds, Watch the Sunset From Your Deck, holiday rental in Pineland
Easy Walk to Beautiful Beach, Sleep 10 In Beds, Watch the Sunset From Your Deck, holiday rental in Pineland

Easy Walk to Beautiful Beach, Sleep 10 In Beds, Watch the Sunset From Your Deck

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Nice spacious & charming home. Kayak, golf carts , bikes & free wine included., holiday rental in Pineland
Nice spacious & charming home. Kayak, golf carts , bikes & free wine included., holiday rental in Pineland
Nice spacious & charming home. Kayak, golf carts , bikes & free wine included., holiday rental in Pineland

Nice spacious & charming home. Kayak, golf carts , bikes & free wine included.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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LAST MINUTE SPECIALS, PRIVATE BEACHES, COME GET AWAY! HEATED POOL & PRIVATE BAR!, holiday rental in Pineland
LAST MINUTE SPECIALS, PRIVATE BEACHES, COME GET AWAY! HEATED POOL & PRIVATE BAR!, holiday rental in Pineland
LAST MINUTE SPECIALS, PRIVATE BEACHES, COME GET AWAY! HEATED POOL & PRIVATE BAR!, holiday rental in Pineland

LAST MINUTE SPECIALS, PRIVATE BEACHES, COME GET AWAY! HEATED POOL & PRIVATE BAR!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Steps from the beach, Gulf and Sound Views, Pool and Cabana, holiday rental in Pineland
Steps from the beach, Gulf and Sound Views, Pool and Cabana, holiday rental in Pineland
Steps from the beach, Gulf and Sound Views, Pool and Cabana, holiday rental in Pineland

Steps from the beach, Gulf and Sound Views, Pool and Cabana

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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PEACE OF PARADISE - Private Resort Style Pool & Private Beach Access - Sleeps 10, holiday rental in Pineland
PEACE OF PARADISE - Private Resort Style Pool & Private Beach Access - Sleeps 10, holiday rental in Pineland
PEACE OF PARADISE - Private Resort Style Pool & Private Beach Access - Sleeps 10, holiday rental in Pineland

PEACE OF PARADISE - Private Resort Style Pool & Private Beach Access - Sleeps 10

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Happy Hours Beach House - Your Happiness Begins Here - Luxury, Pool, 2 Golf Cart, holiday rental in Pineland
Happy Hours Beach House - Your Happiness Begins Here - Luxury, Pool, 2 Golf Cart, holiday rental in Pineland
Happy Hours Beach House - Your Happiness Begins Here - Luxury, Pool, 2 Golf Cart, holiday rental in Pineland

Happy Hours Beach House - Your Happiness Begins Here - Luxury, Pool, 2 Golf Cart

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Romantic beach cottage with golf cart kayaks and bikes. Remodeled Coastal charm, holiday rental in Pineland
Romantic beach cottage with golf cart kayaks and bikes. Remodeled Coastal charm, holiday rental in Pineland
Romantic beach cottage with golf cart kayaks and bikes. Remodeled Coastal charm, holiday rental in Pineland

Romantic beach cottage with golf cart kayaks and bikes. Remodeled Coastal charm

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Bayfront Beach Escape, holiday rental in Pineland
Bayfront Beach Escape, holiday rental in Pineland
Bayfront Beach Escape, holiday rental in Pineland

Bayfront Beach Escape

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to paradise! You're now on island time!, holiday rental in Pineland
Welcome to paradise! You're now on island time!, holiday rental in Pineland
Welcome to paradise! You're now on island time!, holiday rental in Pineland

Welcome to paradise! You're now on island time!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Near beach, includes golf cart , bikes , kayaks and pool , 5 stars, Boat Slip !, holiday rental in Pineland
Near beach, includes golf cart , bikes , kayaks and pool , 5 stars, Boat Slip !, holiday rental in Pineland
Near beach, includes golf cart , bikes , kayaks and pool , 5 stars, Boat Slip !, holiday rental in Pineland

Near beach, includes golf cart , bikes , kayaks and pool , 5 stars, Boat Slip !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Villa Island Getaway - ALL INCLUDED! Beach villa w. boat included in the price., holiday rental in Pineland
Villa Island Getaway - ALL INCLUDED! Beach villa w. boat included in the price., holiday rental in Pineland
Villa Island Getaway - ALL INCLUDED! Beach villa w. boat included in the price., holiday rental in Pineland

Villa Island Getaway - ALL INCLUDED! Beach villa w. boat included in the price.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Coconut Castaway | New Rental, Newly remodeled, Ocean Views, Hot Tub, Golf Cart, holiday rental in Pineland
Coconut Castaway | New Rental, Newly remodeled, Ocean Views, Hot Tub, Golf Cart, holiday rental in Pineland
Coconut Castaway | New Rental, Newly remodeled, Ocean Views, Hot Tub, Golf Cart, holiday rental in Pineland

Coconut Castaway | New Rental, Newly remodeled, Ocean Views, Hot Tub, Golf Cart

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury private pool home, stunning views, just steps to beach on Captiva Island, holiday rental in Pineland
Luxury private pool home, stunning views, just steps to beach on Captiva Island, holiday rental in Pineland
Luxury private pool home, stunning views, just steps to beach on Captiva Island, holiday rental in Pineland

Luxury private pool home, stunning views, just steps to beach on Captiva Island

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Newly Built Floridays, Pool, Beachview, Lots Amenities, holiday rental in Pineland
Newly Built Floridays, Pool, Beachview, Lots Amenities, holiday rental in Pineland
Newly Built Floridays, Pool, Beachview, Lots Amenities, holiday rental in Pineland

Newly Built Floridays, Pool, Beachview, Lots Amenities

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Island Queen, Luxury in Paradise, 200ft to Beach, holiday rental in Pineland
Island Queen, Luxury in Paradise, 200ft to Beach, holiday rental in Pineland
Island Queen, Luxury in Paradise, 200ft to Beach, holiday rental in Pineland

Island Queen, Luxury in Paradise, 200ft to Beach

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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NEW LISTING! SERENITY NOW, SLEEPS 14, 4 KINGS, SCREENED-IN HEATED POOL, CLUB, holiday rental in Pineland
NEW LISTING! SERENITY NOW, SLEEPS 14, 4 KINGS, SCREENED-IN HEATED POOL, CLUB, holiday rental in Pineland
NEW LISTING! SERENITY NOW, SLEEPS 14, 4 KINGS, SCREENED-IN HEATED POOL, CLUB, holiday rental in Pineland

NEW LISTING! SERENITY NOW, SLEEPS 14, 4 KINGS, SCREENED-IN HEATED POOL, CLUB

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico, holiday rental in Pineland
Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico, holiday rental in Pineland
Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico, holiday rental in Pineland

Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Frequently Asked Questions about Pineland