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Pineland Holiday Homes

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    Pineland is popular with travellers just like you. Don’t let them get your perfect place first—book today!
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    NEW PROPERTY: Upscale Beach Home with Screened-in Pool, Hot Tub, Outdoor Kitchen1 / 48
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oceanfront Luxury Home with Secluded Private Beach1 / 22
    (32)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beachfront, pet friendly home with free grocery delivery - 2021 / 47
    (23)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    177 - The Big Easy1 / 27
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Reviewed 13 February 2020
    This house was phenomenal. It's well stocked and a wonderful location to explore everything that North Captiva Island has to offer. The house cart worked well for us - one tip...
    Reviewed 25 November 2019
    First of all, the house is huge! It slept 6 of us very comfortably, but can accommodate many more for entertaining! The pool area was great to hang around on, the grill was...
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    About this property
    Book your next vacation to stay at The Big Easy, which is located on Upper Captiva, the island is only accessible by boat or ferry and nearest airport to fly-in are RSW or PGD. The Big Easy is a 3 Bedroom 2 Bathroom Beach View Home with a large private pool, outdoor shower, Tiki bar, gas grill,...
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Waterfront
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    About this property
    BRAND NEW BEACHFRONT HOME! Welcome to Green On The Gulf! Just completed (New Construction) January, 2019!  This 3 bedrooms 2.5 bathrooms custom built upside down home has sweeping and unobstructed Gulf of Mexico views from the top floor living area. The home is beautifully landscaped, is equipped...
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Happy Hours Beach House - Your Happiness Begins Here - Luxury, Pool, 2 Golf Cart1 / 45
    (13)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    About this property
    Hummingbird Hideaway is Located on North Captiva Island were you can treat yourself to the real Florida experience, away from busy streets, crowded beaches, and the commercial scene. The beauty and seclusion of this barrier island will captivate your senses and restore your soul. North Captiva...
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    Pineland, Florida 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
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    About this property
    A real get away from the hustle a bustle of life, you must take a ferry from North Captiva Island Club or Island Girl Charters to get to the island. This freshly renovated town home awaits your arrival away from the hectic world. Whether you plan to fish, beach-comb, relax in the sun, play in the...
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Captivation - Sunrise-to-sunset views–walk to beach– 2 golf carts, bikes, pool1 / 49
    (24)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
    Reel Paradise - Everything You Need And More - Pr. Pool & Tiki Bar - 3BR + Den1 / 37
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
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    About this property
    Pelican's Perch is a perfect newly renovated cottage that has 2 bedroom 2.5 bathrooms and a private heated pool. The house has a fully equipped kitchen. You can watch the sunset from either the first or second level deck. When you book your stay at Pelican Perch you will have access to 2 House Golf...
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    Pineland, Florida 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    The Pearl Beach House, North Captiva Island, FL1 / 27
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Pineland, Florida 33924
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Doc Holiday - ‘Old Florida’ Cottage, 600 ft frm beach, Sleeps 8 in beds, pets ok1 / 33
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Beachfront Oasis w/AmazingViews! Steps to beach.Boat Rental Avail.Priv Doc. WiFi1 / 24
    (11)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Beach's Edge, One Of A Kind Beachfront Experience1 / 40
    (52)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Walk to Private Beach and Island Club/Free kayaks/Bikes/Olympic Sized Pools1 / 35
    (70)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Snow More Worries - Sleeps 12 -Private Pool -2 Golf Carts -Resort Membership1 / 43
    (13)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Spring Warrior Fish Camp Lodge, Located on the Gulf of Mexico.1 / 17
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Location Information
    Pineland, Florida 32348
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    Ocean Boulevard-New Steps To The Beach - Professionally Decorated -2 Golf Carts1 / 43
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
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    Pineland, Florida 33924
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Coconut Breeze, 4 bedrrom, pool ,2 private beach access, elevator, free docking1 / 24
    (14)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Will you decide on Breakfast in the Kitchen/Dining area or on the screened in porch? How about a dip in the hot tub off the kitchen before or after the beach? Should you go shelling, bike riding, kayaking, fishing, play a game of tennis or basketball or take a dip in one of two resort pools at...
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Newly renovated BEACHFRONT home on Gulf in North Captiva, Florida1 / 50
    (3)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    If you are looking for great vacation home look no further. Your family will love the Tipsy Turtle, a 3 Bedroom 3 Bathroom home that sleeps 8 with spectacular 360 views of the island. You can watch the sunrise on one side and the sunset on the other. First level has a Queen Bedroom, Hall Bathroom,...
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Vitamin SEA 365.  Off the grid Bliss.  Private Beach and Dock1 / 39
    (19)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    *** SUMMER 2020 IS FULLING UP!!! BOOK YOUR AMAZING ISLAND VACATION NOW!!!***1 / 48
    (31)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Rockstar Beach House North Captiva Island (accessible by ferry boat only)1 / 40
    (38)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Breathtaking Designer Home 3BR/4 BA - Sleeps 10 - Steps to the Beach1 / 40
    (19)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Tropical paradise awaits at the Blue Tortuga1 / 50
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico1 / 17
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pineland, Florida 32348
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    About this property
    Floridays is loaded with amenities for your family to enjoy. Newly Built, beautifully landscaped, 4 bedroom 4 bathroom private pool home can comfortably sleeps a family up to 11. 2 Golf Carts Included As a member of the marina club bring your boat and get dockage for just $40 per day with your...
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    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    1 Minute to Beach, Luxury New pool home, Gulf sunrise and sunset Views1 / 50
    (49)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    Pineland, Florida 33924
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    463B - The Morganite Nest Located off Hidden Lane, in a nice secluded area of North Captiva Island Welcome to The Morganite Nest this beautiful rare gem has 3 Bedroom 4 Bathroom, private pool and is built with a Reserve Plan layout, so you and your family can enjoy the views where you gather the...
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    • Waterfront
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    About this property
    Picturesque 2 bedroom 2 bath Bayfront cottage with private fishing dock. Just steps to your own private beach! Best spot to watch dolphin on the island. Bayfront home has a screened-in porch overlooking the water. Watch the dolphin go by and see the tarpon jumping in the sun. If you like to fish,...
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    Pineland, Florida 33924
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Enjoy luxury in Paradise at Captain Jack's retreat. This amazing home will surely knock your socks off. Situated near surrounding state park area and just a few hundred feet to one of the nicest wide sandy beach on North Captiva Island make this an amazing vacation getaway. This one level...
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    Welcome to the Emeraude Nest located in one of the most desirable locations on North Captiva. Right off of Panama Shell Drive, you’re within walking distance to the nature preserve and state park beach. Emeraude Nest has 3 Bedroom 4 Bathroom, private pool and is built with a Reserve Plan layout ,...
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    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    Look no further…you have found the perfect vacation location! This brand new, beautiful home is located just a few short steps from the largest beach on North Captiva and offers many features that will make your stay memorable and leave you wanting to make The Beachy Keen your regular vacation...
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    Location Information
    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Oh Say Can You Sea   North Captiva1 / 29
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Hot Tub
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    • Terrace
    • Private Outdoor Pool (Unheated)
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    • Patio
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Grill
    • Balcony
    • Private Outdoor Pool (Heated)
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    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come experience this brand new (2019) amazingly charming vacation get-away! Everyone will enjoy this large,1800 square foot, open floor plan that is a very functional, beach friendly vacation home. It has 3 bedrooms, 3 baths, with high ceilings and fans in every room, big windows and well-appointed...
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    Location Information
    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Stardance  Pool, 2 golf carts1 / 28
    (32)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    The Maine Deck  Breathtaking Views - Pool- Steps to the beach - 2 Golf Carts!1 / 45
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Spring Warrior Fish Camp #1 Located on the Gulf of Mexico1 / 10
    (10)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Pineland, Florida 32348
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Rum Point - 5BR/Pool - 2 Golf Carts - Sleeps up to 121 / 49
    (32)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
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    Pet friendly
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    Location Information
    Pineland, Florida 33924
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Serendipity - Pool, 2 Golf Carts, NCIC, location, location, location!1 / 43
    (26)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
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    Location Information
    Pineland, Florida 33924
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    021 - Lost Shaker of Salt1 / 25
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Washer
    • Grill
    • Balcony
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2019
    We loaded up the kids, dog and our boat and went out for the week. Unfortunately, the people before us overstayed their checkout time but, the Island Club staff was super...
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    About this property
    Come stay at Lost Shaker of Salt, newly built in 2017, 3 bedroom 3 bath Island house with private heated pool. Just a 1 minute golf cart ride to the beach or a 5 minute walk. First bedroom has a king bed in the master with a large master bath, separate luxurious soaking tub and walk-in shower. 2nd...
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    Location Information
    Pineland, Florida 33924
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Spring Warrior Fish Camp #6 located on the Gulf of Mexico1 / 10
    (12)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Pineland, Florida 32348
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    • Wi-Fi
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    • Patio
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfy old-timey mobile home w pretty garden on historic Pine Island. Nearby fishing, kayaking, birding, good eats. Visit pristine Cayo Costa (catch ferry from PI) & Ft. Myers Beach/Sanibel (45 min). Retro furn, quiet A/C, ceiling fans. Sleeps 6, but 1 or 2 is just fine. Full kitch, living, lanai,...
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    Location Information
    Pineland, Florida 33922
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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