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Holiday Homes near Waterside Shops

5415 Tamiami Trl N, Naples, Florida 34108-2853
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    Travellers to Naples are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 560 Rentals in Naples
    Walk to Beach from Stunning Tropical Pool Home1 / 15
    (5)Excellent
    2.0 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    0.8 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Luxury Lakefront Villa in Gated Community1 / 20
    (7)Excellent
    12.3 kilometres from Waterside Shops
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Beautiful 2 BR/2 BA, Huge Heated Pool, 3 Miles to Downtown 5th Ave & The Beach1 / 41
    (3)Excellent
    9.7 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Washer
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Naughty in Naples! Seasonal Three Month Rate/Jan 1-March 31-$11,500. Inclusive.1 / 18
    (1)Excellent
    13.1 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 2
    Pelican Bay, North Naples
    1.9 kilometres from Waterside Shops
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    About this property
    Seasonal Vacation Rental in Naples, FL - $12,000 Monthly - 30 day Minimum Fabulous residence right in the heart of Pelican Bay! Completely updated and modernized to reflect today's 'contemporary casual elegance' design style. Unique courtyard style residence with completely private walled-in...
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Winter Rental in Montreux Village * Fiddlesr Creek.. Professionally decorated.1 / 20
    (1)Excellent
    23.8 kilometres from Waterside Shops
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Brand new, modern pool villa, just minutes from beaches, golf & shopping1 / 24
    (1)Excellent
    1.4 kilometres from Waterside Shops
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Balcony
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2016
    It's was great to get away with sibling and rekindling memories while creating new ones with our kids. The property is a remodeled beach home with all amenities and house goods...
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    About this property
    Villa Sophia is a true coastal gem that is fresh and breathy as well as warm and cozy. It is just 1,5 miles away from the beautiful beaches of Naples and right in the middle of everything Naples has to offer. The 4-bedroom house with its open-concept living space features soaring 12-foot vaulted...
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Pelican Bay, North Naples
    1.8 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
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    About this property
    Seasonal Vacation Rental in Naples, FL - $6,500 Monthly Wonderful lake views from this spacious three bedroom residence located right in the heart of Pelican Bay and so close to everything this premier development has to offer. Furnished in a casual neutral decor scheme with accents of color...
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.9 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Westlake Villa offers guests a lovely comfortable vacation home full of old Naples charm. It has 3 bedrooms, the master suite with king sized bed is en-suite and has a flat screen TV. The queen has a flat screen tv and twin room has a dvd flat screen tv, there is a 2nd full bathroom with shower....
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.2 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ****Phase 3 on the reopening of Florida instituted which includes beach access, hair salons & barber shops, fitness centers, restaurants, bars and retail shops operating at normal capacity. Cleaning and disinfecting our properties are highest priority and we are following all CDC guidelines Park...
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Newly Renovated Top Floor Condo! Gated community, close to Olde Naples. Pool!1 / 49
    (3)Excellent
    11.8 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    22.4 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    15.2 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    8.8 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    8.5 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Leave the chill of Fall/Winter behind by visiting Florida's  Beautiful Beaches!1 / 42
    (4)Excellent
    15.2 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
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    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.2 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Seasonal Vacation Rental in Naples, FL - $6,000 Monthly Right in the heart of the Naples area and so close to everything the city has to offer! Totally renovated beauty boasting all luxury modern features and appointments. The owner has spared no expense in the reimagining of this residence....
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    7.7 kilometres from Waterside Shops
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    12.9 kilometres from Waterside Shops
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Private Outdoor Pool (Unheated)
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    13.6 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pet friendly
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    21.4 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Terrace
    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Quite/rural 3 bedroom 2.5 bathroom home with pool & lanai, fenced with gates1 / 27
    (1)Excellent
    14.4 kilometres from Waterside Shops
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    1.7 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    8.8 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Remodeled Condo Near 5th Avenue & Beach with amazing amenities1 / 37
    (6)Excellent
    8.6 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    9487 Campanile Circle - Stunning 3 Bed Plus Den Home/ Award Winning Amenities1 / 21
    (1)Excellent
    23.5 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Old Naples
    7.6 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    8.8 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Stunning 3 Bedroom plus Den Pool home in Naples Gated Briarwood Community1 / 35
    (12)Excellent
    7.7 kilometres from Waterside Shops
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    This 3/2 home enjoys a Southwest facing lakefront view with pool and spa1 / 35
    (2)Excellent
    8.0 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lely Resort
    18.7 kilometres from Waterside Shops
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    17.5 kilometres from Waterside Shops
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    16.4 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    8.5 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    South Naples 2/2 1200' Condo in Bundled Golf / Tennis with Golf Course Views1 / 17
    (5)Excellent
    10.9 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Lely Resort
    19.0 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    13.7 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Naples Condo. 2/2 with Golf Course view. Near Marco Island1 / 15
    (3)Average
    26.3 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    9.7 kilometres from Waterside Shops
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    King Studio with Pool and Canal Access1 / 14
    (8)Very good
    10.7 kilometres from Waterside Shops
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    8.6 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Villa w/Heated, Saltwater Pool in Fiddlers Creek1 / 35
    (1)Excellent
    23.7 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful one bedroom one bath unit in country like setting on horse ranch1 / 24
    (7)Very good
    16.7 kilometres from Waterside Shops
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    23.7 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Old Naples
    8.3 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Park Shore Paradise- Naples Florida1 / 37
    (1)Excellent
    2.0 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lely Resort
    16.6 kilometres from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    10.2 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Washer
    • Internet Access
    • Terrace
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Moorings
    4.7 kilometres from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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