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Holiday Rentals 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 513 Rentals in Naples
    0.5 miles from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Park Shore Resort,1st- West of 41, 1.25 miles to beach; Free WiFi1 / 45
    (1)Average
    0.8 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Park Shore Resort-Stunningly renovated; 1.25 miles to Beach! Free High Speed Int1 / 28
    (2)Excellent
    0.8 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    0.8 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    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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    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Luxury Lakefront Villa in Gated Community1 / 20
    (7)Excellent
    7.6 miles from Waterside Shops
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Beautiful 2 BR/2 BA, Huge Heated Pool, 3 Miles to Downtown 5th Ave & The Beach1 / 41
    (3)Excellent
    6.0 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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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
    (2)Excellent
    8.1 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 2
    Winter Rental in Montreux Village * Fiddlesr Creek.. Professionally decorated.1 / 20
    (1)Excellent
    14.7 miles 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
    0.8 miles from Waterside Shops
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    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 - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Park Shore Resort-EXTENSIVE HIGH END LUXURIOUS RENOVATION! 1.25 Miles to Beach!1 / 28
    (1)Excellent
    0.8 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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    • Cable/satellite TV
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2017
    We've stayed at Park Shore Resort before but in a unit that had not been updated. This unit is absolutely fantastic - updated down to the last detail - we loved it and had a...
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    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 **IN...
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.7 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    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
    Brand new, modern pool villa, just minutes from beaches, golf & shopping1 / 24
    (1)Excellent
    0.9 miles from Waterside Shops
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Balcony
    • Grill
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    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
    1.1 miles 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
    0.5 miles 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
    0.7 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    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
    (8)Excellent
    7.3 miles from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Balcony
    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    13.9 miles from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.5 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    9.4 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
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    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5.3 miles 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
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    Convenient and well-appointed Vacation Home ! NEW JACUZZI !1 / 48
    (6)Excellent
    4.7 miles from Waterside Shops
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Leave the chill of Fall/Winter behind by visiting Florida's  Beautiful Beaches!1 / 42
    (4)Excellent
    9.4 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    • Hot Tub
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    • Washer
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    Pet friendly
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    8.0 miles 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
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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, 3 Bathrooms, Sleeps 6
    0.7 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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
    8.4 miles 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
    1.1 miles 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
    Quite/rural 3 bedroom 2.5 bathroom home with pool & lanai, fenced with gates1 / 27
    (1)Excellent
    8.9 miles 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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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    13.3 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Terrace
    • Cable/satellite TV
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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
    (2)Excellent
    14.6 miles from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Remodeled Condo Near 5th Avenue & Beach with amazing amenities1 / 37
    (6)Excellent
    5.3 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5.4 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Lely Resort
    11.6 miles 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
    Old Naples
    4.7 miles 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
    Stunning 3 Bedroom plus Den Pool home in Naples Gated Briarwood Community1 / 35
    (16)Excellent
    4.8 miles from Waterside Shops
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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
    (4)Excellent
    5.0 miles 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
    5.4 miles 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
    South Naples 2/2 1200' Condo in Bundled Golf / Tennis with Golf Course Views1 / 17
    (5)Excellent
    6.7 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    FRESHLY REMODELED TOP FLOOR LUXURY CONDO in Coral Falls, part of Lely Resorts1 / 16
    (17)Excellent
    Lely Resort
    11.8 miles 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
    10.9 miles from Waterside Shops
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    6.0 miles from Waterside Shops
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    10.2 miles from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
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    • Balcony
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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
    Old Naples
    5.2 miles 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
    8.5 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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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 - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Villa w/Heated, Saltwater Pool in Fiddlers Creek1 / 35
    (1)Excellent
    14.7 miles from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    5.4 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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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 4
    14.7 miles from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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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
    Park Shore Paradise- Naples Florida1 / 37
    (3)Excellent
    1.2 miles 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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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lely Resort
    10.3 miles from Waterside Shops
    3 Bedrooms, 2 Bathrooms, Sleeps 6 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    8.7 miles from Waterside Shops
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Patio
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    King Studio with Pool and Canal Access1 / 14
    (11)Very good
    6.6 miles from Waterside Shops
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Naples, Southwest Gulf Coast
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1
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