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Holiday Rentals with Pools in Naples Park

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    Travellers to Naples Park are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    29 Matching Rentals in Naples ParkView all 43 rentals
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    New Chic Dream Home Heated Pool!1 / 25
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Beach Cottage! New Listing,Pool,Spa,Cabana,Hanging Swing,Privacy, Walk to Beach1 / 30
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    **Unlimited Golf, Tennis** - 2BR/BA + Den, Naples1 / 35
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Park Shore Resorts1 / 41
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 February 2016
    Beautiful landscaping from our second story condo overlooking the central island plus colorful wildlife to watch every day float by to the sound of waterfalls by day and...
    Reviewed 28 September 2015
    This rental is ideally located if you're interested in exploring the Naples area. The owner was very responsive to questions. The unit is fairly well equipped and maintained...
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    About this property
    This Park Shore Resort Condo is in the heart of Naples, next to all what Naples has to offer. You are in walking distance to Waterside Shops, restaurants, supermarket, beach and much more. 5th Ave and 3rd St just minutes away from Art Galleries, Restaurants, Shops and Night life and the Pier of...
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    Naples Park, Florida 34103
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Single family Pool Home Close to the Gulf.1 / 15
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Parking
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 2018
    This home is close to the Gulf. I was pleased that the home had bikes to use. Very clean and comfy. The pool is a nice addition. I like the location and would stay there again...
    Reviewed 8 January 2018
    great house,best value for the money,close to everything,short walk to beach,house was very clean,dan was great to work with,thanks again,jim
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    About this property
    single House, 3 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 7 conformable ) Single Pool Home! Everything you'll need for a great vacation, close to gulf. Our Newer single family home has a gorgeous pool and Lanai with palm trees, 3 bedrooms that offer a king size bed in the master, queen in...
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    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxurious holiday condo with oversize pool1 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Terrace
    • Washer
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2015
    This place is simply picture perfect!!! The location is excellent, the unit is spotless and has everything one may need and more. Fully equipped kitchen, full size washer and...
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    About this property
    This condo located in Winterpark community known for its fabulous location and one of the largest swimming pools in Naples (You may see it on Google map). Less then 10 minutes drive from white sandy beaches, close to shops, restaurants, minutes drive from Naples 5th Avenue and other attractions....
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    Naples Park, Florida 34112
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very comfortable villa 'Summer Dream', 2 storeys, built in 1980 in 2016. In a quiet, sunny position residential area (villas), 1 km from the sea. Private: garden (fenced), swimming pool heated (01.01.-31.12.). Parking at the house, single garage. Supermarket, restaurant 900 m, sandy beach 1.2 km....
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    Naples Park, Florida 34108
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Private Pool Renovated Beach Cottage1 / 18
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2018
    Gina and Anthony's home was wonderful! It was very clean, equipped with everything we needed, close to stores and within walking distance to Vanderbilt Beach! I was in...
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    About this property
    This is not a rental, this is a home! Everything in the home has been replaced and updated with the pride of ownership evident in every detail. The Gourmet Kitchen features Granite Counter tops. All new Stainless Steel Appliances are set off by the white wood cabinetry and the glass tile...
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    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Wi-Fi
    • Parking
    • Washer
    • Balcony
    • Air Conditioning
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    End unit on 4th floor of a 7 story high rise SCREENED LANAI FACES WEST FOR THE VIEWING OF ALL THE SUNSETS OUT OVER BAREFOOT BEACH FULL SIZE LAUNDRY IN UNIT. OWNER WILL SUPPLY INTERNET AND CABLE TV.. 3BEDROOMS KING BED IN MASTER, TWINS IN GUEST, AND QUEEN IN OTHER GUEST ROOM ,AND TWO FULL BATHS...
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    Location Information
    Naples Park, Florida 33410
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunny Naples on the Florida coast is calling with this spacious vacation rental, boasting 3 bedrooms, 2-1/2 baths, and accommodations to sleep up to 6, possibly 8. Private heated pool for relaxation, bike over to Vanderbilt Beach to witness a spectacular sunset, or drive to nearby Mercato (an...
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    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Naples Park Home -Stunning Heated Pool/ 3 Bed+Den / Pet Friendly/ Sleeps 6 / 2 Full Bath/ 7 Night Min. Beautifully furnished beach retreat, fully equipped. Bike/walk to Vanderbilt Beach, Wiggins Park Beach, Mercato Shopping District and so much more! Simply and elegantly decorated, this home is...
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    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ARE YOU READY FOR A LUXURIOUS VACATION? A hidden treasure tucked away on the 500 block in Naples Park. Meticulously maintained and tastefully decorated. 3BR/2BA pool home is perfect to accommodate your family and friends. Updated kitchen cabinetry, new bathroom vanities, tile throughout. Outdoor...
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    Location Information
    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Terrific distant Gulf views across the street from this fifth floor residence in one of Vanderbilt Beach's most popular high rise communities. Enjoy the cool Gulf breezes while having an afternoon drink on the screened lanai. Pleasing light Florida style decor throughout with accents of beach...
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    Naples Park, Florida 34108
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy southwest facing water views and spectacular sunsets from this sprawling ranch! Fabulous floorpan with many rooms leading to the outdoor living - pool, lanai, yard, gulf access canal and expansive dock. You and your guests are sure to enjoy! Sprawling split bedroom ranch with master suite on...
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    Naples Park, Florida 34108
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2006 built house looks like it has never been lived in! Brand new carpet in 4 bedrooms and tile on the diagonal throughout balance of house, including front porch and lanai. Immaculately clean and crisp, vaulted ceilings, 8' doors, 5.25' baseboards, Granite counter-tops, laundry tub in laundry...
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    Naples Park, Florida 34108
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect Florida Beach Vacation Getaway! Call Louise at Phase III realty, for more details and pricing. Rent this fabulous and spacious pool home in the highly desirable 500 block in North Naples, a short 10 minute walk to the BEACH! This beautifully furnished home was professionally designed and...
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    Location Information
    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Parking
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise at the Dunes. Enjoy this spectacular complex with its world class amenities including large community pool, tennis courts, clubhouse with five-star dining and close proximity to the beach. You will be just a short drive to the area's newest hotspot The Mercatto, where you can...
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    Naples Park, Florida 34110
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located within walking distance to Vanderbilt Beach, Barefoot Pelican gated complex located on the bay and canal. Properties amenities include pool, BBQ Grill and hot tub. Unit 237 is a two bedroom, two bathroom third floor condo with elevator in the building. Bedding includes King and two...
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    Naples Park, Florida 34108
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a classic Florida escape at this 3-bedroom, 2-bath vacation rental house in Naples! Offering 2,271 square feet of pristine living space and accommodations for up to 8, this home is perfect for friends, family, and pets. Enjoy the perks of a screened-in backyard lanai, complete with a gas...
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    Location Information
    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Balcony
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very comfortable villa 'Summer Dream', 2 storeys, built in 1980 in 2016. In a quiet, sunny position residential area (villas), 1 km from the sea. Private: garden (fenced), swimming pool heated (01.01.-31.12.). Parking at the house, single garage. Supermarket, restaurant 900 m, sandy beach 1.2 km....
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    Naples Park, Florida 34108
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Feel a sense of calmness come over you when you stay at 'Casa Tranquilidad,' a 4-bedroom, 2.5-bathroom vacation rental house in Naples. This beautiful home boasts 2,200 square feet, high-end furnishings, comfortably sleeps up to 8 guests, and has everything you need for a comfortable stay in the...
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    Naples Park, Florida 34108
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rejuvenate and revel in the beauty of Florida's white sandy beaches and crystal clear ocean in this Vanderbilt Villas condo less than a mile from Vanderbilt Beach. About 10 miles from downtown Naples, this 3-bed, 2-bath vacation rental home can host the quintessential Florida beach vacation for 6....
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    Naples Park, Florida 34110
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Hot Tub
    • Air Conditioning
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the whole family to explore Naples from your personal oasis at this 3-bedroom, 4-bath vacation rental house! Up to 8 guests can look forward to lazy days by the sandy shore of Vanderbilt Beach, just 2 miles away before returning to this beautiful home to relax some more in the modern interior...
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    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 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
    Kid friendly
    Smoking allowed
    About this property
    Experience your own tropical paradise when staying at this 3-bedroom, 2-bathroom vacation rental house in Naples! This tastefully designed abode features luxurious amenities such as a screened lanai and private pool that create an unforgettable retreat for up to 6 guests. Everyone will relish easy...
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    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover an impressive shopping scene, high-end golf courses, and pristine Gulf Coast beaches while staying at this lovely vacation rental house in Naples. Situated in a peaceful neighborhood 10 minutes from Mercato and only 1.5 miles from Vanderbilt Beach, your dining experiences, shopping...
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    Location Information
    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * Please note that this property features exterior security cameras and motion lights. These do not look into any interior spaces * Experience scenic Southern Florida at this lavish 4-bedroom, 2.5-bath vacation rental house in Naples! This modern beach abode offers just under 2,300 square feet...
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    Naples Park, Florida 34108
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Patio
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Palm Retreat. This home will be spotless when you arrive. Equipped with two master suites. Only used a few months out of the year by the owner. this home was never a rental property. It is fully equipped home and includes a child protection removal screen system which allows you to keep the...
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    Location Information
    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gulf Breeze.This home will be spotless when you arrive. Note: The street that this home is located on is currently having new water mains installed. There is construction on the street and the road is not currently paved. We provide a garage remote to park your car in the garage. All residents can...
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    Location Information
    Naples Park, Florida 34108
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunshine Daydream. This home will be spotless when you arrive. Fantastic location. Walk or ride to the beach ( we supply 4 adult bikes and 1 teenage bike free of charge). Just purchased and never rented before. 4 bedroom pool home with new everything - furniture, bedding outdoor furniture,...
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    Location Information
    Naples Park, Florida 34108
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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