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Holiday Rentals in Naples, FL

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    Travellers to Naples are booking March dates now. Secure your holiday home today, and have the perfect trip.
    1 / 15
    5 of 5 stars (5) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Walking distance to the beach and 5th Avenue in Olde Naples, Florida. Located in residential area of multi-million dollar homes. Only 14 units, super quiet. Plenty of parking, but you don't even need a car, walk to everything. All units overlook courtyard where pool & spa is located. View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    THE BEST OF EVERYTHING! DOWNTOWN NAPLES WITH THE ADDITION OF BEING SO CLOSE TO THE OCEAN !!! SUMMER RATES HELD THROUGH OCTOBER 2015! 'A Home From Home' 'A Place to Relax and Recover' plus Netflix! Beautiful apartment to rent, in a 'bijou' complex, 14 condos in all set on two levels, private... View all property information
    Location Information
    Naples, Southwest Gulf Coast FL34102
    1 / 21
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Welcome to our resort style, luxurious villa in Paradise! 'Tivoli Paradise' is set on a beautiful, lush and tropical property, with plenty of trees to provide privacy, our guests can enjoy their own private oasis only 5-10 minutes from all that Naples has to offer. Unlike other rental properties... View all property information
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    Naples, Southwest Gulf Coast 34104
    1 / 21
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
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    About this property
    Location location location! Beautifully and professionally maintained house within the quiet, pristine waterfront neighborhood of Royal Harbor and just a short bicycle-ride to downtown Olde Naples. This unique 3 bedroom/ 2 bath, courtyard style house offers great privacy for extended family or 2... View all property information
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    Naples, Southwest Gulf Coast 34102
    1 / 13
    3.5 of 5 stars (2) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful heated pool home is situated in Briarwood, a gated community, only 10 minutes from the beach and downtown. It is decorated with tropical furnishings and overlooks a lake surrounded with palm trees. The house is equipped with WiFi and there are new flat screen televisions in all the... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34104
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    A great condo in North Naples near Vanderbilt Beach! A short 6/10 of a mile walk to the beach, this condo is everything your looking for. Short walks to the beach and beautiful sunsets, yet close to all the shopping, restaurants and theaters. This great condo has three bedrooms. The master bedroom... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34110
    1 / 22
    5 of 5 stars (8) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    About this property
    Location, location, location!!! This professionally managed 3 bedroom, 3 bath property in a spacious, lush and private garden is nestled in the heart of Olde Naples. The property is on a quiet street, lined with beautiful trees and just 3.5 blocks to Naples' pristine, white, sandy beaches as well... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
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    1 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Accommodations: First Floor Condo, 2 Bedrooms + 2 Baths Winterpark is in an ideal location close to all the attractions Naples has to offer. Five minute drive to both the public beach on Gulf of Mexico with white sand and clean rest rooms, and 5th Avenue in historic Olde Naples with its trendy... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34112
    1 / 31
    5 of 5 stars (8) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This casually elegant 3700 sq. ft. 4 bedroom home is located in the upscale neighborhood of Olde Naples. Located just steps away from one of Naples most pristine beaches and the Naples Pier. Charmingly designed, this home boasts 25 foot ceilings and lavish windows which provide for an open and... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Park Shore Resorts prime location west of Hwy.41 (Tamiami Trail) is within close proximity to restaurants, shopping, and famous downtown Naples. There's even a local supermarket, pharmacy, and post office just across the street. This sought after community is also convenient for walking, biking, or... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34103
    1 / 14
    5 of 5 stars (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Come escape into a cute cottage near the beach for your Florida vacation! Enjoy soaking up the sun at Delnor Wiggins Pass Park (1.2 miles away) or Vanderbilt Beach (1.9 miles away), both so close to you that it's tempting to go everyday for the spectacular sunsets! Ride a bike, take a stroll, and... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34108
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    If you wish to enjoy the treasures of Naples in a professionally redecorated four bedroom home - then you have found your vacation paradise. Located in the private (double gated) and exclusive Majors community in Lely Resort, this beautifully appointed open floor plan features high ceilings, crown... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34113
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    The exterior is so ornate people sometimes mistake it for the entrance to a resort. They pull into the brick driveway, see the manicured hedges and arched windows framed by clusters of palms, and they wait for the doorman to approach. No, this isn’t a resort. It’s a house. But it’s located in one... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34114
    1 / 24
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Can’t decide whether to vacation in Naples or Marco Island? Why not both? The Lesina is a gated community located in Naples but just a few minutes from Marco Island. This 14th floor, 2,300 square foot condo sleeps four, with one king bed and one queen. It comes with 2.5 bathrooms and secure... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34114
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    You’ve just discovered the ideal location for people who want to experience the best of Naples and Marco Island. This 900 square foot first floor condo sleeps four, with one queen bed and two twins, and it comes with two bathrooms. It’s also ideal for people who love sitting on the lanai in the... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34114
    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    The tropical and the elegant unite in this world-class community. Welcome to Fiddler’s Creek. They’ve taken the best features of resorts and placed them in the stunning natural surroundings of Southern Naples. It’s the best of both worlds. Make that the best of three luxurious worlds, because this... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34114
    1 / 26
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Why choose between two fantastic tropical destinations when you can have them both? This 2600 square foot, third floor condo is located in Naples but it’s only a short drive to Marco Island, so you get to fully experience two gems of Paradise Coast. It’s the best of both worlds. Make that the best... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34114
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome to Marco Island and its miles of warm sands, turquoise waters and sunsets that leave you breathless. Marco Island is located in the Gulf of Mexico, in Southwest Florida. That’s what the map says, but the map only tells a small part of the story. It doesn’t tell you how this tropical... View all property information
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    Naples, Southwest Gulf Coast 34114
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Marco Island or Naples? You can’t make up your mind which one to visit. Naples or Marco Island? You could flip a coin, but here’s a better solution: visit them both at the same time. The Falling Waters community is located at the intersection of 951 and 41, so you’re in Naples but just a few... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34114
    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    How’s this for the best both of both worlds? You’re in Naples but just a few minutes from Marco Island. You get a stunning water view, and you’re just a few steps from a heated pool. This 800 square foot first floor condo sleeps four, with two queen beds, and it comes with two bathrooms. It... View all property information
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    Naples, Southwest Gulf Coast 34114
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Park Shore Resorts prime location west of Hwy.41 (Tamiami Trail) is within close proximity to restaurants, shopping, and famous downtown Naples. There's even a local supermarket, pharmacy, and post office just across the street. This sought after community is also convenient for walking, biking, or... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34103
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Wedge Wood Trace is an upscale condominium neighborhood within the prestigious gated North Naples community of The Strand. This incredibly gorgeous development is located on Immokalee Road, west of I-75, just minutes to the beaches & all of the fine dining & shopping Naples has to offer. This well... View all property information
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    Naples, Southwest Gulf Coast 34110
    1 / 28
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Charming home with spacious floorplan and interesting architectural details. The master suite is separate from the other bedrooms for added privacy. There is also a living room as well as an additional separate den area. The home features a fantastic large screened-in lanai for breakfast or... View all property information
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    Naples, Southwest Gulf Coast 34108
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Greenlinks 1414 is a luxury renovated Greenlinks Golf Villa, offered for rental exclusively through The Holiday Life! Greenlinks at Lely Resort was designed as a tropical haven for golf enthusiasts, complete with plenty of features to keep non-golfers happy too! Unit 1414 is a 2 bedroom, 2 bath... View all property information
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    Naples, Southwest Gulf Coast 34113
    1 / 28
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome to the gated community of Briarwood! This spacious (2280 sq.ft.), single story, 4BR/3BA, 2 car garage, pool home is centrally located within minutes to famous downtown 5th Ave. restaurants and shopping, as well as nearby white sandy beaches. This home was recently purchased and has... View all property information
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    Naples, Southwest Gulf Coast 34104
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to the gated community of Briarwood! This spacious (1943 sq.ft.), well appointed 3 bedroom, 2 bath, 2 car garage pool home is centrally located within minutes to famous downtown 5th Ave. restaurants and shopping, as well as nearby white sandy beaches. This tastefully decorated home boasts a... View all property information
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    Naples, Southwest Gulf Coast 34104
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Wiggins Lakes & Preserve is your premier Naples vacation destination for the entire family! This meticulously maintained hidden gem is tucked away between U.S. 41 (Tamiami Trail) and Vanderbilt Drive, off Wiggins Pass Road (West of 41) in North Naples. The neighborhood is conveniently located... View all property information
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    Naples, Southwest Gulf Coast 34110
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Experience the ultimate in Naples waterfront living at the Vista Pointe Estate of Aqualane Shores. Located on over an acre with 300 feet of Naples Bay water frontage, the custom built home offers panoramic bay views from all rooms and an incredible indoor outdoor living experience. A gated entry... View all property information
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    Naples, Southwest Gulf Coast 34102
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    4 Bed 4.5 Bath Spacious home with a gorgeous view This beautiful two story home is inspired by the exotic style of Mediterranean homes. It sits right off of the prestigious Arthur Hills-designed Creek Golf Course with exceptional lake and course views. You'll have more than 3,700 sq. ft. of... View all property information
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    Naples, Southwest Gulf Coast 34114
    1 / 27
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to Wharfside on Naples Bay! Location, location, location…….sets this charming bay front townhouse apart from other rentals. In addition to its incredible views of Naples bay from any one of three waterfront lanais, this prime location is within walking distance to Tin City, Fifth Ave., and... View all property information
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    Naples, Southwest Gulf Coast 34102
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The best location to vacation in all of Naples! This beautifully furnished and decorated 3 bedroom/2 bath home is located 1/2 mile from the Vanderbilt beach and immediately down the street from the shopping and dining of the brand new Mercato lifestyle center, including Whole foods, movie theater... View all property information
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    Naples, Southwest Gulf Coast 34108
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Looking for a fabulous Naples pied-à-terre on the beach? You can't beat the location of the Surfside Club of Coquina Sands...located just to the north of downtown Olde Naples, you'll find yourself situated on a pristine stretch of sugar sand beach, right next door to the iconic Naples Beach Hotel &... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Greenlinks at Lely Resort was designed as a tropical haven for golf enthusiasts, complete with plenty of features to keep non-golfers happy too! Unit 1313 is a 2 bedroom, 2 bath first floor condo which also has a den to sleep a total of 6 people comfortably. Extra amenities offered by this... View all property information
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    Naples, Southwest Gulf Coast 34113
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Greenlinks at Lely Resort was designed as a tropical haven for golf enthusiasts, complete with plenty of features to keep non-golfers happy too! Unit 426 is a 3 bedroom, 2 bath second floor condo which sleeps 6 people in beds plus 2 more on the Queen size sleeper sofa. Extra amenities offered by... View all property information
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    Naples, Southwest Gulf Coast 34113
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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    • x
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    About this property
    Coral Falls The Coral Falls is a cozy condo located in the exclusive area of south Naples. Thanks to its great location the condo is close to the beautiful Naples beaches, various shopping malls, and a wide variety of exclusive dining options. To relax, you can enjoy the heated community pool and... View all property information
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    Naples, Southwest Gulf Coast 34113
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • x
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    About this property
    ​Elegance and Sophistication Elegance and sophistication is the way to describe this beautifully decorated 1652 sq. ft 3 bedroom 3 bathroom courtyard home with private pool located in the prestigious gated Prestwick Place Community in Lely Resort. Walk into the courtyard and you can see why this... View all property information
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    Naples, Southwest Gulf Coast 34113
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to beach vacation paradise at Sandcastle Villas! Unit 1 is a three level bayfront townhome located across the street from Vanderbilt Beach on Gulf Shore Drive. The villa is walking distance from the Ritz Carlton and La Playa beach resorts and just minutes from North Naples’ downtown... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34108
    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
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    About this property
    The finest Fiddler’s Creek has to offer…Amador is a 4 bedroom, 4 bath single family home tucked into the beautiful Veneta community. Built for entertaining, this home welcomes you and your guests through the lofty foyer to home’s ground floor with spacious open living and dining areas, a separate... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34114
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
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    • ?
    • ?
    About this property
    This beautifully furnished and decorated 3 bedroom/2 bath home with private pool in Naples Park is located 1/2 mile from the Vanderbilt beach and immediately down the street from the shopping and dining of the brand new Mercato lifestyle center, including Whole foods, movie theater, Blue Martini... View all property information
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    Naples, Southwest Gulf Coast 34108
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Greenlinks at Lely Resort was designed as a tropical haven for golf enthusiasts, complete with plenty of features to keep non-golfers happy too! Unit 924 is a 2 bedroom, 2 bath second floor condo which also has a den so it sleeps a total of 6 people comfortably. Extra amenities offered by this... View all property information
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    Naples, Southwest Gulf Coast 34113
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Greenlinks at Lely Resort was designed as a tropical haven for golf enthusiasts, complete with plenty of features to keep non-golfers happy too! Unit 911 is a 3 bedroom, 2 bath first floor condo which sleeps 6 people in beds. Extra amenities offered by this privately managed condo include a private... View all property information
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    Naples, Southwest Gulf Coast 34113
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • x
    • ?
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Rent Greenlinks Golf Villa Unit 1712, offered exclusively by The Holiday Life! Greenlinks at Lely Resort was designed as a tropical haven for golf enthusiasts, complete with plenty of features to keep non-golfers happy too! Unit 1712 is a 2 bedroom, 2 bath ground floor condo that sleeps 4 people... View all property information
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    Naples, Southwest Gulf Coast 34113
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    • Terrace
    • Washer
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    • Wi-Fi
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This well-decorated Trafalgar Square condo in Berkshire Village is centrally located within 15 minutes of beautiful beaches and downtown Naples with its world-famous restaurants and shopping. This picturesque, meticulously landscaped condominium community offers a heated outdoor swimming pool, gas... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34116
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The best location to vacation in all of Naples! This beautiful 3 bedroom/2 bath charming home is located 1/2 mile from the Vanderbilt beach and immediately down the street from the shopping and dining of the brand new Mercato lifestyle center, including Whole foods, movie theater and Trader Joe`s.... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34108
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Terrace
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Rent Greenlinks Golf Villa Unit 423, offered exclusively by The Holiday Life! Greenlinks at Lely Resort was designed as a tropical haven for golf enthusiasts, complete with plenty of resort features to keep non-golfers happty too! Unit 423 is a 2 bedroom, 2 bath second floor condo which has a den... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34113
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
    • Wi-Fi
    • Hot Tub
    • Terrace
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Park Shore Resorts prime location west of hwy 41 (Tamiami Trail) is within close proximity to restaurants, shopping, & famous downtown Naples. This sought after community is also convenient for walking, biking, or driving to nearby Clam Pass Beach. The resort offers free wifi inside and outside the... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34103
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Rent this 3 bedroom Greenlinks Golf Villa, offered exclusively by The Holiday Life! Greenlinks at Lely Resort was designed to be a tropical haven for golf enthusiasts, complete with plenty of features and a convenient Naples location to keep non-golfers happy too! Unit 1011 is a 3 bedroom, 2 bath... View all property information
    Location Information
    Naples, Southwest Gulf Coast 34113