Naples offers stunning beaches, engaging art galleries and performances, world-class dining, challenging golf courses and endless shopping experience. With all these options, it’s no wonder we are one of the top vacation destinations! Once you decide to visit Naples, picking the perfect vacation rental makes the rest of the trip that much better.

Pick a Locale

Imagine your perfect vacation; do you spend your days lounging by the beach, golfing or dining? Picking the right area of Naples guarantees you’ll be able to make the most of your trip.

Waldorf Condominium at Moorings Beach


We have plenty of stunning beachfront or beach-adjacent listings that offer some of the most celebrated beaches in the world just outside your door. Choose a home further south to be close to downtown Naples’ dining and shopping.

Beach Area Listings


A rare find! Live in luxurious coastal comfort directly on one of Naples best stretches of beach. This sprawling, newly renovated condo in the prestigious Waldorf building lives like a beachfront home and is appointed with the highest level of finishes and decor to offer a 5-star living experience.

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Olde Naples, reimagined for contemporary luxury living! Gulf Shore Grand is a brand new estate-style home nestled in the center of town just steps to the white sand gulf beach and only two blocks from 5th Ave S. The home is a modern masterpiece, featuring clean lines and the highest level of luxury finishes inside and out.

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The Olde Naples home you’ve been searching for! This completely renovated Florida home is set on a lushly landscaped lot just steps from the sugar sand gulf beach. The interior offers 3 bedrooms, 3 baths (2 en suite, plus a guest/pool bath!) a living room, dining room, open kitchen and den with sliders out to the pool area.

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Golf Course/Country Club

Are you looking to enjoy a quiet home away from home experience close to the links? Our golf course homes and condos offer complete relaxation and all the amenities you’d expect from a country club lifestyle.

Country Club Listings


Modern luxury at Fiddler’s Creek. This ground floor coach home in Cherry Oaks offers convenience and plenty of space for your seasonal stay. Light, contemporary style lends a sense of calm to this open floor plan which includes 3 bedrooms plus a den/TV room. A screened lanai, accessible from the living room, dining room and master overlooks a lushly landscaped area and the golf course beyond.

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The ultimate golfer’s destination…Watercourse Villa II is a spacious single family home in Talis Park, one of Naples’ most coveted club communities and comes with a fully transferable golf membership! Beautifully decorated in a contemporary Florida style, the home has calming feel of a luxury resort, inviting relaxation! An open great room offers views out to the West facing private pool, spa and yard space overlooking the lake.

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Our Waterlily golf villa is a newly updated condo in Lely Resort’s Greenlinks community, offered for rental exclusively through The Holiday Life! This end-unit has the luxury of the most desirable location within the community, offering a captivating golf course and lake view from the master bedroom and screened lanai.

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Downtown Naples

Downtown Naples is home to countless celebrated restaurants, boutique shopping experiences, and inviting artistic experiences all in a walkable waterside environment.

Downtown Listings


Experience the best of Naples in luxurious coastal style…this newly updated and impeccably furnished condo in the Cottages at Naples Bay Resort offers resort-style living right downtown. The Naples Bay Resort is an amenity-rich property ideally located on US 41 adjacent to historic Tin City and 5th Avenue South. The screened and covered balcony offers views of the lushly landscaped area outside and is furnished with a sectional sofa – perfect for enjoying the balmy breezes flowing in off of Naples Bay.

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Canary Cove Cottage is a private, tropical oasis nestled in the perfect location, right in the heart of Olde Naples! The classic Key West style home invites relaxed Florida living with all the modern amenities you could hope for in a beach house. Walk 2 blocks west to Third Street South, home of the renowned Naples farmer’s market, Tommy Bahama’s and many more elegant shops and eateries. Three more blocks west you’ll find yourself at the pristine white sand beach and historic Naples Pier – a community landmark!

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La Galleria Loft is a spacious Olde Naples apartment perched directly above our beach town’s most charming shopping and dining district, 3rd Street South. Completely renovated to a designer luxury standard, the loft apartment offers the ultimate in downtown living with fabulous amenities including a private 2-car garage, a huge screened and covered outdoor living room with a hot tub, wet bar and TV and a sun deck with chaise lounges.

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Feeling overwhelmed?

We’re local experts and are happy to help you find the perfect luxury vacation rental. Call us at (239) 349-2494 or send us an email at for help with your holiday.

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