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LUXURY VACATION RENTALS Resort-Style Service With The Comforts Of Home

LUXURY VACATION RENTALS Resort-Style Service With The Comforts Of Home


The Holiday Life offers upscale vacation and seasonal home rentals along Southwest Florida’s Paradise Coast. From Marco Island and Naples, each of our beautifully appointed private properties offers guests a unique and authentically local experience paired with the service and amenities you’d expect at a fine hotel.

Our Approach and Key Prinicples


All properties in our portfolio meet detailed maintenance, furnishing, and amenities requirements that we have developed based on experience and guest feedback over the past decade. We know what goes into a comfortable stay and we don’t represent anything less!


We take the hassle out of short term rental ownership by managing the entire process, making our program ideal for absentee vacation homeowners and investors. We handle marketing, booking, the detailed guest turnover cleaning and inspection process, and providing thorough owner reporting on rental activity and financials.


Our local team is available seven days a week to ensure guest needs are promptly met throughout the stay. We have dedicated property services coordinators out in the field inspecting our units and providing exceptional guest services upon request.

Featured Developments

So|Ce Flats NAPLES, FL

Olde Naples…reimagined for the modern lifestyle! SoCe Flats is an exciting new condominium development in the most desirable neighborhood in Naples, the Paradise Coast’s most coveted beach town. SoCe, named for the ideal location South of Central Avenue in Olde Naples, offers the unique opportunity for a luxurious short-term vacation stay, walking distance to both the beach and the elegant 5th Ave S shopping and dining district.

GreenLinks Golf Villas at Lely Resort NAPLES, FL

Centrally located in a resort community 15 minutes from downtown Naples and Marco Island. GreenLinks Resort features fully furnished 2 & 3 bedroom villas surrounded by 36 holes of championship golf, a resort-style swimming pool, and an on-site restaurant.

Marco Beach Ocean Resort MARCO ISLAND, FL

Privately managed hotel condos in a luxury boutique setting directly on Marco Island’s white sand beach. Onsite dining is available at the casual beachside bar and grill and at Sale e Pepe, Marco Island’s only AAA Four Diamond restaurant, offering authentic Italian cuisine and an award-winning 500+ label wine list.

Owner & Guest Testimonials


Peter Jahn


"Casey and the Holiday Life team has made my decision to rent my house an easy one. Casey is extremely professional, dedicated and great to work with. When ever there is an issue (which is seldom) Casey can be counted on to go above and beyond for both me and renters of my house. I would recommend The Holiday Life and Casey to anyone. If I ever need to rent a vacation home, I am using The Holiday Life."


Kyle O'Neill


"Casey provided my family with one of the most exceptional vacation experiences while visiting Marco island. Her attention to detail and willingness to go above and beyond for her clients is the reason why we will only use The Holiday Life for any of our vacation needs!"


Sue Elsasser


"We have loved working with Casey these past few months since we joined The Holiday Life. After having two rental agents who did not look out for their owners, we feel Casey is doing a great job and cares for her owners as well as prospective clients. We look forward to a long relationship with her, and would strongly recommend The Holiday Life for vacation plans in SW Florida."


Vincent Fiscella


As always excellent. The best

Featured Properties

Recent Blog Posts

In the Aftermath of Hurricane Ian

First and foremost, The Holiday Life hopes you and your loved ones are safe and sound. We are heartbroken over the devastation throughout our community and the coastal areas impacted by Hurricane Ian, and sympathize with all who have lost loved ones or experienced displacement or irreversible damage to their property. We are still working assessing damage mitigation to our properties and figuring out how to best help our community,...


Historical Landmarks in Olde Naples

Staying in Olde Naples is often a lavish adventure. Olde Naples is a charming combination of old beach cottages and mansions resting peacefully among hundreds of tall coconut palms and banyan trees. Some of the houses are almost 100 years old! This Florida neighborhood known as Olde Naples does not have a precise location. It is, however, between the Third Street South shopping area and the Naples Beach Hotel and...


Summer in Southwest Florida? Activities to stay cool during your stay

Everyone loves the clean beaches, beautiful outdoor sights, and perfect tanning summer weather in Southwest Florida, but how do you beat the summer heat when out of the water? Are you looking for a break from the pool or beaches during your summer vacation? We’ve put together a list of activities that will keep you busy without being overwhelmed by the heat. Visit a historical Museum Visiting a historical museum...


THE HOLIDAY LIFE Homeowner Services

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(239) 349-2494

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