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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

Effortless Escapes. Elevated Stays.

Your escape begins here—where every detail is curated for comfort, style, and coastal ease.

At The Holiday Life, we create exceptional vacation experiences in some of Southwest Florida’s most sought-after destinations. Whether you’re planning a quiet family getaway, a sun-soaked celebration, or a season of remote work by the sea, our handpicked homes offer more than just a place to stay—they offer a feeling of home, elevated.

From the moment you book to the day you depart, our local team is here to make your stay seamless. Expect beautifully maintained properties, personalized touches, and concierge-style service designed to help you relax, recharge, and make the most of your time away.

Coastal Stays, Curated for You.
This is The Holiday Life.

FIND YOUR ESCAPE

Beachfront Rentals

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Gulf Access Waterfront Rentals

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Single Family Pool Home Rentals

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Private Club Community Rentals

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Walk to Beach Rentals

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Walk to Town Rentals

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Your Personal Concierge: Elevate Your Rental Experience

Experience effortless living with our personalized Concierge Services—designed exclusively for renters who want more than just a place to stay. From pre-arrival grocery stocking and professional cleaning to coordinating bike and golf cart rentals, our dedicated team handles all the little details so you can focus on enjoying your stay. Need a welcome basket filled with locally sourced treats? We’ve got it covered. Want seamless delivery and setup of amenities before you arrive? Consider it done. Our concierge service transforms your rental experience into a stress-free, luxury retreat tailored just for you.

Book Your Concierge Experience

Spotlight on Signature Communities

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The Mark on 8thNaples, FL

Located just off Fifth Avenue South and minutes from the beach, The Mark blends modern luxury with unbeatable walkability in Old Naples. Enjoy stylish residences with access to a resort-style pool, fitness center, and golf simulator—all available with flexible weekly rentals.

Luxury Meets Location

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GreenLinks Golf Villas at Lely ResortNaples, FL

Experience the resort-style club lifestyle at GreenLinks, where golf, dining, and relaxation come together. Enjoy on-site access to championship courses, a clubhouse restaurant, and flexible rental options—all surrounded by lush, tropical scenery.

Where Club Living Meets Vacation Flexibility

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Refined Stays. Trusted Partnerships. Real Words.Owner & Guest Testimonials

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Kevin Z

Guest

Everything was seamless—beautiful home, spotless and stylish, with thoughtful touches throughout. Dan and the team made us feel like VIPs.

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Sylvia G

Owner

Professional, responsive, and trustworthy. Dan treats our property like it’s his own.

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Louis M

Guest

The Holiday Life went above and beyond. Incredible property, easy check-in, and prompt, friendly communication.

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Jason J

Owner

The Holiday Life delivers five-star service—for both guests and owners. We’re beyond impressed.

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David C

Guest

Luxury-level service with a local, personal feel. Dan and Kelly made sure everything was perfect.

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Joey C

Owner

Dan and his team are pros. Our home is consistently booked, immaculately cared for, and we have total peace of mind.

Luxury Management for Exceptional Homes

Whether it’s your family vacation home, future retirement escape or investment property, our dedicated local team takes the hassle out of short-term rental ownership. From professional marketing and guest communication to maintenance coordination and five-star hospitality touches, we handle every detail—so you can enjoy the rewards of ownership without the day-to-day demands.

Discover Our Services

THE HOLIDAY LIFEHomeowner Services

Give Us A Call At:

(239) 349-2494

Free Rental Evaluation

Discover Your Property’s True Potential

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Featured Properties

Mariana Court

  • 5 Beds
  • 3 Baths
  • 10 Guests

Neapolitan Sky

  • 6 Beds
  • 6 Baths
  • 12 Guests

Esperanza 102 at Tiburon

  • 3 Beds
  • 3.6 Baths
  • 6 Guests

Sea Winds 504

  • 2 Beds
  • 2 Baths
  • 6 Guests

From the Coast: Insights & StoriesDiscover coastal secrets and insider tips for your best stay yet.

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,...

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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...

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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...

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