Welcome to Our Naples Family
5+
Who We Are
Naples-Based Superhosts. 4.95★ & 4.96★ Approaching 400 Five-Star Reviews. Two Exceptional Homes.
Meet Your Hosts
Naples Holiday Houses was built on a simple belief: vacation rentals should feel like a five-star experience without the five-star price tag. We stock our homes like we're the guests - quality coffee, real cookware, beach gear, bikes, board games, and pool floats. We respond fast. Every time.
Whether you're a family of eight needing bikes and beach gear, a group of couples wanting private pool time, or a snowbird extending the season - we have the perfect home for you. And when you book direct through naplesholidayhouses.com, you keep 10% more of your vacation budget.
- Airbnb Superhosts since 2021
- 4.95★ & 4.96★ (Almost 400 5-Star Reviews!)
- Top 5% of all homes on Airbnb
- 100% response rate
- 5★ for Accuracy, Amenities, Cleanliness, &Communication
The Real Estate Team
About Matt Brown
Matt's Bio: Matt Brown is a luxury real estate advisor with William Raveis Real Estate, a brokerage ranked among the Top 100 Luxury Real Estate Brokers in the World and named Best Real Estate Luxury Brokerage in Florida for 2025 by Luxury Lifestyle Awards. Over a 23+ year career, he has closed more than $700 million in residential sales across Florida and New Jersey, including over $50 million in 2024. RealTrends Verified has ranked him #922 nationally and #13 in Naples by sales volume (2024), placing him in the Top 1.5% of agents nationwide (2025). He was also named one of the Top 50 Naples Real Producers for 2025 and Top Realtor 2026 by Haute Living.
Owning and managing Naples Holiday Houses is an extension of that same approach. Matt and Lindsey handle both properties directly, with the same attention to detail and client care that defines the real estate practice. When you stay with us, you are not dealing with a management company. You are working with owners who know Naples deeply and care about your experience.
Outside of real estate and hosting, Matt is a golfer, boater, and family man who supports local organizations including Grow Church, the Conservancy of Southwest Florida, and Captains for Clean Water. He and Lindsey relocated from Jersey City, New Jersey to Naples in 2018 with their two daughters, drawn by the Gulf Coast lifestyle they now share with every guest who walks through our doors.
Know More About Matt
Our Properties
Browse Our Properties
Each property offers a unique Naples experience. Beach proximity or pet-friendly paradise, find your perfect match.
Naples Holiday House
Parrot Holiday House
Why Us
Our Commitment to You
Every guest is treated like family with our white-glove service approach.
Personal Touch
We personally oversee every aspect of your stay, from pre-arrival communication to ensuring your home is perfectly prepared.
24/7 Support
Questions at midnight? Need restaurant recommendations? We're always just a message away, ready to help.
Quality Guaranteed
Professional cleaning, regular maintenance, and quality amenities ensure your comfort throughout your stay.
Your Local Naples Experts
After years of exploring every corner of Naples, we’ve compiled the ultimate insider’s guide for our guests. From the best sunset spots to hidden restaurant gems, we share it all.
Every guest receives our curated Naples guidebook with personalized recommendations based on their interests — whether you’re seeking adventure, relaxation, family fun, or culinary experiences.
- Best Beaches
- Family Activities
- Top Restaurants
- Hidden Gems
Best of Naples
Best of Naples
Taste the best of
traditional cuisine
Let yourself be delighted with the range of content available about Naples and Naples activities.
Best Naples Beaches + : Where Sunsets Paint The Sky
Discover the best beaches in Naples and Southwest Florida, where warm waters, sunny skies, and stunning shorelines await.
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Top Ice Cream Shops in Naples, Florida: A Guide for Dessert Lovers
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Top 15 Public Golf Courses in Naples, FL
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Upscale Waterfront Restaurants In Naples, FL
Discover upscale waterfront restaurants for fine dining with ocean views, fresh seafood, and elegant ambiance.
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Naples Family Activities
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Healthy Dining Options in Naples, Florida: From Vegan Cafes to Organic Restaurants
Discover Naples’ best organic and healthy food spots, from farm-to-table eateries to vegan and gluten-free options.
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Top Parks in Naples, Florida: Nature, Family Fun & Outdoor Living
Naples, Florida, offers a lifestyle built around sunshine, comfort, and outdoor living.
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Naples Florida Art Scene
Explore Naples, Florida’s art scene with us! Each year, Naples witnesses an influx of individuals from all over…
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Naples Organic Grocery Stores and Apothecaries
Explore Naples’ best organic grocery stores and apothecaries for fresh produce and natural skincare.
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Shopping Paradise in Naples, FL
Shopping Paradise in Naples, FL: Top Malls, Boutiques & Lifestyle Destinations
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Top Marinas in Naples and Bonita Springs: Ultimate Boating Guide
Discover the best marinas in Naples and Bonita Springs, each offering unique amenities like boat slips, fuel services
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12 Best Spa in Naples, Florida
Renowned for high end spas in Southwest Florida, Naples is one of the premier places in the country…
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