The Holiday Life

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Naples, FL
The Holiday Life

The Holiday Life offers upscale vacation and seasonal home rentals in Naples & Marco Island, Florida Our company name gets us excited.

The Holiday Life is licensed and insured for short-term rental management and rated "Excellent" on TripAdvisor by past guests! Each of our beautifully appointed properties has something special to offer visitors to the Paradise Coast and comes equipped with the type of amenities and concierge services you’d expect at a fine hotel. All of our homes are privately owned and managed exclusively by The

Holiday Life. We value the time you set aside to relax, make memories with your family, or set out on an adventure so we treat our selection of homes with care to ensure that when you book with us, your holiday life is just what you want it to be. Please follow us on Facebook for updates on our property inventory and local happenings in Southwest Florida! For reservations and details, please visit our website: www.theholidaylife.com

05/30/2025

Welcome to Windward at Regatta 🥂
3 Beds | 2 Baths | 6 Guests

Resort-style weekly rental in North Naples at The Regatta on Vanderbilt Beach!🌴

Enjoy a tropical waterfall pool, lap pool, spa, tiki hut, and fitness center—just a short walk to the beach, Ritz Carlton, and top dining like Turtle Club & Baleen. Mercato shops & Whole Foods are only 2 miles away!

☀️Book your Summer vacation stay at The Windward at Regatta today — https://theholidaylife.com/882281/?beds=

05/28/2025

Welcome to Sea Winds 504 🌴

2 Beds | 2 Baths | 6 Guests
📍Located in Marco Island, is this newly renovated beachfront condo!

This is the prime location on Marco Island's south end - just next door is the Sunset Grille, where you can enjoy beachfront dining and drinks, while also just steps from the Sea Winds pool area and beach access path. Enjoy access to the tennis courts right on the property as well!🎾

Also walking distance, find an abundance of shops and restaurants at Marco Walk Plaza!🛍️

Book your Summer vacation at Sea Winds 504 today: https://theholidaylife.com/587151/?beds= #
✨Available for weekly rentals✨

05/23/2025

Memorial Day Flash Sale – Up to 15% Off! 🎉
�Kick off summer with The Holiday Life! 🌞 Book any time May 23–26 for stays through December 18, 2025, and save up to 15% with code HOLIDAYFLASH.

Whether you’re craving a beach weekend or a fall escape, now’s your chance to lock in your dream trip.

🌴 Use code: HOLIDAYFLASH�📅 Booking Dates: May 23–26�🏡 Stay Dates: Now–Dec 18, 2025�⚠️ Not valid on existing bookings or combined with other promos.

Book now → https://theholidaylife.com

05/16/2025

Mornings on Marco at Doreen’s Breakfast!🥞

From fluffy pancakes to island-style omelets, it’s the perfect way to start your day in paradise.

Staying with us at The Holiday Life? You’re just minutes away from this local gem!

05/06/2025

Stroll, shop, and savor the charm of Tin City — a must-visit waterfront destination in Naples! From the boutiques and local art to fresh seafood and boat tours, it’s the perfect way to spend a sunny Florida day. ☀️🌴

Even better? Holiday Life Luxury Vacation Rentals has beautiful properties just minutes away. Stay close to all the fun while enjoying the comfort and style you deserve.

📍Naples, FL

05/01/2025

Lunch on Third Street ✨

Dining at is an experience in every bite — fresh seafood + refreshing cocktails, right in the heart of Third Street South.

When you’re renting a Naples vacation home with The Holiday Life, you are just a short walk or quick drive to the most incredible shops, restaurants, and beaches!

04/22/2025

Sun, sand, and your own slice of luxury—Naples is calling! ☀️🌴

Make this summer unforgettable with a stay at Holiday Life Luxury Vacation Rentals. From sparkling private pools to pet-friendly homes and top-tier amenities, we’ve got everything you need for the perfect Florida escape.🥂

Why book with us?

✨Prime Naples locations
✨Beautifully curated homes
✨Personalized guest experience from start to finish
✨Your summer dream vacation starts here.

Book and explore all of our rentals on our website or on the Hopper app!🌴

04/18/2025

Date night at Alberto’s Fine Italian 🍝

Nothing says romance like a stay at one of our luxury vacation rentals in Naples paired with a candlelit dinner at Alberto’s Fine Italian in Naples. 🥂

From homemade pasta to fine wine, it’s the perfect setting for unforgettable moments.
Book your getaway, make your reservation, and let the sparks fly. ✨

04/12/2025

Summer plans in Southwest Florida 🌴☀️

Whether you’re dreaming of beach days, poolside lounging, or exploring the best of Southwest Florida, our family-friendly vacation rentals in Naples put you right where you want to be.

✨Now’s the time to book your summer getaway with The Holiday Life: https://theholidaylife.com

04/10/2025

Elevate your mornings with a curated coffee experience at — a hidden Naples treasure just minutes from your Holiday Life luxury rental. ☕️

Artful brews, cozy ambiance, and thoughtful details make it more than a coffee stop—it’s a lifestyle moment ✨

04/03/2025

Enjoying the beautiful views on Third Street South - Naples, Florida 🌴✨

Eat at all of the delicious restaurants, venture around the local shops, and enjoy the beautiful views of Third Street in downtown Naples.

02/05/2025

3 pet friendly beaches in Naples, Florida (save this post for later) 🐶☀️

🦴Keewaydin Island
Located in between Naples and Marco Island (only accessible by boat)

🦴Bonita Beach Dog Park
Located between Fort Myers Beach and Bonita Beach

🦴Delnor - Wiggins Pass State Park
Located in North Naples
(Leashed dogs are only allowed in certain areas here)

Address

3255 Tamiami Trl N
Naples, FL
34103

Website

http://www.theholidaylife.com/

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