Luxury Vacation Rentals with a Private Pool in Naples

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 19 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Naples

Home in Naples

2 bedrooms•2 baths

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Home in Naples

3 bedrooms•3 baths

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Home in Marco Island

4 bedrooms•3 baths

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Luxury

Home in Marco Island

3 bedrooms•3 baths

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Wander Marco Island Villa

4 bedrooms•4 baths

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Luxury

Home in Marco Island

3 bedrooms•3 baths

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Home in Naples

3 bedrooms•2 baths

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New

Home in Marco Island

5 bedrooms•3 baths

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New

Welcome to private poolside luxury in Naples

Escape to Naples with Wander. Our collection of luxury private pool vacation rentals in Naples, Florida brings the ease of a five-star stay to the comfort of a private home.

Swim in your own crystal-clear pool, professionally maintained and often heated, framed by generous patios for lounging and long afternoons in the sun. Inside, expect chef-ready kitchens, plush bedding, dedicated workstations, and ultra fast WiFi for seamless remote work and streaming.

Every stay includes pristine cleaning, 24/7 concierge, and thoughtful smart-home features. What you see is exactly what you get, so you can arrive relaxed and settle straight into vacation mode.

Available soon in Naples

Home in Naples

2 bedrooms•2 baths

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Home in Naples

3 bedrooms•3 baths

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Home in Marco Island

4 bedrooms•3 baths

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Luxury

Home in Marco Island

3 bedrooms•3 baths

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Luxury

Home in Marco Island

3 bedrooms•3 baths

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Home in Marco Island

5 bedrooms•3 baths

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New

Luxury

Home in Marco Island

5 bedrooms•3 baths

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New

Home in North Naples

3 bedrooms•2 baths

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New

Featured private pool vacation rentals in Naples

Home in Marco Island

4 bedrooms•4.5 baths

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New

Highlights in Naples

Discover Naples' pristine white-sand beaches, upscale shopping districts, and lush tropical gardens along Florida's paradise coast.

Naples Pier

Fifth Avenue South

Naples Botanical Garden

Naples Zoo at Caribbean Gardens

Tin City Waterfront Shops

Clam Pass Park

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Naples

Home in Naples

2 bedrooms•2 baths

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Home in Naples

3 bedrooms•3 baths

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Home in Marco Island

4 bedrooms•3 baths

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Luxury

Home in Marco Island

3 bedrooms•3 baths

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Wander Marco Island Villa

4 bedrooms•4 baths

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Luxury

Home in Marco Island

3 bedrooms•3 baths

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Home in Naples

3 bedrooms•2 baths

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New

Home in Marco Island

5 bedrooms•3 baths

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New

View all homes

Most popular amenities for private pool vacation rentals in Naples

Beach essentials (14)

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Discover more beyond the pool in Naples

On the Gulf of Mexico, Naples pairs sugar-soft beaches with coastal sophistication. Sunrise tee times, Naples Pier sunsets, and palm-lined streets set an unhurried rhythm along Fifth Avenue South and Third Street South.

Glide past mangroves in Rookery Bay, boat to shell-strewn Keewaydin Island, or venture toward the Everglades for unforgettable wildlife. With calm surf, clear light, and a thriving arts scene, the city excels in every season. This is why Wander's luxury vacation rentals in Naples, Florida are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Naples

Why should I book a Wander in Naples over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.

Every home in Naples delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Naples?

Some of our most popular private pool vacation rentals in Naples include GreenLinks Retreat - Pool, Hot Tub, Tennis, Golf, Sports Ranch Luxe Estate, and Amazing 4 bed 3 bath Marco Island home w/ Heated Pool. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Naples?

Wander offers 19 private pool vacation rentals in Naples, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Naples?

You can check-in to Wander private pool vacation rentals in Naples after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Naples have WiFi access?

Yes. Every Wander home in Naples has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.