Entire condo

Olde Naples 5th Ave S Penthouse

Photo gallery for Olde Naples 5th Ave S Penthouse

A spacious living room with a large sofa, a coffee table, and a television on a cabinet. - Olde Naples 5th Ave S Penthouse (Naples)
A rooftop pool with red and white lounge chairs, a pool ladder, and a white railing. - Olde Naples 5th Ave S Penthouse (Naples)
A modern living room with a sofa, coffee table, TV, and a ceiling fan. - Olde Naples 5th Ave S Penthouse (Naples)
A modern kitchen with wooden cabinets, a gas stove, and a dishwasher. - Olde Naples 5th Ave S Penthouse (Naples)
A beach with a pier extending into the water, sandy shore, and people walking along the beach. - Olde Naples 5th Ave S Penthouse (Naples)
Near Fifth Avenue South and Naples Beach, Olde Naples 5th Ave S Penthouse provides a garden, laundry facilities, and a hot tub. Stay connected with in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning

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About this property

Olde Naples 5th Ave S Penthouse

  • Summary:

    Enjoy the life of luxury in the heartbeat of Naples in your own high end penthouse overlooking Naples 5th Ave. 5th Ave offers world class fine dining and shopping. Just a few blocks away lies the beautiful white sand beaches of Naples. To the south, you'll find the famous Naples Pier. Relax in the pool or spa right across from your front door, enjoy people watching from your own private balcony. Your rental includes beach chairs, bikes, and more!



    Guest Access:

    Guests will have one reserved parking spot, access to the rooftop communal pool and hot tub (only shared between 8 units!), communal BBQ grill, owner storage room with bikes and beach gear!



    The Neighborhood:

    Located directly on Old Naples Downtown 5th Avenue! Guests will find the area very walkable.



    Getting Around:

    Walking distance to Naples fine dining and shopping. Guests will have access to one reserve parking spot. Only 5 blocks from the beach!



    Other Things to Note:

    Please note our exclusive condo does require an online rental application that must be approved 20 days before check in! This application is $150 per person 18+ or $150 for married couples. This screening application does require you to enter personal information, driver's license / passport information, SSN, and vehicle information (if applicable.) Upon booking, we will send you a link to complete the application and send you a rental agreement via Docusign.

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About the neighborhood

Located near the beach, this condo is in Old Naples, a neighborhood in Naples. Shoppers can check out Fifth Avenue South, while everyone can enjoy the natural beauty of Naples Beach and Vanderbilt Beach. Ready for a night out? Consider Dimension Nightclub and Shula's Steak House. Take an opportunity to explore the area for outdoor excitement like cycling. Visit our Naples travel guide
View more Condo Rentals in Naples
Map
Naples, FL

What's nearby

  • A bustling street with palm trees, a yellow building, and people walking.
    Fifth Avenue South
    1 min walk - 0.0 km
  • A wooden pier extending into the sea with a sunset in the background.
    Naples Beach
    10 min walk - 0.9 km
  • A red barn with a blue door and a wooden staircase leading up to it.
    Tin City
    12 min walk - 1.0 km
  • A beach with people walking and a pier extending into the water.
    Naples Pier
    18 min walk - 1.6 km
  • Cambier Park
    3 min walk - 0.3 km

Getting around

  • Southwest Florida Intl. Airport (RSW)
    40 min drive

Restaurants

  • Starbucks
    4 min walk
  • Slice
    3 min walk
  • 5th avenue coffee company
    1 min walk
  • Caffe Milano
    4 min walk
  • Del Mar
    3 min walk

Frequently asked questions

Does Olde Naples 5th Ave S Penthouse have a pool?

Yes, this property has a pool.

Is Olde Naples 5th Ave S Penthouse pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Olde Naples 5th Ave S Penthouse?

Check-in begins at 4:00 PM.

What time is check-out at Olde Naples 5th Ave S Penthouse?

Check-out is at 10:00 AM.

Where is Olde Naples 5th Ave S Penthouse located?

Located in Old Naples, this condo building is within a 15-minute walk of Fifth Avenue South and Naples Beach. Cambier Park and Norris Center are also within 10 minutes.

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Reviews

Olde Naples 5th Ave S Penthouse Reviews

9.8

Exceptional

8.0

Cleanliness

10

Location
Rating 10 - Excellent. 6 out of 7 reviews
Rating 8 - Good. 1 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Heart of Naples!

Great weather, beautiful co.ndo! Beach, restaurants, shops all within walking distance. Swimming pool right outside the door. The rental agency was professional and very responsive.
Stayed 56 nights in Feb 2025
From a partner site

10/10 Excellent

My absolute favorite repeat retreat

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Found this amazing place 3 years ago, and never looked back. You want for nothing...the amenities, the 's all there. The kitchen is fabulous as someone who loves to cook, the peaceful rooftop pool, a fun balcony to people watch, best location for a 5 mile daily walk! And the beach is right at the end of the avenue. Great coffee shop below, lovely and friendly neighbors. Simply won't look elsewhere. Hannah and team get an A+ for response time and communication! Love it here.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!!

The only reason I didn't give 5 stars all the way was I found a few hairs on the bathroom counter which is a pretty peeve of mine
Stayed 7 nights in May 2022
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
The real-estate mantra about location, location, location applies to this condo more than any other condo we've ever rented in Naples. In the heart of 5th Ave. S, it is a perfect spot, and we loved it. The host was very helpful providing everything we asked for, but there is a need for improvements in the following areas - clean rugs, better seating in the living area, newer sheets (they have seen better days), a toaster that works in all 4 slots, the dining table and coffee table are pockmarked and unsightly, and most important - grab bars are needed in the showers. This is an expensive property, and the renter deserves better amenities.
Stayed 14 nights in Jan 2026
From a partner site

10/10 Excellent

Blissful retreat, what more could I want?

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Another absolutely delightful stay at 555 5th! The location is so central to everything from the beach, shops, 3rd St to my favorite morning diner! A delightful walkable neighborhood whether you choose Gulfshore drive, a beach stroll or exploring the neighborhood streets. Everything is so picturesque. The condo feels like a vacation all it's own... rooftop pool steps from the door, a fabulous balcony overlooking 5th really is pretty amazing. This condo spoils me when it comes to other places. I shall return again. The management team is first class and so easy to work with. I enjoyed meeting Hannah and she created such a seamless process. I could go one and on...the condo won't leave you wanting for anything! It's gorgeous and well equipped. Bravo!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 21 nights in Mar 2026
Verified review

10/10 Excellent

Stayed 27 nights in Feb 2026