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Olde Naples 5th Ave S Penthouse

Photo gallery for Olde Naples 5th Ave S Penthouse

Pool
Living area
Exterior
The patio overlooking 5th Avenue
Pool

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 5

Popular amenities

  • Indoor pool
  • Spa pool on site
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View map
Naples, FL
  • Place, Fifth Avenue South
    ‪1 min walk‬
  • Place, Naples Beach
    ‪10 min walk‬
  • Place, Tin City
    ‪12 min walk‬
  • Airport, Fort Myers, FL (RSW-Southwest Florida Intl.)
    ‪50 min drive‬

Rooms & beds

2 bedrooms (sleeps 5)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

2 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Kitchen
Office
Balcony
Garden
Dining area

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 area

Naples

Located near the beach, this condo is in Old Naples, a neighbourhood in Naples. Shoppers can check out Fifth Avenue South, while everyone can enjoy the natural beauty of Naples Beach and Vanderbilt Beach. Looking to enjoy an event or a game while in town? See what's happening at USOP National Pickleball Center or Swamp Buggy Races. Take the opportunity to explore the area for outdoor excitement like cycling.
Map
Naples, FL

What's nearby

  • Fifth Avenue South - 1 min walk - 0.0 km
  • Cambier Park - 3 min walk - 0.3 km
  • Naples Beach - 10 min walk - 0.9 km
  • Tin City - 12 min walk - 1.0 km
  • Naples Pier - 18 min walk - 1.6 km

Getting around

  • Fort Myers, FL (RSW-Southwest Florida Intl.) - 40 min drive

Restaurants

  • ‪Starbucks - ‬4 min walk
  • ‪Vergina - ‬2 min walk
  • ‪Osteria Tulia - ‬3 min walk
  • ‪Caffe Milano - ‬4 min walk
  • ‪5th avenue coffee company - ‬1 min walk

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 5 out of 6 reviews
Rating 8 - Good. 1 out of 6 reviews
Rating 6 - Okay. 0 out of 6 reviews
Rating 4 - Poor. 0 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

8.0/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jon M.

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
Verified

10/10 Excellent

Penny C.

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

8/10 Good

RoseLynn M.

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

laura h.

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.
From a partner site

10/10 Excellent

laura h.

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

10/10 Excellent

Bill S.

Stayed 27 nights in Feb 2026
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