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Entire condo

Olde Naples 5th Ave S Penthouse

Photo gallery for Olde Naples 5th Ave S Penthouse

A beach with a pier extending into the water, sandy shore, and people walking along the beach. - Olde Naples 5th Ave S Penthouse (Naples)
A modern kitchen with wooden cabinets, a black countertop, and pendant lighting. - Olde Naples 5th Ave S Penthouse (Naples)
A wooden deck with railings, benches, and a pergola overhead. - Olde Naples 5th Ave S Penthouse (Naples)
A hotel with a red and white striped awning, palm trees, and a street view with cars and pedestrians. - Olde Naples 5th Ave S Penthouse (Naples)
A bedroom with a large bed, a nightstand with a lamp, a ceiling fan, and a window with curtains. - Olde Naples 5th Ave S Penthouse (Naples)
Experience the epitome of luxury in Naples with a stay at your own penthouse overlooking Olde Naples 5th Avenue. Relax by the pool or unwind in the spa, both steps from your front door, and enjoy people-watching on your private balcony.

Reviews

9.8 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 5

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • 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.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Hot tub

Internet

  • Available in the condo: WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shower

Living spaces

  • Dining table

Entertainment

  • TV

Outdoor areas

  • Balcony
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Things to do

  • Cycling nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden

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Exterior
La Quinta Inn & Suites by Wyndham Naples Downtown
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  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
8.2 out of 10, Very good, 2,052 reviews
The price is €69
includes taxes & fees
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Rental Agreement and Homeowners Association Application required for all tenants 18+. Booking includes fees for two adults 18+ and tenant will be r...

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

About the area

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. 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 beach with white sand, turquoise water, and a rocky area in the foreground. There are palm trees and a building 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 a wooden pier extending into the ocean, a person walking along the shore, and a sunset in the background.
    Naples Pier
    18 min walk - 1.6 km
  • Cambier Park
    3 min walk - 0.3 km

Getting around

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

Restaurants

  • Starbucks
    4 min walk
  • Slice
    3 min walk
  • Osteria Tulia
    3 min walk
  • Caffe Milano
    4 min walk
  • 5th avenue coffee company
    1 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?

Checkout 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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Olde Naples 5th Ave S Penthouse Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

8.0

Cleanliness

10

Location

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
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.
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.

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