2 Bedrooms, 2 Blocks to Gulf, Boutique Shopping, Arts and Dining in Old Naples.
The Upstair's Retreat can be found on the Historic Coquina Cottage Estate. Located at the corner of Broad Ave S and Gordon Drive, we are within walking distance to the water and all that Old Naples is renowned for. This Historic Estate features five separate rentals on the property: The Main House, The Upstair's Retreat, and Cottages A, B, and C.
*** Each rental has its own ID # and can be viewed by putting the ID # in the guest's "Where To" finder.
Main House #3984466: Is an independent rental that offers a king and a queen bedroom, with ensuite bathrooms, kitchen, extra sitting room, deck, and brick patio.
The Upstairs Retreat #3947948: Is an independent rental that offers 2 kings bedrooms, 1 bathroom, kitchen, laundry, and porch.
Cottage A #3980277: Queen efficiency with no stove or laundry. With a non covered porch.
Cottage B #3980383: King bedroom with a sitting room, 1 bathroom, kitchen, laundry, covered porch, and brick patio.
Cottage C #3980651: Is a studio with a Queen bed, 1 bathroom, kitchen, laundry, and brick patio.
You will enter The Upstair's Retreat by parking in the shared driveway and following the shelled path that runs parallel to Broad Ave S. to the back side of the Main House where you will find your brick landing and entrance.
The Upstair's Retreat is an independent rental. You will only see other guests in the shared spaces - The driveway, the greens and garden, the trash area, and the grill space where extra beach supplies live.
Once you unlock your door with a code, you will enter a hallway where we keep your beach supplies. The stairway is approximately 16 steps up, leading to the second floor /The Upstairs Retreat. The door at the top of the stairs must remain closed at all times to ensure the air conditioning works properly. When left open for even a short amount of time, the system needs to work harder to keep up.
The Upstairs has an open floor plan, cathedral ceilings with two large airplane fans, central air conditioning and heating, a mounted television, a desk, antiques, art, and a comfortable seating arrangement.
A large, white marble counter flows around the kitchen workspace, forming the four-seat bar area. The kitchen includes a four-burner stove, deep farmhouse sink, built-in under-the-counter refrigerator and freezer units and cabinetry. The wall of windows behind the sink allows for beautiful views of the grounds and the night sky. We recently added white wooden shades that help with the sun that pours in.
There are two king bedrooms in the Upstairs Retreat. On king bedroom, with a dresser, comfortable chair and small closet is located on the Broad Avenue S, side of the property. The second king bedroom faces Gordon Drive and over looks the driveway. This bedroom has an antique desk, a dresser, smart television bed side tables and a walk in closet.
Adjacent to the kitchen is the utility room with a stackable laundry. We ask guests to no run the machines after 8 pm to ensure that the downstairs guests do not hear any buzzers. We store cleaning supplies, and the Wi-Fi router for the property.
The one bathroom is directly across the kitchen, with a step-up. The tub/shower combination functions well. Below a wall-mounted mirror, the marble vanity features a single sink wth the bath linens stored beneath. The toilet is tucked in behind this mirrored wall.
We supply beach chairs, beach umbrella, beach bag, an insulated cooler and Igloo ice packs. We work very hard to keep weather umbrellas stocked, but often loose them to guests walk about. Games and books are also available.
We have built a spot on the grass with Adirondack Chairs and a large umbrella for you. The brick landing also has a small metal table and chairs for coffee.
Due to the location and this being one of five rentals, we are not pet-friendly. We appreciate you following our guidelines and trusting that we are acting in the best interest of all our guests.
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BEAUTIFUL, PERFECT LOCATION ON 5TH AVENUE~1.5 BLOCK FROM BEACH, DINING, SHOPPING
Old Naples
BEAUTIFUL, PERFECT LOCATION ON 5TH AVENUE~1.5 BLOCK FROM BEACH, DINING, SHOPPING
The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds, gather used towels and store extra beds
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Thank you for putting all trash in tied plastic bags. It really helps in this hot climate
Turn the air conditioning to 74 please.
Failure to complete these may result in a negative review from the host.
Please read and acknowledge the Rental Agreement to ensure that we are all on the same page.
No animals on the property.
No flame or smoking on or in the property.
Important information
You need to know
Property # 3947948vb
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
Long-term renters welcome
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, a first aid kit and a deadlock
About the area
Naples
Located near the beach, this apartment 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. Ready for a night out? Consider Dimension Nightclub and Off The Hook Comedy Club. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and horse riding nearby.
Naples Historical Society's Historic Palm Cottage - 2 min walk - 0.2 km
Naples Pier - 3 min walk - 0.3 km
Naples Beach - 3 min walk - 0.3 km
Fifth Avenue South - 9 min walk - 0.8 km
Getting around
Fort Myers, FL (RSW-Southwest Florida Intl.) - 47 min drive
Restaurants
Slice - 18 min walk
5th avenue coffee company - 17 min walk
The Dock At Crayton Cove - 13 min walk
Del Mar - 15 min walk
Vergina - 19 min walk
Frequently asked questions
Is 2 Bedrooms, 2 Blocks to Gulf, Boutique Shopping, Arts and Dining in Old Naples. pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at 2 Bedrooms, 2 Blocks to Gulf, Boutique Shopping, Arts and Dining in Old Naples.?
As of 15 Oct 2026, prices found for a 1-night stay for 2 adults at 2 Bedrooms, 2 Blocks to Gulf, Boutique Shopping, Arts and Dining in Old Naples. on 20 Nov 2026 start from AU$8,239, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at 2 Bedrooms, 2 Blocks to Gulf, Boutique Shopping, Arts and Dining in Old Naples.?
On-site parking is available at the property.
What time is check-in at 2 Bedrooms, 2 Blocks to Gulf, Boutique Shopping, Arts and Dining in Old Naples.?
Check-in begins at 4:00 PM.
What time is check-out at 2 Bedrooms, 2 Blocks to Gulf, Boutique Shopping, Arts and Dining in Old Naples.?
Checkout is at 10:00 AM.
Where is 2 Bedrooms, 2 Blocks to Gulf, Boutique Shopping, Arts and Dining in Old Naples. located?
Located in Old Naples, this apartment building is within a 5-minute walk of Third Street South, Naples Beach and Naples Pier. Fifth Avenue South is 0.5 mi (0.8 km) away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We had a wonderful stay at this house, literally a 3 minute walk to the beach, also a very short walk to 3rd Avenue and 5th Avenue where all the great restaurants and shops are, the house is decorated beautifully, with some very very nice mid century modern antiques and any questions we had were responded to immediately, just a really nice visit all around
This was the single most CLEAN and WELL-STOCKED Vacation Rental we've ever stayed in, EVER, and we have stayed in many from coast-to-coast and top-to-bottom of the USA over the last 30 years! It's a great apartment with a great location, minutes from a great beach!!! 100% recommendation.
This is a wonderful place to relax in lovely surroundings. You can walk right out into the pretty neighborhood, take a short stroll down to the beach, or walk to the shops and great restaurants on Third Street.
Stayed 5 nights in Sep 2024
Response from VrboOwner on 25 Sept 2024
Thank you, Daria, for your great review. The Upstairs is in a pretty, relaxing, and quiet neighborhood. I always overlook that as I focus on the white sands and the hopping downtown within blocks. Reach out if we can host you again. K
The location of the property was 1 1/2 blocks from the Gulf which was perfect. In addition, it was just a block from 3rd Street and walkable to 5th Avenue. The unit was comfortable and clean. Kate was wonderful with excellent communication skills and I would certainly stay at any VRBO in the future that she offered.
We love staying here. It’s the perfect location. There was a minor issue with the A/C but the house was quick to resolve. Easily one of the best vacations we’ve had.
Stayed 5 nights in Jun 2026
About the host
Hosted by Kate Williams-Hewitt
Hello—I have a great life. After 30 years of teaching and raising my family in Maine, I could spend more time with my mother and sister as they found unique properties in Florida and Nantucket, Massachusetts. They are equally talented in color, design, and scale - especially with historic properties. I do not have that eye, but I love taking care of the properties and sharing them with guests.
Why they chose this property
My mother and sister both love historic houses. This c.19120 estate has always been a favorite for years. When Pam Watson put it on the market, my sister was ready. It is two blocks from the beach and just a few blocks from Old Naples. What's not to love?
What makes this property unique
Besides the location, we have kept the c.1910 structure and beauty. Historical Florida Estates are vanishing...we honor the old and add highlights of new.
Languages:
English
Premier Host
They consistently provide great experiences for their guests