Naples · Florida’s Gulf Coast

Old Naples

Fifth Avenue South, Third Street South and the pier, all within a few blocks.

19 homes
0.2 mi to the Gulf
Direct Gulf access, no bridges

The original town grid, laid out in the 1880s and still walkable end to end. Galleries and restaurants on Third Street South, shopping on Fifth Avenue South, and the pier at the end of Twelfth Avenue.

Homes in Old Naples

19 homes

6 bedrooms · Sleeps 12

Second Avenue Cottage

Six bedrooms and eight baths spread across two stories give this Old Naples cottage room to gather, with a chef's kitchen, wine room and wet bar anchoring the great room for easy entertaining. Days settle around the pool and integrated spa, screened lanai and open porch, while the fenced yard and pool bath keep things simple for a group of twelve. Concierge service, four-car garage parking and high-speed Wi-Fi handle the rest, so the household can focus on the pool, not the logistics.

6 Bed
8 Bath
Sleeps 12

From $1,800 a night

Discover Second Avenue Cottage

5 bedrooms · Sleeps 10

The Fifth Avenue Residence

Old Naples living unfolds across three floors, with the screened lanai and outdoor kitchen sitting at the center of daily life alongside the heated pool and spa. Five bedrooms and seven baths give the group room to spread out, while the wine room and great room set the stage for evenings in. Partial Gulf glimpses reach past the landscaped corner lot, and concierge service handles the rest.

5 Bed
7 Bath
Sleeps 10

From $1,650 a night

Discover The Fifth Avenue Residence

4 bedrooms · Sleeps 8

Sabre Cay House

Wood floors and a wall of built-in cabinets set a calm tone across two stories of living space in Old Naples, with a den for quiet mornings and a family room for everyone else. Four bedrooms and five bathrooms give a group of eight room to spread out, while the chef's kitchen and gas cooktop keep dinner simple after a day at the private dock or in-ground pool. Concierge service, a two-car garage, and full laundry handle the rest, leaving the hot tub and landscaped grounds for the evening.

4 Bed
5 Bath
Sleeps 8

From $1,575 a night

Discover Sabre Cay House

5 bedrooms · Sleeps 10

Thirteenth Avenue House

Five bedrooms and six bathrooms spread across two stories give this Old Naples home room for ten guests to settle in without crowding. Mornings start at the outdoor kitchen beside the heated pool and spa, marble and wood floors carrying the flow from the chef's kitchen to the screened lanai. Evenings close in the wine room or by the outside fireplace, with concierge service and a three-car garage handling the rest.

5 Bed
6 Bath
Sleeps 10

From $1,575 a night

Discover Thirteenth Avenue House

5 bedrooms · Sleeps 10

Broad Avenue House

Five bedrooms and five and a half baths over 3,631 square feet, a block from the beach at the quiet end of Old Naples. Days here run short: sand in the morning, the avenues for lunch, back for the afternoon. The pool and the lanai sit behind the house, out of the street.

5 Bed
5.5 Bath
Sleeps 10

From $1,500 a night

Discover Broad Avenue House

4 bedrooms · Sleeps 8

Eighth Avenue House

Four bedrooms and six baths spread across two stories give this Old Naples home room to gather without crowding, with a great room, wet bar, and wine cooler ready for the group to settle in. Days move outside easily, from the screened lanai and outdoor kitchen to the salt-water pool and heated spa overlooking the lake, all enclosed behind a fenced yard for peace of mind. Evenings settle by the outdoor fireplace, dinner handled on the gas grill and cooktop, with concierge service and high-speed Wi-Fi keeping the details out of the way.

4 Bed
6 Bath
Sleeps 8

From $1,475 a night

Discover Eighth Avenue House

5 bedrooms · Sleeps 10

Gulf Shore House

Five bedrooms and six baths spread across two levels give a group of ten room to spread out, with a fireplace, wired sound, and wood floors setting a calm, grown-up tone. Mornings move easily between the chef's kitchen and the screened lanai, where the outdoor kitchen and gas-heated pool anchor long, unhurried afternoons. A three-car garage, impact windows and doors, and concierge service handle the practical side, so the corner-lot courtyard and private pool stay the focus of the day.

5 Bed
6 Bath
Sleeps 10

From $1,450 a night

Discover Gulf Shore House

4 bedrooms · Sleeps 8

Fourth Street House

Four bedrooms and six bathrooms give this Old Naples home room for eight guests across 2,957 square feet, with a chef's kitchen and wine room set for evenings in. Days settle around the heated pool and spa, screened by the lanai, with the outdoor kitchen ready for grilling under cover. Wood floors, custom mirrors, and impact windows run through two stories, while a garage, concierge service, and high-speed Wi-Fi handle the rest.

4 Bed
6 Bath
Sleeps 8

From $1,450 a night

Discover Fourth Street House

5 bedrooms · Sleeps 10

Sixth Avenue House

Five bedrooms and five baths spread across two stories give this Old Naples home room for ten to settle in without crowding the great room or the fireplace. Days move between the screened lanai, the outdoor kitchen, and the heated pool and spa, with the chef's kitchen and wine room ready when the group comes back inside. A two-car garage, circular driveway, and concierge service handle the practical side, leaving the bar, den, and balcony for the rest.

5 Bed
5 Bath
Sleeps 10

From $1,425 a night

Discover Sixth Avenue House

4 bedrooms · Sleeps 8

The Eleventh Avenue Villa

Four bedrooms and six bathrooms give a family real breathing room across 4,258 square feet, with a chef's kitchen and outdoor grill built for slow mornings and long dinners. Days settle around the screened lanai, where the heated saltwater pool and spa combo sit behind a safety fence, and evenings often end at the outdoor fireplace. Impact windows, a wired sound system, and an EV charger in the three-car garage round out a property built for both comfort and ease, all backed by concierge service.

4 Bed
6 Bath
Sleeps 8

From $1,425 a night

Discover The Eleventh Avenue Villa

4 bedrooms · Sleeps 8

The Canal House

Four bedrooms and five bathrooms spread across three levels give this Old Naples canal house room to gather without crowding. Mornings start on the screened lanai beside the heated infinity pool and spa, afternoons move to the private dock with direct Gulf access, and evenings settle by the fireplace or the wine room. Impact windows, a tankless water heater, and concierge service keep the mechanics quiet, leaving the focus on the water.

4 Bed
5 Bath
Sleeps 8

From $1,400 a night

Discover The Canal House

4 bedrooms · Sleeps 8

The Coach House

Coffered ceilings and a great room set the tone for four bedrooms and five bathrooms across two floors, with a chef's kitchen fitted with a gas cooktop, double oven, and pot filler for anyone cooking at scale. Days settle around the screened lanai, private pool and spa, and outdoor fireplace, while the fenced yard and pool bath keep things easy for a full group of eight. Three-car garage parking, a wine room, and concierge service round out a stay built for guests who want space indoors and out.

4 Bed
5 Bath
Sleeps 8

From $1,400 a night

Discover The Coach House

4 bedrooms · Sleeps 8

The Mangrove House

Mangrove and preserve views frame the bay frontage, where a private dock offers direct Gulf access for a morning on the water. Four bedrooms and five bathrooms spread across two stories, with a chef's kitchen, wine room, and screened lanai anchoring the ground floor. Evenings settle around the heated pool and spa, with the outdoor kitchen ready for dinner under the fireplace's glow.

4 Bed
5 Bath
Sleeps 8

From $1,375 a night

Discover The Mangrove House

4 bedrooms · Sleeps 8

Seventh Avenue Cottage

Two stories of wood and tile floors open onto a screened lanai, where the pool-and-spa combo, gas heat, and outdoor kitchen anchor the day outside. Four bedrooms and five bathrooms give a group of eight room to spread out, with the chef's kitchen, double oven, and wet bar keeping meals easy indoors. Evenings settle around the outside fireplace, and Engaged Destinations' concierge service handles arrangements while the three-car garage and full laundry take care of the rest.

4 Bed
5 Bath
Sleeps 8

From $1,350 a night

Discover Seventh Avenue Cottage

4 bedrooms · Sleeps 8

Fourth Avenue Residence

Four bedrooms and six baths span two stories in Old Naples, with wood floors, a fireplace, and a wine room setting the tone inside. Days move between the heated pool and spa, both fenced for safety, out to the screened lanai and outdoor grill, or through the private garage for a walk to the beach. Impact windows and doors, central air, and concierge service keep the practical side handled, leaving room for wine before dinner and a soak after.

4 Bed
6 Bath
Sleeps 8

From $1,350 a night

Discover Fourth Avenue Residence

4 bedrooms · Sleeps 8

The Boathouse

Vaulted ceilings and a fireplace set the tone in a four-bedroom Old Naples retreat where the chef's kitchen and wine room anchor the ground floor. Mornings begin poolside or on the screened porch before the private dock and direct Gulf access call for a day on the water; evenings settle back in along the salt canal. Impact windows, zoned cooling, and a two-car garage round out a home built for eight guests who want the water at the doorstep and every comfort inside.

4 Bed
5 Bath
Sleeps 8

From $1,350 a night

Discover The Boathouse

4 bedrooms · Sleeps 8

Bougainvillea House

Four bedrooms and four baths sit under coffered ceilings and a fireplace glow, with French doors opening the great room to a screened lanai. The heated saltwater pool and above-ground spa anchor a private, landscaped quarter-acre, while the gas grill and chef's kitchen with gas cooktop keep meals moving outdoors. Concierge service, a two-car garage, and full laundry round out days that start slow and end by the water.

4 Bed
4 Bath
Sleeps 8

From $1,325 a night

Discover Bougainvillea House

4 bedrooms · Sleeps 8

Fourteenth Avenue House

Four bedrooms and six bathrooms spread across two stories give eight guests room to spread out, with a den, a loft, and coffered and tray ceilings marking each space. Mornings start at the gas cooktop and double oven in the chef's kitchen, then move outside to a screened lanai and concrete pool framed by a privacy wall. French doors, wide-plank wood floors, and a fireplace carry the day inside, while concierge service and a two-car garage handle the rest.

4 Bed
6 Bath
Sleeps 8

From $1,325 a night

Discover Fourteenth Avenue House

4 bedrooms · Sleeps 8

Eleventh Avenue Cottage

Two stories built around a courtyard, French doors, and a screened lanai give this Old Naples cottage room to spread out for eight guests across four bedrooms. Days start in the chef's kitchen with its gas cooktop and wine cooler, move to the fenced private pool, and end with drinks from the wine room. Detached garage parking, an outdoor shower, and concierge service handle the practical side, leaving the rest of the stay open.

4 Bed
3 Bath
Sleeps 8

From $1,300 a night

Discover Eleventh Avenue Cottage

No home in Old Naples has that just now — but one in Park Shore almost certainly does.

In and around Old Naples

Experiences our guests here book most — arranged by us, on your dates, before you arrive.

All experiences

Experience

Florals and centrepieces

From $1,800

Arrangements built the morning of, from what came in that week — heavy on local greenery and light on anything that has flown.

Discover

Experience

Private Chef's Table

From $450

A seven-course tasting menu prepared in your residence, sourced from the morning's catch.

Discover

Experience

Ottimo on 5th

From $0

"Ottimo" is excellent, and the kitchen means it: traditional Italian recipes with a modern hand, from a long lunch through to a late glass at the bar. Warm, elegant, and easy to drop into.

Discover

Getting here

What is nearby

Gulf beach access0.2 mi
Third Street South shops and galleries0.7 mi
Fifth Avenue South restaurants1.2 mi
Naples Pier1.5 mi
Gordon Pass, out to the Gulf2.4 mi by water
Naples Municipal Airport (APF)5.0 mi
Southwest Florida International (RSW)42 mi

Arriving

Most guests fly into RSW and drive down, about fifty minutes. Private aircraft come into Naples Municipal, ten minutes from the house. We can meet either one.

Arrange a transfer