Holiday houses in Old Naples

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Top-rated holiday rentals in Old Naples

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Condo in Old Naples
4.67 out of 5 average rating, 3 reviews

Naples Pier Condo 123

Enjoy a relaxing coastal escape in this beautifully appointed 2-bedroom, 2-bath condo just steps from the Gulf of Mexico. The bright, open living space is designed for comfort, with stylish furnishings and a layout perfect for unwinding after a day in the sun. A well-equipped kitchen and comfortable bedrooms make extended stays easy and enjoyable. Guests will love the peaceful atmosphere and easy access to pristine white-sand beaches. This condo offers the perfect blend of comfort, convenience, and classic Naples coastal living.

Guest favourite
Condo in Old Naples
4.92 out of 5 average rating, 177 reviews

Downtown Condo at Naples Pier Beach

Come enjoy a restful beach escape at the Naples Mariner, formerly a beautiful Motel built in 1966! Relax while enjoying your fully renovated condo located 60 yards from the Olde Naples Fishing Pier beach and 1 block from the 3rd Street Shops/Restaurants. A quick drive, bike or walk 1 mile north will place you on 5th Avenue - an area of shops, restaurants, bars and a playhouse. The condo has one designated parking spot, wifi, washer/dryer on premises, heated pool, courtyard & more. 'Sea' Ya!

Top Guest favourite
A modern kitchen features white cabinetry and a spacious island with white quartz countertops. Stainless steel appliances, including a microwave and oven, are visible. A television displaying a beach scene adds a touch of relaxation, while natural light fills the open layout.
Condo in Old Naples
5 out of 5 average rating, 40 reviews

Luxurious condo steps to beach with heated pool!

Relax Off 5th is a perfectly located 1 bedroom condo in the heart of Old Naples, just a 1/2 block from vibrant 5th Avenue with its restaurants, boutiques, and cafés, and only four short blocks to the beach. Set in a charming Old Florida building surrounded by multi-million-dollar estates, the condo offers access to a heated pool perfect for a refreshing dip after a day at the beach. Inside, you’ll enjoy fast WiFi with a dedicated workspace, and the convenience of keyless, contactless entry.

Top Guest favourite
A private, landscaped patio features two swivel chairs positioned around a small table. Lush greenery and flowering plants surround the area, providing a serene view of a lake in the background. The natural setting invites relaxation and enjoyment of the outdoors.
Condo in Old Naples
5 out of 5 average rating, 90 reviews

Little Gem By the Beach and 5th w/Patio Old Naples

JUST A SHORT WALK TO THE BEACH AND 5th AVE, IN THE HEART OF OLD NAPLES, WITH A RARE, PRIVATE PATIO! Totally renovated in January 2023! A beautiful, one-bedroom, one-bath home, with only a 5-minute stroll to the beach and dining! Just outside the living room is a private, landscaped patio overlooking a pretty lake, which is an unusual and lovely feature of this home! Inside, you'll enjoy a fully-equipped kitchen with granite countertops, a comfortable king bed, and washer/dryer in the condo.

Guest favourite
A bright and airy living area features a comfortable sofa paired with decorative pillows. A glass coffee table rests atop tiled flooring, while a dining table is positioned nearby. A flat-screen TV is mounted on the wall, and wall art adds a coastal touch.
Condo in Old Naples
4.94 out of 5 average rating, 96 reviews

Luxury 2-Bedroom. Steps to Naples Beach & Town.

**Newly renovated, reopened December 2024** Spend your Naples getaway in this completely renovated sun drenched, luxury corner unit. Cross the street to the sunny beaches of the Gulf of Mexico. Stroll to the famous Naples Fishing Pier. Walk a block to 3rd St S for fine dining, casual eateries, boutiques, and more. Relax indoors with 3 flat-screen TV's or by the pool. At the end of your day grab your beach chair an view the spectacular Naples sunsets. It does not get any better than this!

Top Guest favourite
A spacious heated pool invites relaxation, surrounded by lounge chairs placed along the deck. Lush palm fronds frame the view, enhancing the tropical ambiance. The pool area is well-maintained, with clear water reflecting the sun. Parking is visible beyond the poolside greenery.
Condo in Old Naples
4.93 out of 5 average rating, 137 reviews

NEW! ONE BLOCK to the Beach, Restaurants & Shops!

Welcome to your newly renovated condo in the heart of Olde Naples! Just ONE BLOCK to the beautiful Naples beaches and all of the shops and dining on 3rd Street! Your first floor condo suite is ideally situated just steps from the oversized heated pool. And with large windows you can let that warm Florida sunshine in. The studio also has a designated parking space, common laundry, kitchen, bathroom, dining table, king size bed, pull out single trundle bed and can sleep up to 3 people.

Top Guest favourite
Condo in Old Naples
4.98 out of 5 average rating, 42 reviews

Downtown Naples Beach Condo, Off of Famous 5th Ave

This peaceful Olde Naples condo is just half a block from dining and shops on famous Downtown 5th Ave and 4 blocks from Naples Beach. This first-floor end-unit condo is perfect for a beach getaway. This clean, modern unit has a pool just feet from the front door, a complete kitchen with updated appliances, a new washer and dryer, comfy furniture, beach chairs and umbrella, and high-speed internet. This property offers a perfect blend of relaxation and convenience to sleep up to 4 guests.

Top Guest favourite
A bright bedroom features a spacious bed with a soft yellow coverlet. A small dining table with two chairs is positioned nearby. A painting adorns the wall, with light entering through the window. A laundry area is visible, providing added convenience.
Apartment in East Naples
4.99 out of 5 average rating, 109 reviews

Rare Gem, Fast WiFi, 3 Min to Town, King Bed

For Guests Who Love Privacy! Sunny Studio where Art is highlighted. French Doors to Lg Screened Porch for Outside Dining/Working. Peaceful. Stilt home (8 steps) in Safe, Quiet area w parking right outside. Backyard is yours w BBQ grill, table & chairs. Charmingly Furnished w Recliner, Heavenly King Bed, Convection/Microwave oven, Kitchen Aid stove top & Full Fridge. FAST WiFi at antique desk. SMALL quiet pets ok. Attached to owner's home but Studio is Completely Private! Only One Bed!

Guest favourite
A light-filled living area features a large, comfortable sectional sofa arranged around a white coffee table. Floor-to-ceiling glass doors lead to a balcony, while a stylish television is mounted on the wall. Soft, neutral colors enhance the serene atmosphere.
Condo in Old Naples
4.92 out of 5 average rating, 12 reviews

Amazing Old Naples Property!

Indulge in this beautifully appointed two-bedroom, two-bath retreat nestled in the heart of Old Naples. Soaring ceilings and an open-concept layout create an airy, welcoming ambiance, complemented by a sleek modern kitchen, in-unit laundry, and a private balcony perfect for al fresco dining or sunset cocktails. Retreat to plush hotel-quality linens and premium mattresses in the primary king suite and secondary full bedroom—each featuring an ensuite bathroom for privacy and convenience.

Guest favourite
Apartment in Old Naples
4.88 out of 5 average rating, 16 reviews

Modern 5th Ave Beach Condo!

Where Fifth Avenue Meets the Gulf! Located just two blocks from the beach, ON 5th Avenue South & 1 block from 3rd Street South. Walk to world-class restaurants, shops, art galleries and more. Or just simply relax and unwind at home in this newly renovated, never-lived-in 2BR/2BA end unit with outdoor space to enjoy the coastal breeze. The heated pool & modern coastal finishes complete this perfect retreat. Unbeatable location. Parking included. Available weekly, monthly, or annually.

Top Guest favourite
Home in Old Naples
5 out of 5 average rating, 13 reviews

Newly Restored Old Naples Estate - Best Location!

Main House is one of five quaint rental opportunities on a magnificently rebuilt Old Naples Cottage Estate, built c.1910. It is two blocks from the Gulf and two minutes walking distance from everything 5th Avenue and 3rd Street have to offer. Two beautiful bedrooms, each with its own bathroom. Large living room, fully equipped eat-in kitchen, laundry, deck, patio, and game room with a mini ping pong table. Upstairs is a standalone or can be rented, accommodating eight combined.

Top Guest favourite
A sandy beach is seen leading to a wooden pier extending into the ocean. Waves crash against the shore, with gentle greenery framing the view. The sky is blue with scattered clouds, enhancing the serene coastal atmosphere.
Condo in Old Naples
4.99 out of 5 average rating, 88 reviews

FUN AT THE BEACH #2

This second story unit (with a common elevator) has that Naples Beach Vibe all through out. Building has a retro old Miami appeal. 1 block from the beach and 1 block from dining and shopping. Pier is being rebuilt at the moment. Primary has a king and secondary room has twin beds that can be converted to a king upon request. I am always available to assist with any questions and concerns. I have a first floor unit and had nothing but great experiences with my guests.

Popular amenities for Old Naples holiday rentals

When is the best time to visit Old Naples?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$542 NZD$697 NZD$689 NZD$519 NZD$436 NZD$366 NZD$370 NZD$354 NZD$364 NZD$425 NZD$504 NZD$523 NZD
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Quick stats about holiday rentals in Old Naples

  • Total holiday rentals

    Explore 330 holiday rentals in Old Naples

  • Nightly prices starting at

    Old Naples holiday rentals start at $122 NZD per night before taxes and fees

  • Verified guest reviews

    Over 5,210 verified reviews to help you choose

  • Family-friendly holiday rentals

    230 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 70 rentals that welcome pets

  • Holiday rentals with a pool

    260 properties feature pools

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wi-Fi availability

    330 of Old Naples holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Old Naples rentals

  • 4.9 Average rating

    Old Naples stays are highly rated by guests—averaging 4.9 out of 5!

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