Holiday rentals in Old Naples

4.97 out of 5 average rating, 38 reviews

Flat in Old Naples

Upstairs - 2 Blocks From Everything

This is one of five quaint rental opportunities on a magnificently restored Old Naples Cottage Estate c. 1910. Located two blocks from the Gulf of Mexico & Naples Pier and within walking distance of everything 5th Avenue and 3rd Street have to offer. The private entrance to the stairs brings you to a newly renovated, magical spot. Comfortable seating arrangement, full kitchen with marble counters forming a sitting bar, all new equipment, two king bedrooms, and a full bathroom off the kitchen.

4.96 out of 5 average rating, 129 reviews

A serene beach scene captures a vibrant sunset, with hues of pink and orange reflected on the water's surface. Gentle waves lap at the shoreline, while soft sand stretches along the beach, interspersed with small scattered shells.

Home in Naples

Magical Gateway in Naples FL

You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

4.92 out of 5 average rating, 179 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!

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.

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.

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.

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.

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.

4.93 out of 5 average rating, 138 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.

4.98 out of 5 average rating, 44 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.

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.

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.

4.89 out of 5 average rating, 18 reviews

Flat in Old Naples

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.

5 out of 5 average rating, 29 reviews

Apartment in East Naples

Naples Luxurious Resort Retreat with Lazy River

Naples Tyme Retreat is an elegant, newly renovated, 2-bedroom, 2-bath condo that sleeps 6. Enjoy luxurious resort amenities, including 5 pools, a spa, gym, tennis, and world-class dining (see below for resort fees). Just steps from vibrant 5th Avenue and Naples' stunning beaches, this serene retreat offers a private lanai, modern kitchen, and sophisticated decor. Perfect for families or mature travelers seeking a blend of relaxation and upscale living.

An aerial view captures the condo complex positioned near the Gulf of Mexico. The scene features the peaceful sea, sandy beach, and palm trees, with a glimpse of the community pool nestled within the property.

5 out of 5 average rating, 17 reviews

Old Naples Beach Condo

Whether you are looking to join us for a short or extended stay, enjoy the perfect blend of comfort and convenience in this delightful 2 bedroom, 2 bath condo located on the top floor of the complex in the heart of Old Naples. With its cozy atmosphere and ideal location, this condo is perfect for those seeking a relaxing retreat just steps from the beach and downtown Naples. Book with us today and take advantage of everything Old Naples has to offer!