Vacation rentals in Old Naples

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Top-rated vacation rentals in Old Naples

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Superhost
Apartment in Old Naples
5 out of 5 average rating, 4 reviews

Modern & Chic 5th Ave Historic Naples

Highly desirable & exclusive condo directly on 5th Ave S in Olde Naples. Experience the night life and luxury Naples has to offer right just a few steps away. We're only 5 blocks from Naples famous white sand beaches. 5th Ave offers some of Naples most prestigious and high-end dining and shopping. From cafes, bistros, boutiques, ice cream parlors, designer jewelers, fine art, 5th Ave's modern and historic district has it all. Your condo is completely outfitted for a luxury and stress-free vacati

Guest favorite
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
4.96 out of 5 average rating, 124 reviews

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.

Top guest favorite
The image captures a view of a sandy beach leading to a pier extending into the ocean. Waves can be seen crashing against the pier, while green foliage frames the foreground, enhancing the natural coastal scenery under a clear blue sky.
Condo in Old Naples
4.98 out of 5 average rating, 120 reviews

FUN AT THE BEACH

2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier( to be rebuilt)and 3rd Ave Famous Dining and Shopping. Private entrance to unit with designated parking. The pool is outside your door for easy access. The unit provides a master suite with a king mattress and the extra room has 2 twins that can convert into a king. Please request upon booking. A laundry facility is located on the premises. Kitchenette provides cooktop and microwave/convection oven & a small refridgerator.

Guest favorite
Condo in Old Naples
4.91 out of 5 average rating, 174 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 favorite
Apartment in Naples
5 out of 5 average rating, 8 reviews

A Find! Just 3 blocks to the Gulf and Old Naples

387 is in a duplex- back unit offers off-street quiet and has everything you need for your home away from home: a king bedroom, a full bath, a dining area, a workspace, and a large living room. Beach equipment that other guests have suggested, including a small cart to walk it down to the Gulf or Norris Community Center - we hope the wagons last. Renovated in 2022 with new equipment- we kept the sweetness of the pink bathroom. Sidewalks and street lights all the way to Old Naples/Gulf.

Top guest favorite
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, 89 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.

Top guest favorite
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 Naples
4.99 out of 5 average rating, 106 reviews

Aesthetic Lush Landscape, 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. 624/34 Mbps at antique desk. SMALL quiet pets ok. Attached to owner's home but Studio is Completely Private! Only One Bed!

Top guest favorite
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, 135 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 favorite
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 favorite
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
5 out of 5 average rating, 10 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 favorite
Home in Naples
4.94 out of 5 average rating, 223 reviews

4BR Near Downtown Naples |Beach, Bikes, BBQ& Games

Relax in this spacious 4-bedroom Naples home minutes from the beach, 5th Ave shopping, and downtown dining. Ideal for families and groups, this 1,864 sq ft retreat offers king beds, bikes, beach gear for 8, outdoor games, BBQ, and two outdoor lounge areas everything needed for an easy Southwest Florida getaway. We have stellar reviews, come check us out & see for yourself. ⭐ Consistently 5-star rated | Superhost owned & operated

Top guest favorite
An outdoor living space features a screened lanai overlooking a pool. Comfortable loungers are positioned around the pool. A dining table with multiple chairs is set under a ceiling fan, complemented by a large area rug. The scene is bathed in natural light.
Home in Naples
4.99 out of 5 average rating, 134 reviews

Sunside House, 3/2 Pool Home in Gated Community

Prepare to be impressed as you enter this beautiful home in the sought-after Community of Briarwood. It certainly has the 'WOW' factor. The open aspect of this great-room floor plan, which flows out to a large, very private SW facing Patio and Pool area, makes this a perfect home for entertaining, family time or your golf time. You will love how light, bright and spotless this gorgeous home is. So much NEW.

Popular amenities for Old Naples vacation rentals

When is the best time to visit Old Naples?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$62,670 GYDG$66,023 GYDG$61,831 GYDG$62,460 GYDG$52,400 GYDG$44,016 GYDG$44,435 GYDG$42,548 GYDG$43,806 GYDG$51,142 GYDG$60,574 GYDG$62,879 GYD
Avg. temp18°C20°C21°C24°C26°C28°C29°C29°C28°C26°C23°C20°C

Quick stats about vacation rentals in Old Naples

  • Total vacation rentals

    Explore 330 vacation rentals in Old Naples

  • Nightly prices starting at

    Old Naples vacation rentals start at G$14,672 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,210 verified reviews to help you choose

  • Family-friendly vacation rentals

    230 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation 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 vacation 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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  4. Collier County
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  6. Old Naples