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, 3 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 spacious deck extends over the canal, surrounded by lush palm trees. Comfortable seating is arranged around a fire pit, with a paddleboard propped nearby. A BBQ grill is visible, inviting outdoor dining in a serene waterfront setting.
Home in Naples
4.95 out of 5 average rating, 130 reviews

Boaters Bayshore Bungalow w/HOT TUB view of water.

BRING YOUR BOAT! This ranch home is located on a canal with direct access to the Gulf/Naples Bay(no bridges). Amazing water sports access. In the cool/hip Bayshore Arts district! Great restaurants, Naples Botanical Gardens, boating, 3 miles to DT Naples and 4 to the best beaches. This is a perfect family/friends vacation spot. We have all the gear to enjoy this location. Quiet neighborhood/newly renovated/great views. Coffee on the deck with sunrise in front of you or drinks at sunset. Serenity

Top guest favorite
Condo in Old Naples
4.98 out of 5 average rating, 119 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.

Top guest favorite
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, 34 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 favorite
Guesthouse in Lake Park
5 out of 5 average rating, 171 reviews

By the Beach and 5th - Studio Apartment with Pool

Great location! Newly renovated! A studio guest apartment with your own private entrance, full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining & shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention there's also a pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth speaker? This home is 325 square feet of clean cuteness!

Superhost
A bright living area features a spacious sectional sofa and a large flat-screen TV. A fan above provides airflow. Natural light enters through large windows framed with sheer curtains, while a tasteful rug and decorative lamps enhance the room's comfort.
Apartment in Naples
4.92 out of 5 average rating, 49 reviews

Remodeled Condo at Resort Near 5th Avenue & Beach

Enjoy the beauty of this completely remodeled condo. The new white wash wood floors, and the upscale furnishings will make your vacation that much more enjoyable. Naples Bay Resort offers you a luxury hotel complex that features 5 pools, a state of the art gym, spa and tennis. The beach is just a 10 min ride and 1.5 miles away. Take a complimentary shuttle and enjoy the luxury hotel van. Rent bikes, kayaks, paddleboat and boats from the marina. Please see our GUEST ACCESS For Club Info-

Guest favorite
A clear pool is surrounded by palm trees and tropical foliage, offering a serene outdoor setting. Several lounge chairs are positioned along the edge of the pool, which reflects the blue sky and wispy clouds above. The spacious patio features light-colored stone flooring.
Condo in Old Naples
4.9 out of 5 average rating, 52 reviews

Renovated Studio Steps to Naples Beach & Downtown!

Your next Sunshine State retreat begins at this beautiful Naples studio condo! Cross the street to the sunny beaches of the Gulf of Mexico, take a short stroll to the famous Naples Fishing Pier, or walk a block to Third Street South - Naples' destination venue for fine dining, casual eateries, boutiques, and galleries. After a day in the sun, relax in your second-story home-away-from-home featuring a flat-screen cable TV, free WiFi, all new furnishings, and a remodeled kitchen and bathroom.

Top guest favorite
A stilt home is visible among lush tropical landscaping, featuring a mixture of palm and flowering plants. The entrance, framed by greenery, leads up a set of wooden steps. A clear blue sky is seen above, enhancing the serene atmosphere of the exterior.
Apartment in Naples
4.99 out of 5 average rating, 103 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
Condo in Old Naples
4.93 out of 5 average rating, 134 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
4.97 out of 5 average rating, 38 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
The studio features a spacious bed dressed in soft linens, accompanied by a bedside lamp. An open closet with a hanging rod is visible, and natural light filters through the window, adorned with sheer curtains. A wall-mounted television is positioned across from the bed.
Condo in Old Naples
4.96 out of 5 average rating, 103 reviews

Gulfside Sleeper in the ❤ of Historic Old Naples

Bright, clean 2nd floor studio is ideal for 1 or 2 travellers. Minimalist design with an emphasis on comfort and relaxation is perfect for executive business travellers or sun seeking beachgoers. No car necessary. The small space is hard flooring of wood and tile. There is an open closet with hanging rod. The shower access is a bit tight, and may not be suitable for big and tall or plus sized individuals. The westward view from the window is one block from the beach sunsets.

Superhost
An outdoor seating area features a comfortable arrangement of a sectional sofa and matching chairs with vibrant orange cushions. A glass-topped coffee table sits at the center on a stone-paved floor, while double French doors lead to the interior space.
Townhouse in Naples
4.83 out of 5 average rating, 213 reviews

Royal Palm flat Bay side shoppes

Royal Palm flat first floor charming Just remolded, updated new on market fresh, with large back porch and shared garage with beach toys, close to the beach 1 block from 5th Ave. one mile from beach 3 blocks from Naples bay. close to many restaurants and shops on 5th ave. The beach is at the end of 5th Ave. great walk down the heart of Naples down town and charming tin city shops and dinning. view 5th ave from rear porch. entire first floor with many games in garage.

Popular amenities for Old Naples vacation rentals

When is the best time to visit Old Naples?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR4,764 ZARR5,019 ZARR4,700 ZARR4,748 ZARR3,983 ZARR3,346 ZARR3,378 ZARR3,234 ZARR3,330 ZARR3,887 ZARR4,604 ZARR4,780 ZAR
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 370 vacation rentals in Old Naples

  • Nightly prices starting at

    Old Naples vacation rentals start at R1,115 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 5,410 verified reviews to help you choose

  • Family-friendly vacation rentals

    260 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Vacation rentals with a pool

    280 properties feature pools

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wi-Fi availability

    370 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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