Old Naples holiday rentals

We found 1,240 holiday rentals — enter your dates for availability
Select from 22 houses, 99 flats and other holiday rentals to find the perfect place for your stay in Old Naples. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you expect for your stay, which might include parking and a garden. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Old Naples

Showing deals for:11 Dec - 18 Dec

Marina
Pool
Private kitchen
Property grounds
Exceptional
(21 reviews)

Luxurious Naples Bay Resort Pool, Spa & Beach Club!

Naples

7% off
AU$10,636
for 7 nights, 1 cottage
AU$1,519 per night
includes taxes & fees
Luxurious Naples Bay Resort Pool, Spa & Beach Club!
Interior
Pool
Tin City Shops & Restaurants - Less Than 1 Mile Away
Private kitchen
Exceptional
(120 reviews)

Tropical Retreat Pool Home close to Downtown & Naples Beaches

Naples

8% off
AU$3,914
for 7 nights, 1 home
AU$559 per night
includes taxes & fees
Tropical Retreat Pool Home close to Downtown & Naples Beaches
Room
Outdoor dining
Private kitchen
Exterior detail
Exceptional
(9 reviews)

Near DownTown & Napes Beach! Cottage House 2QueenBeds Fenced Back Yard with deck

Naples

7% off
AU$2,402
for 7 nights, 1 cottage
AU$343 per night
includes taxes & fees
Near DownTown & Napes Beach! Cottage House 2QueenBeds Fenced Back Yard with deck
Exterior
Please note, this is not a private balcony/deck
Room
Living area
Exceptional
(65 reviews)

Stay in the Heart of Olde Naples - Steps to the Beach, Restaurants and Shops

Naples

8% off
AU$5,028
for 7 nights, 1 apartment
AU$718 per night
includes taxes & fees
Stay in the Heart of Olde Naples - Steps to the Beach, Restaurants and Shops
Interior
Private kitchen
Dining
Terrace/patio
Exceptional
(122 reviews)

Boaters Paradise : 3 bedroom waterfront home close to downtown Naples Fl.

Naples

8% off
AU$8,861
for 7 nights, 1 home
AU$1,266 per night
includes taxes & fees
Boaters Paradise : 3 bedroom waterfront home close to downtown Naples Fl.
Exterior
Private kitchen
Fitness facility
Property grounds
Wonderful
(17 reviews)

C-224 - End Unit with Private Views & Sleeps 6

Naples

7% off
AU$2,894
for 7 nights, 1 apartment
AU$413 per night
includes taxes & fees
C-224 - End Unit with Private Views & Sleeps 6
Heated pool
Check-in lobby with helpful staff
Grill area
Hogfish Harry’s is a favorite of the locals and it’s right next to the pool.
Exceptional
(8 reviews)

Resort Condo with Heated Pool, Tennis, Gym, Pickle Ball, On-Site Restaurant

Naples

8% off
AU$3,693
for 7 nights, 1 apartment
AU$528 per night
includes taxes & fees
Resort Condo with Heated Pool, Tennis, Gym, Pickle Ball, On-Site Restaurant
Room
Private kitchen
Outdoor dining
Dining
Wonderful
(10 reviews)

Blue Banyan Boathouse w/POOL/DOCK!

Naples

8% off
AU$5,293
for 7 nights, 1 home
AU$756 per night
includes taxes & fees
Blue Banyan Boathouse w/POOL/DOCK!
Pool
Dining
Interior
Dining
Excellent
(13 reviews)

Naples Haven – Walk to Beach & 5th Ave

Naples

8% off
AU$4,408
for 7 nights, 1 apartment
AU$630 per night
includes taxes & fees
Naples Haven – Walk to Beach & 5th Ave
Interior
Dining
Interior
Living area
Very good
(5 reviews)

F-236 - Deluxe Condo With Resort Views & Sleeps 6

Naples

7% off
AU$2,946
for 7 nights, 1 apartment
AU$421 per night
includes taxes & fees
F-236 - Deluxe Condo With Resort Views & Sleeps 6
Living area
Interior
Sports court
Private kitchen
Very good
(5 reviews)

B-116 - Resort Views and Close to the Lobby

Naples

8% off
AU$4,287
for 7 nights, 1 apartment
AU$612 per night
includes taxes & fees
B-116 - Resort Views and Close to the Lobby
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Old Naples

  • Charming Historic District: Explore the picturesque streets of Olde Naples, filled with unique historic houses and a romantic vibe.
  • Beautiful Beaches: Enjoy relaxing days on the sandy shores of Naples, perfect for families and beach lovers alike.
  • Cultural Experiences: Visit the stunning Naples Cathedral and unwind at local pubs for a taste of regional culture.
  • Outdoor Activities: Stroll through urban parks and enjoy outdoor adventures along the serene Naples Bay.
  • Diverse Accommodations: Choose from spacious condos, charming vacation homes, and luxurious villas to suit your stay.

Popular types of accommodation around Old Naples

Planning a getaway to Old Naples? You're in for a treat! With a variety of accommodation options, including spacious condos, charming houses, and luxurious villas, you’ll find the perfect spot to unwind. Explore the local charm, and if you're considering hotels, the Olde Naples hotel and Hyatt House Naples on 5th Avenue are excellent choices. Discover your ideal vacation rental in Old Naples and make the most of your stay!

  • Condos: The top choice for visitors in Old Naples, offering modern amenities and a community feel.
  • Houses: A fantastic option for families and groups, providing privacy and space for a homely stay.
  • Villas: Elegant and spacious, these rentals provide a luxurious experience in a picturesque setting.
  • Apartments: Ideal for solo travellers or couples, offering convenience and access to local attractions.
  • Cottages: Quaint and charming, perfect for a peaceful retreat away from the hustle and bustle.**

Top attractions in and around Old Naples

Old Naples offers a delightful mix of beach, family, and city-themed experiences. Visitors can explore sandy shores, the charming Naples Historic District, and the serene Naples Bay. Don't miss the stunning Naples Cathedral and the unique historic houses scattered throughout the area. For a taste of local culture, unwind at the old Naples pub or stroll through the urban parks. It's a perfect destination for those seeking outdoor adventures and cultural immersion.

  • Naples Beach: A stunning stretch of sandy shoreline, perfect for sunbathing and swimming. Enjoy the relaxing beach vibes, take a leisurely stroll, or indulge in water sports, all while soaking up the Floridian sun.
  • Fifth Avenue South: A vibrant street filled with boutique shops, art galleries, and delightful eateries. Experience the lively city vibes as you explore local culture, enjoy al fresco dining, and attend various events.
  • Naples Pier: This historic jetty offers breathtaking sunset views and opportunities for fishing and dolphin spotting. Embrace the excursions vibes as you stroll along the pier, soaking in the coastal atmosphere.

Things to do recommended for couples

Looking for a romantic getaway in Old Naples? Try a fun round at Coral Cay Adventure Golf, just 3.2km away, or enjoy thrilling water sports at Marco Island, 24.1km away. Both offer adventure and a chance to create unforgettable memories together!

Things to do recommended for families

Families visiting Old Naples can experience the wellness vibes at East Naples Community Park, just 4.8km away, or have a splashing good time at Sun N Fun Lagoon, a thrilling waterpark located 14.5km away, perfect for entertainment and adventure.

Things to do recommended for groups

Explore Tin City for a unique shopping experience with lively entertainment. Enjoy a round of golf at New Smyrna Beach Municipal Golf Course or Evergreen Golf and Country Club, both offering fantastic outdoor vibes just a short drive from Old Naples.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking with Stayz is simple

Are you keen to save some dollars on your next getaway? Being flexible with your travel dates can really help, as prices often vary. Additionally, opting for a longer stay typically allows for significant savings. To discover the perfect Stayz property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Old Naples

Old Naples offers a delightful blend of charm and relaxation, perfect for a beach or family-themed getaway. Stroll through historic downtown Naples, where friendly locals and vibrant boutiques create a welcoming atmosphere. Explore the picturesque streets of Olde Naples, with its romantic vibe and stunning coastal views. Whether you’re seeking a laid-back day at the beach or a taste of local culture, this enchanting neighbourhood has something for everyone.

  • Naples: Naples is a vibrant city where Old Naples is located and is well-known for its stunning beaches and outdoor activities. Visitors flock to this area for a quintessential family experience, enjoying pristine sandy shores and picturesque sunsets. The city boasts an array of attractions, including luxurious resorts, upscale shopping centres, and world-class golf courses. Key landmarks include the beautiful beaches and family-friendly parks, making it an ideal destination for relaxation and recreation.
  • Redevelopment Area: The Redevelopment Area is a charming neighbourhood situated a short 1.3km from Old Naples. This area attracts families and beach lovers alike, offering a delightful city-themed experience. Visitors can explore various shopping centres and enjoy leisurely strolls in the nearby streets. The local beaches provide a perfect spot for family outings, enhancing the appeal of this vibrant community.
  • East Naples: Located 3.2km away from Old Naples, East Naples is another fantastic neighbourhood that caters to those seeking outdoor adventures and family fun. This area is renowned for its excellent golf courses and shopping experiences, appealing to both sports enthusiasts and avid shoppers. With easily accessible beaches and lush parks nearby, East Naples offers visitors a chance to unwind and enjoy the natural beauty of the Florida coastline.

Best time to go to Old Naples

If you're planning a trip to Old Naples, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from February to April, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January65.7°F (18.7°C)No Rain (Dry)Mostly SunnyAverageAverage
February68.2°F (20.1°C)No Rain (Dry)SunnyModerately HighSlightly High
March70.3°F (21.3°C)No Rain (Dry)SunnyModerately HighSlightly High
April75.4°F (24.1°C)No Rain (Dry)SunnyModerately HighAverage
May78.8°F (26.0°C)Light RainMostly SunnyAverageAverage
June82.2°F (27.9°C)Light RainMostly SunnyAverageAverage
July83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
August84.0°F (28.9°C)Light RainMostly SunnyModerately LowSlightly Low
September82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly Low
October78.6°F (25.9°C)Light RainMostly SunnyModerately LowSlightly Low
November73.0°F (22.8°C)No Rain (Dry)Mostly SunnyModerately LowAverage
December69.3°F (20.7°C)No Rain (Dry)Mostly SunnyAverageSlightly High

What do I need to keep in mind when booking a vacation around Old Naples

If you’re planning a trip with friends, family, or even your furry companions, or if you’re considering an extended stay, be sure to refine your search based on what matters most to you. Here are some helpful booking tips for using Stayz.

  • Travelling to Old Naples with a group: Think about how many bedrooms you'll require, as well as amenities like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options, and more, on Stayz.
  • Travelling to Old Naples with young kids: Travelling with little ones can be a bit of a handful. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Old Naples: For many, a family holiday isn't truly fulfilled without their furry companion by their side. If that resonates with you, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels completely at home.
  • Planning for a long term stay visiting Old Naples: If you're searching for holiday rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Stayz Trips: Effortless planning

Stayz's Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous arrangements, and manage your itinerary. Here, you'll find the properties you've saved or booked neatly organised into categories such as Potential, Upcoming, or Current Trips. To begin exploring the benefits of Trip Boards, simply head over to: https://www.stayz.com.au/trips.

**Based on Stayz properties bookings.

Frequently asked questions

When is the best time to visit Old Naples for a holiday rental?
The best time to visit Old Naples for a holiday rental is during the peak season from February to April, with March being particularly popular. This vibrant period attracts a mix of tourists seeking sun-soaked days and a lively option. With temperatures averaging between 20 to 27 degrees Celsius, visitors can enjoy outdoor activities such as relaxing on the pristine beaches, exploring the charming shops along Fifth Avenue South, or indulging in al fresco dining at delightful local restaurants.Springtime in Old Naples offers plenty of opportunities for sightseeing and enjoying the natural beauty of the area, including the stunning sunsets over the Gulf of Mexico. The warm, pleasant climate is superb for leisurely strolls along the beach or participating in various water sports, making it an ideal destination for those looking to soak up the sun.If you're looking for a more budget-friendly option, consider planning your visit in October. While this month is outside the main tourist season, it offers a quieter experience with the warm weather still lingering. October is a great time to explore the local art galleries and enjoy the beautiful parks without the crowds, allowing for a more relaxed holiday.Ultimately, choosing the right time to visit Old Naples depends on whether you prefer the energetic buzz of peak season or the serene charm of the quieter months.
What are the top attractions in Old Naples, Florida, United States of America?
In Old Naples, visitors can enjoy a delightful mix of attractions that embody the charm of this coastal town. The historic Third Street South is a must-visit, lined with boutique shops, art galleries, and a variety of dining options, offering a vibrant setting, especially during the evening. Nearby, the beautiful Naples Pier provides stunning views of the Gulf of Mexico and is an ideal spot for fishing, sunset watching, or simply enjoying a leisurely stroll along the beach.Additionally, the pristine beaches of Naples are a major draw, where visitors can relax on soft white sands and partake in water sports. For those interested in nature, the nearby Naples Botanical Garden is a serene escape, showcasing a diverse collection of plants and themed gardens that reflect the region's ecology.
Are all fees included in the Old Naples holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Old Naples holiday homes with parking?
Stayz offers a wide selection of holiday homes in Old Naples with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Old Naples holiday homes?
You can find great discounts on holiday homes in Old Naples on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Old Naples holiday home booking on Stayz?
To find Old Naples holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Old Naples?
A long-stay holiday home in Old Naples is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Old Naples holiday home?
Book your Old Naples holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Old Naples?
Prices for holiday homes in Old Naples vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Old Naples to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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