Old Naples holiday homes

We found 1,161 holiday rentals — enter your dates for availability

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August 2025

September 2025

Select from 54 houses, 211 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:14 Nov - 21 Nov

A view of the beach just steps away. Fish abound, shelling and birds too!

Exceptional

(119 reviews)

BEACH, POOL, SUNSETS in the Heart of Old Naples!

Naples, FL

8% off

NZ$787 per night

includes taxes & fees

Exceptional

(11 reviews)

Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!

Naples, FL

7% off

NZ$350 per night

includes taxes & fees

Exceptional

(6 reviews)

Bamboo Oasis A - 5 miles to Beach & Downtown

Naples, FL

8% off

NZ$329 per night

includes taxes & fees

Exceptional

(8 reviews)

Just 2 block walk to the Gulf of Mexico Beaches in Olde Naples

Naples, FL

7% off

NZ$1,667 per night

includes taxes & fees

Exceptional

(13 reviews)

NEW POOL! Naples Home 2 miles to Beach/5th Ave, 2 King Beds, Hot Tub, Bikes

Naples, FL

8% off

NZ$726 per night

includes taxes & fees

Tropical heated outdoor pool area provides an abundance of entertaining space for guests, as well as BBQ (propane/gas) grill for outdoor cooking.

Exceptional

(19 reviews)

Totally Renovated Home: Screened in Lanai w/Heated Pool & Dining-2 Blocks to Beach-Coquina Sands

Naples, FL

5% off

NZ$882 per night

includes taxes & fees

Exceptional

(13 reviews)

Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.

Naples, FL

12% off

NZ$530 per night

includes taxes & fees

Steps to the famous Naples Pier and white sand beach

Exceptional

(70 reviews)

NAPLES BEACH!- In Olde Naples - Just Steps Away - Summer & Fall Available!!!

Naples, FL

8% off

NZ$599 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Find properties near top attractions in Old Naples

Fifth Avenue South

Naples Pier

Naples Historical Society's Historic Palm Cottage

Find the best place to stay - Old Naples

Downtown Naples Beach Condo, Half block from Famous 5th Ave

Sleeps 5 · 1 bedroom · 1 bathroom

Bellasera Resort

Sleeps 4 · 1 bedroom

Olde Naples Luxury Condo Steps to Pier, Beach, Sunsets and fabulous Restaurant

Sleeps 4 · 2 bedrooms · 2 bathrooms

BEST LOCATION IN Naples! 300 steps to white sand beaches. All new!!!

Sleeps 4 · 2 bedrooms · 2 bathrooms

The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.

Sleeps 2 · 1 bedroom · 1 bathroom

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Old Naples?

Condos are the most popular style of holiday home in Old Naples, according to our data. Even if you've got a different idea about what you want, Bookabach has properties in all sizes and shapes. Browse our many options to find your perfect fit.

How much does it cost to rent a holiday home in Old Naples?

Property type, length of stay and season are among the factors that can influence the price of a holiday home. Simply add your travel dates to find the ultimate escape. From comfy cottages to expansive luxury villas, all Bookabach holiday homes provide amazing value.

How much does it cost to rent a beach house in Old Naples?

The average price for a holiday home close to the beach in Old Naples will depend on when you'll be there and the size and type of property you're looking for. You can easily find prices on Bookabach by entering your preferred travel dates. Then use the filter tool to pick the number of bedrooms and amenities important to you, like a pool, WiFi and air conditioning.

Are there pet-friendly holiday homes in Old Naples?

Pack a bone and a squeezy toy for your canine companion because Old Naples has 271 properties that put out the welcome mat to pets. Let your happy hound get in on the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates then check the "Pets allowed" filter box.

Can I rent a house with a pool in Old Naples?

Check the "pool" box in our handy filter tool and pick from 221 houses with private pools in Old Naples on Bookabach. Gentle soak, ball games or noodle joust? Leisure activities are up to you when your Bookabach holiday home has its own pool.

What are popular home amenities in Old Naples?

A barbecue grill, a fireplace and an ocean view are the most popular home amenities in Old Naples. Whether you plan to travel as a party of one, with your other half or a group of best friends, Bookabach will help you find a holiday home that matches your tastes with all the features you're looking for.

Are there large group holiday homes in Old Naples?

You can pick from 10 holiday homes in Old Naples that can accommodate a group of 10 or more people. Whether you're organising a trip with the family or an event like an anniversary, there's plenty of room to get your loved ones together under the same roof.

Are there holiday homes in Old Naples that welcome kids?

Gather your entire family for an unforgettable adventure in Old Naples at one of our 271 family-friendly holiday properties. A lot of these stays offer conveniences that are ideal for trips with children, like dining rooms, extra bedrooms and entertainment areas. Just check the "Properties good for families" filter and pick your favourite.

What are the top attractions for families in Old Naples?

Keep the kids entertained at these fun family-friendly attractions in Old Naples:

Vanderbilt Beach
Naples Beach
Naples Pier

Are there one-bedroom holiday homes in Old Naples?

Yes, you can pick from 67 one-bedroom homes in Old Naples. Whether you're searching for a cosy chalet or a condo, Bookabach's one-bedroom homes are perfect if you don't need tons of space. One of the main perks of having your own place? You won't need to share your getaway with strangers.

Can I find two-bedroom holiday homes in Old Naples?

Old Naples has 137 two-bedroom holiday properties that you can choose from. Discover a holiday home with all the privacy and comfort you need at a fantastic price on Bookabach.

Are there holiday homes with WiFi in Old Naples?

Old Naples has 85 holiday homes with WiFi, so you'll be able to stay connected while travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to posting pics on social media, these Bookabach homes make it a breeze to get online.

How can I find holiday homes with air conditioning in Old Naples?

You'll have a choice of 268 holiday homes with air conditioning in Old Naples giving you that gentle, cool breeze and extra level of comfort. Simply enter your preferred travel dates and then make use of our filter tool to find properties with air conditioning.

How old do you have to be to rent a holiday home in Old Naples?

The minimum age is typically 16, 18 or 21. It can vary across properties on Bookabach, so look at the rules of your preferred Old Naples stay before booking your escape.

How long can I rent a holiday home in Old Naples for?

How long you can book a holiday home in Old Naples depends on the property. Just enter your desired dates to look at a list of options offering extended stays. With loads of creature comforts like laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get a terrific place to call your home away from home in Old Naples.