Old Naples holiday lettings

We found 1,093 holiday rentals — enter your dates for availability

your current months are October, 2023 and November, 2023.
October 2023
November 2023
Select from 52 houses, 182 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.

Find spaces that suit your style

  • 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, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Frequently asked questions

What are the top holiday rentals in or near Old Naples?

Whatever holiday experience you're seeking, you'll find a rental in or around Old Naples that's a match made in heaven. Here are some of our faves:

  • "My Favourite Apartment In Naples" is popular with guests. Around 7 miles from Old Naples, it has 3 bedrooms and loads of handy amenities, including lowered locks and beach towels.
  • "Upscale Home With Private Pool" is another top-notch choice, offering 2 bedrooms, towels, a boat and more. It's around 8 miles from Old Naples.

For even more great options, use the search bar at the top of the page to find the perfect Old Naples holiday rental for you.

What are the top-rated holiday rentals for weekend getaways in or near Old Naples?

Clock out on Friday and then forget all about the office. If you're up for some fun and relaxation, these properties in and near Old Naples promise the ideal weekend getaway:

  • Enjoy a change of scenery at "Naples Paradiso'. Remodeled Villa. . Heated Salt Water Pool", which is around 4 miles to the east of central Old Naples. There's lots of adventure and nature to keep you happy here. Do some windsurfing and sailing or simply take in the sights of Valencia Golf and Country Club and San Carlos Golf Club.
  • Alternatively, enjoy a rejuvenating getaway at "Waterfront/canal Walk To Beachlarge Pool Bayview Dock". Stay in and relax, or get active and try surfing and boogie boarding and cycling. When you're ready to explore more of the area, check out Kensington Golf & Country Club and Sanibel Island Golf Club. This fantastic holiday rental is around 8 miles north of Old Naples.

Can I find studio apartments for rent in and around Old Naples?

Enjoy a taste of the vibe and culture of Old Naples from the comfort and privacy of your own studio apartment. Whether you plan to take a break on your own or paint the town red with pals, you'll find the perfect studio apartment for rent in or near Old Naples:

  • Throw your bags down at "Charming Beach Condo Without The Beachfront Price". Amenities including a microwave oven and air conditioning help make guests feel at home here.
  • Alternatively, switch to holiday mode at "Coquina Cottage - Steps To The Beach", which comes with conveniences including a nearby laundromat and a fridge.

When you're ready to step out of your studio apartment and go exploring, there's loads to entertain you around Old Naples. Into culture? Organise a visit to Von Liebig Art Centre and The Baker Museum.

Can I find short term rentals in or near Old Naples?

Every once in a while, you just need to take a break from it all, even if it's only for one or two days. Enjoy the perfect combination of rest and recreation at one of these short-term rentals in or around Old Naples:

  • Nice and close to the centre of Old Naples, "Tivoli Oasis | Boutique Luxury Oversized Salt Pool And Spa Villa. King Beds" is great for a quick break. While you're around, make sure you get to well-known attractions like Naples Pier and Naples Zoo at Caribbean Gardens.
  • Eat, sleep and explore from "Tivoli Paradise | Boutique Luxury Oversized Salt Pool And Spa Villa. King Beds", another good option. Tin City and Naples Beach should be on your itinerary when you're ready to see the sights.

What are the best romantic weekend getaways in or near Old Naples?

Forget flowers and chocolates. Sometimes all you need is to get away for a weekend, just you and your beloved. At Vrbo, we've got romantic getaways in and around Old Naples that would make even Cupid swoon. Here are a few that'll sweep you off your feet:

  • Sneak away on Friday for a couple of passion-filled evenings at "My Favourite Apartment In Naples". Approximately 7 miles from Old Naples, this property comes with plenty of nice touches, including beauty services and beach sun loungers.
  • Another place where you can enjoy a few dreamy days together is "Upscale Home With Private Pool". Located 8 miles from Old Naples, beauty services and a nearby bay add to the atmosphere here.

Are there mansions for rent in or near Old Naples?

Nothing screams "Best. Holiday. Ever." like staying in a mansion. Treat your nearest and dearest to a truly unforgettable escape at one of these mansions for rent in or near Old Naples:

  • Situated approximately 10 miles to the east of Old Naples, "1 Bed / 1 Bath Suite In Luxurious Mansion In Naples" is the perfect place to relax in the lap of luxury. Amenities on offer here include a chef and golf.
  • With a swimming pool, a barbecue grill and loads of other top-notch amenities, "1 Bed / 1 Bath Suite In Luxurious Mansion In Naples" will get your team's tick of approval. This sumptuous retreat is roughly 10 miles to the east of Old Naples.

What's the best place to stay if you're looking to rent a house for a weekend in or near Old Naples?

A weekend of fresh coastal air and laid-back vibes at Barefoot Beach in Naples will work wonders. Check in to a rental home and stay a couple of nights or longer at this picture-postcard stretch of shoreline located 1 mile east of Old Naples.

What are the best large group holiday rentals in or near Old Naples?

Sneak a peek at these large group holiday rentals in or near Old Naples and forget about leaving anyone off your invite list:

  • There's plenty of space to move around at "Water Front In Royal Harbour. Brand New Home - Built 2014 - Featuring 5 Bedrooms". Around 1 mile southeast of Old Naples, this welcoming retreat has 4 bedrooms that sleep up to 12 guests. It comes with a host of amenities, including a water view and a nearby waterfront.
  • Nothing is more important than spending precious time with loved ones, and "Naples, Florida Beachfront Home Rental On The Gulf" makes it easy to do that. Located around 1 mile to the south of Old Naples, as many as 14 people can stay in this holiday rental which has 6 bedrooms. A kitchen and a swimming pool are among the numerous amenities on offer here.

Are there large holiday rentals that sleep 30 or more in or near Old Naples?

Whether you're planning a wedding, a birthday party or a holiday with your extended family, we'll help you find the right place for your group. Round up your posse and browse these large holiday rentals in or near Old Naples:

  • "Condo With Pool Access: Walk To Shopping And Beach": The more guests the merrier to this popular escape. It has 2 bedrooms, accommodates up to 100 people and includes ample amenities, such as a kitchen and a swimming pool.
  • "Downtown Naples 7 Units - 2/1 - Pool": This impressive retreat was tailor-made for large groups and includes a swimming pool and a kitchen. It contains 16 bedrooms and caters for up to 48 guests.

What are the best houses for rent with a pool in or near Old Naples?

From lively games of sharks and minnows to leisurely afternoon dips, a pool promises fun for both adults and kids. Score major brownie points with the fam by booking a house with a swimming space in or near Old Naples:

  • Pack your swimming gear and enjoy a fun stay at "2nd Ave Beach House - Stylish Pool Home Steps To Naples' Best Beach". Other amenities here include a TV and cable/satellite TV services.
  • "Pelican House Royal Harbour On Naples Bay" is another highly rated option. After you've enjoyed a refreshing dip with the kiddos, make the most of other conveniences like childrens activities and towels.

What are the best large family holiday rentals in or near Old Naples?

Whether your ideal escape is high in the hills or down by the sea, you'll have a lot more fun if you share it with those closest to you. Choose one of these large family holiday rentals in or near Old Naples and bring the whole gang:

  • Around 4 miles to the northeast of Old Naples, "Tivoli Oasis | Boutique Luxury Oversized Salt Pool And Spa Villa. King Beds" has 4 bedrooms and sleeps up to 8 guests. It's equipped with a range of amenities, including a TV and childrens activities.
  • Another great option is "Tivoli Paradise | Boutique Luxury Oversized Salt Pool And Spa Villa. King Beds". This large rental is 4 miles northeast of Old Naples and features beach sun loungers, a meal delivery service and more. With 4 bedrooms accommodating up to 8 people, don't worry about leaving anyone off your guest list.

When it's time to explore, there are loads of family-friendly attractions nearby to keep everyone entertained and happy. Naples Pier, Naples Zoo at Caribbean Gardens and Corkscrew Swamp Sanctuary should be top of your to-do list.

What are the best large houses to rent with indoor pools in or near Old Naples?

Nothing says fancy-schmancy like your own indoor pool. Pack your favourite bikini and take a dip in the comfort and privacy of one of these roomy houses in or near Old Naples:

  • Stay at "Holiday Apartment Ascona For 2" and while away your days poolside. This sprawling getaway has 3 bedrooms sleeping up to 8 guests and a range of other quality amenities. Mountain views and a nearby waterfront are among them.
  • Besides its impressive indoor pool, "Private 3bedroom 3ba Villa In Gorgeous Resort" features a swimming pool and a water view. It has 3 bedrooms that can accommodate up to 7 people, so you can bring the extended family along.

If you're curious about other options, use the search bar at the top of the page and adjust the filters to find the Old Naples holiday rental that's perfect for your needs.

Explore destinations around Old Naples

More Holiday Rentals ideas

People also search for