Naples has been consistently rated as one of the USA’s best vacation spots, and for good reason. With white sand beaches, high-end shopping, and heaps of great places to eat and drink, this Florida city is a vacationer’s dream come true! The area can get a little expensive when it comes to accommodation, but don’t stress. This list of 20 great vacation rentals in Naples has you covered, with something to suit every travel budget and style.

Golf fans will also have a whale of a time in Naples, as the city is known to have some of the best golf courses in the entire country. The city also gets some fantastic weather, with about 264 days of the year being sunny and warm. There are truly so many reasons to visit Naples.

So if you’re dreaming of a trip to Florida and fancy checking out this beachside paradise, here’s a great guide to kickstart your plans.

Quick Answer: These are the Top 5 Vacation Rentals in Naples, FL

Overall Best Value Vacation Rental in Naples, FL
Nautical style home with 3 Bedrooms
Overall Best Value Vacation Rental in Naples, FL

Nautical style home with 3 Bedrooms

  • > $$
  • > 6 guests
  • > Includes a private pool and spa
  • > Located close to Vanderbilt Beach
Best Budget Vacation Rental in Naples, FL
Waterfront 1 BR condo
Best Budget Vacation Rental in Naples, FL

Waterfront 1 BR condo

  • > $
  • > 2 guests
  • > Cosy and bright condo
  • > Located in downtown Naples
Best Vacation Rental for Couples in Naples, FL
Cute condo for a couple
Best Vacation Rental for Couples in Naples, FL

Cute condo for a couple

  • > $
  • > 2 guests
  • > 5-minute walk to the beach
  • > Located in the heart of Old Naples
Best Vacation Rental for Families in Naples, FL
3 BR with pool and putting green
Best Vacation Rental for Families in Naples, FL

3 BR with pool and putting green

  • > $$
  • > 6 guests
  • > Beautifully designed outdoor space
  • > Located close to Sun N Fun Waterpark
Over-the-Top Luxury Vacation Rental in Naples, FL
Mediterranean-style private estate home
Over-the-Top Luxury Vacation Rental in Naples, FL

Mediterranean-style private estate home

  • > $$$$
  • > 8 guests
  • > Custom-built four-bedroom luxury home
  • > 5 minute drive to Naples Beach

Looking for other types of accommodation? Check out our guide to Where to Stay in Naples, Florida!

Types of Accommodation in Naples

Before we look at our top picks, here’s an overview of the most common types of vacation rentals you can expect to find in Naples, Florida.

East Naples, Florida

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Apartments and Condos

Naples has a plethora of apartments and condominiums to choose from. Most of them have three to four bedrooms, sleeping about six to eight people. It is possible to find apartments with more space, but we reckon they’re ideal for couples, small families or small groups of friends.

You’ll find the nicest apartments around the Vanderbilt Beach area. Here, most condos will have amazing sea views and are steps away from the beach.

Beachfront Vacation Rentals

If you want to wake up to the sound of waves and enjoy your morning coffee watching the sunrise over the water, this is for you. Naples has endless holiday homes along its coastline, allowing you to make the most of this stunning area. These rentals are usually furnished in a modern, tasteful style, with all the creature comforts you could ask for.

Naples Beach Florida USA
Not bad for a backyard!

Private Suites in Resorts

Naples is home to some of America’s best resorts and timeshares. Because Florida is where many Americans either holiday or retire, there are so many private timeshares available to rent here! The best thing about renting a private suite is that you get access to all the resort amenities at a fraction of the price you would pay normally.

Naples Florida Coastline
Waterfront villas are commonplace here

The Top 20 Vacation Rentals in Naples

If you’re like me and hate the generic cookie-cutter hotel room, Naples will not disappoint. The rentals here are stylish, comfortable and most feel like they have been decorated by people who actually care about making your holiday better. After all, it is always the little details that make the most difference!

Best Overall Vacation Rental in Naples | Nautical style home with 3 Bedrooms

Nautical style home with 3 Bedrooms
A private resort-style pool awaits you!
  • $$
  • Includes a private pool and spa
  • 6 guests
  • Close to Vanderbilt Beach

Somehow, cottages or houses that are decorated in pastel colours or shades of white always seem so peaceful and tranquil to me. If you’re a fan of coastal chic homes that are tastefully decorated with thoughtful touches, I’ll eat my hat if you don’t end up falling in love with this home.

The holiday home boasts a fully-equipped kitchen, bedrooms with comfortable beds that you will want to melt into, and super clean interiors throughout. Outside, your private lanai area with a pool and a spa awaits. With all the space and facilities, this place is the ideal vacation rental for a family.

Best Budget Holiday Rental in Naples | Budget condo with great views    

Budget condo with great views
Views from the apartment
  • $
  • Direct access to the beach
  • 6 guests
  • Walking distance to Venetian Village

This condo is so close to the ocean that you can hear the waves crashing onto the beach from almost every room! Although the rental only has two bedrooms, there is a sofa bed in the living room. This place is super affordable for the budget traveller or a group of friends who want to spend less on accommodation and more on sightseeing, shopping and eating out.

The apartment isn’t flash but has pretty much everything you might need on holiday, including a washing machine, bathroom essentials, and cooking facilities.

Best Vacation Rental in Naples for a Family Getaway | 3 BR with pool and putting green

3 BR with pool and putting green
This home will be loved by adults and kids alike
  • $$
  • Beautiful outdoor space
  • 6 guests
  • Close to Sun N Fun Waterpark

This vacation rental in Naples is the perfect blend of a beautiful backyard and some seriously stunning interiors. The house is great for travellers of any age, offering superb amenities like a heated pool, a spa and even a little putting area.

Inside, high ceilings give the house a spacious look. The kitchen is complete with modern appliances, while the living and dining area has enough room for everyone. The rental does allow pets, but note there is an extra fee of $100 per booking.

Best Vacation Rental in Naples for a Family on a Budget | Affordable 3 BR home

Affordable 3 BR home
Another great pick for adventurous families
  • $
  • Spacious backyard with heated pool
  • 6 guests
  • Close to Vanderbilt Beach

This rental is perfect if you’re travelling with the whole clan, as there are heaps of amenities for younger children to enjoy. The house comes with bikes and a shallow pool, perfect for the kids. There are also games and toys in the house to keep everyone occupied on rainy days.

The house has many restaurants, supermarkets, and other eateries nearby if you don’t fancy cooking. If you do, a full chef’s kitchen awaits you. The interiors are spacious and roomy with large sliding doors that open out to the pool.  

Best Vacation Rental in Naples for Couples | Waterfront 1 BR condo

Waterfront 1 BR condo
Cheerful interiors in this cosy rental
  • $
  • Cosy and bright condo
  • 2 guests
  • Downtown Naples

If you’re travelling with your partner and want to stay close to all that Naples has to offer, then this cute apartment is the place for you! The condo is within walking distance of the famous Tin City, 5th Avenue South, and the beach.

While this Naples vacation rental is by no means luxe or super flash, it’s bright throughout and offers a view of the boats docked below. Guests also have access to the shared pool in the complex.

Best Pet Friendly Vacation Rental in Naples | Private fenced yard for your fur baby

Private fenced yard for your fur baby
Look at this cheery pet-friendly home!
  • $$
  • 2 pets allowed
  • 6 guests
  • 5 minute bike ride to Delnor Wiggins State Park

This home does charge an extra fee if you bring your pet, but we reckon it’s absolutely worth it. The three-bedroom house is close to the beach and has a fenced-in backyard, so your pets can roam around leash-free. The on-site pool is for human use only, however.

The house has an open and spacious lanai area, with a saltwater pool that can be heated on request. The house has recently been renovated and features two full bathrooms. The master bedroom has a king bed, while the other two rooms have a queen and two twin beds, making it great for a family travelling with children.

Best Value for Money Holiday Rental in Naples | 4 BR spacious home

4 BR spacious home
Classy interiors open up to the pool area
  • $$
  • Affordable luxury
  • 8 guests
  • In the Briarwood neighbourhood

This is my personal favourite vacation rental on the list. The sheer value for money that this place offers is insane. The house is gorgeous, with heaps of space filled with premium quality furnishings. The full kitchen is equipped with all the pots and pans you need to cook up a storm.

Outside, the relaxing lanai with the pool has enough seating for everyone to lie back and soak up some Vitamin D. There’s a little fitness area for the people who want to work out, with weights and other equipment included.

Best Holiday Rental in Naples for a Weekend Getaway | Comfy 4 BR private house

Comfy 4 BR private house
The spacious outdoor lanai area
  • $$
  • Florida-style heated pool
  • 8 guests
  • 1 mile from Vanderbilt Beach

For a quick weekend getaway with friends or family, this vacation rental in Naples is a great option. It’s super affordable and offers amenities that one would expect from a holiday home. The pool can be heated and the lanai area is full of space for everyone to chill out.

The house is a short drive or bike ride to the Ritz Carlton and some amazing golf courses. There are also some great Florida boat rentals, fishing charters, and sunset cruises if you want a relaxing weekend to simply unwind and relax.

Most Modern Vacation Rental in Naples | Oceanfront 2 BR Condo

Oceanfront 2 BR Condo
Your beautiful private balcony in this vacation rental in Naples
  • $$$
  • Sweeping ocean views
  • 4 guests
  • Close to Vanderbilt Beach

If you’re a beach bum, this vacation rental in Naples is the one for you. The apartment complex has direct access to the sand and is close to the premium shopping and dining places of Mercato, Waterside Shops and downtown Naples. The Gumbo Limbo at The Ritz Carlton is also only a short walk away.

Guests also have access to the shared Jacuzzi spa, BBQ and seating area by the beach. The apartment itself is furnished with modern appliances and comfortable furnishings that will leave you wanting for nothing. The private balcony is the perfect place to sip your morning coffee or unwind in the evenings with a glass of your favourite wine.

Best Vacation Rental in Naples for a Friends Getaway | Modern 3 BR apartment

Modern 3 BR apartment
  • $$$
  • Private balconies in every room
  • 6 guests
  • Close to Artis- Naples

This luxe apartment is great for a group of friends travelling together. There’s so much to do in the area, but the condo is just far enough to get you away from the hustle and bustle. Oh, and this awesome Naples vacation rental also has its own private beach!

The house features lots of neutrals and calming details. Comfortable furniture and chic metallic accents give the interiors a modern feel. The views alone are worth choosing this place! Spotlessly clean and stocked with amenities like beach gear, kitchen equipment and quality linen, the apartment also gives guests access to a shared fitness centre and pool downstairs.

Best Vacation Rental in Naples for a Large Group | 5 BR home close to the beach

5 BR home close to the beach
Covered pool for a lazy pool day
  • $$$
  • Backyard pool
  • 10 guests
  • Steps from Vanderbilt Beach

It isn’t always easy to find a house that ticks all the boxes when you’re travelling in a large group. However, we’re confident that this vacation rental in Naples hits the sweet spot. Very luxurious but surprisingly affordable when split between 10 guests, this house might just blow your mind!

This Naples Airbnb offers heaps of living space for everyone to stretch out. The pool area is great for a relaxed day, or if you want to go exploring, you’ll find that the beach is also close by.  

Vacation Rental in Naples with a Covnenient Location | 3 BR Modern Bungalow

3 BR Modern vacation rental Naples
Stay a stone’s throw from all the action!
  • $$
  • Newly remodelled home
  • 6 guests
  • Close to the Ritz Carlton

This bungalow is beautifully decorated with stylish interiors, but the best thing about it is its location! A short 3-minute drive away is Vanderbilt Beach and the Delanor- Wiggins Pass State Park. The Ritz Carlton is half a mile away, as is Mercato, Naples’ upscale shopping and restaurant development.

The house itself has been recently redone and hence is offers modern appliances and comforts. There’s a huge backyard with many fruit trees and flowers, giving the space a very tropical paradise kind of vibe.

The Vacation Rental in Naples with the Best Pool | Landscaped pool area that will blow your mind!

best vacation rental in Naples with a pool
Resort-style oasis pool
  • $$$
  • 3 acres of tropical gardens
  • 6 guests
  • Located in Rural Estates

You know how people visit other cities but never leave their rental to actually explore the area? I’ve never understood how that works… until now. Because honestly, I wouldn’t blame you if you didn’t step out of the pool at all!

The house has three Tiki Huts, one on the pool level, the second with a huge screen for movie nights, and the third for quieter times like morning yoga or cosy conversations. The entire property has speakers throughout that can be used to play music from your phone. There’s a stunning pool that has a waterfall, a slide, a cave spa and a beach sitting area. What more could you need?!

Most Affordably Luxurious Vacation Rental in Naples | 4 BR private estate home  

luxurious vacation rental in Naples
This place is seriously stunning
  • $$
  • Spacious home in Lely Resort
  • 10 guests
  • Golf course and lake views

This expansive home in a golf resort sleeps 10 people across four bedrooms and a den area. Guests can enjoy a game of golf as well as beautiful views of the lake nearby.

The house has an open plan living and dining room opens out to extensive views. Guests also get access to the resort’s private Players Club and Spa – what a bonus!

Best Holiday Rental in Naples with a View | 22nd floor apartment with Gulf and Bay views     

22nd floor vacation rental Naples
Open expansive views in this vacation rental in Naples
  • $$$
  • Floor to ceiling windows with gorgeous views
  • 8 guests
  • North Naples location

Staying on the 22nd floor practically guarantees views that go on and on from every room! Soak in the stunning vistas of the Gulf of Mexico, Wiggins Pass, and a wildlife sanctuary if you choose to stay here.

The house is filled with luxurious, plush furniture that gives it a stylish and opulent vibe. The sunsets from the lanai are utterly gorgeous, while the 3,200+ feet open living area with a  great room makes for the perfect Instagram-worthy background. There’s a modern kitchen, private elevator and even a separate butler’s pantry and bar.

Best Cottage Holiday Rental in Naples | Cosy Cottage with a pool

Cosy vacation rental with a pool Naples
  • $
  • Open plan living
  • 6 guests
  • Park Shore

If you’re heading to Florida with friends, this cottage would honestly be perfect! It sits in a quiet, exclusive residential area and features cosy and bright interiors.

Three bedrooms sleep six guests, while the open-plan living area creates plenty of space for everyone to relax. Outdoors you can enjoy a private saltwater pool, or grab your beach essentials and embark on the two-minute drive to Clam Pass Beach! Shopping and dining options are also within easy reach.

Most Luxurious Vacation Rental in Naples | Sophisticated 5 BR home

Sophisticated 5 BR vacation rental Florida
This house is the real deal
  • $$$$
  • Contemporary style house close to the beach
  • 10 guests
  • Located in Port Royal

This house is all kinds of fancy and luxe. It boasts over 6,400 square feet of space, and offers no less than five bedrooms and seven bathrooms!

The master bedroom has a walk-in closet, a massive bathtub, and a walkthrough shower, as well as expansive views of Cutlass Cove. The huge lounge area opens up onto the deck, where you’ll find a massive pool and a Jacuzzi that can fit 12.

Most Accessible Vacation Rental in Naples | Wheelchair friendly single level home

Wheelchair friendly vacation rental in Naples
Check out this stylish ground floor home
  • $$
  • Step-free home for easy accessibility
  • 6 guests
  • 1 mile from 5th Avenue South, Downtown Naples

This single level home has beautiful boho-chic interiors that instantly soothe your soul as soon as you walk into the house. The entire place is bright and airy and is spacious enough to accommodate everyone with people bumping elbows.

The tropical backyard features a private hot tub for you to relax in after a long day of exploring Naples’ coolest attractions. Relax on the hanging day bed under a fan or in the hammock under the palm trees, for a lazy day. If you want to go out, the house is conveniently close to shopping and several eateries. 

Most Romantic Vacation Rental in Naples | Cute condo for a couple

Cute condo for a couple
Relax and enjoy the quiet life
  • $
  • 5-minute walk to the beach
  • 2 guests
  • In the heart of Old Naples

This condo is great for couples looking for a private retreat in the outdoors. The private patio overlooks the lake, and the beach is just five minutes away. If you’re after some fine dining, shopping, or fancy anything from tennis to performing arts, then this is the ideal place to base yourself.

The apartment itself boasts modern amenities and is the perfect cosy space for two. Interiors are bright, with natural light flowing in through the atrium doors that open out onto the patio.

Most OTT Luxurious Vacation Rental in Naples | Mediterranean-style private estate home

Mediterranean-style luxury Naples vacation rental
Dripping in opulent style
  • $$$$
  • Custom-built four-bedroom luxury home
  • 8 guests
  • 5 minute drive to Naples Beach

Got a few thousand dollars to spare? Me neither. But for those looking for something extra special or are celebrating a very special occasion, prepare to have your mind blown. Yes, this vacation rental in Naples is really, really expensive. Having said that, true luxury often comes at an eye-watering cost.

Set on 300 feet of frontage on calm Naples Bay, the house has an infinity pool that looks out to the bay. It’s close to golf courses and the busy downtown area of Naples but is also far enough for you to savour the peace and privacy that this villa offers.  

Naples Travel Insurance

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing.

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

Final Thoughts

There’s a huge variety of vacation rentals in Naples to suit every budget and travel style. Whether you want something budget-friendly or something super flashy and flamboyant, this Floridian city has it all.

While the nightlife might not be something to write home about, seeing that Naples is a place where many come to retire, the city makes up for it with its amazing beaches and laid back lifestyle. If this sounds like something you might enjoy, all that’s left to do is pick your favourite rental and get packing!

Till next time!  

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