Holiday Rentals in Naples, FL

2560 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Naples, FL holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Naples, FL

Best family friendly Naples, FL holiday rentals

Among the 2560 accommodations in Naples, FL, here are the 4 best family friendly rentals

Naples Getaway - Naples, FL
9.5 49 reviews
Naples, FL
14/08 – 16/08
SG$439/nighttotal: SG$878 (2 )

Naples Getaway

1 7
apartment , Naples
This Naples, Florida single-family home provides excellent proximity to Naples' beaches, Fifth Avenue South, and Mercato, all within under 6.4 kilometres.
Sleeping eight guests, this four-bedroom, three-bathroom property boasts a spacious open-plan layout, modern amenities including a fully equipped kitchen and smart TVs, plus a private garden and parking.
Tranquil Waterfront* 5th Ave/beach 3mi* Fastwifi - Naples, FL
9.6 60 reviews
Naples, FL
05/07 – 28/07
SG$259/nighttotal: SG$5957 (23 )

Tranquil Waterfront* 5th Ave/beach 3mi* Fastwifi

1 2
apartment , Naples
This luxurious four-bedroom, three-bathroom Naples waterfront property, situated in a quiet neighbourhood, is a 6.4km (10-minute) drive from Naples Beach and Fifth Avenue.
Offering direct waterfront access, a heated pool, Jacuzzi, garden, parking, and amenities including Publix, Walmart, and Starbucks nearby, this self-catering apartment comfortably sleeps eight guests and features five smart TVs, high-speed internet (200 Mbps), and a BBQ grill.
Condo ∙ 1 Bedroom ∙ 4 Guests - Naples, FL
9.3 3 reviews
Naples, FL
27/06 – 04/07
SG$225/nighttotal: SG$1575 (7 )

Condo ∙ 1 Bedroom ∙ 4 Guests

1 2
apartment , Naples
White Sands, an apartment in Old Naples, is located a short walk from the beach and Fifth Avenue South's shops and restaurants.
This family-friendly apartment offers a heated swimming pool, a spa tub, and complimentary bicycles, accommodating up to four guests with one bedroom and one bathroom.
2 Miles To The Beach And 5th Ave - Naples, FL
9.2 5 reviews
Naples, FL
03/07 – 05/07
SG$476/nighttotal: SG$952 (2 )

2 Miles To The Beach And 5th Ave

3 7
apartment , Naples
This East Naples holiday home, situated in a quiet coastal neighbourhood less than 3.2km from Naples' Fifth Avenue South, Naples beaches, and the Naples Zoo, offers convenient access to key attractions.
Sleeping seven guests, this three-bedroom, two-bathroom property boasts a gourmet kitchen, game room with air hockey and ping pong, a shared laundry room, and proximity to guided kayak tours on the intercoastal waterways.

Best Naples, FL holiday rentals with a pool

Among the 2560 accommodations in Naples, FL, here are the 4 best rentals with a pool

Awesome Apartment Near The Beach - Naples, FL
9.8 19 reviews
Naples, FL
07/09 – 10/09
SG$293/nighttotal: SG$879 (3 )

Awesome Apartment Near The Beach

2 1
apartment , Naples
This two-bedroom, two-bathroom apartment in Central Naples, Florida, is situated within The World Tennis Club, approximately 6.4 kilometres from Naples' beaches and Fifth Avenue South's upscale shopping.
The 7-guest property boasts a fully equipped kitchen, including a dishwasher, air conditioning, a private garden, access to two heated pools, a jacuzzi, sauna, parking, and on-site tennis courts, pickleball, and bocce ball facilities.
Naples Oasis - Naples, FL
9.8 14 reviews
Naples, FL
06/10 – 07/10
SG$765/nightfor 1 night

Naples Oasis

2 2
house , Naples
This Naples, Florida villa is conveniently located 1.9km from the Collier Museum of the Everglades, 3.7km from Gulf Shores Marina, and 1.9km from Naples Municipal Airport.
The two-bedroom, two-bathroom property sleeps eleven guests and boasts a private pool and patio, fully equipped kitchen with dishwasher, free on-site parking, and is within walking distance of local amenities.
3 Mi To Naples Beach: Chic Group Getaway W/ Pools! - Naples, FL
Naples, FL
22/12 – 26/12
SG$2720/nighttotal: SG$10880 (4 )

3 Mi To Naples Beach: Chic Group Getaway W/ Pools!

8 11
apartment , Naples
This East Naples waterfront property offers direct canal access and is located 1.6 kilometres from the Naples Botanical Garden, 3.2 kilometres from the USOP National Pickleball Centre, and 6.4 kilometres from Naples Beach.
This expansive residence, totalling 511 square metres, features eight bedrooms, eight bathrooms, two heated swimming pools, two kitchens, and accommodates up to 16 guests, with four bicycles provided for exploring the area.
Naples Tennis Escape With Resort Amenities - Naples, FL
10 4 reviews
Naples, FL
27/06 – 04/07
SG$221/nighttotal: SG$1547 (7 )

Naples Tennis Escape With Resort Amenities

1 2
apartment , Naples
This furnished 2-bedroom, 2-bathroom condominium offers a prime location within Naples' World Tennis Centre, a short drive from Naples beaches and 5th Avenue South shopping and dining.
This apartment provides accommodation for up to 4 guests and features a private balcony, on-site tennis and pickleball courts, a swimming pool, a spa, and clubhouse dining, with a mandatory club facility fee for access to all amenities.

Frequently asked questions about holiday rentals in Naples, FL

  • What should a first-time visitor not miss in Naples, FL?

    You definitely need to visit the Naples Pier, which is a great spot to watch the sunset over the Gulf of Mexico. Also, you should check out the Naples Botanical Garden, which has a wide variety of plants and flowers from all over the world. And if you're interested in art, the Naples Art Museum is a must-see.
  • What are the best Airbnb and vacation rentals in Naples, FL?

  • What are the hotels like in Naples?

    When it comes to booking a hotel in Naples, a bed and breakfast is the most abundant accommodation in the city, however, these are not your usual quaint family-run B&Bs. Bed and breakfasts in Naples resemble a normal hotel here, just you can be sure of a delicious Italian spread in the morning to start the day. Many B&Bs in Naples have the four-star label. You can also find a range of hotels of different categories, such as luxury hotels in historic palaces and those with stunning views over the Bay of Naples. There are also lower budget guesthouses and hostels if you're traveling to Naples on a budget.
  • Which neighborhood in Naples, FL should you consider for a vacation rental?

    If you want to be close to the beach and the action, then Old Naples is a great choice. It has lots of restaurants and shops, and it's within walking distance of the beach. If you're looking for something a bit quieter, then Aqualane Shores is a good option. It's a bit further from the centre, but it has beautiful beaches and a more relaxed atmosphere.
  • What are the most popular Airbnbs in Naples, FL?

  • Where's the best place to book a hotel in Naples?

    On your first visit to Naples, you'll want to stay in the Centro Storico, the Old Town. This is the heart of the city, set between medieval houses and cobbled streets. Budget travelers may want to book a hotel in the Quartieri Spagnoli, the former home to the Spanish garrisons in the 16th century. Although the area had an unsavory reputation, its crime and prostitution have mostly gone and is a safe area to stay, but cheaper due to its seedy past. On the other hand, families will want to find accommodation in and around Piazza del Plebiscito, as it's close to the center but close enough to the sea as well. For nightlife (and amazing views), book a place in the Vomero neighborhood, set on the hilly part of the city. Finally, if you want luxury and a cool vibe, you can't beat the upscale neighborhood of Chiaia, where Italian designer fashion and arty boutiques line the streets.
  • What are the top family-friendly attractions in Naples, FL?

    The Naples Zoo is a great place to spend a day with the family. It has over 100 different animal species, and there are lots of interactive exhibits for kids. The Golisano Children's Museum of Naples is another great option. It has hands-on exhibits that teach kids about science, art, and culture.
  • What are the best vacation rentals with a pool in Naples, FL?

  • What are the must-see sights in Naples?

    Many of Naples's main sites will take you outside the city. The ruined city of Pompeii is an absolute must if you're staying in Naples and expect to spend a whole day there. If you've caught the history bug, then head over to the ruins of Herculaneum nearby, too. The more adventurous traveler may want to hike up the infamous Mount Vesuvius, the dormant volcano looming over the city. In the city, sites to add to your itinerary include the Naples National Archaeological Museum, the San Gennaro Catacombs, and Castel Nuovo.
  • When is the best time to book a vacation rental in Naples, FL?

    The best time to book a vacation rental in Naples is during the shoulder seasons, which are spring (April-May) and autumn (September-October). The weather is still good during these months, but the crowds are smaller and the prices are lower.
  • What are the best rentals for families and kids in Naples, FL?

  • What should I eat in Naples?

    You cannot visit Naples without trying pizza. After all, this is the homeland of pizza, so you leave the diet at the door and enjoy this Neapolitan classic. Of course, Naples offers many other tasty snacks, and pastries being one of them. Try Taralli, a local cracker made with toasted almonds, lard, and black pepper, Sfogiatelli, a flaky pastry sometimes stuffed with ricotta, and Struffoli, deep-fried dough topped with honey and a popular dish around Christmas.
  • What events or festivals should visitors check out in and around Naples, FL?

    The Naples Winter Wine Festival is a major event that takes place every January. It's a charity event that raises money for children in need. The Naples Stone Crab Festival is another popular event that takes place in October. It celebrates the local stone crab industry.
  • What are the best rentals or Airbnbs with a jacuzzi in Naples, FL?

  • How can I get around from my hotel in Naples?

    You can explore Naples on foot, but take care as Neapolitan drivers tend to ignore red lights. Alternatively, you have great public transport options, with two subway lines, an extensive tram network that's been in operation since 1875! Don't want to climb hills? Well, that's what the funiculars are for! Of course, there are also many buses to get around, and it is the most popular option for locals.
  • What are the best budget-friendly activities in Naples, FL?

    You can enjoy a free walk along the Naples Pier and watch the sunset, or you can visit the Naples Botanical Garden for a small entrance fee. You can also take a free guided tour of the Naples Historic District.
  • What are the best restaurants with local dishes in Naples, FL?

    For fresh seafood, you should try The Dock at Crayton Cove. It has a beautiful location on the water and serves some of the best seafood in Naples. If you're looking for something more casual, then try The Local, which has a great selection of local beers and pub food.
  • What are the best walking or cycling routes in Naples, FL?

    The Naples Beachfront Walk is a great place to walk or cycle. It stretches for over 3 km along the beach and offers stunning views of the Gulf of Mexico. You can also cycle along the Gordon River Greenway, which is a 16 km paved trail that runs through mangrove forests and coastal areas.
  • Are there pet-friendly attractions in Naples, FL?

    Yes, there are a few pet-friendly attractions in Naples. The Naples Botanical Garden allows well-behaved dogs on leashes on their trails, and many restaurants have outdoor seating where you can bring your dog.
  • What are the benefits of choosing a vacation rental in Naples, FL?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities that you wouldn't find in a hotel room. They can also be a more affordable option, especially if you're travelling with a family or a group of friends.
  • What are the top sports attractions and facilities in Naples, FL?

    Naples is home to the Naples Beach & Golf Club, which has two championship golf courses. The city also has several public tennis courts and a number of fitness centres.

Destinations nearby

Best Naples, FL holiday rentals with a balcony

102 M² Condo ∙ 2 Bedrooms ∙ 6 Guests - Naples, FL
9.0 4 reviews
Naples, FL
27/06 – 27/07
SG$154/nighttotal: SG$4620 (30 )

102 M² Condo ∙ 2 Bedrooms ∙ 6 Guests

2 2
apartment , Naples
This Naples flat is situated within 160 acres of mature green space, offering immediate access to a lake and proximity to golf courses and beaches, with extensive shopping including Publix, Target, Walmart, and Costco within 500 metres.
This family-friendly 102 square metre condominium sleeps six and features two bedrooms and two bathrooms, boasting a private pool, sauna, Jacuzzi, terrace, garden, fitness centre, and parking within a gated community.
Ultimate Tennis Condo At World Tennis Center - Naples, FL
10 12 reviews
Naples, FL
05/07 – 28/07
SG$148/nighttotal: SG$3404 (23 )

Ultimate Tennis Condo At World Tennis Center

2 2
apartment , Naples
This Naples, Florida condo is centrally located, within 5km of three golf courses (Quail Run, Kensington, Naples Grande) and 10km of Coastland Center and Waterside Shops.
The two-bedroom, two-bathroom apartment sleeps four, boasts a private balcony, swimming pool, fitness centre, parking, and a fully equipped kitchen including a dishwasher, microwave and fridge; free Wi-Fi is also provided.
H-346 -Third Floor - Sunset Views From The Lanai! - Naples, FL
Naples, FL
15/08 – 17/08
SG$428/nighttotal: SG$856 (2 )

H-346 -Third Floor - Sunset Views From The Lanai!

2 4
apartment , Naples
This Park Shore flat in Naples offers resort-style living within a 13-acre subtropical oasis, located a short drive from downtown Naples and 2.9 kilometres from Horizon Way beach and 3.2 kilometres from Seagate/North Gulfshore Beach.
This 80 square metre apartment sleeps six, featuring two bedrooms and two bathrooms, with amenities including a kitchen with a fridge, microwave and dishwasher, air conditioning, a swimming pool, a terrace, and on-site tennis and pickleball courts.
Brick Enclave With Mini Golf & Spa, 5mins To Beach - Naples, FL
9.6 18 reviews
Naples, FL
17/08 – 24/08
SG$226/nighttotal: SG$1582 (7 )

Brick Enclave With Mini Golf & Spa, 5mins To Beach

2 2
house , Naples
This recently renovated two-bedroom holiday home is situated in Naples' Brick Enclave neighbourhood, a short 8km drive from Naples beach, 2.6km from the Naples Museum of Art, and 7.7km from Tin City.
The 80 square metre property sleeps seven, boasting a fully equipped kitchen, jacuzzi, private parking, and access to on-site amenities including a mini-golf course, spa, and outdoor fireplace, all within easy reach of local attractions.

Best Naples, FL holiday rentals with parking

I-352 - Beautiful Lake Views- Walk To Amenities - Naples, FL
10 2 reviews
Naples, FL
04/08 – 05/08
SG$577/nightfor 1 night

I-352 - Beautiful Lake Views- Walk To Amenities

2 2
apartment , Naples
This Park Shore flat in Naples, Florida, offers a tranquil tropical setting, located just a 12-minute drive from downtown Naples and 2.9 kilometres from Horizon Way beach and 3.2 kilometres from Seagate/North Gulfshore Beach.
This 79 square metre flat accommodates up to six guests with two bedrooms and two bathrooms, featuring a king bed, two twin beds, a pull-out sofa, a private washer/dryer, a fully equipped kitchen, air conditioning, a swimming pool, a terrace, parking, and on-site tennis and pickleball courts.
Park Shore Resort By Mike Z Rentals - Naples, FL
8.7 846 reviews
Naples, FL
20/07 – 23/07
SG$425/nighttotal: SG$1275 (3 )

Park Shore Resort By Mike Z Rentals

2 5
resort , Naples
Park Shore Resort by Sunstream is located in Naples, Florida, just a short drive from the beautiful North Gulfshore beach and close to attractions like Tin City and the Naples Museum of Art. This resort has consistently received very good ratings for its cleanliness, location, and overall experience.
The resort offers a range of accommodation options, including comfortable rooms with private bathrooms and modern amenities. Guests can enjoy a variety of facilities, including a swimming pool, hot tub, tennis court, fitness centre, and BBQ facilities, making it a great choice for families and couples alike.
Steps To The Beach With Heated Pool In Old Naples, Fl! - Naples, FL
9.9 54 reviews
Naples, FL
24/11 – 30/11
SG$484/nighttotal: SG$2904 (6 )

Steps To The Beach With Heated Pool In Old Naples, Fl!

1 2
apartment , Naples
This one-bedroom apartment in Old Naples is ideally located just 1 kilometre from the bustling Fifth Avenue South shopping district and the beautiful Naples Beach, making it perfect for exploring the area's charm. The apartment has received excellent ratings for location, cleanliness and overall user experience.
This comfortable flat is suitable for up to 4 guests and features a fully equipped kitchen, a private patio, and access to a swimming pool and jacuzzi. Guests can also enjoy free Wi-Fi, air conditioning and a washing machine.
"La Casa Delmar" Heated Pool! Close To Beaches And 5th Ave. - Naples, FL
9.7 146 reviews
Naples, FL
06/08 – 11/08
SG$344/nighttotal: SG$1720 (5 )

"La Casa Delmar" Heated Pool! Close To Beaches And 5th Ave.

4 1
apartment , Naples
This smoke-free holiday home is located in East Naples, just a 2.4 km walk from Village Plaza Shopping Center and Fifth Avenue South, with Gordon River and Brookside Marina also within a 2.4 km radius. This property has received excellent ratings for user experience, location, and cleanliness.
The house has 4 bedrooms and 2 bathrooms, spanning 111 square meters, comfortably accommodating up to 10 guests. It features a private pool, a fenced yard, a garden, a barbecue grill, air conditioning, parking, and a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher.
©2026 cozycozy.com