Condo
10.0(238 Reviews)
1 Bedroom
2 Guests
Hot Tub
Parking
Pool
Ocean View
US $376/Night
7 Nights - US $2,635
Naples Holiday Rentals
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Compare Villas, Resorts, & Rentals in Naples
10.0
Apartment
10.0(23 Reviews)
2 Bedrooms
4 Guests
Oceanfront- Hot Tub
Breakfast- Parking
US $272/Night
7 Nights - US $1,902
Cottage
10.0(7 Reviews)
1 Bedroom
- Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $758/Night
7 Nights - US $5,303
House
10.0(207 Reviews)
2 Bedrooms
6 Guests
Private Pool- Oceanfront
- Parking
- Pool
US $381/Night
7 Nights - US $2,667
House
10.0(10 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $481/Night
7 Nights - US $3,367
Condo
10.0(204 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $275/Night
7 Nights - US $1,922
Condo
10.0(199 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $323/Night
7 Nights - US $2,260
House
10.0(192 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $368/Night
7 Nights - US $2,575
Condo
10.0(170 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $288/Night
7 Nights - US $2,014
Luxury Holiday Rentals in Naples
Over 10000+ Luxury Holiday Rentals in or Near Naples
House
3 Bedrooms
6 Guests
View- Air Conditioner
Internet
Pet Friendly
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New
House
3 Bedrooms
10 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
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New
House
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
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House
4 Bedrooms
10 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
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House
8.4(6 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
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Resort
10.0(2 Reviews)
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
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Resort
10.0(2 Reviews)
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
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Resort
10.0(2 Reviews)
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
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Top-Rated Holiday Rentals with a Pool in Naples
Over 10000+ The Best Private Villas and Holiday Rentals in Naples with a Pool
House
10.0(328 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $268/Night
7 Nights - US $1,876
House
10.0(257 Reviews)
5 Bedrooms
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,300/Night
7 Nights - US $9,097
New
Condo
10.0(233 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $273/Night
7 Nights - US $1,910
House
10.0(211 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $289/Night
7 Nights - US $2,021
House
10.0(188 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $596/Night
7 Nights - US $4,172
House
10.0(184 Reviews)
6 Bedrooms
20 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $2,294/Night
7 Nights - US $16,061
House
10.0(180 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $401/Night
7 Nights - US $2,804
House
10.0(175 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $467/Night
7 Nights - US $3,272
House
10.0(164 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $596/Night
7 Nights - US $4,172
Pet-Friendly Holiday Rentals in Naples
Over 4026+ Pet-Friendly Holiday Rentals in or Near Naples
Condo
10.0(94 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $226/Night
7 Nights - US $1,582
House
10.0(9 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
US $268/Night
7 Nights - US $1,876
Cottage
10.0(3 Reviews)
1 Bedroom
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $693/Night
7 Nights - US $4,854
House
10.0(78 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $225/Night
7 Nights - US $1,572
Apartment
10.0(7 Reviews)
3 Bedrooms
7 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $230/Night
7 Nights - US $1,610
House
10.0(77 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $323/Night
7 Nights - US $2,260
House
10.0(64 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $436/Night
7 Nights - US $3,055
House
10.0(62 Reviews)
2 Bedrooms
7 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $300/Night
7 Nights - US $2,100
Apartment
10.0(61 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $233/Night
7 Nights - US $1,634
Large Holiday Rentals and Private Villas in Naples
Over 2155+ Large Holiday Rentals and Private Villas in or Near Naples
Villa
10.0(55 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $431/Night
7 Nights - US $3,020
Villa
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
US $483/Night
7 Nights - US $3,383
US $359/Night
7 Nights - US $2,513
Villa
10.0(40 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $290/Night
7 Nights - US $2,032
House
10.0(6 Reviews)
4 Bedrooms
11 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Internet
US $347/Night
7 Nights - US $2,429
Villa
10.0(28 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $187/Night
7 Nights - US $1,307
House
10.0(17 Reviews)
2 Bedrooms
60 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $373/Night
7 Nights - US $2,611
House
10.0(15 Reviews)
2 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $853/Night
7 Nights - US $5,973
Villa
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $245/Night
7 Nights - US $1,713
Wheelchair Accessible Holiday Homes in Naples
Over 3847+ Wheelchair Accessible Holiday Homes in or Near Naples
Condo
10.0(163 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $356/Night
7 Nights - US $2,490
Apartment
10.0(6 Reviews)
1 Bedroom
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $260/Night
7 Nights - US $1,820
Condo
9.6(100 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $672/Night
7 Nights - US $4,702
Condo
10.0(163 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $288/Night
7 Nights - US $2,014
House
10.0(2 Reviews)
4 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
US $476/Night
7 Nights - US $3,332
Condo
10.0(154 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $308/Night
7 Nights - US $2,158
Condo
10.0(145 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $326/Night
7 Nights - US $2,285
Condo
10.0(143 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $393/Night
7 Nights - US $2,750
Condo
10.0(142 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $241/Night
7 Nights - US $1,686
Naples Private Villas and Holiday Homes Under $200
Over 3911+ Naples Private Villas and Holiday Homes Under $200
Condo
10.0(94 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $182/Night
7 Nights - US $1,274
House
10.0(5 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $161/Night
7 Nights - US $1,127
Apartment
1 Bedroom
- Oceanfront
- Parking
- Pool
- Ocean View
US $189/Night
7 Nights - US $1,322
Condo
10.0(76 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $195/Night
7 Nights - US $1,366
Apartment
10.0(4 Reviews)
1 Bedroom
2 Guests
EV Charge Station- Parking
- View
- Air Conditioner
US $145/Night
7 Nights - US $1,015
Apartment
10.0(76 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $188/Night
7 Nights - US $1,319
Condo
10.0(71 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $163/Night
7 Nights - US $1,138
Condo
10.0(67 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $172/Night
7 Nights - US $1,206
Condo
10.0(66 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $177/Night
7 Nights - US $1,236
Instantly Bookable Holiday Homes in Naples
Over 10523+ Instantly Bookable Holiday Homes in or Near Naples
Condo
10.0(147 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $426/Night
7 Nights - US $2,981
House
6.5(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Internet
Child Friendly
US $367/Night
7 Nights - US $2,569
Condo
8.8(71 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $181/Night
7 Nights - US $1,265
House
10.0(143 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $245/Night
7 Nights - US $1,714
Condo
10.0(133 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $403/Night
7 Nights - US $2,823
Condo
10.0(131 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $279/Night
7 Nights - US $1,951
Apartment
10.0(122 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $282/Night
7 Nights - US $1,971
Condo
10.0(114 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $337/Night
7 Nights - US $2,358
Condo
10.0(112 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $303/Night
7 Nights - US $2,118
Book a Last Minute Place to Stay in Naples
About Casai's Private Villas and Holiday Rentals in Naples
Discover more than 19130 vacation rentals available in Naples. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Naples.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Naples, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Naples. On average, places to stay near Naples offer 970.01 ft², with nightly prices averaging US $445.
With Casai, finding and comparing holiday rentals in Naples is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Naples, FL
There are 19130 Naples, FL Holiday Rentals
- Prices for a holiday home in Naples start at US $46
- Top rated vacation home in Naples is Perfect recipe for relaxing, heated pool, walk to beach, bikes, stunning sunsets
- Most popular short term in Naples is La Quinta by Wyndham Naples East (I-75)
- Cheapest place to stay in Naples is Come Stay in Beautiful Marco Island at Marco Comfort!
- Most expensive holiday rental in Naples is Beautiful home w/Pool & soaker tub!
Recently Booked Holiday Rentals in Naples
Frequently Asked Questions About Naples?
What are the top holiday rentals in Naples?
With numerous options available in Naples, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Naples:
- Perfect recipe for relaxing, heated pool, walk to beach, bikes, stunning sunsets
- Beautiful home, ideal for a larger group to gather.
- 🐬 HIGHLY RATED! Remodeled Beachfront Apollo Condo, 9th Floor w/GREAT VIEW
- Great Beach Views, Direct Access, Pickleball, New Kitchen & Heated Pool! Tower 3
- Charming Beach Cottage with private pool! One mile to stunning Horizon Beach!
- NEW PINBALL & LOUNGERS! Cute Designer Home, Heated Pool, Close Beach, FREE Bikes
- Beautiful beachfront, along with breathtaking sunset views
- Newly remodeled beach front! SPECIAL RATE SEPTEMBER and OCTOBER
- Beautiful Naples Home: Private Pool, 4-Minute Drive to Vanderbilt Beach
- Waterview 3 ensuite home with pool HGTV chose as ideal vacation home!
How many holiday rentals have private pools in Naples?
Discover a selection of holiday rentals with private pools near Naples with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Naples are best for families?
If you're searching for a family-friendly holiday home in Naples, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Naples:
How many Casai.com holiday rentals are available in Naples?
As of 2026, Casai boasts over 19130 properties listed in the Naples area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Naples.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| West Naples Vacation Rentals in Naples, Florida | 1476 |
| Old Naples Vacation Rentals in Naples, Florida | 1470 |
| Bonita Shores Vacation Rentals in Naples, Florida | 1376 |
| Naples Park Vacation Rentals in Naples, Florida | 937 |
| Central Naples Vacation Rentals in Naples, Florida | 426 |
| East Naples Vacation Rentals in Naples, Florida | 408 |
| Park Shore Vacation Rentals in Naples, Florida | 347 |
| Vanderbilt Beach Vacation Rentals in Naples, Florida | 317 |
| Rural Estates Vacation Rentals in Naples, Florida | 156 |
| Moorings Vacation Rentals in Naples, Florida | 114 |
| Bonita Bay Vacation Rentals in Naples, Florida | 88 |
| Pelican Bay Vacation Rentals in Naples, Florida | 57 |
| Redevelopment Area Vacation Rentals in Naples, Florida | 37 |
| Coquina Sands Vacation Rentals in Naples, Florida | 24 |
| Aqualane Shores Vacation Rentals in Naples, Florida | 1601 |
| Estero Bay Shores Vacation Rentals in Naples, Florida | 974 |
