New
Apartment
10.0(18 Reviews)
2 Bedrooms
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $225/Night
7 Nights - US $1,576
Naples, FL Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
- No markup
- Trusted partners
Compare Holiday Rentals, Villas & Resorts in Naples
10.0
Apartment
10.0(23 Reviews)
2 Bedrooms
4 Guests
Hot Tub
Breakfast- Parking
Pool
US $272/Night
7 Nights - US $1,902
House
9.8(55 Reviews)
4 Bedrooms
10 Guests
Private Pool- Parking
- Pool
- Balcony/Terrace
US $439/Night
7 Nights - US $3,076
New
House
10.0(12 Reviews)
2 Bedrooms
5 Guests
- Parking
Ocean View- Balcony/Terrace
View
US $286/Night
7 Nights - US $2,002
House
10.0(10 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- View
- Air Conditioner
US $481/Night
7 Nights - US $3,367
Condo
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- View
US $116/Night
7 Nights - US $813
New
Condo
10.0(4 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $863/Night
7 Nights - US $6,040
House
10.0(2 Reviews)
4 Bedrooms
13 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,451/Night
7 Nights - US $10,155
New
House
10.0(1 Review)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $747/Night
7 Nights - US $5,228
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
Unlock the Best Price
House
8.4(6 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
Unlock the Best Price
Resort
10.0(2 Reviews)
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
Unlock the Best Price
Condo
3 Bedrooms
6 Guests
- Hot Tub
- Balcony/Terrace
Child Friendly
Security/Safety
US $9,116/Night
7 Nights - US $63,812
Resort
10.0(16 Reviews)
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $6,619/Night
7 Nights - US $46,333
Resort
9.8(19 Reviews)
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $6,619/Night
7 Nights - US $46,333
Resort
10.0(17 Reviews)
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $6,619/Night
7 Nights - US $46,333
Resort
10.0(16 Reviews)
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $6,583/Night
7 Nights - US $46,083
Resort
10.0(18 Reviews)
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $6,583/Night
7 Nights - US $46,083
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
- Parking
- Pool
- Ocean View
US $280/Night
7 Nights - US $1,963
House
10.0(257 Reviews)
5 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,396/Night
7 Nights - US $9,773
Condo
10.0(242 Reviews)
1 Bedroom
2 Guests
Oceanfront- Hot Tub
- Parking
- Pool
US $465/Night
7 Nights - US $3,252
House
10.0(240 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $334/Night
7 Nights - US $2,341
New
Condo
10.0(233 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $289/Night
7 Nights - US $2,025
House
10.0(220 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $382/Night
7 Nights - US $2,671
House
10.0(216 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $479/Night
7 Nights - US $3,352
House
10.0(207 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $419/Night
7 Nights - US $2,932
Condo
10.0(205 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $290/Night
7 Nights - US $2,031
Pet-Friendly Holiday Rentals in Naples
Over 4154+ Pet-Friendly Holiday Rentals in or Near Naples
House
10.0(1 Review)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $403/Night
7 Nights - US $2,823
House
10.0(9 Reviews)
3 Bedrooms
6 Guests
- Breakfast
- Parking
- Pool
- Balcony/Terrace
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
New
Apartment
10.0(1 Review)
2 Bedrooms
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $149/Night
7 Nights - US $1,041
Apartment
10.0(7 Reviews)
3 Bedrooms
7 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $230/Night
7 Nights - US $1,610
House
9.8(11 Reviews)
3 Bedrooms
9 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $423/Night
7 Nights - US $2,963
House
9.8(7 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $736/Night
7 Nights - US $5,153
New
House
9.6(5 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,460/Night
7 Nights - US $17,219
New
House
9.6(5 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $174/Night
7 Nights - US $1,220
Large Holiday Rentals and Private Villas in Naples
Over 2214+ Large Holiday Rentals and Private Villas in or Near Naples
New
House
6 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,527/Night
7 Nights - US $17,687
House
10.0(9 Reviews)
4 Bedrooms
10 Guests
- Parking
- Pool
- View
- Air Conditioner
US $575/Night
7 Nights - US $4,025
US $359/Night
7 Nights - US $2,513
New
House
5 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,383/Night
7 Nights - US $9,678
Villa
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Breakfast
- Parking
- Balcony/Terrace
US $307/Night
7 Nights - US $2,152
House
4 Bedrooms
10 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,057/Night
7 Nights - US $7,396
New
Villa
1 Bedroom
16 Guests
- Parking
Spa- Balcony/Terrace
- Kitchen
US $1,032/Night
7 Nights - US $7,226
House
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,026/Night
7 Nights - US $7,183
New
House
6 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $964/Night
7 Nights - US $6,751
Wheelchair Accessible Holiday Homes in Naples
Over 4028+ Wheelchair Accessible Holiday Homes in or Near Naples
Condo
9.8(94 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $626/Night
7 Nights - US $4,382
Apartment
10.0(6 Reviews)
1 Bedroom
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $260/Night
7 Nights - US $1,820
Apartment
8.0(1 Review)
1 Bedroom
- Oceanfront
- Parking
- Pool
- Ocean View
US $504/Night
7 Nights - US $3,528
US $659/Night
7 Nights - US $4,614
US $476/Night
7 Nights - US $3,332
New
Condo
2 Bedrooms
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $581/Night
7 Nights - US $4,066
Condo
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $420/Night
7 Nights - US $2,942
New
Apartment
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $356/Night
7 Nights - US $2,492
New
Condo
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- View
US $351/Night
7 Nights - US $2,458
Naples Private Villas and Holiday Homes Under $200
Over 3782+ Naples Private Villas and Holiday Homes Under $200
New
Condo
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $196/Night
7 Nights - US $1,371
House
10.0(5 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Internet
US $161/Night
7 Nights - US $1,127
US $160/Night
7 Nights - US $1,119
Condo
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $194/Night
7 Nights - US $1,360
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
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $193/Night
7 Nights - US $1,350
New
Apartment
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
Bedding/Linens
US $187/Night
7 Nights - US $1,309
New
Condo
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $184/Night
7 Nights - US $1,285
New
Condo
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $183/Night
7 Nights - US $1,278
Instantly Bookable Holiday Homes in Naples
Over 10982+ Instantly Bookable Holiday Homes in or Near Naples
House
9.6(19 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $407/Night
7 Nights - US $2,850
House
6.5(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Internet
- Child Friendly
US $367/Night
7 Nights - US $2,569
US $203/Night
7 Nights - US $1,422
New
House
8.8(6 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $409/Night
7 Nights - US $2,860
New
Condo
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $2,888/Night
7 Nights - US $20,214
New
House
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,653/Night
7 Nights - US $11,570
New
Condo
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,225/Night
7 Nights - US $8,577
New
House
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $586/Night
7 Nights - US $4,101
New
House
3 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $585/Night
7 Nights - US $4,094
Book a Last Minute Place to Stay in Naples
About Casai's Private Villas and Holiday Rentals in Naples
Discover more than 19827 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 983.18 ft², with nightly prices averaging US $456.
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 in Naples, FL
There are 19827 Naples, FL Holiday Rentals
- Prices for a holiday home in Naples start at US $61
- Top rated vacation home in Naples is Perfect recipe for relaxing, heated pool, just remodeled new pictures coming.
- Most popular short term in Naples is La Quinta by Wyndham Naples East (I-75)
- Cheapest place to stay in Naples is Tollgate Inn
- Most expensive holiday rental in Naples is 102nd Christina Jason Maria Moore Sand and Sea Pool Bungalow
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, just remodeled new pictures coming.
- Beautiful home, ideal for a larger group to gather.
- 🐬 Beachfront Paradise, 9th Floor Apollo Condo with Gulf Views & King Bed
- Stunning Beach Cottage with private pool! 2 miles to Beach!
- Great Beach Views, Direct Access, Pickleball, New Kitchen & Heated Pool! Tower 3
- Three block walk to beach, private pool, designer home
- Charming Beach Cottage with private pool! One mile to stunning Horizon Beach!
- NEW Pinball & Loungers! OCT SPECIAL! Cute Designer Home, Heated Pool, Near Beach
- Beautiful beachfront, along with breathtaking sunset views
- Newly remodeled beach front! SPECIAL RATE SEPTEMBER and OCTOBER
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.nz holiday rentals are available in Naples?
As of 2026, Casai boasts over 19827 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 | 1534 |
| Old Naples Vacation Rentals in Naples, Florida | 1526 |
| Bonita Shores Vacation Rentals in Naples, Florida | 1451 |
| Naples Park Vacation Rentals in Naples, Florida | 989 |
| Central Naples Vacation Rentals in Naples, Florida | 450 |
| East Naples Vacation Rentals in Naples, Florida | 418 |
| Park Shore Vacation Rentals in Naples, Florida | 360 |
| Vanderbilt Beach Vacation Rentals in Naples, Florida | 333 |
| Rural Estates Vacation Rentals in Naples, Florida | 165 |
| Moorings Vacation Rentals in Naples, Florida | 116 |
| Bonita Bay Vacation Rentals in Naples, Florida | 87 |
| Pelican Bay Vacation Rentals in Naples, Florida | 59 |
| Redevelopment Area Vacation Rentals in Naples, Florida | 42 |
| Coquina Sands Vacation Rentals in Naples, Florida | 24 |
| Estero Bay Shores Vacation Rentals in Naples, Florida | 1007 |
| Aqualane Shores Vacation Rentals in Naples, Florida | 1671 |
