Condo
10.0(131 Reviews)
2 Bedrooms
4 Guests
Parking
Pool
Ocean View
View
US $306/Night
7 Nights - US $2,143
Old Naples Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Old 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
Condo
10.0(1 Review)
1 Bedroom
- Parking
- Pool
- Ocean View
Balcony/Terrace
US $899/Night
7 Nights - US $6,293
Condo
10.0(101 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $376/Night
7 Nights - US $2,629
Villa
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Breakfast
- Parking
- Balcony/Terrace
US $307/Night
7 Nights - US $2,152
Condo
10.0(97 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
Spa
US $398/Night
7 Nights - US $2,783
Condo
10.0(78 Reviews)
2 Bedrooms
5 Guests
Private Pool- Parking
- Pool
- Ocean View
US $391/Night
7 Nights - US $2,734
Apartment
10.0(76 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $228/Night
7 Nights - US $1,597
Apartment
10.0(61 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $194/Night
7 Nights - US $1,357
Luxury Holiday Rentals in Old Naples
Over 2921+ Luxury Holiday Rentals in or Near Old Naples
Unlock the Best Price
US $4,564/Night
7 Nights - US $31,945
US $4,484/Night
7 Nights - US $31,391
US $4,429/Night
7 Nights - US $31,002
House
10.0(6 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,510/Night
7 Nights - US $24,567
House
10.0(9 Reviews)
11 Bedrooms
30 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,357/Night
7 Nights - US $23,498
US $3,241/Night
7 Nights - US $22,686
Apartment
8.7(3 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $3,000/Night
7 Nights - US $21,000
House
4 Bedrooms
8 Guests
- Private Pool
- Pool
Kitchen
Air Conditioner
US $2,967/Night
7 Nights - US $20,771
Top-Rated Holiday Rentals with a Pool in Old Naples
Over 2082+ The Best Private Villas and Holiday Rentals in Old Naples with a Pool
House
10.0(57 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $862/Night
7 Nights - US $6,033
Condo
10.0(57 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $197/Night
7 Nights - US $1,381
Condo
10.0(56 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $381/Night
7 Nights - US $2,666
Condo
10.0(54 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $423/Night
7 Nights - US $2,962
US $308/Night
7 Nights - US $2,158
Condo
10.0(49 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $287/Night
7 Nights - US $2,010
Apartment
10.0(47 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $355/Night
7 Nights - US $2,487
Condo
10.0(45 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $517/Night
7 Nights - US $3,621
Condo
10.0(45 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- View
US $380/Night
7 Nights - US $2,662
Pet-Friendly Holiday Rentals in Old Naples
Over 589+ Pet-Friendly Holiday Rentals in or Near Old Naples
Condo
10.0(18 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $219/Night
7 Nights - US $1,532
US $338/Night
7 Nights - US $2,368
Villa
9.4(17 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $743/Night
7 Nights - US $5,201
Condo
10.0(17 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $187/Night
7 Nights - US $1,312
Apartment
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $393/Night
7 Nights - US $2,749
Condo
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Air Conditioner
Internet
Pet Friendly
Child Friendly
US $816/Night
7 Nights - US $5,710
Condo
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $135/Night
7 Nights - US $946
Condo
10.0(9 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $278/Night
7 Nights - US $1,945
House
10.0(8 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,181/Night
7 Nights - US $8,264
Large Holiday Rentals and Private Villas in Old Naples
Over 286+ Large Holiday Rentals and Private Villas in or Near Old Naples
Villa
10.0(40 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $308/Night
7 Nights - US $2,158
House
10.0(3 Reviews)
3 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $695/Night
7 Nights - US $4,865
Villa
10 Bedrooms
6 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $1,612/Night
7 Nights - US $11,286
Villa
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $246/Night
7 Nights - US $1,719
Villa
9.8(57 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $207/Night
7 Nights - US $1,450
House
10.0(5 Reviews)
2 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $359/Night
7 Nights - US $2,516
Villa
10.0(5 Reviews)
2 Bedrooms
5 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $262/Night
7 Nights - US $1,831
US $127/Night
7 Nights - US $888
Villa
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $280/Night
7 Nights - US $1,957
Wheelchair Accessible Holiday Homes in Old Naples
Over 349+ Wheelchair Accessible Holiday Homes in or Near Old Naples
Condo
10.0(44 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $627/Night
7 Nights - US $4,387
US $228/Night
7 Nights - US $1,598
Apartment
8.0(1 Review)
1 Bedroom
- Oceanfront
- Parking
- Pool
- Ocean View
US $504/Night
7 Nights - US $3,528
Condo
10.0(34 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $278/Night
7 Nights - US $1,947
Apartment
9.6(23 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $251/Night
7 Nights - US $1,755
Condo
10.0(31 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $347/Night
7 Nights - US $2,427
Condo
10.0(24 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $631/Night
7 Nights - US $4,415
Apartment
10.0(21 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $390/Night
7 Nights - US $2,728
Condo
10.0(18 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $459/Night
7 Nights - US $3,214
Old Naples Private Villas and Holiday Homes Under $200
Over 874+ Old Naples Private Villas and Holiday Homes Under $200
House
10.0(24 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $192/Night
7 Nights - US $1,344
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
1 Bedroom
- Oceanfront
- Parking
- Pool
- Ocean View
US $189/Night
7 Nights - US $1,322
Condo
10.0(24 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $180/Night
7 Nights - US $1,262
US $122/Night
7 Nights - US $854
Condo
10.0(22 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $160/Night
7 Nights - US $1,117
Condo
10.0(15 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $137/Night
7 Nights - US $957
US $191/Night
7 Nights - US $1,339
Condo
10.0(14 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $157/Night
7 Nights - US $1,101
Instantly Bookable Holiday Homes in Old Naples
Over 1339+ Instantly Bookable Holiday Homes in or Near Old Naples
Condo
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $315/Night
7 Nights - US $2,202
Condo
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $174/Night
7 Nights - US $1,219
Condo
10.0(27 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $273/Night
7 Nights - US $1,910
Condo
10.0(25 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $326/Night
7 Nights - US $2,283
Cottage
10.0(25 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $300/Night
7 Nights - US $2,102
Cottage
10.0(22 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $831/Night
7 Nights - US $5,816
Cottage
10.0(21 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $683/Night
7 Nights - US $4,779
Condo
10.0(21 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $420/Night
7 Nights - US $2,939
Condo
10.0(17 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- View
US $226/Night
7 Nights - US $1,579
Book a Last Minute Place to Stay in Old Naples
About Casai's Private Villas and Holiday Rentals in Old Naples
Discover more than 2930 vacation rentals available in Old 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 Old Naples.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Old 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 Old Naples. On average, places to stay near Old Naples offer 923.81 ft², with nightly prices averaging US $371.
With Casai, finding and comparing holiday rentals in Old 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 Old Naples, FL
There are 2930 Old Naples, FL Holiday Rentals
- Prices for a holiday home in Old Naples start at US $70
- Top rated vacation home in Old Naples is 2024 NEWLY RENOVATED CONDO BY THE BEACH #1
- Most popular short term in Old Naples is La Quinta by Wyndham Naples East (I-75)
- Cheapest place to stay in Old Naples is Charming Guest Quarters in Separate Building Available/Monthly Summer Bookings
- Most expensive holiday rental in Old Naples is Beautiful home w/Pool & soaker tub!
Recently Booked Holiday Rentals in Old Naples
- 2024 NEWLY RENOVATED CONDO BY THE BEACH #1
- Spacious 2BR Lely Resort Condo with Lake View steps to Pool Hot Tub Gym
- Genoa Vacation Rental: Stylish 2-BR Condo with Golf & Lake Views. Resort-Style Pool, Hot Tub, and Easy Access to Championship Golf. Minutes from Naples Beaches, 5th Avenue S, and Marco Island
- Amazing Old Naples Location! Center of Fifth Ave & Walk to Beach
- Cozy Coastal Cottage at Naples Bay, Pickleball, Botanical Garden
Frequently Asked Questions About Old Naples?
What are the top holiday rentals in Old Naples?
With numerous options available in Old Naples, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Old Naples:
- 2024 NEWLY RENOVATED CONDO BY THE BEACH #1
- Amazing Old Naples Location! Center of Fifth Ave & Walk to Beach
- ALL 5 STAR REVIEWS for our 2Br.Cottage at Naples Bay Resort
- 1 Block to Beach, heart of Old Naples, newly renovated, perfect location
- Lovely 2-Bedroom + Den Condo in Greenlinks Resort
- Vacation in paradise at Lely Resort
- Old Naples Luxury 4BR Home - Truly Close to Beach & 5th Ave
- 5-8 MINUTE WALK TO BEACHES, DINING & SHOPPING! RARE PRIVATE PATIO & LAKE VIEW!
- Beautifully Updated Naples Condo, Walk to Beach & 3rd St
- HOME SUITE HOME! 3 Bedroom, Ground Floor, Beautiful Golf Course View
How many holiday rentals have private pools in Old Naples?
Discover a selection of holiday rentals with private pools near Old 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 Old Naples are best for families?
If you're searching for a family-friendly holiday home in Old Naples, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Old Naples:
How many Casai.nz holiday rentals are available in Old Naples?
As of 2026, Casai boasts over 2930 properties listed in the Old Naples area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Old Naples.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| West Naples Vacation Rentals in Naples, Florida | 1447 |
| Redevelopment Area Vacation Rentals in Naples, Florida | 38 |
| Coquina Sands Vacation Rentals in Naples, Florida | 2181 |
| Lake Park Vacation Rentals in Naples, Florida | 2586 |
| Aqualane Shores Vacation Rentals in Naples, Florida | 1601 |
| Ridge Lakes Vacation Rentals in Naples, Florida | 1958 |
