House
10.0(207 Reviews)
2 Bedrooms
6 Guests
Private Pool
Parking
Pool
Ocean View
US $354/Night
7 Nights - US $2,481
Waterside Shops Holiday Rentals
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Compare Villas, Resorts, & Rentals in Waterside Shops
10.0
House
10.0(2 Reviews)
4 Bedrooms
12 Guests
Oceanfront- Parking
- Ocean View
View
US $468/Night
7 Nights - US $3,275
House
8.0(1 Review)
1 Bedroom
- Parking
- Pool
- Ocean View
- View
US $1,410/Night
7 Nights - US $9,869
Condo
10.0(154 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
Hot Tub- Parking
- Pool
US $308/Night
7 Nights - US $2,158
House
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $347/Night
7 Nights - US $2,432
US $523/Night
7 Nights - US $3,662
Apartment
10.0(122 Reviews)
1 Bedroom
2 Guests
- Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $278/Night
7 Nights - US $1,948
House
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Air Conditioner
Internet
US $266/Night
7 Nights - US $1,862
House
1 Bedroom
- Pool
- Balcony/Terrace
- Kitchen
- Internet
US $1,043/Night
7 Nights - US $7,298
Condo
10.0(48 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $376/Night
7 Nights - US $2,634
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $201/Night
7 Nights - US $1,406
Condo
10.0(46 Reviews)
1 Bedroom
3 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $237/Night
7 Nights - US $1,662
House
10.0(1 Review)
6 Bedrooms
12 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $646/Night
7 Nights - US $4,522
Condo
10.0(44 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $692/Night
7 Nights - US $4,845
House
10.0(38 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $285/Night
7 Nights - US $1,994
Condo
10.0(33 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $179/Night
7 Nights - US $1,253
House
10.0(32 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $317/Night
7 Nights - US $2,220
Condo
10.0(31 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $371/Night
7 Nights - US $2,600
Condo
10.0(28 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $306/Night
7 Nights - US $2,143
Condo
10.0(27 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $536/Night
7 Nights - US $3,753
Condo
10.0(25 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $221/Night
7 Nights - US $1,545
House
10.0(24 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $259/Night
7 Nights - US $1,815
Condo
10.0(23 Reviews)
1 Bedroom
5 Guests
- Parking
Spa- Balcony/Terrace
- Kitchen
US $213/Night
7 Nights - US $1,491
Condo
10.0(18 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $185/Night
7 Nights - US $1,298
About Casai's Private Villas and Holiday Rentals in Waterside Shops
Discover more than 2178 vacation rentals available in Waterside Shops. 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 Waterside Shops.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Waterside Shops, 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 Waterside Shops.
With Casai, finding and comparing holiday rentals in Waterside Shops is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
There are 2178 Waterside Shops, FL Holiday Rentals
- Prices for a holiday home in Waterside Shops start at US $86
- Top rated vacation home in Waterside Shops is Charming Beach Cottage with private pool! One mile to stunning Horizon Beach!
- Most popular short term in Waterside Shops is Best Western Naples Inn & Suites
- Cheapest place to stay in Waterside Shops is Naples Charming Condo close to the Beach & Downtown
- Most expensive holiday rental in Waterside Shops is Naples Pool Home | 4BR Sleeps 10 Nr Beach
Recently Booked Holiday Rentals in Waterside Shops
- NEW Pinball & Loungers! OCT SPECIAL! Cute Designer Home, Heated Pool, Near Beach
- A Private Oasis Complex in Naples
- Neapolitan - Newly Renovated 3-BR Luxury Home with Private Pool. Enjoy a Fully Equipped Kitchen and Free Wi-Fi
- Luxurious Beach Front Condo with Spectacular Views!
- Luxury Golf-Front Retreat 3BR3BA HTD Pool, Jacuzzi, GOLF AVAILABLE
Frequently Asked Questions About Waterside Shops?
What are the top holiday rentals in Waterside Shops?
With numerous options available in Waterside Shops, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Waterside Shops:
- Charming Beach Cottage with private pool! One mile to stunning Horizon Beach!
- NEW Pinball & Loungers! OCT SPECIAL! Cute Designer Home, Heated Pool, Near Beach
- Luxurious Beach Front Condo with Spectacular Views!
- Luxurios beach condo with balcony in every room and private beach access
- 1 Mi to Vanderbilt Beach! Walkable Couple’s Haven
- Walk to Vanderbilt Beach, Heated Resort Pool & Spa, Kids Gear
- Deluxe End Unit Condo with georgeous Gulf and Clam Pass views
- Naples Oasis - Heated Pool, Pizza Oven, Fire Pit & Near Vanderbilt Beach
- REGATTA Condo on the intercoastal waters-steps to the beach
- Summer is available! Villa with Heated Pool & Spa.Walk to the Beach & Mercado.
How many Casai.com holiday rentals are available in Waterside Shops?
As of 2026, Casai boasts over 2178 properties listed in the Waterside Shops area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Waterside Shops.
Nearby Neighborhood (12)
| Neighborhood | Property Count |
|---|---|
| West Naples Vacation Rentals in Naples, Florida | 1448 |
| Old Naples Vacation Rentals in Naples, Florida | 1441 |
| Bonita Shores Vacation Rentals in Naples, Florida | 1377 |
| Naples Park Vacation Rentals in Naples, Florida | 940 |
| Central Naples Vacation Rentals in Naples, Florida | 429 |
| East Naples Vacation Rentals in Naples, Florida | 408 |
| Park Shore Vacation Rentals in Naples, Florida | 352 |
| Vanderbilt Beach Vacation Rentals in Naples, Florida | 315 |
| Moorings Vacation Rentals in Naples, Florida | 113 |
| Bonita Bay Vacation Rentals in Naples, Florida | 82 |
| Pelican Bay Vacation Rentals in Naples, Florida | 56 |
| Redevelopment Area Vacation Rentals in Naples, Florida | 38 |
