Vacation Rentals in Waterside Shops, FL: Compare 10+ Sites & Save

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  4.  Florida
  5.  Naples
  6.  Waterside Shops

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2214 Best Vacation Rentals in Waterside Shops (Starting from $162)

Luxury Penthouse near Beach
Luxury Penthouse near Beach
Apartment
Naples, FL, USA
0.4k from Waterside Shops center

Apartments, Luxury, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$361
Average price / night
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Close to the beach \nCozy 2-bedroom apartment in serene Naples with AC and gym
Close to the beach \nCozy 2-bedroom apartment in serene Naples with AC and gym
Apartment
Naples, FL, 34103, United States
0.4k from Waterside Shops center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$223
Average price / night
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Naples LaStrada - Private pool, 12 mins to beach
Naples LaStrada - Private pool, 12 mins to beach
House
Naples, FL, USA
0.6k from Waterside Shops center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$541
Average price / night
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Saltwater Pool & Spa Retreat in Central Naples
Saltwater Pool & Spa Retreat in Central Naples
House
Naples, FL, 34103, United States
0.4k from Waterside Shops center

AC, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
New to Booking
$423
Average price / night
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Coastal Vibes, Pickleball Court, One Mile to the Beach
Coastal Vibes, Pickleball Court, One Mile to the Beach
House
Naples, FL, USA
0.8k from Waterside Shops center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$227
Average price / night
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LaStrada: Heated Pool & Mins to Beach
LaStrada: Heated Pool & Mins to Beach
House
Naples, FL, 34103, United States
0.4k from Waterside Shops center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
8.6

Fabulous

4 reviews

$339
Average price / night
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Lakefront, Pool, outdoor kitchen, lush garden
Lakefront, Pool, outdoor kitchen, lush garden
House
Naples, FL, USA
0.8k from Waterside Shops center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
3.0

Review score

1 reviews

$275
Average price / night
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Welcome to CocoBaba!
Welcome to CocoBaba!
House
Naples, FL, 34108, United States
0.5k from Waterside Shops center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

5 Bedrooms10 Guests
New to Booking
$2893
Average price / night
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Peace on Pompei
Peace on Pompei
House
Naples, FL, USA
0.8k from Waterside Shops center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms6 Guests
8.6

Fabulous

9 reviews

$293
Average price / night
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Lux/Heated Pool/Jacuzzi/Firepit/Games/1mile to beach
Lux/Heated Pool/Jacuzzi/Firepit/Games/1mile to beach
House
Naples, FL, 34103, United States
0.6k from Waterside Shops center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms10 Guests
6.0

Review score

3 reviews

$881
Average price / night
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Alhambra Circle Memories
Alhambra Circle Memories
House
Waterside Shops, Naples, Florida, USA
1.0k from Waterside Shops center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

3 Bedrooms8 Guests
New to Booking
$274
Average price / night
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Naples Coastal Beach Cottage W/ Private Pool - Walk to the Beach & Waterside!
Naples Coastal Beach Cottage W/ Private Pool - Walk to the Beach & Waterside!
House
Naples, FL, 34103, United States
0.7k from Waterside Shops center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms10 Guests
New to Booking
$1237
Average price / night
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The Shore Club at Park Shore
The Shore Club at Park Shore
House
Waterside Shops, Naples, Florida, USA
1.1k from Waterside Shops center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom4 Guests
New to Booking
$196
Average price / night
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Spacious 1-bedroom apartment in central Naples with AC, W/D, pool and gym access
Spacious 1-bedroom apartment in central Naples with AC, W/D, pool and gym access
Apartment
Naples, FL, 34103, United States
0.7k from Waterside Shops center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$272
Average price / night
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Designer Furnished and Views
Designer Furnished and Views
House
FL, USA
1.2k from Waterside Shops center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$876
Average price / night
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Amazing A-Frame home  with beautiful heated pool, in great location to beaches.
Amazing A-Frame home with beautiful heated pool, in great location to beaches.
House
Naples, FL, 34103, United States
0.7k from Waterside Shops center

Fireplace, Kitchen, No Smoking, Pool, TV

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$333
Average price / night
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Completely renovated first floor condo
Completely renovated first floor condo
House
Naples, FL, USA
1.2k from Waterside Shops center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

2 Bedrooms5 Guests
New to Booking
$514
Average price / night
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Close to the Beach, Heart of Naples. 3 B-rooms +  office and outdoor living area
Close to the Beach, Heart of Naples. 3 B-rooms + office and outdoor living area
House
Naples, FL, 34103, United States
0.8k from Waterside Shops center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$342
Average price / night
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End Unit with Private Views
End Unit with Private Views
House
Naples, FL, USA
1.2k from Waterside Shops center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
New to Booking
$206
Average price / night
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Lovely 2-bedroom house with AC in Naples
Lovely 2-bedroom house with AC in Naples
House
Naples, FL, 34103, United States
0.8k from Waterside Shops center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

2 Bedrooms5 Guests
New to Booking
$162
Average price / night
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Lakeshore: Pool, Outdoor Kitchen, & Garden
Lakeshore: Pool, Outdoor Kitchen, & Garden
House
Naples, FL, 34103, United States
0.8k from Waterside Shops center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.4

Superb

32 reviews

$346
Average price / night
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Single level family home w/private pool & furnished patio w/grill, dog-friendly.
Single level family home w/private pool & furnished patio w/grill, dog-friendly.
House
Naples, FL, 34103, United States
0.8k from Waterside Shops center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.2

Superb

66 reviews

$322
Average price / night
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Walk to the Beach! Private Villa with Pool & Lanai – Perfect Naples Getaway
Walk to the Beach! Private Villa with Pool & Lanai – Perfect Naples Getaway
Villa
Naples, FL, 34103, United States
0.8k from Waterside Shops center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$441
Average price / night
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Naples Outdoor Paradise/HEATED Pool & Spa/Only 1.2mi from Beaches!
Naples Outdoor Paradise/HEATED Pool & Spa/Only 1.2mi from Beaches!
House
Naples, FL, 34103, United States
0.8k from Waterside Shops center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

11 reviews

$611
Average price / night
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Park Shore Naples 3 bed 2.5 bath Villa near beach!
Park Shore Naples 3 bed 2.5 bath Villa near beach!
Villa
Naples, FL, 34103, United States
0.8k from Waterside Shops center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms5 Guests
8.8

Fabulous

5 reviews

$229
Average price / night
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5BR/6BTH Heated Pool/Spa Home 1 Mile to Beach! 5 min to Downtown Naples
5BR/6BTH Heated Pool/Spa Home 1 Mile to Beach! 5 min to Downtown Naples
House
Naples, FL, 34103, United States
0.9k from Waterside Shops center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms14 Guests
New to Booking
$995
Average price / night
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Woodridge: Work Friendly, Pool, Near Beach
Woodridge: Work Friendly, Pool, Near Beach
House
Naples, FL, 34103, United States
0.9k from Waterside Shops center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.4

Superb

29 reviews

$272
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Waterside Shops.

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Frequently Asked Questions

You can explore 2214 verified vacation rentals in Waterside Shops. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Waterside Shops vary depending on the season, property size, and location. Rates typically start from around $162 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Waterside Shops include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Waterside Shops welcome pets. Currently, 24 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Waterside Shops often include amenities such as Fireplace/Heating, Wellness Facilities, and Pool. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.