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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Naples
  6.  Waterside Shops

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2185 Best Vacation Rentals with Pool in Waterside Shops (Starting from $196)

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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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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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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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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★Cozy Beach Escape★ 0.9 miles from Clams Pass Beach !
★Cozy Beach Escape★ 0.9 miles from Clams Pass Beach !
Condo
Naples, FL, 34108, United States
0.4k from Waterside Shops center

AC, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$263
Average price / night
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Naples Grande Beach Resort
Naples Grande Beach Resort
Resort
Waterside Shops, Naples, Florida, USA
1.0k from Waterside Shops center

Accommodations, Pools, Resorts, Parking, Spa, Pet-friendly, 4-star, Lodgings, Beach

509 Bedrooms64 Guests
8.3

Very Good

872 reviews

$719
Average price / night
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Totally Renovated 3 BR / 2Bath condominium with access to Pelican Bay Beach
Totally Renovated 3 BR / 2Bath condominium with access to Pelican Bay Beach
Condo
Naples, FL, 34108, United States
0.6k from Waterside Shops center

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

3 Bedrooms5 Guests
New to Booking
$419
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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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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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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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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Second Floor With Lake and Fountain View
Second Floor With Lake and Fountain View
House
Naples, FL, USA
1.2k from Waterside Shops center

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

2 Bedrooms4 Guests
9.4

Superb

7 reviews

$251
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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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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Naples/ Parkshore 2 bedroom/2 bath condo with garage. Less than 1 mile to beach.
Naples/ Parkshore 2 bedroom/2 bath condo with garage. Less than 1 mile to beach.
Condo
Naples, FL, 34103, United States
0.9k from Waterside Shops center

AC, Dryer, Free Parking, Heater, Internet, Laundry, No Smoking, Pool, TV

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$428
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
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Pelican Bay Condo overlooking pool and gardens, with private beach access.
Pelican Bay Condo overlooking pool and gardens, with private beach access.
Condo
Naples, FL, 34108, United States
0.9k from Waterside Shops center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$301
Average price / night
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NaplesHammock
NaplesHammock
House
Naples, FL, 34103, United States
0.9k from Waterside Shops center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
7.6

Good

5 reviews

$444
Average price / night
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Cozy Vacation Home * Heated Pool*Near The Beach !
Cozy Vacation Home * Heated Pool*Near The Beach !
House
Naples, FL, 34103, United States
0.9k from Waterside Shops center

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

3 Bedrooms1 Guest
New to Booking
$457
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 with Pool in Waterside Shops.

Where to stay in Waterside Shops? Best neighborhoods & areas

Waterside Shops Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 2185 verified vacation rentals with a pool in Waterside Shops. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Waterside Shops vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $196 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Waterside Shops offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Waterside Shops welcome pets. Currently, 13 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Waterside Shops often include additional outdoor features such as Pool, Wellness Facilities, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Waterside Shops offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.