Vacation Rentals with Pool in 21st Avenue South Beach, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Naples
  6.  21st Avenue South Beach

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1269 Best Vacation Rentals with Pool in 21st Avenue South Beach (Starting from $220)

Naples Studio 1 Block to Beach and Restaurants!
Naples Studio 1 Block to Beach and Restaurants!
Apartment
Naples, FL, USA
1.2k from 21st Avenue South Beach center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$220
Average price / night
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Naples Beach Port Royal Luxe Coastal Mansion & Guesthouse with Pool & Hot Tub
Naples Beach Port Royal Luxe Coastal Mansion & Guesthouse with Pool & Hot Tub
House
Naples, FL, 34102, United States
0.5k from 21st Avenue South Beach center

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

6 Bedrooms12 Guests
New to Booking
$3759
Average price / night
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Evolve Dtwn Studio Steps to Naples Pier and Beach!
Evolve Dtwn Studio Steps to Naples Pier and Beach!
Apartment
21st Avenue South Beach, Naples, Florida, USA
1.2k from 21st Avenue South Beach center

View, Wheelchair Accessible, Internet, Parking, Ocean View, Laundry, Pool

1 Bedroom4 Guests
8.3

Very Good

4 reviews

$337
Average price / night
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Port Royal - Sweeping Lake Views
Port Royal - Sweeping Lake Views
House
Naples, FL, 34102, United States
0.5k from 21st Avenue South Beach center

AC, Free Parking, Hot Tub, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool

5 Bedrooms10 Guests
New to Booking
$2014
Average price / night
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Coastal Downtown Naples Condo - Walk to the Beach!
Coastal Downtown Naples Condo - Walk to the Beach!
Apartment
Naples, FL, USA
1.2k from 21st Avenue South Beach center

Apartments, Cheap, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms4 Guests
9.3

Superb

12 reviews

$457
Average price / night
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Port Royal Newly Renovated Contemporary Home On 3/4 Acres Walking Distance Beach
Port Royal Newly Renovated Contemporary Home On 3/4 Acres Walking Distance Beach
House
Naples, FL, 34102, United States
0.5k from 21st Avenue South Beach center

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

4 Bedrooms8 Guests
New to Booking
$1362
Average price / night
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Condo with Pool Access Walk to Shopping and Beach!
Condo with Pool Access Walk to Shopping and Beach!
Apartment
Naples, FL, USA
1.2k from 21st Avenue South Beach center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals, Condos

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$412
Average price / night
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Port Royal residence nestled among Royal Palms
Port Royal residence nestled among Royal Palms
House
Naples, FL, 34102, United States
0.9k from 21st Avenue South Beach center

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

4 Bedrooms8 Guests
New to Booking
$1540
Average price / night
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Luxe Naples Escape Walk to Beach and Downtown!
Luxe Naples Escape Walk to Beach and Downtown!
Apartment
Naples, FL, USA
1.2k from 21st Avenue South Beach center

Apartments, Cheap, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms5 Guests
9.6

Exceptional

10 reviews

$865
Average price / night
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Gables by the Sea - Naples, FL
Gables by the Sea - Naples, FL
House
Naples, FL, 34102, United States
0.9k from 21st Avenue South Beach center

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

5 Bedrooms10 Guests
New to Booking
$2785
Average price / night
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Sleek Coastal Abode 1 Block to Naples Beach!
Sleek Coastal Abode 1 Block to Naples Beach!
Apartment
Naples, FL, USA
1.2k from 21st Avenue South Beach center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms6 Guests
9.0

Fabulous

4 reviews

$516
Average price / night
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Aqualane Oasis | Waterfront Luxury Home Walkable to Beach & 3rd Street South
Aqualane Oasis | Waterfront Luxury Home Walkable to Beach & 3rd Street South
House
Naples, FL, 34102, United States
1.0k from 21st Avenue South Beach center

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

5 Bedrooms10 Guests
New to Booking
$1154
Average price / night
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Upscale Naples Condo with Pool Access Walk to Pier!
Upscale Naples Condo with Pool Access Walk to Pier!
Apartment
Naples, FL, USA
1.3k from 21st Avenue South Beach center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals, Condos

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$340
Average price / night
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Port Royal elegance for the traveler who desires the luxury and location.
Port Royal elegance for the traveler who desires the luxury and location.
House
Naples, FL, 34102, United States
1.0k from 21st Avenue South Beach center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms8 Guests
New to Booking
$2362
Average price / night
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Hilton Vacation Club Charter Club Naples Bay
Hilton Vacation Club Charter Club Naples Bay
Resort
Naples, FL, USA
2.2k from 21st Avenue South Beach center

Accommodations, Pools, Resorts, Parking, Golf, Hilton , 3-star, Lodgings, Hot tubs

33 Bedrooms18 Guests
9.2

Superb

131 reviews

$240
Average price / night
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Old Naples Beach Condo
Old Naples Beach Condo
Apartment
Naples, FL, 34102, United States
1.2k from 21st Avenue South Beach center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

17 reviews

$378
Average price / night
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Marina Manor
Marina Manor
House
Naples, FL, USA
2.6k from 21st Avenue South Beach center

Kitchen, Pool, Internet, Child Friendly

1 Bedroom4 Guests
New to Booking
$262
Average price / night
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Olde Naples Luxury Condo Steps to Pier, Beach, Sunsets and restaurants!
Olde Naples Luxury Condo Steps to Pier, Beach, Sunsets and restaurants!
Condo
Naples, FL, 34102, United States
1.2k from 21st Avenue South Beach center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

34 reviews

$735
Average price / night
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BeauMer 102B
BeauMer 102B
Apartment
Naples, FL, USA
2.7k from 21st Avenue South Beach center

Apartments, Accommodations, Pools, Lodgings, Jacuzzis, Places to stay, Family

2 Bedrooms4 Guests
New to Booking
$362
Average price / night
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Fully renovated upscale 2-bedroom condo in the heart of Old Naples.
Fully renovated upscale 2-bedroom condo in the heart of Old Naples.
Condo
Naples, FL, 34102, United States
1.2k from 21st Avenue South Beach center

AC, Free Parking, Heater, Laundry, Microwave, No Smoking, Pool, TV

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$224
Average price / night
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The Cottages at Naples Bay Resort
The Cottages at Naples Bay Resort
Apartment
Naples, FL, USA
2.8k from 21st Avenue South Beach center

Apartments, Cheap, Accommodations, Pools, Lodgings, Hot tubs, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$253
Average price / night
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Naples Pier Condo 123
Naples Pier Condo 123
Condo
Naples, FL, 34102, United States
1.2k from 21st Avenue South Beach center

AC, Dryer, Internet, Kitchen, Microwave, No Smoking, Pool, TV, Washer

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$436
Average price / night
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1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt
1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt
Condo
Naples, FL, 34102, United States
1.2k from 21st Avenue South Beach center

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

2 Bedrooms4 Guests
9.8

Exceptional

197 reviews

$735
Average price / night
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2 BD/ 2BA.  Just steps to Beach, Walk to 3rd St South
2 BD/ 2BA. Just steps to Beach, Walk to 3rd St South
Condo
Naples, FL, 34102, United States
1.2k from 21st Avenue South Beach center

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

2 Bedrooms4 Guests
9.8

Exceptional

98 reviews

$480
Average price / night
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One block to beach and to dining. Best location in Naples !!
One block to beach and to dining. Best location in Naples !!
Condo
Naples, FL, 34102, United States
1.2k from 21st Avenue South Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

82 reviews

$459
Average price / night
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Great location!!! Old Naples Pool Home - Walk to the beach, shops, restaurants.
Great location!!! Old Naples Pool Home - Walk to the beach, shops, restaurants.
House
Naples, FL, 34102, United States
1.2k from 21st Avenue South Beach center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
9.2

Superb

9 reviews

$532
Average price / night
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CONDO BY THE BEACH #2
CONDO BY THE BEACH #2
Condo
Naples, FL, 34102, United States
1.2k from 21st Avenue South Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

77 reviews

$390
Average price / night
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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 21st Avenue South Beach.

Where to stay in 21st Avenue South Beach? Best neighborhoods & areas

21st Avenue South Beach Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1269 verified vacation rentals with a pool in 21st Avenue South Beach. 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 21st Avenue South Beach vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $220 per night, with private pool homes and peak travel periods often costing more.

Many rentals in 21st Avenue South Beach 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 21st Avenue South Beach welcome pets. Currently, 23 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 21st Avenue South Beach often include additional outdoor features such as Pool, Laundry, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in 21st Avenue South Beach 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.