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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  South Beach

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485 Best Vacation Rentals with Private Pool in South Beach (Starting from $328)

Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
House
South Beach, Key West, Florida, USA
1.2k from South Beach center

Pool, Private Pool, Kitchen, Parking, Internet, Air Conditioner, Child Friendly

1 Bedroom4 Guests
New to Booking
$348
Average price / night
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NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
House
Key West, FL, 33040, United States
0.1k from South Beach center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Free Parking, Heater, Internet

5 Bedrooms12 Guests
10.0

Exceptional

149 reviews

$2141
Average price / night
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Casa Grande by AvantStay | Dt Key West | Near South Beach w/ Pool
Casa Grande by AvantStay | Dt Key West | Near South Beach w/ Pool
House
Key West, FL, 33040, United States
0.1k from South Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, No Smoking, Patio

5 Bedrooms12 Guests
9.8

Exceptional

86 reviews

$2161
Average price / night
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**HALFWAY TO HAVANA @ DUVAL** Two Cottages w/ Pool + LAST KEY SERVICES...
**HALFWAY TO HAVANA @ DUVAL** Two Cottages w/ Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from South Beach center

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

4 Bedrooms8 Guests
New to Booking
$1523
Average price / night
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**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from South Beach center

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

7 Bedrooms16 Guests
10.0

Exceptional

89 reviews

$2676
Average price / night
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**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.2k from South Beach center

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

5 Bedrooms12 Guests
10.0

Exceptional

49 reviews

$2304
Average price / night
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**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
House
Key West, FL, 33040, United States
0.2k from South Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$458
Average price / night
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Green Goddess - 4 BD/3 BA Amazing 360 Degrees Rooftop Views! RealKeyWest
Green Goddess - 4 BD/3 BA Amazing 360 Degrees Rooftop Views! RealKeyWest
House
Key West, FL, 33040, United States
0.2k from South Beach center

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

4 Bedrooms8 Guests
8.4

Very Good

5 reviews

$559
Average price / night
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Southernmost View - Private Pool
Southernmost View - Private Pool
House
Key West, FL, 33040, United States
0.2k from South Beach center

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

4 Bedrooms8 Guests
9.8

Exceptional

7 reviews

$415
Average price / night
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SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!
SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!
House
Key West, FL, 33040, United States
0.2k from South Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$703
Average price / night
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Tropical Dreaming by AvantStay | 4 BLKS to Beach! Private Pool!
Tropical Dreaming by AvantStay | 4 BLKS to Beach! Private Pool!
House
Key West, FL, 33040, United States
0.2k from South Beach center

AC, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

2 Bedrooms6 Guests
9.6

Exceptional

104 reviews

$1350
Average price / night
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SEA FOREVER ~  Downtown Ocean View Home w/ 3 BR, 3.5 Ba w/ Pool!
SEA FOREVER ~ Downtown Ocean View Home w/ 3 BR, 3.5 Ba w/ Pool!
House
Key West, FL, 33040, United States
0.2k from South Beach center

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

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$412
Average price / night
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**SOUTHERNMOST VISTAS @ SOUTHERNMOST** Gorgeous Home & Pool + LAST KEY SERVICES…
**SOUTHERNMOST VISTAS @ SOUTHERNMOST** Gorgeous Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.2k from South Beach center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$482
Average price / night
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**A ROYAL AFFAIR @ DUVAL** Three Home Compound + LAST KEY SERVICES…
**A ROYAL AFFAIR @ DUVAL** Three Home Compound + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

14 Bedrooms34 Guests
10.0

Exceptional

1 reviews

$4014
Average price / night
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Catch a BAHAMA BREEZE at this quiet 3bd/3.5ba Monthly rental
Catch a BAHAMA BREEZE at this quiet 3bd/3.5ba Monthly rental
House
Key West, FL, 33040, United States
0.3k from South Beach center

AC, Barbecue, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
New to Booking
$362
Average price / night
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HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$328
Average price / night
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**DOS CASITAS @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES
**DOS CASITAS @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

2 Bedrooms14 Guests
New to Booking
$2219
Average price / night
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4-bedroom resort style home in awesome Key West with large pool and private deck
4-bedroom resort style home in awesome Key West with large pool and private deck
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1414
Average price / night
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Hidden away near the Southernmost Point, Louisa's Hideaway is it!
Hidden away near the Southernmost Point, Louisa's Hideaway is it!
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

200 reviews

$1376
Average price / night
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Louisa House: A comfortable four bedroom vacation hideaway
Louisa House: A comfortable four bedroom vacation hideaway
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

4 Bedrooms10 Guests
9.4

Superb

177 reviews

$1464
Average price / night
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Catherine House: A charming Old Town Key West cottage
Catherine House: A charming Old Town Key West cottage
House
Key West, FL, 33040, United States
0.3k from South Beach center

AC, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

2 Bedrooms4 Guests
9.8

Exceptional

191 reviews

$816
Average price / night
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Key West Dreamin` - Private Pool Steps Off Duval
Key West Dreamin` - Private Pool Steps Off Duval
House
Key West, FL, 33040, United States
0.3k from South Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

56 reviews

$899
Average price / night
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SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
House
Key West, FL, 33040, United States
0.3k from South Beach center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
9.8

Exceptional

210 reviews

$1057
Average price / night
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LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

3 Bedrooms8 Guests
9.8

Exceptional

239 reviews

$1282
Average price / night
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~ GRAND MAISON ~ Spacious home on Duval St with pool and 4 ensuite bedrooms.
~ GRAND MAISON ~ Spacious home on Duval St with pool and 4 ensuite bedrooms.
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

130 reviews

$2293
Average price / night
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~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Pool ON DUVAL.
~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Pool ON DUVAL.
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

6 Bedrooms12 Guests
10.0

Exceptional

100 reviews

$3154
Average price / night
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LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!
LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!
House
Key West, FL, 33040, United States
0.3k from South Beach center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$492
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 Private Pool in South Beach.

Where to stay in South Beach? Best neighborhoods & areas

South Beach Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 485 verified vacation rentals with a private pool in South Beach. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in South Beach vary depending on the property size, location, and travel season. Rates typically start from around $328 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in South Beach also welcome pets. Currently, 26 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in South Beach often include additional features such as Pool, Private Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in South Beach include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.