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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  South Beach

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1469 Best Vacation Rentals with Pool in South Beach (Starting from $370)

The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
0.1k from South Beach center

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

130 Bedrooms42 Guests
7.6

Good

287 reviews

$418
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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Santa Maria Suites Resort
Santa Maria Suites Resort
Resort
Key West, FL, USA
0.1k from South Beach center

Accommodations, Pools, Resorts, Parking, Romantic, Boutique, 4-star, Lodgings, Places to stay

35 Bedrooms20 Guests
9.3

Superb

674 reviews

$432
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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Southernmost Hospitality VII by Last Key Realty
Southernmost Hospitality VII by Last Key Realty
House
Key West, FL, USA
0.2k from South Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

7 Bedrooms16 Guests
New to Booking
$1607
Average price / night
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Santa Maria Suites
Santa Maria Suites
Resort
1401 Simonton St, Key West, FL, 33040, United States
0.1k from South Beach center

AC, Balcony, Bar, Crib, Fitness Equipment, Frontdesk 24 Hour, Housekeeping, Internet, Kitchen

9.6

Exceptional

1000 reviews

$684
Average price / night
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Southernmost Hospitality V by Last Key Realty
Southernmost Hospitality V by Last Key Realty
House
Key West, FL, USA
0.2k from South Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

5 Bedrooms12 Guests
New to Booking
$1385
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 View -Pool & Water Views
Southernmost View -Pool & Water Views
House
Key West, FL, USA
0.2k from South Beach center

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

4 Bedrooms8 Guests
New to Booking
$1894
Average price / night
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Kona Kai Oasis
Kona Kai Oasis
House
630 South Street, Key West, FL, 33040, United States
0.2k from South Beach center

AC, Barbecue, Free Parking, Internet, Outdoor Space, Pool, TV

8.2

Very Good

620 reviews

$370
Average price / night
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Casa Amarilla by Last Key Realty
Casa Amarilla by Last Key Realty
House
Key West, FL, USA
0.3k from South Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$1138
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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Duchess of Catherine by Last Key Realty
Duchess of Catherine by Last Key Realty
House
Key West, FL, USA
0.3k from South Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

5 Bedrooms14 Guests
New to Booking
$1367
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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Duke of Catherine by Last Key Realty
Duke of Catherine by Last Key Realty
House
Key West, FL, USA
0.3k from South Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs

2 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1747
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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Queen of Louisa by Last Key Realty
Queen of Louisa by Last Key Realty
House
Key West, FL, USA
0.3k from South Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms12 Guests
New to Booking
$856
Average price / night
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The Duke and The Duchess by Last Key Realty
The Duke and The Duchess by Last Key Realty
House
Key West, FL, USA
0.3k from South Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

8 Bedrooms22 Guests
New to Booking
$3397
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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Poolside Paradise Tropical Village
Poolside Paradise Tropical Village
Apartment
Key West, FL, USA
0.3k from South Beach center

Pool, Parking, Security/Safety, View, Sports/Activities, Spa, Barbecue/Outdoor Cooking

1 Bedroom2 Guests
New to Booking
$400
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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The Southern Cross Tropical Village
The Southern Cross Tropical Village
House
Key West, FL, USA
0.3k from South Beach center

Pool, Parking, Security/Safety, View, Sports/Activities, Spa, Barbecue/Outdoor Cooking

2 Bedrooms6 Guests
New to Booking
$607
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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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 South Beach.

Where to stay in South Beach? Best neighborhoods & areas

South Beach Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1469 verified vacation rentals with a pool in 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 South Beach vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $370 per night, with private pool homes and peak travel periods often costing more.

Many rentals in 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 South Beach welcome pets. Currently, 48 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 South Beach often include additional outdoor features such as Pool, Internet, and Wellness Facilities. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in 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.