Vacation Rentals with Private Pool in Waterfront Playhouse, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Waterfront Playhouse

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485 Best Vacation Rentals with Private Pool in Waterfront Playhouse (Starting from $348)

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
Waterfront Playhouse, Key West, Florida, USA
1.0k from Waterfront Playhouse 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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**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$730
Average price / night
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Conch House at the Truman Annex in Key West
Conch House at the Truman Annex in Key West
House
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

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

4 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$623
Average price / night
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Rose Key Cottage - Private Pool & Near Duval
Rose Key Cottage - Private Pool & Near Duval
House
Key West, FL, 33040, United States
0.4k from Waterfront Playhouse center

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

2 Bedrooms6 Guests
5.6

Review score

4 reviews

$1929
Average price / night
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The Rigby House - Pool, One block from Duval St
The Rigby House - Pool, One block from Duval St
House
Key West, FL, 33040, United States
0.4k from Waterfront Playhouse center

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

6 Bedrooms12 Guests
10.0

Exceptional

14 reviews

$3552
Average price / night
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SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Annex Home w/Private Heated Pool!
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Annex Home w/Private Heated Pool!
House
Key West, FL, 33040, United States
0.4k from Waterfront Playhouse center

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

3 Bedrooms6 Guests
9.8

Exceptional

96 reviews

$525
Average price / night
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BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
House
Key West, FL, 33040, United States
0.4k from Waterfront Playhouse center

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

4 Bedrooms8 Guests
10.0

Exceptional

90 reviews

$571
Average price / night
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SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
Condo
Key West, FL, 33040, United States
0.4k from Waterfront Playhouse center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

2 Bedrooms6 Guests
8.0

Good

1 reviews

$894
Average price / night
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Sunset views at the Galleon
Sunset views at the Galleon
Condo
Key West, FL, 33040, United States
0.4k from Waterfront Playhouse center

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

2 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$898
Average price / night
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Takeover at the Grand Maloney
Takeover at the Grand Maloney
House
Key West, FL, 33040, United States
0.4k from Waterfront Playhouse center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Internet, Laundry, No Smoking

6 Bedrooms16 Guests
8.6

Fabulous

7 reviews

$3386
Average price / night
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1 Block to Duval St | Banana's Foster Guesthouse
1 Block to Duval St | Banana's Foster Guesthouse
House
Key West, FL, 33040, United States
0.4k from Waterfront Playhouse center

AC, Balcony, Barbecue, Extra Bed, Free Parking, Internet, Kitchen, Microwave, No Smoking

7 Bedrooms19 Guests
9.8

Exceptional

7 reviews

$3421
Average price / night
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A Palm Tree Haven at the Truman Annex in Key West
A Palm Tree Haven at the Truman Annex in Key West
House
Key West, FL, 33040, United States
0.4k from Waterfront Playhouse center

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

4 Bedrooms8 Guests
9.6

Exceptional

23 reviews

$575
Average price / night
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3 Bedroom Key West Home - Perfect Location & Private Pool
3 Bedroom Key West Home - Perfect Location & Private Pool
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

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

3 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$1394
Average price / night
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**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

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

5 Bedrooms8 Guests
10.0

Exceptional

28 reviews

$1726
Average price / night
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**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

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

6 Bedrooms12 Guests
10.0

Exceptional

91 reviews

$3128
Average price / night
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The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

AC, Dryer, Hot Tub, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms10 Guests
9.8

Exceptional

22 reviews

$1816
Average price / night
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SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

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

5 Bedrooms10 Guests
9.8

Exceptional

206 reviews

$2516
Average price / night
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**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

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

3 Bedrooms6 Guests
9.8

Exceptional

38 reviews

$458
Average price / night
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Waterfront Views from Dolphin Watch
Waterfront Views from Dolphin Watch
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

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

4 Bedrooms8 Guests
9.8

Exceptional

92 reviews

$1157
Average price / night
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Hemingway Hideaway in the Truman Annex
Hemingway Hideaway in the Truman Annex
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

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

2 Bedrooms6 Guests
9.8

Exceptional

68 reviews

$469
Average price / night
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Casa Rosa: 4BR/4BA house, pool, near Duval
Casa Rosa: 4BR/4BA house, pool, near Duval
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

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

4 Bedrooms8 Guests
9.6

Exceptional

85 reviews

$911
Average price / night
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Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

AC, Balcony, Barbecue, Dryer, Hot Tub, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
New to Booking
$717
Average price / night
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Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
House
Key West, FL, 33040, United States
0.5k from Waterfront Playhouse center

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

6 Bedrooms16 Guests
9.8

Exceptional

247 reviews

$2154
Average price / night
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PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
House
Key West, FL, 33040, United States
0.6k from Waterfront Playhouse center

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

4 Bedrooms8 Guests
9.8

Exceptional

37 reviews

$2591
Average price / night
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**CASA AVILA @ OLD TOWN** Private Home & Pool + LAST KEY SERVICES…
**CASA AVILA @ OLD TOWN** Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.6k from Waterfront Playhouse center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
New to Booking
$486
Average price / night
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Luxe Designer Oasis + Guest House steps off Duval
Luxe Designer Oasis + Guest House steps off Duval
House
Key West, FL, 33040, United States
0.6k from Waterfront Playhouse center

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

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1050
Average price / night
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THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!
THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!
House
Key West, FL, 33040, United States
0.6k from Waterfront Playhouse center

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

4 Bedrooms10 Guests
New to Booking
$525
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 Private Pool in Waterfront Playhouse.

Where to stay in Waterfront Playhouse? Best neighborhoods & areas

Waterfront Playhouse Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

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

Prices for rentals with a private pool in Waterfront Playhouse vary depending on the property size, location, and travel season. Rates typically start from around $348 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 Waterfront Playhouse also welcome pets. Currently, 13 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 Waterfront Playhouse 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 Waterfront Playhouse 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.