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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Waterfront Playhouse

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1469 Best Vacation Rentals with Pool in Waterfront Playhouse (Starting from $279)

Ocean Key Resort & Spa, a Noble House Resort
Ocean Key Resort & Spa, a Noble House Resort
Resort
Key West, FL, USA
0.1k from Waterfront Playhouse center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, 4-star, Lodgings, Jacuzzis

97 Bedrooms46 Guests
8.7

Fabulous

116 reviews

$578
Average price / night
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Feather Queen at Custom House Inn | Two Vibrant Suites!
Feather Queen at Custom House Inn | Two Vibrant Suites!
Apartment
Key West, FL, 33040, United States
0.1k from Waterfront Playhouse center

AC, Dryer, Free Parking, Internet, Living Area, Microwave, No Smoking, Pool, TV

2 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1074
Average price / night
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Pier House Resort & Spa
Pier House Resort & Spa
Resort
Key West, FL, USA
0.2k from Waterfront Playhouse center

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

140 Bedrooms62 Guests
8.3

Very Good

664 reviews

$534
Average price / night
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2-bedroom condo in the heart of Key West- private beach & pool, tiki bar on-site
2-bedroom condo in the heart of Key West- private beach & pool, tiki bar on-site
Condo
Key West, FL, 33040, United States
0.1k from Waterfront Playhouse center

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

2 Bedrooms6 Guests
New to Booking
$652
Average price / night
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Opal Key Resort & Marina
Opal Key Resort & Marina
Resort
Key West, FL, USA
0.2k from Waterfront Playhouse center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Hot tubs

188 Bedrooms106 Guests
8.6

Fabulous

1178 reviews

$716
Average price / night
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Ocean Key Resort - A Noble House Resort
Ocean Key Resort - A Noble House Resort
Resort
Zero Duval St., Key West, FL, 33040, United States
0.1k from Waterfront Playhouse center

AC, Balcony, Bar, Breakfast Available, Business Services, Crib, Elevator, Fitness Equipment, Frontdesk 24 Hour

9.2

Superb

1002 reviews

$592
Average price / night
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Darling of Duval by Last Key Realty
Darling of Duval by Last Key Realty
House
Key West, FL, USA
0.3k from Waterfront Playhouse center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

2 Bedrooms4 Guests
New to Booking
$929
Average price / night
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Hyatt Centric Key West Resort & Spa
Hyatt Centric Key West Resort & Spa
Resort
Key West, FL, USA
0.3k from Waterfront Playhouse center

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

118 Bedrooms30 Guests
8.2

Very Good

545 reviews

$387
Average price / night
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Luxury Waterfront Stay @ The Galleon, Mins from Downtown
Luxury Waterfront Stay @ The Galleon, Mins from Downtown
Apartment
Key West, FL, 33040, United States
0.1k from Waterfront Playhouse center

AC, Dryer, Extra Bed, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
New to Booking
$675
Average price / night
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Last Minute
Last Minute
House
Key West, FL, USA
0.3k from Waterfront Playhouse center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

3 Bedrooms6 Guests
8.0

Good

2 reviews

$1115
Average price / night
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Ann Street Gardens - Downtown Key West
Ann Street Gardens - Downtown Key West
Cottage
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$489
Average price / night
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New Rose Retreat - Pool & Parking
New Rose Retreat - Pool & Parking
House
FL, USA
0.4k from Waterfront Playhouse center

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

2 Bedrooms6 Guests
New to Booking
$1180
Average price / night
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2 Sunset Harbor Resort, Pool, Hot Tub, In Town!
2 Sunset Harbor Resort, Pool, Hot Tub, In Town!
Resort
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Balcony, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms2 Guests
New to Booking
$2137
Average price / night
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New Rose Petal Petite Suite - Pool & Parking
New Rose Petal Petite Suite - Pool & Parking
Apartment
FL, USA
0.4k from Waterfront Playhouse center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom2 Guests
7.0

Good

1 reviews

$324
Average price / night
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2 Sunset Harbor Resort Key West, Hot Tub, Pool!
2 Sunset Harbor Resort Key West, Hot Tub, Pool!
Resort
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Balcony, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
New to Booking
$2025
Average price / night
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New Coastal Rose - Bright Loft with High Ceilings
New Coastal Rose - Bright Loft with High Ceilings
Apartment
FL, USA
0.4k from Waterfront Playhouse center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom4 Guests
7.3

Good

3 reviews

$427
Average price / night
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2 Sunset Harbor Resort Key West Florida
2 Sunset Harbor Resort Key West Florida
Resort
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Balcony, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms2 Guests
New to Booking
$11248
Average price / night
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Rigby House - Brand New with Private Pool
Rigby House - Brand New with Private Pool
House
Key West, FL, USA
0.4k from Waterfront Playhouse center

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

6 Bedrooms12 Guests
New to Booking
$2937
Average price / night
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Ann Street Cottage: A bright and airy home near Duval Street
Ann Street Cottage: A bright and airy home near Duval Street
Cottage
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio, Pool

1 Bedroom2 Guests
9.8

Exceptional

179 reviews

$524
Average price / night
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New The Cottage at James House
New The Cottage at James House
House
Key West, FL, USA
0.4k from Waterfront Playhouse center

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

1 Bedroom3 Guests
8.8

Fabulous

6 reviews

$358
Average price / night
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Amsterdam's Curry Mansion Inn
Amsterdam's Curry Mansion Inn
House
511 Caroline St, Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Business Services, Elevator, Heater, Internet, Laundry, Outdoor Space, Pool, TV

8.2

Very Good

1004 reviews

$279
Average price / night
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Trumans Trove by Last Key realty
Trumans Trove by Last Key realty
House
Key West, FL, USA
0.4k from Waterfront Playhouse center

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

2 Bedrooms6 Guests
New to Booking
$946
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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\"Tranquility \" At Ann Street Gardens Steps From Duval
\"Tranquility \" At Ann Street Gardens Steps From Duval
Cottage
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

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

1 Bedroom2 Guests
10.0

Exceptional

80 reviews

$1378
Average price / night
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Old Town Bali Hideaway For 2, Just Steps From Duval
Old Town Bali Hideaway For 2, Just Steps From Duval
House
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Patio, Pool, TV

1 Bedroom2 Guests
9.8

Exceptional

92 reviews

$590
Average price / night
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Hyatt Sunset Harbour Resort-Prime location on Key West!!
Hyatt Sunset Harbour Resort-Prime location on Key West!!
Resort
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Dryer, Elevator, Extra Bed, Fitness Equipment

2 Bedrooms6 Guests
8.0

Good

1 reviews

$740
Average price / night
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Two-bedroom townhouse overlooking the harbor.\n  \nONLY AVAILABLE Nov. 8 - Nov 15
Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 8 - Nov 15
Resort
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
New to Booking
$900
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 Waterfront Playhouse.

Where to stay in Waterfront Playhouse? Best neighborhoods & areas

Waterfront Playhouse Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1469 verified vacation rentals with a pool in Waterfront Playhouse. 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 Waterfront Playhouse vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $279 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Waterfront Playhouse 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 Waterfront Playhouse welcome pets. Currently, 25 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 Waterfront Playhouse often include additional outdoor features such as Pool, Laundry, and Internet. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Waterfront Playhouse 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.