Short-Term Rentals in Waterfront Playhouse, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida
  5.  Key West
  6.  Waterfront Playhouse

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2250 Best Short-Term Rentals in Waterfront Playhouse (Starting from $159)

Luxury 4BDR/4BA Penthouse
Luxury 4BDR/4BA Penthouse
House
Key West, FL, USA
0.1k from Waterfront Playhouse center

Laundry, Security/Safety, Child Friendly

4 Bedrooms8 Guests
New to Booking
$977
Average price / night
Check Availability
Chicken Run at Custom House Inn | Unbeatable Location!
Chicken Run at Custom House Inn | Unbeatable Location!
Apartment
Key West, FL, 33040, United States
0.1k from Waterfront Playhouse center

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

1 Bedroom4 Guests
9.8

Exceptional

10 reviews

$550
Average price / night
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Harbor Luxe Celebration Suites
Harbor Luxe Celebration Suites
Apartment
Key West, FL, USA
0.1k from Waterfront Playhouse center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

1 Bedroom20 Guests
New to Booking
$3894
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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Great Old Town Location, Steps from Mallory Square
Great Old Town Location, Steps from Mallory Square
Apartment
Waterfront Playhouse, Key West, Florida, USA
0.1k from Waterfront Playhouse center

Air Conditioner, Internet

1 Bedroom2 Guests
New to Booking
$159
Average price / night
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Underwater Cabana at Custom House Inn
Underwater Cabana at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$481
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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Chicken Run at Custom House Inn
Chicken Run at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$514
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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Citrus Queen at Custom House Inn
Citrus Queen at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$544
Average price / night
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Harbor House Penthouse- A
Harbor House Penthouse- A
Condo
Key West, FL, 33040, United States
0.1k from Waterfront Playhouse center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms12 Guests
10.0

Exceptional

23 reviews

$1914
Average price / night
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Birds of a Feather at Custom House Inn
Birds of a Feather at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$549
Average price / night
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Harbor House Penthouse- B
Harbor House Penthouse- B
House
Key West, FL, 33040, United States
0.1k from Waterfront Playhouse center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

4 Bedrooms8 Guests
9.6

Exceptional

15 reviews

$1691
Average price / night
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Chicken Water Cabana at Custom House Inn
Chicken Water Cabana at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$837
Average price / night
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Sandbar Suite | 2 bed near Duval & waterfront
Sandbar Suite | 2 bed near Duval & waterfront
Apartment
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

2 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$1092
Average price / night
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Feather Queen at Custom House Inn
Feather Queen at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$867
Average price / night
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Coral Reef Suite | 1 bed near Duval & waterfront
Coral Reef Suite | 1 bed near Duval & waterfront
Apartment
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$952
Average price / night
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Sunshine State at Custom House Inn
Sunshine State at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom3 Guests
New to Booking
$541
Average price / night
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Sundown Refuge | Top Location w/ Outdoor Dining & Shared Pool | Month Long Stays
Sundown Refuge | Top Location w/ Outdoor Dining & Shared Pool | Month Long Stays
Condo
Key West, FL, 33040, United States
0.2k from Waterfront Playhouse center

AC, Balcony, Barbecue, Dryer, Extra Bed, Internet, Kitchen, Laundry, No Smoking

2 Bedrooms5 Guests
9.4

Superb

31 reviews

$596
Average price / night
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Custom House Inn All
Custom House Inn All
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Accommodations, Lodgings, Places to stay

8 Bedrooms25 Guests
New to Booking
$5685
Average price / night
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Harbor Walk Hideaways | Group Compound In Old Town, Pool!
Harbor Walk Hideaways | Group Compound In Old Town, Pool!
House
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool, TV

4 Bedrooms14 Guests
9.2

Superb

15 reviews

$1500
Average price / night
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The Penthouse at Custom House Inn
The Penthouse at Custom House Inn
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Accommodations, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$919
Average price / night
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Birds of a Feather at Custom House Inn | Perfect Stay on Duval Street!
Birds of a Feather at Custom House Inn | Perfect Stay on Duval Street!
Apartment
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Internet, Microwave, No Smoking, TV

1 Bedroom4 Guests
10.0

Exceptional

9 reviews

$550
Average price / night
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Sandbar Suite
Sandbar Suite
Apartment
Key West, FL, USA
0.2k from Waterfront Playhouse center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$568
Average price / night
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Chicken Water Cabana at Custom House Inn | Two Modern Suites!
Chicken Water Cabana at Custom House Inn | Two Modern Suites!
Apartment
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Internet, Microwave, No Smoking, TV

2 Bedrooms8 Guests
9.2

Superb

12 reviews

$1028
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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Blanco Luxury Villa
Blanco Luxury Villa
Condo
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, TV

4 Bedrooms8 Guests
New to Booking
$845
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 Short-Term Rentals in Waterfront Playhouse.

Where to stay in Waterfront Playhouse? Best neighborhoods & areas

Waterfront Playhouse Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 2250 verified short-term rentals in Waterfront Playhouse, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Waterfront Playhouse vary depending on location, property size, and travel dates. Rates typically start from around $159 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Waterfront Playhouse include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Waterfront Playhouse, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Waterfront Playhouse often include amenities such as Laundry, Security/Safety, and Child Friendly, providing a comfortable and convenient stay.

Short-term rentals in Waterfront Playhouse are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.