3672+ Vacation Rentals Near Waterfront Playhouse |
  1. USA
  2. Florida
  3. Key West
  4. Waterfront Playhouse

Las Hawaiianas - Vacation Rentals in Waterfront Playhouse

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West From US $269
         

10.0 (189 Reviews)
Condo
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
  • Air Conditioner
  • Parking
  • Pool

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Amsterdam's Curry Mansion Inn From US $563
         

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8.8 (139 Reviews)
Bed & Breakfast
Amsterdam's Curry Mansion Inn
  • Air Conditioner
  • Parking
  • Pet Friendly

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Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub! From US $462
         

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10.0 (5 Reviews)
Cottage
Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
  • Air Conditioner
  • Parking
  • Pool

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Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only From US $575
         

10.0 (181 Reviews)
House
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
  • Air Conditioner
  • Parking
  • Pool

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Old Town Garden Villas From US $258
         

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9.5 (19 Reviews)
House
Old Town Garden Villas
  • Air Conditioner
  • Pool
  • View

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Parrot Perch by Avantstay Old Town Key West w/Shared Pool Month-long Stays Only From US $421
         

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10.0 (5 Reviews)
House
Parrot Perch by Avantstay Old Town Key West w/Shared Pool Month-long Stays Only
  • Air Conditioner
  • Parking
  • Pool

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NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking From US $1,936
         

10.0 (148 Reviews)
House
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
  • Air Conditioner
  • Parking
  • Pool

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Sunshine Corner From US $244
         

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New
House
Sunshine Corner
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Sunnyside Up by Brightwild Pool Parking From US $1,046
         

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10.0 (1 Review)
Apartment
Sunnyside Up by Brightwild Pool Parking
  • Parking
  • Pet Friendly
  • Pool

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Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews From US $344
         

9.8 (162 Reviews)
Condo
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
  • Air Conditioner
  • Parking
  • Pool

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Luxury 3-Bedroom Waterfront Home with Pool AND Dock! From US $1,389
         

9.8 (135 Reviews)
House
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Rent a Piece of Paradise, Best Location on the Island! From US $362
         

9.8 (103 Reviews)
Condo
Rent a Piece of Paradise, Best Location on the Island!
  • Air Conditioner
  • Parking
  • Pool

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STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town! From US $3,307
         

9.6 (76 Reviews)
House
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
  • Air Conditioner
  • Parking
  • Pool

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Prime location, stunning views from 2 decks—walk or ride to explore the island! From US $436
         

10.0 (121 Reviews)
House
Prime location, stunning views from 2 decks—walk or ride to explore the island!
  • Air Conditioner
  • Parking
  • Pool

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"Tranquility " At Ann Street Gardens Steps From Duval From US $1,243
         

10.0 (80 Reviews)
Cottage
"Tranquility " At Ann Street Gardens Steps From Duval
  • Air Conditioner
  • Pool
  • TV

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Namaste 'The Spirit Within Me Salutes The Spirit Within You' From US $1,243
         

10.0 (44 Reviews)
House
Namaste 'The Spirit Within Me Salutes The Spirit Within You'
  • Air Conditioner
  • Pool
  • TV

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*VILLA ANGELITA @ OLD TOWN* Renovated Condo Off Duval + LAST KEY SERVICES. From US $1,197
         

9.8 (86 Reviews)
Condo
*VILLA ANGELITA @ OLD TOWN* Renovated Condo Off Duval + LAST KEY SERVICES.
  • Air Conditioner
  • Pet Friendly
  • TV

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Blue Heaven at The Truman Annex in Key West From US $393
         

9.0 (51 Reviews)
Condo
Blue Heaven at The Truman Annex in Key West
  • Air Conditioner
  • Parking
  • Pool

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*FOLLOW THE SUN @ THE BEACH* Ocean Condo/Pool & Tennis + LAST KEY SERVICES. From US $609
         

10.0 (159 Reviews)
Condo
*FOLLOW THE SUN @ THE BEACH* Ocean Condo/Pool & Tennis + LAST KEY SERVICES.
  • Air Conditioner
  • Parking
  • Pool

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*ATLANTIC REFLECTIONS @ THE BEACH* Ocean Penthouse/Pool + LAST KEY SERVICES. From US $668
         

10.0 (121 Reviews)
Condo
*ATLANTIC REFLECTIONS @ THE BEACH* Ocean Penthouse/Pool + LAST KEY SERVICES.
  • Air Conditioner
  • Parking
  • Pool

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*CONCH CASA GRANDE @ THE ANNEX* Home+ Pool near Duval + LAST KEY SERVICES. From US $2,464
         

10.0 (83 Reviews)
House
*CONCH CASA GRANDE @ THE ANNEX* Home+ Pool near Duval + LAST KEY SERVICES.
  • Air Conditioner
  • Parking
  • Pool

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*SALTWATER HARMONY @ THE ANNEX* Charming Condo & Pool + LAST KEY SERVICES. From US $373
         

10.0 (63 Reviews)
Condo
*SALTWATER HARMONY @ THE ANNEX* Charming Condo & Pool + LAST KEY SERVICES.
  • Air Conditioner
  • Parking
  • Pool

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*PROMENADE TO PARADISE @ THE ANNEX* Ocean Condo & Pool + LAST KEY SERVICES. From US $409
         

10.0 (52 Reviews)
Condo
*PROMENADE TO PARADISE @ THE ANNEX* Ocean Condo & Pool + LAST KEY SERVICES.
  • Air Conditioner
  • Parking
  • Pool

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*THE ROYAL COMPOUND @ THE ANNEX* Lush Estate & Pool + LAST KEY SERVICES. From US $2,022
         

10.0 (28 Reviews)
House
*THE ROYAL COMPOUND @ THE ANNEX* Lush Estate & Pool + LAST KEY SERVICES.
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Lashawaiianas makes it easy to compare the best listings on Lashawaiianas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Lashawaiianas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Waterfront Playhouse.

Weather in Waterfront Playhouse

View the weather forecast for Waterfront Playhouse before booking your Waterfront Playhouse Vacation Rentals to confirm your best time to go.

December - February
High 81°F       Low 67°F
March - May
High 87°F       Low 70°F
June - August
High 91°F       Low 80°F
September - November
High 90°F       Low 73°F

Top Attractions Around Waterfront Playhouse, FL

Lashawaiianas offers a large selection of top attractions around Waterfront Playhouse. Research things to do on your vacation before you visit Waterfront Playhouse.


Duval Street Smathers Beach Southernmost Point Mallory Square South Beach Higgs Beach Key West Harbour Key West Aquarium Ernest Hemingway Home and Museum Fort Zachary Taylor Historic State Park Key West Butterfly and Nature Conservatory Florida Keys Beaches Saddlebunch Keys Harry S. Truman Little White House Key West Shipwreck Museum Key West Golf Club Key West Lighthouse and Keeper's Quarters Museum Ripley's Believe It or Not Audubon House and Tropical Gardens

Waterfront Playhouse Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Waterfront Playhouse?

There are a lot of options in Waterfront Playhouse. If you plan on staying in the Waterfront Playhouse area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Waterfront Playhouse:

How many vacation rentals are available in Waterfront Playhouse?

Currently, the total number of properties listed in 2026 is over 3672 in the Waterfront Playhouse area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Waterfront Playhouse.