Holiday rentals near Waterfront Playhouse
We found 2,434 holiday rentals — enter your dates for availability
Find the perfect holiday rental within close proximity to Waterfront Playhouse. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as parking and a hot tub. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Waterfront Playhouse
Showing deals for:26 Sept - 3 Oct
Image gallery for Waterfront, Private Heated Pool - Capmar House
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Waterfront, Private Heated Pool - Capmar House
Key West, Florida
8% off
Price is AU$11,923
AU$11,923
AU$1,703 per night
includes taxes & fees
Image gallery for Parking, Pet Friendly, Pool, Dock - Suncoast House
9.69.6 out of 10 rating
Exceptional
(36 reviews)
Parking, Pet Friendly, Pool, Dock - Suncoast House
Key West, Florida
8% off
Price is AU$14,232
AU$14,232
AU$2,033 per night
includes taxes & fees
Image gallery for Living the Dream Key West Style
1010 out of 10 rating
Exceptional
(18 reviews)
Living the Dream Key West Style
Key West, FL
8% off
Price is AU$3,505
AU$3,505
AU$501 per night
includes taxes & fees
Image gallery for Parking, Pool & Waterfront - Springtide House
9.89.8 out of 10 rating
Exceptional
(42 reviews)
Parking, Pool & Waterfront - Springtide House
Key West, Florida
8% off
Price is AU$11,795
AU$11,795
AU$1,685 per night
includes taxes & fees
Image gallery for Happy’s Houseboat Key West
9.29.2 out of 10 rating
Wonderful
(20 reviews)
Happy’s Houseboat Key West
Key West, FL
8% off
Price is AU$6,042
AU$6,042
AU$863 per night
includes taxes & fees
Image gallery for 3 bedroom 2 bath Ocean front condo on marina with opt boat slip.
1010 out of 10 rating
Exceptional
(14 reviews)
3 bedroom 2 bath Ocean front condo on marina with opt boat slip.
Key West, FL
8% off
Price is AU$9,380
AU$9,380
AU$1,340 per night
includes taxes & fees
Image gallery for 34’ Catamaran Sailboat
9.49.4 out of 10 rating
Exceptional
(35 reviews)
34’ Catamaran Sailboat
Key West, FL
8% off
Price is AU$3,023
AU$3,023
AU$432 per night
includes taxes & fees
Image gallery for Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
1010 out of 10 rating
Exceptional
(35 reviews)
Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
Key West, FL
13% off
Price is AU$7,022
AU$7,022
AU$1,003 per night
includes taxes & fees
Image gallery for Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
9.69.6 out of 10 rating
Exceptional
(97 reviews)
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
Key West, FL
8% off
Price is AU$5,516
AU$5,516
AU$788 per night
includes taxes & fees
Image gallery for Oceanfront Marina Condo With All Luxuries
9.89.8 out of 10 rating
Exceptional
(146 reviews)
Oceanfront Marina Condo With All Luxuries
Key West, FL
8% off
Price is AU$5,546
AU$5,546
AU$792 per night
includes taxes & fees
Image gallery for Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
9.69.6 out of 10 rating
Exceptional
(96 reviews)
Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
Key West, FL
8% off
Price is AU$6,101
AU$6,101
AU$872 per night
includes taxes & fees
Image gallery for The Cathouse, an Old Town tropical poolside oasis with huge, heated pool
1010 out of 10 rating
Exceptional
(9 reviews)
The Cathouse, an Old Town tropical poolside oasis with huge, heated pool
Key West, FL
10% off
Price is AU$11,581
AU$11,581
AU$1,654 per night
includes taxes & fees
Image gallery for Beautiful Stock Island Rental ~10 Min from Downtown Key West
9.69.6 out of 10 rating
Exceptional
(40 reviews)
Beautiful Stock Island Rental ~10 Min from Downtown Key West
Key West, FL
8% off
Price is AU$5,692
AU$5,692
AU$813 per night
includes taxes & fees
Image gallery for PET FRIENDLY! JUNE SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8
9.69.6 out of 10 rating
Exceptional
(213 reviews)
PET FRIENDLY! JUNE SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8
Key West, FL
15% off
Price is AU$5,727
AU$5,727
AU$818 per night
includes taxes & fees
Image gallery for KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.
9.09.0 out of 10 rating
Wonderful
(105 reviews)
KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.
Key West, FL
8% off
Price is AU$6,146
AU$6,146
AU$878 per night
includes taxes & fees
Image gallery for Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
9.89.8 out of 10 rating
Exceptional
(187 reviews)
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
Key West, FL
8% off
Price is AU$5,279
AU$5,279
AU$754 per night
includes taxes & fees
Image gallery for Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
1010 out of 10 rating
Exceptional
(236 reviews)
Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
Key West, FL
8% off
Price is AU$6,311
AU$6,311
AU$902 per night
includes taxes & fees
Image gallery for Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
8.08.0 out of 10 rating
Very good
(9 reviews)
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Key West, FL
11% off
Price is AU$2,709
AU$2,709
AU$387 per night
includes taxes & fees
Image gallery for Ocean views! <br>I didn’t do it too
1010 out of 10 rating
Exceptional
(21 reviews)
Ocean views! <br>I didn’t do it too
Key West, FL
7% off
Price is AU$5,532
AU$5,532
AU$790 per night
includes taxes & fees
Image gallery for Prime location, stunning views from 2 decks—walk or ride to explore the island!
1010 out of 10 rating
Exceptional
(117 reviews)
Prime location, stunning views from 2 decks—walk or ride to explore the island!
Key West, FL
15% off
Price is AU$4,266
AU$4,266
AU$609 per night
includes taxes & fees
Image gallery for Balcony, Pool, & Pet Friendly - The Grand Turk
8.48.4 out of 10 rating
Very good
(18 reviews)
Balcony, Pool, & Pet Friendly - The Grand Turk
Key West, Florida
7% off
Price is AU$3,675
AU$3,675
AU$525 per night
includes taxes & fees
Image gallery for Ocean views! <br>Luxury suites
1010 out of 10 rating
Exceptional
(26 reviews)
Ocean views! <br>Luxury suites
Key West, FL
11% off
Price is AU$6,267
AU$6,267
AU$895 per night
includes taxes & fees
Image gallery for Newly Updated! The Grand Cayman Suite
9.29.2 out of 10 rating
Wonderful
(22 reviews)
Newly Updated! The Grand Cayman Suite
Key West, Florida
7% off
Price is AU$3,729
AU$3,729
AU$533 per night
includes taxes & fees
Image gallery for Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
9.49.4 out of 10 rating
Exceptional
(47 reviews)
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Key West, FL
8% off
Price is AU$8,020
AU$8,020
AU$1,146 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Waterfront Playhouse
Island Hideaway with Three Pools and Easy Access to Watersports Rentals
Sleeps 4 · 1 bedroom · 1 bathroom
Luxe two 4BDR/4BA Suites
Sleeps 20 · 8 bedrooms · 8 bathrooms
Oceanfront Wellness home w/pool - Mastway House
Sleeps 12 · 4 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Key West Hyatt Charming 2-bedroom resort with WiFi, AC
Sleeps 6 · 2 bedrooms · 2 bathrooms
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value