Oceanfront Rentals in Waterfront Playhouse, FL: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Waterfront Playhouse

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1053 Best Oceanfront Rentals in Waterfront Playhouse (Starting from $230)

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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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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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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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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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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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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Galleon Resort and Marina
Galleon Resort and Marina
Resort
Waterfront Playhouse, Key West, Florida, USA
0.4k from Waterfront Playhouse center

Accommodations, Pools, Resorts, Parking, 3-star, Lodgings, Beach, Jacuzzis, Places to stay

84 Bedrooms20 Guests
7.1

Good

111 reviews

$603
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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Rose Lane Villas
Rose Lane Villas
Villa
Key West, FL, USA
0.4k from Waterfront Playhouse center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

10 Bedrooms26 Guests
8.4

Very Good

299 reviews

$345
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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La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
Resort
Key West, FL, USA
0.5k from Waterfront Playhouse center

Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay, Accessible hotels

12 Bedrooms31 Guests
8.3

Very Good

54 reviews

$306
Average price / night
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Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool
Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool
House
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

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

2 Bedrooms4 Guests
9.0

Fabulous

34 reviews

$230
Average price / night
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Garden of Emma by Last Key Realty
Garden of Emma by Last Key Realty
House
Key West, FL, USA
0.7k from Waterfront Playhouse center

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

4 Bedrooms8 Guests
New to Booking
$1893
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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The Island Suite at KW Vacation
The Island Suite at KW Vacation
Apartment
Key West, FL, USA
0.8k from Waterfront Playhouse center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom4 Guests
9.6

Exceptional

36 reviews

$395
Average price / night
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**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Cottage
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

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

2 Bedrooms4 Guests
10.0

Exceptional

152 reviews

$966
Average price / night
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Tranquillity Guest House
Tranquillity Guest House
Apartment
Key West, FL, USA
0.9k from Waterfront Playhouse center

Apartments, Cheap, Accommodations, Pools, Serviced apartments, 3-star, Lodgings, Places to stay

16 Bedrooms4 Guests
8.2

Very Good

255 reviews

$514
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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Westwinds Inn
Westwinds Inn
House
Key West, FL, USA
0.9k from Waterfront Playhouse center

B&bs, Accommodations, Pools, Guest houses, Homestays, Romantic, Lodgings, Vacation rentals, Places to stay

27 Bedrooms28 Guests
8.8

Fabulous

732 reviews

$475
Average price / night
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**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

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

3 Bedrooms8 Guests
New to Booking
$428
Average price / night
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Key West Villas
Key West Villas
Villa
Key West, FL, USA
0.9k from Waterfront Playhouse center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

9 Bedrooms28 Guests
9.7

Exceptional

379 reviews

$345
Average price / night
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Sunset Harbor - Old Town Key West Location - Beautiful Property
Sunset Harbor - Old Town Key West Location - Beautiful Property
Condo
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

AC, Barbecue, Elevator, Extra Bed, Heater, Hot Tub, Internet, Kitchen, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$698
Average price / night
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Bahama Gardens - Main House
Bahama Gardens - Main House
House
Key West, FL, USA
0.9k from Waterfront Playhouse center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$2211
Average price / night
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Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor
Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor
House
Key West, FL, 33040, United States
0.3k from Waterfront Playhouse center

Elevator, Extra Bed, Internet, Kitchen, Living Area, No Smoking, Patio, Pool, TV

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$482
Average price / night
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Bahama Gardens - Cigar House
Bahama Gardens - Cigar House
House
Key West, FL, USA
0.9k from Waterfront Playhouse center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$1058
Average price / night
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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 Oceanfront Rentals in Waterfront Playhouse.

Where to stay in Waterfront Playhouse? Best neighborhoods & areas

Waterfront Playhouse Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 1053 verified oceanfront rentals in Waterfront Playhouse. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Waterfront Playhouse vary depending on the property size, exact beachfront location, and season. Rates typically start from around $230 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Waterfront Playhouse offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Waterfront Playhouse welcome pets. Currently, 44 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Waterfront Playhouse often include features designed for a comfortable coastal stay, such as Oceanfront, View, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.