Vacation Rentals in Red Barn Theater, FL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  Florida
  5.  Key West
  6.  Red Barn Theater

Refine your search

Price per night

Amenity Filter

Rating

1736 Best Vacation Rentals in Red Barn Theater (Starting from $324)

Sailfish Suite on Duval
Sailfish Suite on Duval
Apartment
Key West, FL, USA
0.0k from Red Barn Theater center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$629
Average price / night
Check Availability
Pilar Cottage | Spectacular Studio w/ Shared Pool
Pilar Cottage | Spectacular Studio w/ Shared Pool
Apartment
Key West, FL, 33040, United States
0.0k from Red Barn Theater center

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

1 Bedroom4 Guests
9.0

Fabulous

14 reviews

$460
Average price / night
Check Availability
New Rose Retreat - Pool & Parking
New Rose Retreat - Pool & Parking
House
FL, USA
0.1k from Red Barn Theater center

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

2 Bedrooms6 Guests
New to Booking
$1180
Average price / night
Check Availability
New Rose Petal Petite Suite - Pool & Parking
New Rose Petal Petite Suite - Pool & Parking
Apartment
FL, USA
0.1k from Red Barn Theater center

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

1 Bedroom2 Guests
7.0

Good

1 reviews

$324
Average price / night
Check Availability
The Penthouse at Custom House Inn | New!
The Penthouse at Custom House Inn | New!
Apartment
Key West, FL, 33040, United States
0.0k from Red Barn Theater center

AC, Internet, Kitchen, Living Area, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

23 reviews

$1174
Average price / night
Check Availability
New Coastal Rose - Bright Loft with High Ceilings
New Coastal Rose - Bright Loft with High Ceilings
Apartment
FL, USA
0.1k from Red Barn Theater center

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

1 Bedroom4 Guests
7.3

Good

3 reviews

$427
Average price / night
Check Availability
Cabana on Duval  |  Monthly studio w/ shared pool
Cabana on Duval | Monthly studio w/ shared pool
Apartment
Key West, FL, 33040, United States
0.0k from Red Barn Theater center

AC, Balcony, Dryer, Internet, Microwave, No Smoking, TV, Washer

New to Booking
$324
Average price / night
Check Availability
New The Cottage at James House
New The Cottage at James House
House
Key West, FL, USA
0.1k from Red Barn Theater 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
Check Availability
Orchid Suite on Duval
Orchid Suite on Duval
Apartment
Key West, FL, 33040, United States
0.0k from Red Barn Theater center

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

New to Booking
$327
Average price / night
Check Availability
Darling of Duval by Last Key Realty
Darling of Duval by Last Key Realty
House
Key West, FL, USA
0.1k from Red Barn Theater center

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

2 Bedrooms4 Guests
New to Booking
$929
Average price / night
Check Availability
\"Island Time\" in Old Town
\"Island Time\" in Old Town
House
Key West, FL, 33040, United States
0.0k from Red Barn Theater center

AC, Dryer, Internet, Kitchen, Laundry, No Smoking, Pool, TV, Washer

2 Bedrooms4 Guests
New to Booking
$390
Average price / night
Check Availability
Takeover at the Grand Maloney
Takeover at the Grand Maloney
House
Key West, FL, USA
0.1k from Red Barn Theater center

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

6 Bedrooms16 Guests
New to Booking
$3083
Average price / night
Check Availability
The Key West Hotel
The Key West Hotel
House
325 Duval St., Key West, FL, 33040, United States
0.0k from Red Barn Theater center

AC, Housekeeping, Internet, Outdoor Space, Pets, Pool, Room Service, TV

9.2

Superb

547 reviews

$490
Average price / night
Check Availability
Rose Lane Villas
Rose Lane Villas
Villa
Key West, FL, USA
0.1k from Red Barn Theater 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
Check Availability
3 Bedroom Key West Home - Perfect Location & Private Pool
3 Bedroom Key West Home - Perfect Location & Private Pool
House
Key West, FL, 33040, United States
0.1k from Red Barn Theater center

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

3 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$1394
Average price / night
Check Availability
New KAMP - Rooftop Penthouse
New KAMP - Rooftop Penthouse
Apartment
Key West, FL, USA
0.2k from Red Barn Theater center

Apartments, Accommodations, Lodgings, Places to stay, Family

1 Bedroom6 Guests
New to Booking
$889
Average price / night
Check Availability
Rose Petal Petite Suite - Near Duval Street
Rose Petal Petite Suite - Near Duval Street
Apartment
Key West, FL, 33040, United States
0.1k from Red Barn Theater center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

5 reviews

$710
Average price / night
Check Availability
Rigby House - Brand New with Private Pool
Rigby House - Brand New with Private Pool
House
Key West, FL, USA
0.2k from Red Barn Theater center

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

6 Bedrooms12 Guests
New to Booking
$2937
Average price / night
Check Availability
Coastal Rose - Private Pool & Near Duval
Coastal Rose - Private Pool & Near Duval
Apartment
Key West, FL, 33040, United States
0.1k from Red Barn Theater center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom4 Guests
9.4

Superb

6 reviews

$725
Average price / night
Check Availability
The Zesty Lime by Last Key Realty
The Zesty Lime by Last Key Realty
House
Key West, FL, USA
0.2k from Red Barn Theater center

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

1 Bedroom8 Guests
New to Booking
$1466
Average price / night
Check Availability
Rose Key Cottage - Private Pool & Near Duval
Rose Key Cottage - Private Pool & Near Duval
House
Key West, FL, 33040, United States
0.1k from Red Barn Theater center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
5.6

Review score

4 reviews

$1929
Average price / night
Check Availability
The Toasted Coconut by Last Key Realty
The Toasted Coconut by Last Key Realty
House
Key West, FL, USA
0.2k from Red Barn Theater center

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

3 Bedrooms8 Guests
New to Booking
$1391
Average price / night
Check Availability
Shared Pool & Parking - The Cottage at James House
Shared Pool & Parking - The Cottage at James House
House
Key West, FL, 33040, United States
0.1k from Red Barn Theater center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

1 Bedroom3 Guests
8.8

Fabulous

9 reviews

$555
Average price / night
Check Availability
Island Pearls
Island Pearls
House
Key West, FL, USA
0.2k from Red Barn Theater center

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

2 Bedrooms4 Guests
New to Booking
$921
Average price / night
Check Availability
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!
Apartment
Key West, FL, 33040, United States
0.1k from Red Barn Theater center

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

2 Bedrooms6 Guests
9.6

Exceptional

31 reviews

$726
Average price / night
Check Availability
Last Minute
Last Minute
House
Key West, FL, USA
0.2k from Red Barn Theater 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
Check Availability
~Hibiscus Cottage~ 18+ Adult Only cottage near Duval St
~Hibiscus Cottage~ 18+ Adult Only cottage near Duval St
Cottage
Key West, FL, 33040, United States
0.1k from Red Barn Theater center

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

2 Bedrooms4 Guests
9.8

Exceptional

16 reviews

$736
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 in Red Barn Theater.

Where to stay in Red Barn Theater? Best neighborhoods & areas

Red Barn Theater Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1736 verified vacation rentals in Red Barn Theater. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Red Barn Theater vary depending on the season, property size, and location. Rates typically start from around $324 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Red Barn Theater include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Red Barn Theater welcome pets. Currently, 52 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Red Barn Theater often include amenities such as Internet, Pool, and Security/Safety. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.