Discover Your Ideal Red Barn Theater Vacation Rental in the Heart of Key West, Florida, USA
Discover Your Perfect Red Barn Theater Vacation Homes
Best Vacation Homes in Red Barn Theater
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- Accessibility
- Air Conditioner
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- Air Conditioner
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- Pet Friendly
- Pool
- Accessibility
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- Pet Friendly
- Pool
- Air Conditioner
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- Pool
- Security/Safety
- Child Friendly
- Internet
- Air Conditioner
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- Pet Friendly
Why Choose Rent By Owner for your Red Barn Theater Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Red Barn Theater Vacation Rentals
Where are the best neighborhoods to stay in Red Barn Theater?
Discover the perfect neighborhood to stay in Key West, Florida, and enjoy an authentic island experience. Whether you prefer the lively atmosphere close to local shops and vibrant nightlife or a more tranquil setting near scenic views, choosing the right area can enhance your visit. Red Barn Theater is situated in a charming part of the city that offers convenient access to cultural attractions and beautiful outdoor spaces. When booking your vacation rentals, consider neighborhoods that provide both comfort and easy exploration of all that this unique destination has to offer. With trusted options available, you can find a space that fits your needs and ensures a memorable stay in Key West.
Key West Historic District
The historic district offers a charming atmosphere where you can immerse yourself in the region's rich cultural heritage and vibrant local life, making it an ideal area for those seeking authentic experiences.
View 2950+ Rentals in Key West Historic DistrictOld Town
In Old Town, you’ll find a lively neighborhood filled with colorful architecture and quaint streets, perfect for exploring the unique character of this island destination.
View 2865+ Rentals in Old TownSunset Key
Sunset Key provides a serene escape with luxurious accommodations just moments from here, offering stunning views and peaceful surroundings for a memorable getaway.
View 3214+ Rentals in Sunset KeyDowntown
Downtown is the bustling heart of the region, where you can experience a mix of lively entertainment, shops, and dining options within walking distance of your stay.
View 1283+ Rentals in DowntownUptown - Upper Duval
Uptown, along with Upper Duval, features a laid-back vibe with convenient access to local attractions and scenic spots, ideal for travelers wanting a relaxed yet central location.
View 890+ Rentals in Uptown - Upper DuvalBahama Village
Bahama Village is known for its vibrant Caribbean influences and welcoming community, offering a lively atmosphere close to the local cultural scene.
View 107+ Rentals in Bahama VillageHistoric Seaport
Close to the historic seaport, this area boasts beautiful waterfront views and easy access to maritime activities, perfect for those seeking a nautical vibe.
View 463+ Rentals in Historic SeaportNew Town
New Town offers a more modern setting with convenient amenities and quieter streets, suitable for travelers looking for comfort and accessibility.
View 126+ Rentals in New TownBest Times to Visit Red Barn Theater
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the shoulder seasons when the area offers pleasant weather and fewer crowds, allowing you to enjoy all that this vibrant destination has to offer with your preferred vacation rentals.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences its peak popularity as travelers seek warmer climates and a vibrant island atmosphere.
Spring (March to May)
Springtime in the region draws visitors with its pleasant weather and lively cultural events, making it an ideal time for exploring the area.
Off-Season Highlights
Summer (June to August)
The summer months see fewer tourists due to higher temperatures and humidity, offering a quiet and relaxed experience here.
Fall (September to November)
Late fall tends to draw fewer visitors, providing a peaceful environment perfect for enjoying the scenic beauty and serene beaches.
Weekly Weather Forecast for Red Barn Theater
How to Book Your Red Barn Theater Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
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Book Online
Explore and book the perfect rental in Red Barn Theater
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor seating area perfect for relaxing and entertaining amidst the tropical climate.
- Take advantage of a lush landscaped backyard ideal for outdoor dining or enjoying the sunshine.
- Make use of a refreshing swimming pool to cool off after exploring the vibrant local scene.
- Benefit from a fully equipped outdoor grilling station for preparing delicious meals in the open air.
- Relax in a shaded patio or porch, providing a comfortable space to unwind outdoors.
- Experience the convenience of off-street parking with easy access to your outdoor amenities.
- Appreciate scenic views of the surrounding region, enhancing your stay in this desirable destination.
Top Attractions Around Red Barn Theater
What attractions are nearby?
While staying here, you can explore the vibrant local scene with nearby beaches, art galleries, and lively dining options that showcase the unique charm of Key West, Florida.

Family Activities
- Visit the Key West Butterfly and Nature Conservatory: Immerse your family in a captivating experience as you walk through lush gardens filled with colorful butterflies and exotic birds, right here in this vibrant destination.
- Explore the Key West Shipwreck Museum: Discover fascinating maritime history and learn about shipwreck salvaging that shaped the area’s heritage through engaging exhibits suitable for all ages.
- Enjoy a sunset cruise along the coast: Relax aboard a family-friendly boat tour and witness breathtaking sunsets over the waters surrounding this popular vacation spot.
- Take a Conch Tour Train adventure: Hop aboard this scenic train ride to explore the highlights of this lively region while providing an entertaining overview for children and adults alike.
Adult Activities
- Attend an Engaging Live Performance: Experience the vibrant arts scene by enjoying a live show or theatrical performance at the Red Barn Theater, renowned for its local productions and intimate setting.
- Participate in Creative Workshops: Enhance your artistic skills through workshops hosted here, offering a unique opportunity to connect with local artists and immerse yourself in the region's cultural flair.
- Explore Local Art Exhibits: Discover contemporary and traditional artwork displayed within the theater space, providing insight into the area's rich artistic community.
- Enjoy Nighttime Cultural Events: Join special evening events such as film screenings or themed performances that showcase the area's diverse cultural offerings and entertain adult visitors.
Red Barn Theater Travel Tips
How Can You Make the Most of Your Stay?
- Explore local attractions nearby: Take advantage of the area's renowned cultural scene and scenic spots to enrich your stay in this vibrant destination.
- Plan outdoor activities early: The region offers pleasant weather year-round, so scheduling boat trips or beach visits during the mornings ensures a more enjoyable experience.
- Discover dining options close to your rental: Savor authentic regional cuisine at nearby eateries to get a true taste of the local flavor during your visit.
- Stay connected with essential amenities: Choose a vacation rental that provides reliable Wi-Fi and modern conveniences to make your time here comfortable and convenient.
Transportation Options
- Rental Car Services: Conveniently explore the area around the Red Barn Theater with a rental car, offering flexibility to visit local attractions at your own pace.
- Public Transit: Local buses provide an affordable and eco-friendly way to navigate here, connecting you easily to key destinations in the region.
- Taxis and Rideshare Services: Reliable transportation options like taxis and rideshare apps ensure quick and comfortable travel to and from your vacation rental near the theater.
- Bicycle Rentals: Rent a bicycle to enjoy scenic routes and experience the charm of this destination at a leisurely pace.
Local Customs Options
- Respect for Local Art and Culture: Visitors often appreciate the vibrant artistic expressions and theatrical traditions that are central to this area's community spirit.
- Celebration of Key West Heritage: Emphasizing historical storytelling and local customs, many find it meaningful to engage with cultural events that highlight the region’s rich history.
- Embracing the Island Lifestyle: The relaxed and friendly attitude prevalent here encourages respectful interactions and laid-back social etiquette among residents and visitors alike.
- Environmental Preservation Respect: Practicing eco-friendly habits and respecting protected natural sites is highly valued in this destination to maintain its natural beauty.
Frequently Asked Questions About Red Barn Theater?
1. What are the top vacation rentals in Red Barn Theater?
There are a lot of options in Red Barn Theater. If you plan on staying in the Red Barn Theater area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Red Barn Theater:
- Almond Tree Inn Hotel - Adults Only
- Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
- Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
- Perfect Location, nPrivate Heated Pool,nPristine Luxury Home!
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
2. How many Rentbyowner vacation rentals are available in Red Barn Theater?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 3563 in the Red Barn Theater area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Red Barn Theater.
3. What is the cancellation policy for this vacation rental in Key West?
4. Are there any additional fees I should be aware of when booking this property?
5. Is there a minimum stay requirement for booking here?
6. How do I access the property upon arrival?
7. Can I inquire about special requests or amenities for my stay?
Best Vacation Homes in Red Barn Theater
- Pet Friendly
- Security/Safety
- Child Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Pool
- Private Pool
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV