Best Vacation Homes in Downtown
10.0
Fireplace/Heating
Pool
Balcony/Terrace
Pet Friendly
10.0- Pool
View
Breakfast
Parking
10.0- Balcony/Terrace
- Parking
Internet
Child Friendly
- Fireplace/Heating
Air Conditioner- Internet
- Child Friendly
10.0- Pool
- View
- Breakfast
- Parking
Private Pool
Oceanfront
Hot Tub- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
Kitchen
- Hot Tub
- Pool
- Balcony/Terrace
- Air Conditioner
Downtown Luxury Rentals
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
9.5- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
Spa- Pool
- Pet Friendly
- Parking
- Pool
- View
- Pet Friendly
- Parking
- Pool
- Pet Friendly
- Parking
- Air Conditioner
- Pool
- View
- Pet Friendly
- Parking
- Pool
- View
- Pet Friendly
- Parking
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
Downtown Pet Friendly Vacation Rentals
10.0- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
10.0- Fireplace/Heating
- Pool
- View
- Pet Friendly
10.0- Pool
- Pet Friendly
- Parking
- Internet
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Fireplace/Heating
- Pool
- View
- Pet Friendly
10.0- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
10.0- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
Downtown Large Vacation Homes
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
10.0- Fireplace/Heating
- Pool
- View
- Pet Friendly
7.4- Pool
- Ocean View
- Balcony/Terrace
- View
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
10.0- Fireplace/Heating
- Pool
- View
- Parking
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
Why Choose Rent By Owner for your Downtown Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Downtown Vacation Rentals
Where are the best neighborhoods to stay in Downtown?
Staying in Downtown Key West puts you at the heart of this vibrant Florida neighborhood, where charming streets and lively establishments create an inviting atmosphere. Whether you're seeking a serene retreat or a dynamic nightlife scene, this area offers a diverse selection of vacation rentals that cater to your preferences. By choosing a property here, you'll enjoy easy access to the local culture and waterfront views, making your stay in this iconic destination both convenient and memorable. Experience the authentic essence of Key West by booking your ideal accommodation in the downtown area, where comfort and accessibility go hand in hand.
Key West Historic District
Staying in the Key West Historic District places you at the heart of the area's vibrant history and culture, offering easy access to charming architecture and local landmarks. This neighborhood provides an authentic experience for those seeking to explore the region's rich heritage through comfortable vacation rentals.
View 2249+ Rentals in Key West Historic DistrictOld Town
In Old Town, you'll find a lively atmosphere with colorful streets and historic sites, making it ideal for discovering the essence of the area. Here, well-appointed vacation rentals allow you to immerse yourself fully in the unique charm of this popular destination.
View 2189+ Rentals in Old TownUptown - Upper Duval
Opting for Uptown - Upper Duval means enjoying a lively neighborhood scene with a variety of dining and entertainment options close by. The area offers convenient vacation rental choices perfect for exploring everything this vibrant part of the city has to offer.
View 711+ Rentals in Uptown - Upper DuvalBahama Village
Located in the region, Bahama Village is known for its colorful character and cultural richness, providing a cozy setting for your stay. Vacation rentals here give you the chance to experience the area's local flavor and welcoming community.
View 77+ Rentals in Bahama VillageHistoric Seaport
The Historic Seaport is perfect for travelers wanting scenic waterfront views and maritime charm, with vacation rentals that place you close to boat tours and seaside activities. It’s an ideal choice for enjoying the region’s nautical atmosphere.
View 366+ Rentals in Historic SeaportTruman Annex
Choosing Truman Annex means staying in a peaceful yet accessible neighborhood, featuring luxurious vacation rentals near scenic parks and historic sites. It’s a prime spot for experiencing the regional blend of tranquility and adventure.
View 306+ Rentals in Truman AnnexBest Times to Visit Downtown
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit this vibrant area ensures you can fully enjoy the unique atmosphere and local charm of your vacation here, making it essential to consider seasonal trends and regional climate when planning your stay.
Peak Season Highlights
Winter (December to April)
During the winter months, this destination experiences its peak season, attracting visitors seeking warm weather and sunny skies. Expect lively atmospheres and higher demand for vacation rentals in the area.
Summer (June to August)
The summer months bring the highest influx of travelers eager to enjoy the region's vibrant atmosphere and outdoor activities. Vacation rentals tend to book quickly during this bustling season.
Off-Season Highlights
Spring (April to June)
In spring, the area sees a slight dip in visitor numbers, offering more availability and relaxed ambiance for those looking to explore at a slower pace. It's an ideal time for affordable vacation rentals.
Fall (September to November)
Autumn offers a quieter experience with fewer crowds, making it perfect for discovering the region’s charms without the peak-season rush. Vacation rentals are often more accessible and budget-friendly.
Weekly Weather Forecast for Downtown
How to Book Your Downtown Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Downtown
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 patio or balcony to relax and soak up the sunny Florida weather.
- Take advantage of lush garden spaces or landscaped courtyards that add to the tropical ambiance.
- Make use of the swimming pool, often available in downtown accommodations for a refreshing escape.
- Utilize outdoor dining areas perfect for al fresco meals in the warm climate.
- Benefit from barbecue grills or outdoor kitchens to host gatherings under the sun or stars.
- Relax on loungers or sun decks designed for soaking up the region’s vibrant sunshine.
- Access nearby waterfront views or dock areas if your rental is close to the coast or harbor.
Top Attractions Around Downtown
What attractions are nearby?
Within this vibrant area, you can enjoy a variety of activities such as exploring historic sites, indulging in local cuisine, and taking scenic boat tours, all conveniently accessible from your downtown Key West vacation rentals.
Family Activities
- Beachfront Family Fun: Spend a day at the sandy shores of this coastal area, where you can enjoy swimming, building sandcastles, and relaxing by the water.
- Historic Lighthouse Tour: Explore the iconic lighthouse, offering educational insights and stunning views that captivate visitors of all ages.
- Conch Republic Marine Park: Discover underwater adventures with family-friendly snorkeling and paddleboarding experiences in the vibrant marine park nearby.
- Old Town Key West Walking Tour: Take a guided stroll through the historic district, immersing your family in the colorful architecture and local stories that make this destination unique.
Adult Activities
- Sunset Sails: Embark on a scenic cruise to enjoy breathtaking sunsets over the Gulf of Mexico, a perfect way to unwind in this vibrant area.
- Duval Street Nightlife: Experience the lively atmosphere and diverse entertainment options along Duval Street, a hub for adult nightlife and local culture.
- Historic Seaport District: Explore the charming waterfront with its unique shops, dining establishments, and opportunities for boat tours that showcase the area's maritime history.
- Conch Tour Train: Take a guided ride through the region’s historic streets and neighborhoods to discover the rich stories and architecture that define this destination.
Other Places to Stay in Downtown, FL
Downtown Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining: Immerse yourself in the area's vibrant culinary scene by trying out popular local eateries and fresh seafood spots near your vacation rental.
- Visit Historic Sites: Take time to discover the region’s rich history by visiting well-known landmarks and museums that capture the essence of this destination.
- Enjoy Waterfront Activities: Make the most of the nearby waters by engaging in activities like boating, fishing, or simply relaxing along scenic waterfronts.
- Experience Nightlife and Events: Dive into the lively atmosphere here by attending evening events or exploring bars and live music venues in the heart of downtown.
Transportation Options
- Walking: Exploring the area on foot allows you to comfortably access many local attractions, shops, and restaurants from your vacation rental in Downtown, Key West.
- Bicycle Rentals: You can rent a bike to enjoy an eco-friendly and flexible way to discover the vibrant streets and scenic waterfronts of this destination.
- Scooter or Moped Rentals: Opt for a scooter or moped to easily navigate through busy streets and reach popular spots around the region with minimal effort.
- Taxi and Rideshare Services: Conveniently get around in the area using reliable taxi or rideshare options that connect you directly to your preferred destinations within downtown Key West.
Local Customs Options
- Conch Shell Blowing: Engaging in the local tradition of blowing conch shells is a respected custom here, often heard during celebrations and special events, adding to the island’s vibrant atmosphere.
- Reef Preservation Etiquette: Respect for marine life is vital when visiting this destination, with locals practicing sustainable snorkeling and diving habits to preserve the region's stunning coral reefs.
- Celebration of Pirates' Heritage: Participating in or observing pirate-themed festivities reflects the area's historical roots and lively culture that you can experience during your stay.
- Supporting Local Artisans: Buying handcrafted goods from market stalls exemplifies the community’s appreciation for its artistic traditions and offers authentic souvenirs to remember your visit.
Frequently Asked Questions About Downtown?
1. What are the top vacation rentals in Downtown?
There are a lot of options in Downtown. If you plan on staying in the Downtown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Downtown:
- Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
- Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach
- Perfect Location, nPrivate Heated Pool,nPristine Luxury Home!
- Casa Caribe Beautiful tropical 2 bedroom sleeps 6
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- Key West Beachfront Luxury 2/2 Condo A212
- Your Condo by the Beach with Ocean View
2. How many vacation rentals have private pools in Downtown?
There are 179 vacation rentals with private pools near Downtown. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Downtown are best for families?
If you are looking for a family-friendly vacation home in Downtown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Downtown:
4. How many Rentbyowner vacation rentals are available in Downtown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1500 in the Downtown 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 Downtown.
5. What is the cancellation policy for vacation rentals in Downtown, Key West?
6. Are there any specific check-in and check-out times I should know about for rentals in this area?
7. How do I find the most suitable vacation rental in the region for my needs?
8. Is there a secure method to pay for my booking in this destination?
9. What should I do if I encounter an issue during my stay at a vacation rental here?
Downtown Top Rated Vacation Rentals
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
10.0- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
10.0- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
