Best Vacation Homes in Key West
10.0
Private Pool
Oceanfront
Pool
Ocean View
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View
Breakfast
Parking
Internet
10.0- Ocean View
Balcony/Terrace- View
Pet Friendly
- Private Pool
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10.0- Internet
Child Friendly
Laundry
Security/Safety
- Private Pool
- Oceanfront
- Pool
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Fireplace/Heating
Air Conditioner- Internet
- Child Friendly
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
Key West Luxury Rentals
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Key West Pet Friendly Vacation Rentals
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
10.0- Fireplace/Heating
- Pool
- View
- Pet Friendly
10.0- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
- Private Pool
- Pool
- Pet Friendly
- Kitchen
10.0- Pet Friendly
- Parking
- Internet
- Child Friendly
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
Key West Large Vacation Homes
- Private Pool
- Oceanfront
Hot Tub- Fireplace/Heating
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
- Pet Friendly
10.0- Hot Tub
- Pool
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- Kitchen
10.0- Hot Tub
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- Balcony/Terrace
- Kitchen
10.0- Hot Tub
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- Breakfast
Why Choose Rent By Owner for your Key West Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Key West Vacation Rentals
Where are the best neighborhoods to stay in Key West?
Discover the best neighborhoods to stay in Key West, Florida, for an unforgettable getaway. Each area offers its own unique charm, whether you're seeking vibrant nightlife, historic streets, or tranquil beaches. Choosing the right neighborhood allows you to immerse yourself in the local culture and enjoy easy access to top attractions. Whether you prefer the lively atmosphere of Old Town or the relaxed vibe of the surrounding residential areas, you'll find the perfect spot to relax and explore while enjoying reliable vacation rentals that make your stay seamless and enjoyable.
Key West Historic District
Staying in this area places you at the heart of the region's rich history and vibrant culture, offering a truly immersive experience. The district’s charming streets and historic landmarks make it an ideal choice for exploring the authentic essence of the destination.
View 2249+ Rentals in Key West Historic DistrictOld Town
This neighborhood provides a perfect blend of quaint charm and lively atmosphere, making it a popular spot for those wanting to enjoy the area's coastal beauty and local character. Here, you'll find easy access to popular attractions, restaurants, and waterfront views that capture the spirit of the region.
View 2189+ Rentals in Old TownSunset Key
Residing on this tranquil island offers a peaceful retreat surrounded by stunning sunsets and lush landscapes, ideal for relaxation and romantic getaways. It’s the perfect location for experiencing serene beachside living just minutes from the bustling city scene.
View 3712+ Rentals in Sunset KeyDowntown
Staying downtown places you at the center of the action, with easy access to vibrant nightlife, shops, and dining options. This area captures the lively essence of the city, making it a convenient base for exploring all the region has to offer.
View 921+ Rentals in DowntownUptown - Upper Duval
This neighborhood offers a quieter, more relaxed atmosphere while still being close to the energetic Duval Street scene, perfect for travelers seeking a balance of tranquility and entertainment. It’s a great spot to enjoy local culture away from the busiest tourist areas.
View 711+ Rentals in Uptown - Upper DuvalBahama Village
Known for its colorful streets and Caribbean-inspired vibe, this neighborhood is perfect for those wanting to experience a unique cultural enclave within the region. Its lively community atmosphere adds a distinctive flavor to your stay in this destination.
View 77+ Rentals in Bahama VillageHistoric Seaport
Positioned along the waterfront, staying here allows you to enjoy scenic views of the harbor and easy access to boating activities, making it ideal for maritime enthusiasts. The seaport area seamlessly blends nautical charm with convenient amenities.
View 366+ Rentals in Historic SeaportNew Town
This area offers a more suburban feel with local shops and eateries, appealing to visitors looking for a comfortable and accessible base outside the busy tourist districts. It provides a practical option for exploring the broader region comfortably.
View 98+ Rentals in New TownBest Times to Visit Key West
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider planning your trip during the shoulder seasons or early in the year when the weather is pleasant and the area offers a more relaxed atmosphere for exploring your ideal vacation rentals here.
Peak Season Highlights
February to April
During these months, the area experiences its peak tourist season, attracting visitors with warm weather and vibrant local events. This is a perfect time to book your vacation rentals for sunny days and lively nightlife.
December to January
The holiday season draws many travelers seeking mild winter temperatures and festive celebrations. Vacation rentals tend to fill up quickly during this period, so early booking is recommended for an ideal stay.
Off-Season Highlights
May to August
This summer period offers fewer crowds and more affordable rates on vacation rentals while still enjoying warm weather. It’s a great time for those looking to explore the region at a more relaxed pace.
September to November
Fall presents a quieter time in this destination, with pleasant temperatures and less competition for securing vacation rentals. It's an excellent choice for tranquil getaways and exploring without the peak-season rush.
Weekly Weather Forecast for Key West
How to Book Your Key West Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Key West
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 pool to relax and unwind in the warm Florida sun.
- Take advantage of spacious patios or decks perfect for outdoor dining and entertaining.
- Make use of a fully equipped outdoor grilling area for cookouts with friends and family.
- Relax in lush, landscaped gardens that offer a tranquil retreat right outside your door.
- Utilize outdoor shower facilities for easy rinsing after days at the nearby beaches.
- Stay active with access to tennis courts or other sports amenities on the property.
- Bask in the sun on a comfortable lounge area overlooking scenic views unique to this destination.
Top Attractions Around Key West
What attractions are nearby?
Here, you can explore a variety of nearby activities such as vibrant local art galleries, scenic boat tours, and lively waterfront dining experiences that capture the essence of this destination for an unforgettable stay.
Family Activities
- Visit the Key West Butterfly and Nature Conservatory: Experience a magical walk through lush gardens and vibrant butterfly exhibits, perfect for family exploration in this tropical paradise.
- Explore Fort Zachary Taylor State Park: Enjoy a day of swimming, picnicking, and beachcombing at this historic park, offering stunning shoreline views and gentle waves ideal for children.
- Discover the Mel Fisher Maritime Museum: Dive into the region’s rich maritime history with engaging exhibits about shipwrecks and treasure hunting that captivate all ages.
- Take a Conch Republic Marine Sea Tour: Embark on an educational boat tour to see local wildlife, colorful reefs, and learn about the area's marine environment firsthand.
Adult Activities
- Sunset Sail Cruises: Experience unforgettable sunsets aboard a sailing cruise that offers breathtaking views of the horizon over this tropical paradise.
- Old Town Trolley Tour: Discover the area's rich history and vibrant culture on a guided trolley tour that takes you through its most iconic landmarks.
- Key West Lighthouse and Keeper's Quarters: Visit this historic lighthouse to learn about maritime history while enjoying panoramic views of the surrounding region.
- Snorkeling at Fort Zachary Taylor Beach: Explore the clear waters and vibrant marine life just off the coast in a prime snorkeling spot nearby.
Other Places to Stay in Key West, FL
Key West Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Savor the region’s fresh seafood and charming eateries to truly experience the culinary culture of this tropical destination.
- Discover Waterfront Activities: Take advantage of the area’s beautiful coastlines by engaging in water sports, boating, or simply relaxing by the harbor.
- Visit Unique Landmarks: Make time to explore the historic sights and iconic landmarks that showcase the area's rich maritime heritage.
- Plan Your Outings Around the Weather: Check the local forecast to make the most of sunny days and outdoor adventures in this vibrant destination.
Transportation Options
- Rental Bikes: You can easily explore the scenic streets of this island destination by renting a bike, enjoying the relaxing breeze and picturesque views at your own pace.
- Golf Carts: Golf cart rentals provide a fun and convenient way to traverse this charming region while taking in its vibrant atmosphere and local sights.
- Public Transportation: The area offers reliable bus services that connect popular spots, making it simple for you to get around without the hassle of driving or parking.
- Taxi and Rideshare Services: Taxis and rideshare options are readily available here, offering quick and comfortable transportation around the region whenever you need it.
Local Customs Options
- Conch Republic Independence Day: Celebrated annually on April 23rd, this region's playful declaration of independence reflects its unique local spirit.
- Duval Street Etiquette: Visitors are encouraged to embrace the relaxed and friendly vibe by greeting locals with a smile and respecting the lively atmosphere of this iconic street.
- Sunset Celebrations at Mallory Square: As the sun sets over the waters here, it’s customary to gather and enjoy the vibrant performances and art displays that mark this daily event.
- Marine Preservation Respect: Since the area is renowned for its marine life, you’ll find that protecting the local environment and avoiding disturbance to wildlife are highly valued customs.
Frequently Asked Questions About Key West?
1. What are the top vacation rentals in Key West?
There are a lot of options in Key West. If you plan on staying in the Key West area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Key West:
- Almond Tree Inn Hotel - Adults Only
- 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
- 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!
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- 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
- Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
2. How many vacation rentals have private pools in Key West?
There are 877 vacation rentals with private pools near Key West. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Key West are best for families?
If you are looking for a family-friendly vacation home in Key West, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Key West:
4. How many Rentbyowner vacation rentals are available in Key West?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 5025 in the Key West 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 Key West.
5. What is the cancellation policy for vacation rentals in Key West, Florida?
6. Are there specific amenities I should expect when booking a rental here?
7. How do I ensure my booking is secure and reliable?
8. What should I know about check-in and check-out procedures?
9. Can I get assistance if I encounter issues during my stay?
Key West Top Rated Vacation Rentals
10.0- Hot Tub
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10.0- Oceanfront
- Fireplace/Heating
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10.0- Oceanfront
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- Pool
- Ocean View
10.0- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
