Key West Cottage Rentals
Balcony/Terrace
Kitchen
Air Conditioner
Internet
9.4
Oceanfront
Fireplace/Heating
Pool
Ocean View
10.0- Ocean View
- Balcony/Terrace
View
Pet Friendly
10.0
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
9.3- Fireplace/Heating
- Balcony/Terrace
Breakfast- Pet Friendly
10.0- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
9.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Balcony/Terrace
- Kitchen
Parking- Air Conditioner
9.0- Pet Friendly
- Internet
Child Friendly
Security/Safety
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
8.8- Pool
- View
- Pet Friendly
- Air Conditioner
10.0- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
Why Choose Rent By Owner for your Key West Cottage Rentals?
What makes our Cottage Rentals special?
Popular Areas for Key West Cottage Rentals
Where are the best neighborhoods to stay in Key West?
When selecting a neighborhood to stay in Key West, Florida, you can enjoy the vibrant atmosphere of Old Town, known for its historic charm and lively streets. For a more relaxed vibe, consider staying in the New Town area, which offers easy access to beaches and local markets. Whichever neighborhood you choose, you'll find that each provides a unique experience perfect for discovering the best of Key West.
Key West Historic District
In this area, you'll find cottages nestled within the charming streets that showcase the rich history and vibrant culture of Key West. Staying here offers easy access to the region’s storied architecture and lively local scene.
View 2249+ Rentals in Key West Historic DistrictOld Town
The neighborhood exudes a quaint and inviting atmosphere, perfect for those seeking cottages close to the historic heart of the region. Here, you can enjoy walking to local attractions and relaxing in a quintessential Florida setting.
View 2189+ Rentals in Old TownSunset Key
This secluded island paradise provides luxurious cottages with stunning views of the Gulf of Mexico, ideal for travelers looking for serenity and upscale accommodations in the region.
View 3712+ Rentals in Sunset KeyDowntown
Stay in the bustling core of the area where cottages are surrounded by lively entertainment, dining, and shopping options, giving you a vibrant and convenient base to explore the region.
View 921+ Rentals in DowntownUptown - Upper Duval
Uptown features a laid-back vibe with cozy cottages near eclectic shops and eateries, making it an excellent spot for relaxed evenings and authentic local experiences.
View 711+ Rentals in Uptown - Upper DuvalBahama Village
This culturally rich neighborhood offers colorful cottages amid vibrant streets, perfect for those wanting an immersive experience in the diverse traditions of the region.
View 77+ Rentals in Bahama VillageHistoric Seaport
Situated along the waterfront, this area provides cottages with scenic views and proximity to the region's maritime history and boat tours, ideal for explorers at heart.
View 366+ Rentals in Historic SeaportNew Town
Here, you’ll discover a modern yet charming setting with cottages offering convenience and comfort, close to key shopping centers and local amenities in the region.
View 98+ Rentals in New TownBest Times to Visit Key West
When should you plan your Cottage Rentals stay?
To make the most of your stay in this vibrant destination, consider planning your vacation during the shoulder seasons when the weather is pleasant and crowds are lighter, allowing you to fully enjoy the charm of the region while securing your ideal cottages through a reliable booking platform.
Peak Season Highlights
Winter (December to April)
During the winter months, you can enjoy warm temperatures and vibrant festivities. This is when the area draws the largest number of visitors seeking refuge from colder climates.
Summer (June to August)
The summer season offers hot and humid weather which appeals to travelers looking for sun and outdoor activities. Expect lively atmosphere and the highest occupancy rates.
Off-Season Highlights
Spring (April to June)
As the crowds lessen, spring provides a pleasant climate ideal for exploring and relaxing without the peak season crowds. The region experiences mild temperatures and lower rates.
Fall (September to November)
This period sees fewer visitors, offering a peaceful retreat. You'll benefit from comfortable weather and better deals on accommodations here.
Weekly Weather Forecast for Key West
How to Book Your Key West Cottage Rentals
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Key West
Common Cottage 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 deck perfect for relaxing and dining al fresco amidst the scenic surroundings.
- Take advantage of lush, tropical gardens that provide privacy and a tranquil atmosphere during your stay.
- Make use of a swimming pool or hot tub to unwind and cool off after a day exploring the area’s attractions.
- Benefit from outdoor grilling facilities to host memorable barbecues under the warm Florida sun.
- Utilize well-maintained walking paths or scenic courtyards that invite exploration and outdoor enjoyment.
- Relax in shaded lounging areas designed to offer comfort while soaking up the region’s sunshine.
- Access outdoor recreation options such as bicycle rentals or water sports gear for active adventures nearby.
Top Attractions Around Key West
What attractions are nearby?
During your stay, you can explore a variety of nearby activities such as vibrant local art galleries, scenic waterfront parks, and lively dining experiences, all easily accessible from this prime Key West location that offers a perfect blend of relaxation and adventure.
Family Activities
- Visit the Key West Aquarium: Engage your family with interactive exhibits and marine life shows at this well-known destination in the region.
- Explore Fort Zachary Taylor Historic State Park: Enjoy a day of swimming, picnicking, and exploring historic fortifications along the scenic shores here.
- Take a Conch Tour Train Ride: Discover local history and sights aboard this family-friendly train tour that showcases the area's unique culture and landmarks.
- Enjoy a Sunset Celebration at Mallory Square: Experience vibrant street performances, local artisans, and breathtaking sunsets perfect for family memories.
Adult Activities
- Sunset Sailing Tours: Experience the breathtaking sunsets over the Gulf of Mexico with a private sailing tour, offering an intimate way to enjoy the area's stunning natural beauty.
- Historic Old Town Exploration: Stroll through this area’s charming streets, discovering unique boutiques, lively cafes, and historic landmarks that reflect its rich cultural heritage.
- Snorkeling and Diving Adventures: Dive into vibrant coral reefs and marine ecosystems along the coast, ideal for exploring the region’s underwater wonders up close.
- Fine Dining Experiences: Indulge in local culinary delights at waterfront restaurants and cozy eateries, where you can savor fresh seafood and regional specialties.
Other Places to Stay in Key West, FL
Key West Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Take time to research local events and outdoor adventures to maximize your experience while staying at a charming cottage here.
- Explore Local Cuisine: Indulge in the region’s culinary delights by visiting popular eateries and trying fresh seafood, enhancing your overall vacation in this vibrant destination.
- Utilize Water Transportation: Make use of ferries or boat rentals to explore the surrounding waters and enjoy scenic views that are unique to this coastal area.
- Book Early for Best Cottages: Secure your preferred property well in advance, especially during peak seasons, to ensure a comfortable and enjoyable stay in this sought-after location.
Transportation Options
- Rental Bikes and Scooters: Exploring the area by bike or scooter offers an eco-friendly and flexible way to see all its scenic spots.
- Public Transit - The Key West Trolley: This hop-on-hop-off trolley provides a convenient way to navigate without worrying about parking or traffic.
- Taxi Services and Rideshares: Reliable taxis and rideshare options like Uber and Lyft are readily available for quick and comfortable transportation around this island destination.
- Car Rentals: Renting a car gives you the freedom to explore beyond the immediate vicinity of your cottage and visit more distant attractions here.
Local Customs Options
- Conch Shell Symbolism: You might notice the conch shell being used to symbolize local heritage and are encouraged to participate respectfully in this tradition, which is deeply rooted here.
- Duval Street Celebrations: Expect lively street festivals and events that embody the vibrant spirit of this destination’s community and its love for live music and art.
- Maritime Heritage Customs: Appreciating the area's rich maritime history includes observing traditional sailing practices and respecting the local nautical culture.
- Sunset Celebrations: Gathering to witness the famed sunset rituals is a cherished custom, offering a perfect opportunity to embrace the relaxed and festive atmosphere of this locale.
Frequently Asked Questions About Key West Rental Cottages
1. What are the top Cottages 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 Cottages in Key West:
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
- Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
- ~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
- Old Town Key West Cottage 3bed/2bath
- Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
- Key Lime Cottage
- Ann Street Gardens - Downtown Key West
- Ann Street Cottage: A bright and airy home near Duval Street
- Conch Cottage - Feels Like Home - 1BD/1Bath - Hot Tub
2. How many Cottages are available in Key West?
Currently, the total number of properties listed by RBO in 2026 is over 136 in the Key West area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Key West.
3. What is the cancellation policy for cottages in this destination?
4. Are there any additional fees or charges I should be aware of when booking a cottage here?
5. What amenities are typically included with cottages in this area?
6. How do I ensure my stay complies with local regulations and property rules?
7. Is parking available at cottages in this region, and are there any restrictions?
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