Key West Resorts
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- Child Friendly
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Why Choose Rent By Owner for your Key West Resorts?
What makes our Resorts special?
Popular Areas for Key West Resorts
Where are the best neighborhoods to stay in Key West?
When visiting Key West, Florida, choosing accommodations in the Old Town neighborhood places you at the heart of the vibrant local culture and historic charm, making it ideal for exploring the city's unique atmosphere. For a more relaxed vibe, the New Town area offers convenient access to beaches and waterfront activities, perfect for those seeking tranquility without sacrificing convenience. Both neighborhoods provide a range of trustworthy resorts that ensure a seamless and enjoyable stay during your trip to this iconic destination.
Key West Historic District
This vibrant area offers a rich blend of history and culture, making it an ideal choice for travelers seeking to immerse themselves in the region’s unique heritage while enjoying convenient access to local attractions.
View 2409+ Rentals in Key West Historic DistrictOld Town
Known for its charming streets and lively atmosphere, Old Town provides a perfect setting for visitors wanting to explore the area's quaint neighborhoods and iconic landmarks with ease.
View 2371+ Rentals in Old TownSunset Key
This exclusive island retreat offers tranquility and spectacular views, ideal for those looking to unwind in a serene environment just minutes from the bustling city center.
View 3595+ Rentals in Sunset KeyDowntown
Downtown is the heart of activity, where you can experience vibrant nightlife, diverse dining options, and easy access to local shops all within a lively urban setting.
View 992+ Rentals in DowntownUptown - Upper Duval
Here, you’ll find a more relaxed vibe with boutique shops and cozy cafes, perfect for those seeking a quieter place to stay while remaining close to the region’s main attractions.
View 761+ Rentals in Uptown - Upper DuvalBahama Village
This culturally rich neighborhood offers vibrant arts, music, and authentic cuisine, making it an excellent choice for travelers interested in experiencing local traditions and lively community events.
View 92+ Rentals in Bahama VillageHistoric Seaport
Set along the waterfront, this area features scenic views and maritime charm, providing a picturesque backdrop for exploring the region’s nautical history and enjoying waterfront activities.
View 387+ Rentals in Historic SeaportNew Town
Offering a modern residential feel, New Town is ideal for visitors seeking convenient access to shopping centers, grocery stores, and practical amenities during their stay here.
View 107+ Rentals in New TownBest Times to Visit Key West
When should you plan your Resorts stay?
To make the most of your stay in this tropical haven, consider visiting during the shoulder seasons when the weather is pleasant and the crowds are smaller, allowing you to enjoy the area’s natural beauty and vibrant culture at a more relaxed pace.
Peak Season Highlights
March to May
This is the most popular time to visit when the weather is warm and sunny, perfect for enjoying the beach and outdoor activities.
December to April
During these months, the region experiences its peak tourist influx with pleasant temperatures and lively events.
Off-Season Highlights
June to August
You’ll find fewer crowds here, though the summer brings hotter weather and occasional rain showers.
September to November
The shoulder season offers a quieter atmosphere with slightly cooler temperatures and less humidity.
Weekly Weather Forecast for Key West
How to Book Your Key West Resorts
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Key West
Common Resorts 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 access to outdoor swimming pools, perfect for relaxing after a day exploring the area.
- Take advantage of private or shared patios and courtyards to unwind in the sunshine.
- Benefit from well-maintained BBQ grills and outdoor dining areas for al fresco meals.
- Experience lush landscaped gardens that add to the tranquility of your stay.
- Make use of outdoor lounge areas equipped with comfortable seating for socializing or reading.
- Utilize dedicated outdoor parking spaces, ensuring convenience during your visit.
- Explore nearby walking tracks or cycling routes that showcase the region’s natural beauty.
Top Attractions Around Key West
What attractions are nearby?
Here, you can enjoy a variety of activities ranging from relaxing on scenic beaches to exploring vibrant local art scenes and water sports that highlight the region's tropical charm, making it an ideal destination for a memorable getaway.
Family Activities
- Snorkeling Excursions: Discover the vibrant marine life just off the coast with family-friendly snorkeling trips around Key West, perfect for exploring the crystal-clear waters and colorful coral reefs.
- Fort Zachary Taylor Historic State Park: Spend a day at this historic park enjoying beach picnics, swimming, and exploring Civil War-era fortifications in a scenic setting ideal for families.
- The Key West Butterfly & Nature Conservatory: Introduce your family to a tropical paradise filled with hundreds of butterflies and exotic birds within a lush, climate-controlled environment.
- Shipwreck Treasure Museum: Engage your family with interactive exhibits that bring to life the region’s maritime history and legendary shipwrecks, offering both education and entertainment in one location.
Adult Activities
- Sailing and Sunset Cruises: Experience the stunning views of the sunset over the horizon while aboard a sailing cruise, offering a relaxing way to enjoy the natural beauty of the area.
- Historic Old Town Exploration: Discover the rich history and vibrant architecture of this destination by strolling through its charming streets and learning about its past.
- Water Sports Adventure: Engage in exhilarating water activities such as snorkeling, paddleboarding, or jet skiing, making the most of the region's clear, warm waters.
- Culinary Tours and Dining Experiences: Savor fresh seafood and local delicacies during guided culinary tours that showcase the area’s vibrant food scene.
Other Places to Stay in Key West, FL
Key West Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: Schedule visits to popular spots early in the day to avoid crowds and make the most of your time here.
- Explore Local Cuisine: Indulge in authentic regional dishes at nearby eateries to fully experience the area’s culinary scene.
- Utilize Water-Based Activities: Take advantage of water adventures such as snorkeling, boating, or paddleboarding for an immersive experience in this destination’s coastal environment.
- Choose Strategic Accommodation: Book a property close to key attractions or beaches to maximize convenience and relaxation during your stay.
Transportation Options
- Rental Cars: Renting a car provides the flexibility to explore the area at your own pace and visit nearby attractions in your own time.
- The Key West Trolley: This hop-on-hop-off trolley offers a convenient and scenic way to see popular sights throughout this island destination.
- Public Transportation: The local bus service is an affordable option for traveling around here, connecting you easily to key points of interest.
- Taxis & Rideshare Services: Taxis and rideshare options like Uber or Lyft provide quick, reliable transportation for getting around the region comfortably.
Local Customs Options
- Conch Republic Celebrations: Participating in local festivities such as the annual Conch Republic Independence Celebration helps you embrace this area's unique sense of community and history.
- Respect for Marine Life: Adhering to guidelines for preserving the region’s vibrant coral reefs and marine ecosystems demonstrates your commitment to protecting this destination’s natural beauty.
- Casual Island Attire: Wearing relaxed, tropical clothing is customary here and reflects the easygoing lifestyle that visitors often seek when staying at resorts in this area.
- Supporting Local Art and Music: Engaging with the region’s artistic expressions and live performances fosters a deeper connection to its vibrant cultural scene while respecting local traditions.
Frequently Asked Questions About Key West Resorts
1. What are the top Resorts 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 Resorts in Key West:
- Ocean Key Resort - A Noble House Resort
- Pier House Resort & Spa
- Hyatt Centric Key West Resort and Spa
- Coconut Beach Resort
- Coconut Beach Resort Timeshare
- The Perry Hotel & Marina Key West
- The Reach Key West, Curio Collection by Hilton
- Oceans Edge Key West
- Coconut Mallory Resort and Marina
- Ocean Key Resort & Spa, a Noble House Resort
2. How many Resorts are available in Key West?
Currently, the total number of properties listed by RBO in 2026 is over 240 in the Key West area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Key West.
3. What is the cancellation policy for resorts in this destination?
4. Are there any specific check-in and check-out times I should be aware of at these resorts?
5. Is it possible to get a customized stay or flexible booking options in this area?
6. What amenities can I expect when booking a resort here?
7. How do I ensure my reservation is secure and reliable when booking a resort in this region?
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