Discover Your Ideal South Beach, Key West Florida Vacation Rentals for an Unforgettable Getaway
Discover Your Perfect South Beach Vacation Homes
Best Vacation Homes in South Beach
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Why Choose Rent By Owner for your South Beach Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for South Beach Vacation Rentals
Where are the best neighborhoods to stay in South Beach?
When planning your stay in South Beach, Florida, selecting the right neighborhood can enhance your entire vacation experience. Each area offers its own unique ambiance, from lively beachfront communities to charming historic districts, ensuring you find the perfect spot that matches your preferences. Whether you desire vibrant nightlife, pristine beaches, or quiet streets lined with local eateries, South Beach provides a variety of neighborhoods ideal for relaxing and exploring. With reliable and seamless booking options for vacation rentals, you can easily secure a comfortable and conveniently located property that suits your lifestyle. Discover the best neighborhoods to stay in South Beach and make your Florida getaway truly unforgettable.
Key West Historic District
Staying in the Key West Historic District places you at the heart of the region's rich history and vibrant culture, offering easy access to charming architecture and local landmarks. It's an ideal spot for travelers seeking an immersive experience in this destination’s storied past.
View 2741+ Rentals in Key West Historic DistrictOld Town
Choosing accommodations in Old Town means you'll be in the center of the area's lively atmosphere, with colorful streets and unique boutiques just steps away. It's perfect for exploring the region’s iconic sights while enjoying a cozy, authentic vibe.
View 2678+ Rentals in Old TownSunset Key
Staying on Sunset Key offers a tranquil retreat with stunning waterfront views, providing a peaceful escape within the region’s scenic surroundings. It’s an excellent choice for those looking to unwind while being close to the area's natural beauty.
View 3214+ Rentals in Sunset KeyDowntown
In downtown, you'll find yourself amid the bustling heart of the city, with easy access to dining, nightlife, and entertainment options that showcase the region’s lively spirit. It's an ideal location for experiencing the energetic side of this destination.
View 1174+ Rentals in DowntownUptown - Upper Duval
Uptown's Upper Duval neighborhood provides a more relaxed atmosphere with quaint streets and local eateries, perfect for visitors seeking a quieter yet engaging stay here. It offers a genuine taste of the area’s laid-back charm.
View 833+ Rentals in Uptown - Upper DuvalBahama Village
Residing in Bahama Village grants you access to an eclectic neighborhood filled with Caribbean influences, lively markets, and friendly local culture. It’s a fantastic spot for immersing yourself in the region’s diverse heritage.
View 103+ Rentals in Bahama VillageHistoric Seaport
Booking accommodations near the Historic Seaport places you in a picturesque setting with boat tours and waterfront dining, making it ideal for enjoying the area's maritime traditions and coastal scenery.
View 434+ Rentals in Historic SeaportNew Town
Opting for New Town provides a convenient base with easy access to shopping centers and local attractions, suitable for travelers seeking a practical yet comfortable stay within the region.
View 119+ Rentals in New TownBest Times to Visit South Beach
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you enjoy the vibrant local atmosphere and beautiful weather, making your experience in this popular destination truly unforgettable.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences its peak season with visitors seeking warm weather and sunny skies, making it ideal for enjoying outdoor activities and vibrant city life.
Spring (March to May)
Spring marks another busy period as travelers flock here to enjoy comfortable temperatures and lively events, ensuring lively beaches and bustling neighborhoods during your stay.
Off-Season Highlights
Summer (June to August)
Summer can be quieter here due to higher temperatures and humidity, providing a more relaxed atmosphere for those looking to escape crowds and enjoy lower rates on vacation rentals.
Fall (September to November)
Early fall offers a shoulder season with fewer tourists, where you can experience pleasant weather and more affordable accommodation options amidst the region's natural beauty.
Weekly Weather Forecast for South Beach
How to Book Your South Beach Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in South Beach
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
- Private outdoor swimming pools to enjoy a refreshing dip under the sun
- Spacious decks or patios perfect for relaxing or entertaining guests
- Outdoor grilling stations to prepare delicious meals with local flavors
- Lush landscaped gardens and tropical landscaping for a serene atmosphere
- Seating areas with lounge chairs and umbrellas for sunbathing and unwinding
- Outdoor dining spaces to savor meals while taking in the scenic surroundings
- Direct access to a private or community beach area, ideal for seaside activities
Top Attractions Around South Beach
What attractions are nearby?
In this vibrant destination, you can enjoy a variety of activities nearby, from relaxing on stunning beaches to exploring lively waterfront areas, ensuring your stay in South Beach offers both adventure and tranquility.
Family Activities
- South Beach Family Fun Park: Enjoy a day of entertainment and outdoor activities at this popular park, perfect for family outings in the area.
- Conch Tour Train: Embark on an informative train tour that takes your family through the highlights and history of this vibrant destination.
- Fort Zachary Taylor Historic State Park: Explore the historic fort and relax on the scenic beaches, ideal for picnics and swimming with the whole family.
- Key West Aquarium: Discover local marine life through interactive exhibits and hands-on experiences at the region’s oldest aquarium.
Adult Activities
- Explore the vibrant nightlife and live music venues: Enjoy lively evenings filled with great entertainment at popular spots within walking distance of your vacation rental.
- Relax on iconic beaches and take part in water sports: Spend your days soaking up the sun or trying out paddleboarding and snorkeling along the scenic shoreline.
- Visit upscale restaurants and local eateries: Indulge in fresh seafood and regional cuisine at renowned dining establishments near your accommodation.
- Experience art galleries and cultural events: Discover contemporary and historic artworks, as well as unique festivals hosted in this lively destination.
South Beach Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Early: Take advantage of the area’s vibrant scene by booking popular attractions and waterfront experiences in advance to ensure a smooth and enjoyable stay.
- Explore Local Cuisine: Savor the region’s unique culinary offerings by dining at local restaurants or preparing fresh seafood in your vacation rental’s kitchen, immersing yourself in the area's flavors.
- Discover Hidden Gems: Wander beyond the main tourist spots to find lesser-known beaches, quaint neighborhoods, and scenic viewpoints that showcase the authentic character of this destination.
- Utilize the Public Transport System: Make the most of available transit options to easily access key areas, reducing travel costs and giving you more time to enjoy your stay in the region.
Transportation Options
- Public Buses: You can rely on the local bus system to easily navigate through the area, offering an affordable and convenient transportation option for exploring South Beach and neighboring destinations.
- Rental Scooters and Bikes: Embrace the scenic surroundings by renting scooters or bikes, allowing you to enjoy the region's vibrant atmosphere at your own pace while reducing your carbon footprint.
- Ride-Sharing Services: Popular ride-sharing apps provide a quick and flexible way to travel around here, especially when you’re looking to get to specific attractions or accommodations efficiently.
- Car Rentals: Renting a car offers the freedom to explore beyond the immediate vicinity, making it ideal for day trips and discovering more of what this destination has to offer at your convenience.
Local Customs Options
- Respect for Local Art and Music: Engaging with the vibrant arts scene and live performances shows appreciation for this destination’s cultural heritage.
- Embracing the Casual Dress Code: Dressing casually, especially in beachwear and summer attire, aligns with the relaxed atmosphere prevalent here.
- Celebrating Variations of Seafood Cuisine: Participating in local seafood dining customs enhances your experience of the region’s culinary traditions.
- Participating in Holiday Festivities: Observing traditional celebrations and public festivals reflects an understanding of this area's community spirit and history.
Frequently Asked Questions About South Beach?
1. What are the top vacation rentals in South Beach?
There are a lot of options in South Beach. If you plan on staying in the South Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in South Beach:
- 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!
- PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- ~ 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
- 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 South Beach?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 4035 in the South Beach 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 South Beach.
3. What is the cancellation policy for booking a vacation rental in this popular Florida destination?
4. How do I find the best vacation rentals in the area that suit my needs?
5. Are there any additional fees I should be aware of when booking a vacation rental in this region?
6. What is the process for checking in and out of a vacation rental in this destination?
7. Can I modify or cancel my reservation if my plans change while staying in the area?
Best Vacation Homes in South Beach
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