Discover Your Perfect Simonton Beach Vacation Homes

Best Vacation Homes in Simonton Beach

|
10.0 (4 Reviews)
House
Mar Y Sol Ocean Front
  • Parking
  • Accessibility
  • Security/Safety
View Availability
|
10.0 (3 Reviews)
House
Somewhere on the beach
  • Pool
  • Accessibility
  • Security/Safety
View Availability
|
10.0 (3 Reviews)
Apartment
The Perch on Duval
  • Security/Safety
  • Child Friendly
  • Internet
View Availability

Why Choose Rent By Owner for your Simonton Beach Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Simonton Beach Vacation Rentals

Where are the best neighborhoods to stay in Simonton Beach?

When choosing a neighborhood to stay in Simonton Beach, Key West, Florida, you'll find this area offers a serene and picturesque setting perfect for relaxing getaways. Known for its tranquil atmosphere, it provides easy access to beautiful waterfront views and local attractions. Whether you're seeking a peaceful retreat or an immersive experience in the vibrant Keys lifestyle, staying nearby will give you convenient access to the charms of Key West while enjoying the comforts of a well-situated neighborhood. Finding the right spot in Simonton Beach ensures a memorable and enjoyable vacation tailored to your needs.

Key West Historic District

Within the historic district, you’ll find charming streets and cultural sites that showcase this destination’s rich heritage, making it a perfect area to experience authentic local charm. Staying here puts you close to key attractions and vibrant neighborhoods, enriching your overall visit.

View 2510+ Rentals in Key West Historic District

Old Town

This area offers picturesque streets and lively community vibes, ideal for those seeking an authentic flavor of the region. It’s the perfect place to immerse yourself in the local culture while enjoying convenient access to popular sights.

View 2445+ Rentals in Old Town

Sunset Key

For a tranquil escape, Sunset Key provides peaceful surroundings with stunning waterfront views, allowing you to unwind just moments from the bustling area. It’s an excellent choice for a serene retreat close to the highlights around here.

View 3214+ Rentals in Sunset Key

Downtown

The downtown neighborhood is the hub of activity, offering vibrant nightlife, dining, and shopping options that capture the energetic spirit of the region. Staying nearby lets you effortlessly explore all the local amenities and entertainment.

View 1085+ Rentals in Downtown

Uptown - Upper Duval

This uptown area features a more relaxed atmosphere with unique shops and eateries, making it ideal for leisurely exploration. Its proximity to central attractions makes it a convenient base for your stay.

View 755+ Rentals in Uptown - Upper Duval

Bahama Village

Known for its lively arts scene and Caribbean-inspired vibe, Bahama Village is perfect for travelers wanting an eclectic neighborhood experience. It offers easy access to local culture and the region’s vibrant community events.

View 95+ Rentals in Bahama Village

Historic Seaport

This scenic waterfront area provides picturesque views and maritime history, ideal for those interested in exploring the region’s nautical roots. Staying here places you right by water-based activities and maritime landmarks.

View 412+ Rentals in Historic Seaport

New Town

Offering a mix of residential comfort and accessibility, New Town is suitable for travelers looking for a quieter neighborhood while remaining within reach of the main attractions. It’s a practical choice for a relaxed yet central stay.

View 115+ Rentals in New Town

Best Times to Visit Simonton Beach

When should you plan your Vacation Rentals stay?

Timing your visit is essential to making the most of your stay in this destination, as choosing the right time to vacation here can enhance your experience and help you enjoy the region’s best weather and events.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, this destination experiences its peak season as travelers seek warm escapes in the region's inviting climate, making it an ideal time to book vacation rentals here.

Average Temperature Daytime: 75°F - Nighttime: 65°F
spring
Spring (March to May)

Spring marks another busy period when visitors flock to enjoy pleasant weather and vibrant atmospheres. Booking your stay during this season ensures you'll experience the area's lively charm at its best.

Average Temperature Daytime: 80°F - Nighttime: 70°F

Off-Season Highlights

image
Summer (June to August)

Summer is considered the off-peak season due to the hotter temperatures and increased humidity, providing a quieter setting for those looking to relax away from larger crowds in the area.

Average Temperature Daytime: 88°F - Nighttime: 78°F
image
Fall (September to November)

Early fall tends to see fewer visitors as temperatures cool down, offering a peaceful atmosphere for booking vacation rentals and enjoying the serene surroundings of this destination.

Average Temperature Daytime: 82°F - Nighttime: 72°F

Weekly Weather Forecast for Simonton Beach

How to Book Your Simonton Beach Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Simonton Beach

More Top-Rated Vacation Rentals in Simonton Beach Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 private outdoor seating areas perfect for relaxing and soaking up the sun in this seaside destination.
  • Benefit from access to communal or private pools that overlook the stunning waters of the region.
  • Take advantage of on-site grilling stations to prepare delicious meals while enjoying the fresh air.
  • Experience the convenience of shaded verandas or patios to unwind after a day of exploring.
  • Make use of outdoor showers, ideal for rinsing off after beach activities along the shoreline.
  • Stroll through lush landscaped gardens surrounding your stay, adding to the tropical ambiance.
  • Utilize dedicated boat docks or fishing areas if available for enhanced leisure on the water.

Top Attractions Around Simonton Beach

What attractions are nearby?

Nearby here, you can enjoy a variety of activities such as relaxing on the beautiful sands, exploring local shops and restaurants, or taking a scenic boat tour to experience the vibrant marine life of this destination.

image
image

Family Activities

  • Snorkeling at the Key West Marine Park: Dive into the clear waters just off the shoreline to explore vibrant marine life and coral reefs, making it a perfect family activity in this coastal area.
  • Relaxing on Simonton Beach: Spend quality time building sandcastles or soaking up the sunshine on the soft sands of this popular beach destination for families visiting here.
  • Kayaking Adventures: Rent kayaks and paddle along calm waters, allowing your family to enjoy scenic views and discover hidden spots around the region.
  • Wildlife Watching at Fort Zachary Taylor Historic State Park: Explore the natural surroundings and observe local bird species and other wildlife in the park's scenic setting near this destination.
image

Adult Activities

  • Sailing and Boating: You can explore the surrounding waters of this region by renting a boat or taking a guided sailing tour, offering a relaxing way to enjoy the scenic coastline.
  • Snorkeling and Swimming: Spend your days discovering vibrant marine life just off the shore, where calm waters provide perfect conditions for snorkeling and swimming.
  • Sunset Cruises: Experience breathtaking sunsets on a romantic cruise, giving you a memorable perspective of the area's beautiful coastline and tranquil atmosphere.
  • Beachside Relaxation and Water Sports: Unwind on the sandy shores while engaging in water sports like paddleboarding or kayaking, making the most of your time here.

Simonton Beach Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the local beaches: Take advantage of the pristine sands and clear waters by spending your days relaxing or engaging in water activities right near your rental.
  • Enjoy sunset views: Make sure to visit the shoreline during sunset hours for breathtaking views that capture the essence of this scenic destination.
  • Sample regional cuisine: Indulge in fresh seafood and local flavors at nearby eateries to immerse yourself in the area’s culinary traditions.
  • Plan outdoor excursions: Utilize the region’s natural beauty by exploring nearby parks and trails, perfect for outdoor adventures close to your accommodations.

Transportation Options

  • Rental Car Services: You can easily explore the area and its surroundings with convenient rental car options available nearby, providing flexibility to visit popular attractions at your own pace.
  • Public Transit: Local bus services connect key parts of the region, offering an affordable and environmentally friendly way to get around during your stay here.
  • Taxi and Ride-Sharing: Taxi services and ride-share apps like Uber and Lyft provide quick and reliable transportation when you prefer door-to-door convenience.
  • Biking and Walking: The area's scenic streets and dedicated bike paths make biking or walking a charming and sustainable way to enjoy this coastal destination.

Local Customs Options

  • Respect for Local Art and History: You should always appreciate the area's vibrant art scene and historical landmarks, reflecting the deep cultural roots of this destination.
  • Celebration of Seafood Cuisine: Embrace the region's maritime heritage by trying local seafood dishes, which are a staple in the area's culinary traditions.
  • Involvement in Water Activities: Participating in or observing water-based customs, such as boating or fishing, is common here and enhances your connection with the coastal community.
  • Respect for Quiet Hours: Being mindful of designated quiet times helps maintain the peaceful atmosphere that residents and visitors alike enjoy in this relaxing seaside locale.

Frequently Asked Questions About Simonton Beach?

1. What are the top vacation rentals in Simonton Beach?

There are a lot of options in Simonton Beach. If you plan on staying in the Simonton 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 Simonton Beach:

2. How many Rentbyowner vacation rentals are available in Simonton Beach?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 4051 in the Simonton 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 Simonton Beach. 

3. What is the cancellation policy for bookings in this area’s vacation rentals?

Cancellation policies vary by listing, so it’s important to review the specific terms on the property’s page. Many rentals offer flexible options, but some may have stricter rules. For detailed information, contact the owner directly before completing your reservation.

4. How do I know if a vacation rental in this destination is available for my travel dates?

Availability calendars are typically displayed on each rental listing. You can check the specific dates you plan to visit and reach out to the host if any questions arise. Booking early ensures the best chance of securing your preferred stay.

5. What amenities should I expect in a rental here to make my stay comfortable?

Most properties in the region come equipped with essential amenities such as Wi-Fi, fully equipped kitchens, air conditioning, and outdoor spaces. For a comprehensive list of what’s included, review the property details or contact the owner directly.

6. Are there any specific check-in or check-out procedures I should be aware of when booking here?

Check-in and check-out times vary by property. Details about key pickup, access instructions, and departure guidelines are provided in the listing description. Contact the owner in advance if you need special arrangements or have specific questions.

7. How can I ensure my safety and security when booking a vacation rental in this popular area?

Choose listings with verified guest reviews and clear, detailed descriptions. Communicate through the platform’s messaging system and avoid sharing sensitive details outside of official channels. The property owner can also provide safety information relevant to their rental.

Best Vacation Homes in Simonton Beach

10.0 (3 Reviews)
House
Yellowfin Ledge
  • Pet Friendly
  • Security/Safety
  • Child Friendly
View Availability