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  3. Key West
  4. Jackson Square
  5. Rentals by Owner

Discover Your Perfect Jackson Square Rentals by Owner

Jackson Square Rentals by Owner

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10.0 (4 Reviews)
House
Mar Y Sol Ocean Front
  • Parking
  • Accessibility
  • Security/Safety
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10.0 (3 Reviews)
House
Somewhere on the beach
  • Pool
  • Accessibility
  • Security/Safety
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10.0 (3 Reviews)
Apartment
The Perch on Duval
  • Security/Safety
  • Child Friendly
  • Internet
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10.0 (3 Reviews)
House
Yellowfin Ledge
  • Pet Friendly
  • Security/Safety
  • Child Friendly
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More Top-Rated Rentals by Owner in Jackson Square Area

Why Choose Rent By Owner for your Jackson Square vacation rental?

What makes our Rentals by Owner special?

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

Popular Areas for Jackson Square Rentals by Owner

Where are the best neighborhoods to stay in Jackson Square?

Discover the vibrant neighborhoods surrounding Jackson Square in Key West, Florida, where charming streets and historic ambiance create a perfect setting for your stay. Staying near this iconic area allows you to immerse yourself in the lively culture and picturesque scenery that define the heart of Key West. Whether you're seeking a cozy rental by owner or a spacious retreat, choosing accommodations in the vicinity of Jackson Square ensures convenient access to local attractions and a truly authentic experience. Trust Rent By Owner to help you find dependable vacation rentals that make your visit to this scenic part of Florida both comfortable and memorable.

Key West Historic District

This area offers a rich blend of history and local culture, making it an ideal spot to find charming rentals that immerse you in the region's unique charm. Staying here connects you to the heart of the island’s storied past while providing convenient access to attractions and vibrant surroundings.

View 2923+ Rentals in Key West Historic District

Old Town

Here, you’ll enjoy a lively neighborhood filled with colorful architecture and a walkable layout that invites exploration. It’s a perfect choice for those seeking authentic experiences and easy access to the region’s popular dining and entertainment options.

View 2836+ Rentals in Old Town

Sunset Key

This exclusive island enclave offers tranquil beaches and luxurious accommodations, ideal for relaxing getaways within close proximity to the main island. Staying on Sunset Key allows you to indulge in serene surroundings while remaining connected to the region’s vibrant lifestyle.

View 3214+ Rentals in Sunset Key

Downtown

In the heart of the city, downtown provides bustling streets full of shops, cafes, and nightlife that capture the region’s energetic spirit. It’s the perfect hub for travelers wanting to experience the region’s dynamic atmosphere and convenient amenities.

View 1279+ Rentals in Downtown

Uptown - Upper Duval

This vibrant neighborhood features a mix of historic sites and lively venues, offering a local vibe away from the more tourist-centric areas. It’s an excellent choice for those looking to enjoy authentic Key West life while staying close to the region’s attractions.

View 875+ Rentals in Uptown - Upper Duval

Bahama Village

Known for its eclectic character and rich cultural heritage, this neighborhood provides a colorful setting for your stay. Here, you can experience a sense of community and discover local art, music, and cuisine that reflect the region’s diverse influences.

View 107+ Rentals in Bahama Village

Historic Seaport

With scenic waterfront views and maritime history, this area offers a peaceful yet lively environment for exploring the region’s nautical traditions. Staying nearby gives you easy access to boat tours and waterfront dining, enriching your visit to this coastal destination.

View 467+ Rentals in Historic Seaport

New Town

A quieter, residential part of the area, New Town provides practical accommodations with proximity to shopping and everyday conveniences. It’s well-suited for travelers seeking a comfortable base from which to explore the broader region.

View 126+ Rentals in New Town

Best Times to Visit Jackson Square

When should you plan your Rentals by Owner stay?

Understanding the optimal time to visit can enhance your experience in this charming area, allowing you to enjoy its vibrant atmosphere and scenic beauty through reliable rental options by owner during peak or off-peak seasons.

Peak Season Highlights

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Winter (December to February)

During the winter months, the region experiences its busiest time as visitors flock here to escape colder climates. Expect lively atmosphere and vibrant local events.

Average Temperature Daytime: around 75°F (24°C) - Nighttime: around 65°F (18°C)
spring
Spring (March to May)

Spring brings warm weather and blooming flora, attracting travelers looking to enjoy outdoor activities and festivals in this popular destination.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: around 70°F (21°C)

Off-Season Highlights

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Summer (June to August)

While summer can be hot and humid, it’s a quieter time with fewer crowds, making it ideal for those seeking a more relaxed experience.

Average Temperature Daytime: around 88°F (31°C) - Nighttime: around 78°F (26°C)
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Fall (September to November)

Fall offers cooler temperatures and fewer visitors, providing a peaceful setting for exploring the area's scenic beauty and local culture.

Average Temperature Daytime: around 82°F (28°C) - Nighttime: around 72°F (22°C)

Weekly Weather Forecast for Jackson Square

How to Book Your Jackson Square vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Jackson Square

More Top-Rated Rentals by Owner in Jackson Square Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 outdoor seating areas such as patios or balconies to relax and take in the coastal ambiance.
  • Take advantage of on-site barbecue grills for outdoor dining experiences with friends and family.
  • Make use of shared or private pools to cool off and unwind after exploring the region.
  • Benefit from lush landscaped gardens or courtyards that add a touch of nature to your stay.
  • Utilize outdoor showers, perfect for rinsing off after a day at nearby beaches or water activities.
  • Access to bike rentals or dedicated bike paths for scenic rides around this vibrant destination.
  • Relish well-maintained outdoor lounging areas or hammocks to enjoy the pleasant weather in the area.

Top Attractions Around Jackson Square

What attractions are nearby?

Within walking distance from your rental here, you can enjoy a variety of vibrant local events, explore charming boutiques, or relax at nearby cafes, making it easy to experience the lively culture and scenic beauty that define this destination.

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Family Activities

  • Visit the Historic Key West Lighthouse and Keeper’s Quarters: Explore this iconic landmark to learn about maritime history while enjoying panoramic views perfect for family photos.
  • Stroll through the colorful streets of the area: Discover vibrant local art, boutique shops, and family-friendly cafes that make the region a lively destination for all ages.
  • Enjoy outdoor performances at nearby venues: Experience entertaining live music and cultural shows that bring the community here to life, creating memorable moments for your family.
  • Participate in interactive museums or activity centers: Engage with educational exhibits designed to entertain and enlighten children while highlighting the area's rich history and culture.
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Adult Activities

  • Historic Walking Tour: Explore the charming streets surrounding the square and discover the rich history that makes this destination unique, with guided or self-guided tours available for an immersive experience.
  • Art Galleries and Local Exhibits: Visit the vibrant art galleries nearby to appreciate local artistry and culture that thrive in this region’s creative community.
  • Cuisine and Dining Experiences: Savor fresh seafood and regional dishes at the renowned restaurants in the area, perfect for relaxing and indulging after your day of exploration.
  • Nightlife and Live Entertainment: Enjoy the lively nightlife scene with live music performances and entertainment options that capture the energetic spirit of this travel destination.

Jackson Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Events and Activities: Take advantage of the vibrant events in this area to immerse yourself in the local culture and enhance your stay.
  • Choose a Central Rental: Opt for a rental close to key attractions and dining options to maximize convenience and experience the best of what this region offers.
  • Visit Early or Late in the Day: Enjoy quieter moments and better photo opportunities by exploring popular spots during off-peak hours.
  • Engage with the Neighborhood: Interact with local residents and vendors to gain insider tips and truly experience the charm of this destination.

Transportation Options

  • Walking: You can easily explore the vibrant surroundings of Jackson Square on foot, enjoying the scenic views and local attractions just steps from your rental.
  • Bike Rentals: Renting a bicycle offers a convenient way to traverse the area's charming streets and nearby points of interest at your own pace.
  • Public Transit: The region is served by reliable bus services that connect you to popular destinations within and around this lively destination.
  • Taxi and Rideshare Services: Convenient and readily available, taxis and rideshare options provide quick transportation for exploring the region comfortably.

Local Customs Options

  • Greetings and Social Interactions: It is customary here to greet locals with friendly nods or waves as a sign of courtesy when visiting public spaces.
  • Respect for Art and Culture: Supporting local artists and respecting the vibrant art displays are important traditions in this area’s lively cultural scene.
  • Dining Etiquette: When enjoying meals at local eateries, tipping generously is appreciated and reflects the region's hospitality standards.
  • Music and Live Performances: Participating in or simply appreciating the live music scenes without disruption helps honor the area's rich musical heritage.

Frequently Asked Questions About Jackson Square Rentals by Owner

1. What are the top vacation rentals in Jackson Square?

There are a lot of options in Jackson Square. If you plan on staying in the Jackson Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Jackson Square:

2. How many Rentbyowner vacation rentals are available in Jackson Square?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 2443 in the Jackson Square 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 Jackson Square. 

3. What is the cancellation policy for rental properties in Jackson Square, Key West?

The cancellation policy varies by individual owner. You should review the specific listing details or contact the property owner directly to understand their cancellation terms before booking.

4. Are there any specific house rules I should be aware of when staying in a vacation rental in this area?

Yes, each rental may have its own set of house rules. It’s recommended to read the house rules section on the listing and communicate with the owner if you have any questions to ensure a smooth stay.

5. How do I securely book a rental in Jackson Square through Rent By Owner?

Booking is designed to be safe and straightforward. You can reserve your stay directly through the platform, which offers secure payment options and detailed property information. Always verify the listing details and communicate with the owner if needed.

6. What amenities are typically included in rentals within this destination?

Amenities vary by property but commonly include essentials like Wi-Fi, kitchen facilities, air conditioning, and outdoor spaces. Review the property listing carefully to ensure it meets your needs.

7. Is it possible to negotiate longer stays or special requests with owners in this region?

Many owners are open to discussing longer stays or specific arrangements. Contact the property owner directly through the platform to inquire about discounts or special accommodations for your travel dates.

More Rentals You May Like Near Jackson Square

More Top-Rated Rentals by Owner in Jackson Square Area