Discover Your Perfect Upper Sugarloaf Key Vacation Homes

Best Vacation Homes in Upper Sugarloaf Key

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9.6 (2 Reviews)
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Pelico Paradise
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Upper Sugarloaf Key Vacation Rental Homes?

What makes our Vacation Rentals 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 Upper Sugarloaf Key Vacation Rentals

Where are the best neighborhoods to stay in Upper Sugarloaf Key?

When exploring Upper Sugarloaf Key and the surrounding area, choosing the right neighborhood can enhance your Florida Keys experience. This tranquil region offers a range of options for those seeking a peaceful retreat close to nature and local charm. Whether you prefer staying near the waterfront or in more secluded areas, Upper Sugarloaf Key provides diverse neighborhoods that cater to various preferences. By selecting a well-situated location within this community, you can enjoy convenient access to outdoor activities and the laid-back Florida Keys lifestyle, ensuring a memorable and relaxing visit.

Geiger Key

Located nearby, Geiger Key offers a peaceful retreat with easy access to the water, perfect for those seeking a tranquil escape in this part of the Florida Keys.

View 35+ Rentals in Geiger Key

Tropical Bay Estates

This area provides a serene setting with beautiful waterfront views, making it an ideal choice for visitors looking to relax surrounded by nature’s beauty.

View 317+ Rentals in Tropical Bay Estates

Doctor's Arm

Here, you can enjoy a quiet atmosphere with close proximity to Key West, suitable for travelers wanting both tranquility and convenience.

View 150+ Rentals in Doctor's Arm

Sands

Sands boasts direct access to the marina and waterfront activities, offering an excellent base for exploring the area's aquatic adventures.

View 318+ Rentals in Sands

Cudjoe Gardens

Known for its scenic waterways, Cudjoe Gardens is perfect for boaters and nature enthusiasts seeking a picturesque setting.

View 459+ Rentals in Cudjoe Gardens

Cutthroat Harbor Estates

Offering waterfront living options, this neighborhood is ideal for guests interested in a nautical lifestyle within reach of nearby attractions.

View 33+ Rentals in Cutthroat Harbor Estates

Port Pine Heights

Positioned conveniently close to local amenities, Port Pine Heights provides a comfortable stay with quick access to the region's scenic parks and trails.

View 98+ Rentals in Port Pine Heights

Long Beach Estates

With its expansive waterfront views, Long Beach Estates offers a relaxing environment perfect for enjoying the natural beauty of this destination.

View 154+ Rentals in Long Beach Estates

Best Times to Visit Upper Sugarloaf Key

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as the region's weather and local events vary throughout the year, making it important to consider seasonal patterns for your perfect getaway.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination sees an influx of visitors seeking warm weather and scenic views, making it the most popular time to explore the area's natural beauty.

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

Spring offers ideal weather conditions with blooming landscapes, attracting travelers looking to enjoy outdoor activities and pleasant days in the region.

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

Off-Season Highlights

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Summer (June to August)

The summer period experiences fewer visitors due to the hot and humid climate, providing a more peaceful environment for those seeking solitude or budget-friendly accommodations.

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

In fall, the area tends to be quieter as many tourists avoid the early hurricane season, offering a calm setting for relaxed stays and longer explorations.

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

Weekly Weather Forecast for Upper Sugarloaf Key

How to Book Your Upper Sugarloaf Key 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 Upper Sugarloaf Key

More Top-Rated Vacation Rentals in Upper Sugarloaf Key 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

  • Private outdoor decks or patios to enjoy the warm Florida sunshine
  • Outdoor grilling areas perfect for family cookouts
  • Swimming pools or hot tubs to unwind after a day exploring the area
  • Direct access to marina or dock facilities for boating and fishing enthusiasts
  • Shade-covered lounging spaces to relax outdoors in comfort
  • Beautifully landscaped gardens or tropical yards for outdoor enjoyment
  • Patio furniture and outdoor dining setups for alfresco meals with scenic views

Top Attractions Around Upper Sugarloaf Key

What attractions are nearby?

Here, you can explore a variety of outdoor activities and water-based adventures that showcase the natural beauty of this destination’s coastal environment.

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Family Activities

  • Snorkeling at the Coral Reef: Explore vibrant marine life just off the shores, making it an ideal activity for families seeking underwater adventures in this region.
  • Wildlife Watching at Marine Parks: Visit local marine parks where you can observe diverse bird species and other wildlife native to the area, perfect for nature-loving families.
  • Kayaking Through Mangroves: Paddle through scenic mangrove tunnels that offer a peaceful escape and memorable family experiences in the region’s calm waters.
  • Fishing Excursions: Enjoy family-friendly fishing trips designed for all skill levels, allowing you to relax and bond while trying your luck in these productive waters.
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Adult Activities

  • Deep Sea Fishing Adventures: Embark on an exhilarating fishing trip in the nearby waters, renowned for their abundant marine life and ideal conditions for a memorable day at sea.
  • Kayaking and Paddleboarding: Explore the serene waterways around this destination, enjoying the opportunity to observe local wildlife and experience the region’s natural beauty firsthand.
  • Snorkeling Excursions: Discover the vibrant underwater ecosystems just off the coast, perfect for immersing yourself in the tranquil marine environment of the area.
  • Sunset Cruises: Unwind while taking in breathtaking views of the horizon during an evening cruise, a popular way to appreciate the region’s scenic coastline.

Upper Sugarloaf Key Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature:** Take advantage of the area's lush surroundings by planning outdoor activities like kayaking or nature walks right from your rental spot.
  • Utilize Water Transportation:** Maximize your stay by renting a boat or using water taxis to easily access nearby islands and hidden coves around this destination.
  • Book Early for Prime Locations:** Secure your preferred vacation rentals early in this region to ensure proximity to key waterfront spots and scenic views.
  • Engage with Local Experts:** Seek recommendations from local hosts for off-the-beaten-path experiences that showcase the true essence of the area.

Transportation Options

  • Rental Cars: Renting a vehicle offers you the flexibility to explore the area at your own pace and access remote spots around Sugarloaf Key with ease.
  • Public Transportation: Local bus services provide an affordable and convenient way to travel around the region without the need for private transportation.
  • Taxi Services: Taxis are readily available for quick trips within the destination, making it simple to reach nearby attractions or get to your vacation rental comfortably.
  • Bike Rentals: Biking is an eco-friendly option that allows you to enjoy the scenic views and navigate through the area’s charming streets at your leisure.

Local Customs Options

  • Respect for Marine Life: Locals in this region hold a deep respect for the surrounding marine environment, encouraging visitors to avoid disturbing wildlife and to follow sustainable boating and fishing practices.
  • Local Seafood Etiquette: When dining out or purchasing fresh produce here, it’s customary to appreciate the region’s seafood heritage by supporting local fishermen and understanding the traditional methods used in preparing and serving seafood dishes.
  • Conservation Practices: Preserving the natural beauty of the area is important, so you’ll find that community members often participate in eco-friendly initiatives and expect visitors to do the same during their stay.
  • Quiet Hours and Respectful Behavior: Maintaining a peaceful atmosphere is valued here, with quiet hours observed in many neighborhoods, making it essential for guests to be considerate of neighbors to ensure an enjoyable visit.

Frequently Asked Questions About Upper Sugarloaf Key?

What are the top vacation rentals in Upper Sugarloaf Key?

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

How many Rentbyowner vacation rentals are available in Upper Sugarloaf Key?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 235 in the Upper Sugarloaf Key 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 Upper Sugarloaf Key. 

Best Vacation Homes in Upper Sugarloaf Key