Best Vacation Homes in Upper Sugarloaf Sound
- 4006 ft² House
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pool
- TV
Why Choose Rent By Owner for your Upper Sugarloaf Sound Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Upper Sugarloaf Sound Vacation Rentals
Where are the best neighborhoods to stay in Upper Sugarloaf Sound?
Discover the charming neighborhoods of Upper Sugarloaf Sound in Sugarloaf Key, Florida, where your ideal vacation begins. Staying in this peaceful area offers a serene escape surrounded by natural beauty and close to tranquil waterways. Whether you're seeking a quiet retreat or a scenic spot to explore additional outdoor activities, the neighborhoods here provide a perfect backdrop for your getaway. With a variety of well-appointed vacation rentals available, you can enjoy a seamless booking experience that combines comfort, convenience, and reliability in this picturesque part of the Florida Keys.
Geiger Key
Located just outside the main hub, Geiger Key offers a peaceful retreat with easy access to the region's serene waters and natural landscapes, making it an ideal spot for relaxing getaways.
View 35+ Rentals in Geiger KeyTropical Bay Estates
This charming neighborhood provides a quiet atmosphere and waterfront views, perfect for those seeking a tranquil stay immersed in the area's natural beauty.
View 317+ Rentals in Tropical Bay EstatesDoctor's Arm
Known for its secluded ambiance, Doctor's Arm is an excellent choice for visitors looking to enjoy the region’s scenic waterways and peaceful surroundings.
View 150+ Rentals in Doctor's ArmSands
Offering beachfront proximity and a relaxed vibe, Sands invites you to unwind near the tranquil waters of this destination’s coastal areas.
View 318+ Rentals in SandsCudjoe Gardens
Nestled along the shoreline, Cudjoe Gardens provides direct access to the water, making it an appealing choice for exploring the region’s aquatic activities.
View 459+ Rentals in Cudjoe GardensCutthroat Harbor Estates
This waterfront community offers stunning harbor views and easy access to boating and fishing, ideal for travelers wanting to experience the area's maritime charm.
View 94+ Rentals in Cutthroat Harbor EstatesPort Pine Heights
Situated on higher ground, Port Pine Heights provides scenic vistas and a peaceful environment, perfect for a relaxing stay away from the hustle.
View 98+ Rentals in Port Pine HeightsLong Beach Estates
With its proximity to the coast, Long Beach Estates is a prime spot for enjoying beachside tranquility while exploring the natural beauty of the region.
View 154+ Rentals in Long Beach EstatesBest Times to Visit Upper Sugarloaf Sound
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you can enjoy the best weather and outdoor activities, making your stay in this destination truly memorable and aligning perfectly with your vacation plans.
Peak Season Highlights
Winter (December to February)
During the winter months, the area experiences its peak season with warm temperatures and clear skies, attracting visitors seeking a sunny escape. This is the ideal time to enjoy outdoor activities and water-based adventures in this popular destination.
Spring (March to May)
Spring brings an influx of travelers eager to explore here as the weather warms up, making it a vibrant period for outdoor pursuits. The region's natural beauty and pleasant climate create perfect conditions for a memorable vacation experience.
Off-Season Highlights
Summer (June to August)
In the summer, the area experiences lower visitor numbers, offering a more relaxed atmosphere and less crowded accommodations. You can enjoy the warm waters and tranquility of this destination during these quieter months.
Fall (September to November)
Autumn sees fewer visitors, providing an excellent opportunity to explore without the crowds. Cooler temperatures and occasional rain create a peaceful environment perfect for unwinding here.
Weekly Weather Forecast for Upper Sugarloaf Sound
How to Book Your Upper Sugarloaf Sound Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Upper Sugarloaf Sound
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 patios or decks perfect for relaxing and entertaining
- Access to waterfront or dock facilities for boat docking and water activities
- Outdoor grilling areas to enjoy meals with scenic views
- Swimming pools or hot tubs for leisure and relaxation in the sun
- Spacious yards or gardens ideal for outdoor recreation or family gatherings
- Direct access to kayaking, paddleboarding, or other water sports gear storage
- Barbecue grills available for open-air cooking amidst lush surroundings
Top Attractions Around Upper Sugarloaf Sound
What attractions are nearby?
Here, you can enjoy a variety of outdoor activities such as kayaking, paddleboarding, and exploring local wildlife, all just moments from your vacation rentals in the scenic region surrounding Upper Sugarloaf Sound.
Family Activities
- Snorkeling Adventures: Explore the vibrant coral reefs and marine life just off the coast, making it a perfect activity for families seeking underwater exploration in the area.
- Kayaking Tours: Paddle through calm waters and enjoy scenic views around Sugarloaf Key, offering an engaging outdoor experience suitable for all ages.
- Wildlife Watching: Discover local bird species and marine animals on guided boat tours that showcase the region's natural beauty and biodiversity.
- Beach Picnics: Relax at nearby beaches with your family, enjoying the serene environment and picturesque sunsets that define this destination’s charm.
Adult Activities
- Charter a Boat Tour: Explore the tranquil waters surrounding this destination by booking a private boat tour to enjoy scenic views and wildlife sightings.
- Snorkeling Adventures: Discover vibrant marine life and colorful coral reefs just off the coast, making the most of your time in this prime snorkeling location.
- Kayaking and Paddleboarding: Engage in water-based activities along the calm shoreline, perfect for enjoying the natural beauty of the region at your own pace.
- Fishing Excursions: Experience a day out on the water trying to catch local fish species, a popular activity in the area for those seeking relaxation and adventure.
Other Places to Stay in Upper Sugarloaf Sound, FL
Upper Sugarloaf Sound Travel Tips
How Can You Make the Most of Your Stay?
- Explore Water Activities: Take advantage of the region's calm waters by engaging in kayaking, paddleboarding, or boating to fully enjoy the scenic beauty and tranquility here.
- Plan for Sunset Views: Make time to relax during sunset hours as the area offers breathtaking views that enhance your overall experience in this destination.
- Choose a Prime Location: Select a vacation rental close to key waterways or natural preserves to maximize access to outdoor adventures and scenic spots.
- Respect the Environment: Practice eco-friendly habits such as proper waste disposal and minimal disturbance to local wildlife, ensuring the pristine nature remains unspoiled for future visitors.
Transportation Options
- Private Boat Charters: You can arrange for private boat charters to explore the stunning waters of this area at your own pace, offering a flexible and scenic way to experience the region.
- Kayak Rentals: Kayak rentals are available nearby, allowing you to enjoy peaceful paddling through the calm waterways that surround your vacation rental here.
- Rental Cars: Car rentals provide convenient access to local attractions and help you easily navigate the region’s scenic routes and surrounding islands.
- Water Taxi Services: Water taxi services operate in this destination, offering quick and convenient transportation across the waterways of Sugarloaf Key and nearby areas.
Local Customs Options
- Reef Respect: Locals here value preserving the vibrant coral reefs, encouraging visitors to avoid anchoring on them and to participate in eco-friendly snorkeling practices.
- Seafood Tradition: Fresh seafood is a staple in the region’s cuisine, with community members often gathering for local fish fries and seafood festivals that celebrate maritime heritage.
- Quiet Hours: Respect for the peaceful atmosphere is important, especially during designated quiet hours in this destination, ensuring a relaxing environment for all visitors.
- Wildlife Appreciation: The area’s residents and visitors alike prioritize observing native wildlife responsibly, maintaining distance from nesting birds and protected marine species.
Frequently Asked Questions About Upper Sugarloaf Sound?
What are the top vacation rentals in Upper Sugarloaf Sound?
There are a lot of options in Upper Sugarloaf Sound. If you plan on staying in the Upper Sugarloaf Sound 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 Sound:
- Florida Keys Beach Getaway
- Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
- Private and Exclusive Beach Getaway
- Pelico Palms Estate.
- Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
- Cassie’s Paradise - Luxury Vacation Rental in the Florida Keys
- The Villa of Pelico Palms
- $and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
- Bungalows Sugarloaf Beach Key West - Hammock House
- Private and Exclusive Beach Getaway
How many Rentbyowner vacation rentals are available in Upper Sugarloaf Sound?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 58 in the Upper Sugarloaf Sound 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 Sound.
Best Vacation Homes in Upper Sugarloaf Sound
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
