Compare Vacation Rentals & Rent By Owner Homes in Upper Sugarloaf Key, Sugarloaf Key, Florida, USA
About Upper Sugarloaf Key Vacation Rentals
With more than 214 Upper Sugarloaf Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Upper Sugarloaf Key.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Upper Sugarloaf Key, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Upper Sugarloaf Key. Places to stay near Upper Sugarloaf Key are 1115.19 ft² on average, with prices averaging US $460 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Upper Sugarloaf Key with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Frequently Asked Questions About Upper Sugarloaf Key?
What are the top vacation rentals in Upper Sugarloaf Key?
- Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
- White Home - Receive 400 dollars ntowards a BOAT RENTAL!
- Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, Bikes, Views!
- Oceanside home, dock,kayaks,bikes,pool,fishing,109
- Oceanside home, dock,kayaks,bikes,pool,fishing,111
- Blue Home - Receive 400 dollars ntowards a BOAT RENTAL!
- Yellow Home - Receive 400 dollars ntowards a BOAT RENTAL!
- Latitudes - Ocean front with salt water pool.
- Sugarloaf Key Home With Beach, Dock and Canal!
- Getaway to the Quiet Florida Keys
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 214 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.
Nearby Neighborhood (12)
| Neighborhood | Property Count |
|---|---|
| Cutthroat Harbor Estates Vacation Rentals in Sugarloaf Key, Florida | 83 |
| Breezeswept Beach Estates Vacation Rentals in Sugarloaf Key, Florida | 30 |
| Sugarloaf Shores Vacation Rentals in Sugarloaf Key, Florida | 26 |
| Eden Pines Vacation Rentals in Sugarloaf Key, Florida | 404 |
| Long Beach Estates Vacation Rentals in Sugarloaf Key, Florida | 154 |
| Doctor's Arm Vacation Rentals in Sugarloaf Key, Florida | 150 |
| Port Pine Heights Vacation Rentals in Sugarloaf Key, Florida | 98 |
| Cudjoe Gardens Vacation Rentals in Sugarloaf Key, Florida | 459 |
| Sands Vacation Rentals in Sugarloaf Key, Florida | 318 |
| Pine Channel Estates Vacation Rentals in Sugarloaf Key, Florida | 415 |
| Geiger Key Vacation Rentals in Sugarloaf Key, Florida | 35 |
| Tropical Bay Estates Vacation Rentals in Sugarloaf Key, Florida | 317 |
