Compare Vacation Rentals & Rent By Owner Homes in Windley Key, Florida, USA
About Windley Key Vacation Rentals
With more than 800 Windley 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 Windley Key.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windley 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 Windley Key. Places to stay near Windley Key are 662.7 ft² on average, with prices averaging AU $1,136 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Windley 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.
Other Places to Stay in Windley Key, FL
Frequently Asked Questions About Windley Key?
What are the top vacation rentals in Windley Key?
- ISLAMORADA, ANGLERS REEF PRISTINE HOME Pool, Dock, Beach, Kayaks, Paddle Boards
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- Oceanside Getaway: Beautiful Home with Boat Slip, Pool & Beach - Gated community
- The Caribbean Resort
- Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- 5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- Serenity by the Sea! Anglers Reef with Boat Slip Available!
- 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
- Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
How many Rentbyowner vacation rentals are available in Windley Key?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 800 in the Windley 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 Windley Key.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Venetian Shores Vacation Rentals in Florida | 41 |
