Windley Key Cottage Rentals
Cottage
10.0(141 Reviews)
1 Bedroom
1 Bath
2 Guests
1100 ft²
Parking
Ocean View
Balcony/Terrace
View
R6,482/Night
7 Nights - R45,375
R9,199/Night
7 Nights - R64,392
Cottage
10.0(19 Reviews)
2 Bedrooms
1 Bath
6 Guests
Oceanfront
Hot Tub- Parking
Pool
R14,912/Night
7 Nights - R104,382
Cottage
10.0(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
R10,072/Night
7 Nights - R70,513
Cottage
10.0(15 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
R11,097/Night
7 Nights - R77,688
Cottage
1 Bedroom
2 Baths
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R12,145/Night
7 Nights - R85,014
Cottage
1 Bedroom
2 Baths
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
R10,148/Night
7 Nights - R71,032
Cottage
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Air Conditioner
Internet
R7,930/Night
7 Nights - R55,511
Cottage
10.0(18 Reviews)
2 Bedrooms
1 Bath
6 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
R12,365/Night
7 Nights - R86,553
Cottage
10.0(13 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
R16,580/Night
7 Nights - R116,056
House
10.0(193 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R7,020/Night
7 Nights - R49,138
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1679.17 ft²
Breakfast- Parking
- Pool
Spa
R16,156/Night
7 Nights - R113,095
People Visiting Windley Key Also Like
Why Choose Rent By Owner for your Windley Key Cottage Rentals?
What makes our Cottage Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Windley Key
How to Book Your Windley Key Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage 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 Windley Key
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage 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
Other Places to Stay in Windley Key, FL
Windley Key Fossil Reef Geological State Park
Theater of the Sea
Frequently Asked Questions About Windley Key Rental Cottages
1. What are the top Cottages in Windley Key?
There are a lot of options in Windley Key. If you plan on staying in the Windley Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Windley Key:
- OCEANSIDE ANGLERS REEF HOME- Gated community- Pool, Dock, Private Beach
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- The Caribbean Resort
- Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- 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 Ocean View in Angler's Reef with View of Sand Bar/Boat slip
- TrulyOceanFRONT-BestPanoramicOceanViews-VLgDecks-QuietestLocation-SlipAvail
- Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
2. How many Cottages are available in Windley Key?
Currently, the total number of properties listed by RBO in 2026 is over 10 in the Windley Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Windley Key.
More Rentals You May Like Near Windley Key
Villa
9.6(77 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
R12,945/Night
7 Nights - R90,617
House
10.0(190 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
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- Ocean View
R8,226/Night
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House
9.5(2 Reviews)
3 Bedrooms
3 Baths
7 Guests
1700.7 ft²
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R12,779/Night
7 Nights - R89,446
House
10.0(148 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
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R6,577/Night
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Villa
9.5(2 Reviews)
2 Bedrooms
3 Baths
6 Guests
1302.43 ft²
Private Beach- Oceanfront
- Parking
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R8,279/Night
7 Nights - R57,953
Villa
10.0(125 Reviews)
2 Bedrooms
2 Baths
6 Guests
1380 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
R7,361/Night
7 Nights - R51,530
Resort
9.1(136 Reviews)
12 Baths
39 Guests
538.19 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
R4,570/Night
7 Nights - R31,995
House
10.0(95 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
R10,994/Night
7 Nights - R76,969
Resort
9.0(1293 Reviews)
19 Baths
58 Guests
448.12 ft²
- Private Beach
- Oceanfront
EV Charge Station- Parking
R11,878/Night
7 Nights - R83,141
Villa
10.0(95 Reviews)
2 Bedrooms
2 Baths
4 Guests
980 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R5,813/Night
7 Nights - R40,692
Resort
8.6(113 Reviews)
26 Baths
80 Guests
418.14 ft²
- Private Beach
- Oceanfront
- EV Charge Station
- Parking
R10,855/Night
7 Nights - R75,982
House
10.0(89 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
R8,337/Night
7 Nights - R58,354
