Cottage
10.0(142 Reviews)
1 Bedroom
2 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $357/Night
7 Nights - US $2,502
Windley Key Cottage Rentals & Holiday Homes
Find the best cottages in Windley Key - We found 9 exact matches
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Compare Cottage Rentals in Windley Key
10.0
US $550/Night
7 Nights - US $3,850
Cottage
10.0(19 Reviews)
2 Bedrooms
6 Guests
Oceanfront
Hot Tub- Parking
Pool
US $930/Night
7 Nights - US $6,508
Cottage
10.0(16 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $627/Night
7 Nights - US $4,392
Cottage
10.0(15 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $664/Night
7 Nights - US $4,645
Cottage
1 Bedroom
4 Guests
- Oceanfront
- Parking
Ocean View- Balcony/Terrace
US $730/Night
7 Nights - US $5,109
Cottage
3 Bedrooms
6 Guests
- Parking
- Pool
- Air Conditioner
Internet
US $490/Night
7 Nights - US $3,428
Cottage
10.0(18 Reviews)
2 Bedrooms
6 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
US $739/Night
7 Nights - US $5,175
Cottage
10.0(13 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $991/Night
7 Nights - US $6,939
People Visiting Windley Key Also Like
House
10.0(193 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $445/Night
7 Nights - US $3,113
House
10.0(2 Reviews)
3 Bedrooms
6 Guests
Breakfast- Parking
- Pool
Spa
US $966/Night
7 Nights - US $6,762
US $185/Night
7 Nights - US $1,293
House
10.0(193 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $415/Night
7 Nights - US $2,903
House
9.5(2 Reviews)
3 Bedrooms
7 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $764/Night
7 Nights - US $5,348
House
10.0(152 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $353/Night
7 Nights - US $2,473
Villa
9.5(2 Reviews)
2 Bedrooms
6 Guests
Private Beach- Oceanfront
- Parking
- Pool
US $495/Night
7 Nights - US $3,465
Villa
10.0(126 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $442/Night
7 Nights - US $3,096
US $177/Night
7 Nights - US $1,242
House
10.0(95 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $507/Night
7 Nights - US $3,552
Resort
9.0(1293 Reviews)
58 Guests
- Private Beach
- Oceanfront
EV Charge Station- Parking
US $659/Night
7 Nights - US $4,611
Villa
10.0(95 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $351/Night
7 Nights - US $2,459
Resort
8.5(768 Reviews)
75 Guests
- Private Beach
- Oceanfront
- Breakfast
- Parking
US $332/Night
7 Nights - US $2,326
House
10.0(91 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $560/Night
7 Nights - US $3,917
House
10.0(90 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $580/Night
7 Nights - US $4,059
House
10.0(72 Reviews)
2 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $371/Night
7 Nights - US $2,598
House
10.0(61 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $440/Night
7 Nights - US $3,083
House
10.0(59 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $496/Night
7 Nights - US $3,470
Apartment
10.0(49 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $400/Night
7 Nights - US $2,800
House
10.0(47 Reviews)
2 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $458/Night
7 Nights - US $3,207
House
10.0(42 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $453/Night
7 Nights - US $3,169
House
10.0(40 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $424/Night
7 Nights - US $2,965
Apartment
10.0(36 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $384/Night
7 Nights - US $2,691
House
10.0(29 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $524/Night
7 Nights - US $3,670
About Windley Key Cottage Rentals on Casai.com
Searching for cottages to rent near Windley Key? Casai features more than 9 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Windley Key have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Casai’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Windley Key.
Are you planning to travel to the lakeside, beach, or mountain area? Casai’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Casai boasts of 9 holiday cottages and places to stay in Windley Key. The site provides unique Airbnb, VRBO, Casai-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Cottage Rentals: Explore Top Destinations
Frequently Asked Questions About Windley Key Rental Cottages
What are the top rated Cottage Rentals 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 Cottage Rentals in Windley Key:
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- OCEANSIDE ANGLERS REEF HOME- Gated community- Pool, Dock, 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
- TrulyOceanFRONT-BestPanoramicOceanViews-VLgDecks-QuietestLocation-SlipAvail
- Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
- Keys Kottage & Bayside Villa W/free onsite boat ramp marina & trailer parking.
How much does it cost to rent a cottage in Windley Key?
The average cost for a cottage rental in Windley Key is $675 per night. Casai has a wide list of great cottages near Windley Key that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Windley Key that allow pets?
Yes, here are the top cottage rentals in Windley Key that allow you to bring your pet:
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- Little Bay Cottage
- Charming Bayfront Cottage in Heart of Islamorada with Heated Pool, Deep Dockage, Kayaks & More
- Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
- Ragged Edge Resort & Marina
- OCEANSIDE ANGLERS REEF HOME- Gated community- Pool, Dock, Private Beach
See all pet-friendly vacation rentals in Windley Key on Casai.com
Do you have any rental cottages in Windley Key that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windley Key to find one that works for you.
Are there quality cottages in Windley Key that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are Over 9 private swimming pools or cottages with indoor pools in the Windley Key area along with other great amenities.
Do any cottages in Windley Key have hot tubs?
About 9 cottages in Windley Key boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Windley Key on Casai.com
Are there luxury cottages in Windley Key?
Yes, there are luxury cottages in Windley Key. Find more luxury, lakefront, winter, & last-minute cottage rentals near Windley Key.
