803+ Private Villas and Holiday Rentals in Windley Key |
Windley Key Holiday Rentals
House
- Florida
- ·
- Islamorada
- 1.83 mi to center
10.0Exceptional
(192 Reviews)
3 Bedrooms
2 Baths
6 Guests
Oceanfront
Fireplace/Heating
Pool
Ocean View
د.إ.1,669/Night
7 Nights - د.إ.11,684
House
- Florida
- ·
- Islamorada
- 0.91 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1679.17 ft²
Spa- Pool
View
Breakfast
د.إ.3,548/Night
7 Nights - د.إ.24,838
House
- Florida
- ·
- Islamorada
- 3.22 mi to center
9.6Exceptional
(246 Reviews)
1 Bedroom
1 Bath
- Pool
- Ocean View
Balcony/Terrace- View
د.إ.948/Night
7 Nights - د.إ.6,637
House
- Florida
- ·
- Islamorada
- 1.86 mi to center
10.0Exceptional
(188 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,748/Night
7 Nights - د.إ.12,235
House
9.6Exceptional
(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
1550 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,469/Night
7 Nights - د.إ.10,285
House
- Florida
- ·
- Islamorada
- 1.17 mi to center
10.0Exceptional
(124 Reviews)
5 Bedrooms
4 Baths
10 Guests
2200 ft²
Private Pool- Oceanfront
- Pool
- Ocean View
د.إ.4,959/Night
7 Nights - د.إ.34,711
House
- Florida
- ·
- Islamorada
- 1.80 mi to center
10.0Exceptional
(116 Reviews)
4 Bedrooms
2 Baths
8 Guests
1928 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
د.إ.2,347/Night
7 Nights - د.إ.16,426
Villa
- Florida
- ·
- Islamorada
- 0.86 mi to center
10.0Exceptional
(95 Reviews)
2 Bedrooms
2 Baths
4 Guests
980 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
د.إ.1,257/Night
7 Nights - د.إ.8,801
House
- Florida
- ·
- Islamorada
- 3.85 mi to center
9.6Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
8 Guests
1360 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,424/Night
7 Nights - د.إ.9,965
Luxury Holiday Rentals in Windley Key
Over 794+ Luxury Holiday Rentals in or Near Windley Key
House
- Florida
- ·
- Islamorada
- 0.84 mi to center
6 Bedrooms
6 Baths
18 Guests
- Oceanfront
- Spa
- Fireplace/Heating
- Ocean View
Unlock the Best Price
Hotel
- Florida
- ·
- Upper Matecumbe Key
- 0.74 mi to center
1 Bath
Air Conditioner
Internet
Child Friendly
Bedding/Linens
د.إ.13,888/Night
7 Nights - د.إ.97,217
Villa
- Florida
- ·
- Islamorada
- 0.89 mi to center
10.0Exceptional
(1 Review)
10 Bedrooms
10 Baths
22 Guests
5826 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.12,685/Night
7 Nights - د.إ.88,795
Condo
- Florida
- ·
- Islamorada
- 0.52 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
10 Guests
- Ocean View
- Balcony/Terrace
- View
Kitchen
د.إ.10,818/Night
7 Nights - د.إ.75,729
House
- Florida
- ·
- Islamorada
- 0.52 mi to center
4 Bedrooms
4 Baths
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
د.إ.10,422/Night
7 Nights - د.إ.72,952
House
- Florida
- ·
- Islamorada
- 0.22 mi to center
8.0Excellent
(1 Review)
6 Bedrooms
5 Baths
12 Guests
3079 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.10,155/Night
7 Nights - د.إ.71,086
House
- Florida
- ·
- Islamorada
- 0.84 mi to center
8 Bedrooms
7 Baths
22 Guests
- Private Pool
- Oceanfront
Hot Tub- Fireplace/Heating
د.إ.9,909/Night
7 Nights - د.إ.69,360
House
- Florida
- ·
- Islamorada
- 0.52 mi to center
4 Bedrooms
4 Baths
10 Guests
- Ocean View
- Balcony/Terrace
- View
Pet Friendly
د.إ.9,579/Night
7 Nights - د.إ.67,053
House
- Florida
- ·
- Islamorada
- 4.16 mi to center
7 Bedrooms
7 Baths
16 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
د.إ.9,411/Night
7 Nights - د.إ.65,878
Top-Rated Holiday Rentals with a Pool in Windley Key
Over 574+ The Best Private Villas and Holiday Rentals in Windley Key with a Pool
Hotel
- Florida
- ·
- Islamorada
- 1.34 mi to center
10.0Exceptional
(166 Reviews)
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
د.إ.2,347/Night
7 Nights - د.إ.16,430
House
- Florida
- ·
- Islamorada
- 1.82 mi to center
10.0Exceptional
(146 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,334/Night
7 Nights - د.إ.9,341
Villa
- Florida
- ·
- Islamorada
- 1.79 mi to center
10.0Exceptional
(122 Reviews)
2 Bedrooms
2 Baths
6 Guests
1380 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,443/Night
7 Nights - د.إ.10,105
House
- Florida
- ·
- Islamorada
- 1.84 mi to center
10.0Exceptional
(119 Reviews)
4 Bedrooms
3 Baths
8 Guests
1980 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.3,177/Night
7 Nights - د.إ.22,241
House
- Florida
- ·
- Islamorada
- 1.81 mi to center
10.0Exceptional
(117 Reviews)
4 Bedrooms
3 Baths
8 Guests
2200 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
د.إ.2,813/Night
7 Nights - د.إ.19,692
House
- Florida
- ·
- Islamorada
- 1.82 mi to center
10.0Exceptional
(105 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
د.إ.2,389/Night
7 Nights - د.إ.16,720
House
- Florida
- ·
- Islamorada
- 1.76 mi to center
10.0Exceptional
(104 Reviews)
4 Bedrooms
2 Baths
8 Guests
1600 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.2,626/Night
7 Nights - د.إ.18,384
House
- Florida
- ·
- Islamorada
- 1.79 mi to center
10.0Exceptional
(95 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.2,472/Night
7 Nights - د.إ.17,308
House
- Florida
- ·
- Islamorada
- 1.77 mi to center
10.0Exceptional
(88 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,926/Night
7 Nights - د.إ.13,480
Pet-Friendly Holiday Rentals in Windley Key
Over 274+ Pet-Friendly Holiday Rentals in or Near Windley Key
Cottage
- Florida
- ·
- Islamorada
- 0.55 mi to center
10.0Exceptional
(114 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
د.إ.990/Night
7 Nights - د.إ.6,928
Resort
- Florida
- ·
- Islamorada
- 1.23 mi to center
8.9Fabulous
(1338 Reviews)
22 Baths
68 Guests
436.91 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.2,609/Night
7 Nights - د.إ.18,259
Hotel
- Florida
- ·
- Islamorada
- 1.61 mi to center
8.2Excellent
(1008 Reviews)
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
د.إ.676/Night
7 Nights - د.إ.4,731
Apartment
- Florida
- ·
- Islamorada
- 0.56 mi to center
10.0Exceptional
(102 Reviews)
2 Bedrooms
2 Baths
8 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
د.إ.1,707/Night
7 Nights - د.إ.11,945
Resort
- Florida
- ·
- Islamorada
- 0.88 mi to center
8.7Fabulous
(90 Reviews)
26 Baths
71 Guests
418.14 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.2,384/Night
7 Nights - د.إ.16,687
House
- Florida
- ·
- Islamorada
- 0.67 mi to center
10.0Exceptional
(52 Reviews)
3 Bedrooms
1 Bath
8 Guests
2000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.5,819/Night
7 Nights - د.إ.40,735
House
- Islamorada
- ·
- Venetian Shores
- 0.19 mi to center
10.0Exceptional
(39 Reviews)
3 Bedrooms
3 Baths
8 Guests
1703 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
د.إ.3,585/Night
7 Nights - د.إ.25,095
House
- Florida
- ·
- Islamorada
- 1.42 mi to center
10.0Exceptional
(34 Reviews)
3 Bedrooms
3 Baths
6 Guests
1860 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.3,729/Night
7 Nights - د.إ.26,101
House
- Florida
- ·
- Islamorada
- 1.32 mi to center
10.0Exceptional
(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1750 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
د.إ.2,088/Night
7 Nights - د.إ.14,619
Large Holiday Rentals and Private Villas in Windley Key
Over 121+ Large Holiday Rentals and Private Villas in or Near Windley Key
House
- Florida
- ·
- Islamorada
- 1.05 mi to center
10.0Exceptional
(72 Reviews)
5 Bedrooms
4 Baths
10 Guests
5000 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
د.إ.5,820/Night
7 Nights - د.إ.40,739
Villa
- Florida
- ·
- Islamorada
- 1.82 mi to center
9.5Exceptional
(2 Reviews)
2 Bedrooms
3 Baths
6 Guests
1302.43 ft²
- Private Beach
- Oceanfront
- Pool
- Ocean View
د.إ.1,818/Night
7 Nights - د.إ.12,727
Villa
- Florida
- ·
- Islamorada
- 0.52 mi to center
9.6Exceptional
(75 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
د.إ.2,682/Night
7 Nights - د.إ.18,773
Villa
- Florida
- ·
- Islamorada
- 1.85 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
3 Baths
6 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
د.إ.2,294/Night
7 Nights - د.إ.16,055
House
- Florida
- ·
- Islamorada
- 3.84 mi to center
8.0Excellent
(3 Reviews)
5 Bedrooms
4 Baths
12 Guests
1582.29 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.661/Night
7 Nights - د.إ.4,628
Villa
- Florida
- ·
- Upper Matecumbe Key
- 0.65 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
3 Baths
6 Guests
1680 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
د.إ.1,700/Night
7 Nights - د.إ.11,905
Villa
- Florida
- ·
- Upper Matecumbe Key
- 0.76 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1680 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
د.إ.2,345/Night
7 Nights - د.إ.16,415
Villa
- Florida
- ·
- Islamorada
- 0.84 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1680 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
د.إ.2,312/Night
7 Nights - د.إ.16,184
Villa
- Islamorada
- ·
- Venetian Shores
- 0.21 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1960 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,791/Night
7 Nights - د.إ.12,536
Wheelchair Accessible Holiday Homes in Windley Key
Over 220+ Wheelchair Accessible Holiday Homes in or Near Windley Key
Condo
- Florida
- ·
- Islamorada
- 4.46 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1536 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
د.إ.1,167/Night
7 Nights - د.إ.8,165
Resort
- Florida
- ·
- Islamorada
- 0.31 mi to center
8.5Fabulous
(768 Reviews)
19 Baths
75 Guests
391.64 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,282/Night
7 Nights - د.إ.8,974
Resort
- Florida
- ·
- Islamorada
- 1.53 mi to center
9.2Exceptional
(1307 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Ocean View
د.إ.1,605/Night
7 Nights - د.إ.11,232
Condo
- Florida
- ·
- Upper Matecumbe Key
- 1.33 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
د.إ.833/Night
7 Nights - د.إ.5,829
Resort
- Florida
- ·
- Islamorada
- 1.70 mi to center
7.9Very Good
(354 Reviews)
11 Baths
43 Guests
234.85 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,326/Night
7 Nights - د.إ.9,278
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
12 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.2,479/Night
7 Nights - د.إ.17,356
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
12 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.2,153/Night
7 Nights - د.إ.15,067
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.901/Night
7 Nights - د.إ.6,307
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.839/Night
7 Nights - د.إ.5,873
Windley Key Private Villas and Holiday Homes Under $200
Over 62+ Windley Key Private Villas and Holiday Homes Under $200
House
- Florida
- ·
- Islamorada
- 3.85 mi to center
9.2Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.711/Night
7 Nights - د.إ.4,981
House
- Florida
- ·
- Islamorada
- 0.16 mi to center
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
د.إ.724/Night
7 Nights - د.إ.5,065
Hotel
- Florida
- ·
- Islamorada
- 1.47 mi to center
9.0Exceptional
(262 Reviews)
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
د.إ.657/Night
7 Nights - د.إ.4,599
Villa
- Florida
- ·
- Islamorada
- 3.84 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1367 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.726/Night
7 Nights - د.إ.5,084
House
- Florida
- ·
- Islamorada
- 0.16 mi to center
2 Bedrooms
2 Baths
4 Guests
1280.91 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
د.إ.705/Night
7 Nights - د.إ.4,937
Condo
- Islamorada
- ·
- Plantation by the Sea
- 0.00 mi to center
9.6Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1033 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
د.إ.485/Night
7 Nights - د.إ.3,394
Villa
- Florida
- ·
- Islamorada
- 3.86 mi to center
9.4Exceptional
(18 Reviews)
3 Bedrooms
2 Baths
6 Guests
1367 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.472/Night
7 Nights - د.إ.3,306
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
8.8Fabulous
(8 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.715/Night
7 Nights - د.إ.5,003
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
8.6Fabulous
(25 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.715/Night
7 Nights - د.إ.5,003
Instantly Bookable Holiday Homes in Windley Key
Over 373+ Instantly Bookable Holiday Homes in or Near Windley Key
House
- Florida
- ·
- Islamorada
- 1.84 mi to center
10.0Exceptional
(83 Reviews)
2 Bedrooms
2 Baths
6 Guests
1650 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
د.إ.1,572/Night
7 Nights - د.إ.11,008
House
- Florida
- ·
- Islamorada
- 1.79 mi to center
3 Bedrooms
3 Baths
6 Guests
1700 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
د.إ.2,686/Night
7 Nights - د.إ.18,803
House
- Florida
- ·
- Islamorada
- 1.76 mi to center
10.0Exceptional
(72 Reviews)
2 Bedrooms
2 Baths
8 Guests
1620 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,939/Night
7 Nights - د.إ.13,572
House
- Florida
- ·
- Islamorada
- 1.15 mi to center
10.0Exceptional
(62 Reviews)
3 Bedrooms
3 Baths
6 Guests
2400 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.3,152/Night
7 Nights - د.إ.22,068
House
- Florida
- ·
- Islamorada
- 1.86 mi to center
10.0Exceptional
(57 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,461/Night
7 Nights - د.إ.10,226
House
- Florida
- ·
- Islamorada
- 1.62 mi to center
10.0Exceptional
(50 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,635/Night
7 Nights - د.إ.11,446
Apartment
- Florida
- ·
- Islamorada
- 0.90 mi to center
10.0Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
د.إ.1,532/Night
7 Nights - د.إ.10,726
House
- Florida
- ·
- Islamorada
- 1.83 mi to center
10.0Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,588/Night
7 Nights - د.إ.11,119
Apartment
- Florida
- ·
- Islamorada
- 0.90 mi to center
10.0Exceptional
(36 Reviews)
2 Bedrooms
2 Baths
4 Guests
620 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
د.إ.1,405/Night
7 Nights - د.إ.9,837
Book a Last Minute Place to Stay in Windley Key
About Casai's Private Villas and Holiday Rentals in Windley Key
Discover more than 803 vacation rentals available in Windley Key. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windley Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windley Key, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windley Key. On average, places to stay near Windley Key offer 662.92 ft², with nightly prices averaging د.إ.2,932.
With Casai, finding and comparing holiday rentals in Windley Key is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Windley Key
| Type | Count |
|---|---|
| Vacation Homes | 501 |
| Holiday Apartments | 79 |
| Villas | 39 |
| Cottages | 10 |
Use these Quick Filters to Find a Holiday Rental in Windley Key
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Windley Key.
Weather in Windley Key, FL
View the weather forecast for Windley Key before booking your Windley Key Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Windley Key, FL
Casai offers a large selection of top attractions around Windley Key . Research things to do on your vacation before you visit Windley Key.
Other Places to Stay in Windley Key, FL
Frequently Asked Questions About Windley Key?
What are the top holiday rentals in Windley Key?
With numerous options available in Windley Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windley Key:
- ISLAMORADA PARADISE in ANGLERS REEF - Pool, Dock, Beach, Kayaks, Paddle Boards
- 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.
- 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.
- Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
How many holiday rentals have private pools in Windley Key?
Discover a selection of holiday rentals with private pools near Windley Key with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Waterfront, boat dock, private oasis in the heart of Islamorada! Pool & Sunsets!
- Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
- 3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .
- Oceanfront 4-BR w/private 31' Boat Slip Included, Pool & Beach, gourmet kitchen
Which holiday homes in Windley Key are best for families?
If you're searching for a family-friendly holiday home in Windley Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windley Key:
How many Casai.ae holiday rentals are available in Windley Key?
As of 2026, Casai boasts over 803 properties listed in the Windley Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windley Key.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Venetian Shores Vacation Rentals in Florida | 25 |
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Finding the best prices in Windley Key
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