803+ Private Villas and Holiday Rentals in Windley Key |
Windley Key Holiday Rentals
House
- Florida
- ·
- Upper Matecumbe Key
- 0.65 mi to center
2 Bedrooms
2 Baths
4 Guests
Fireplace/Heating
Pet Friendly
Kitchen
Parking
R4,617/Night
7 Nights - R32,317
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
R15,919/Night
7 Nights - R111,436
House
- Florida
- ·
- Islamorada
- 3.22 mi to center
9.6Exceptional
(246 Reviews)
1 Bedroom
1 Bath
- Pool
Ocean View
Balcony/Terrace- View
R4,255/Night
7 Nights - R29,779
House
- Florida
- ·
- Islamorada
- 1.83 mi to center
10.0Exceptional
(192 Reviews)
3 Bedrooms
2 Baths
6 Guests
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
R7,489/Night
7 Nights - R52,422
House
9.6Exceptional
(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
1550 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Pool
R6,592/Night
7 Nights - R46,143
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
R7,843/Night
7 Nights - R54,894
House
- Florida
- ·
- Islamorada
- 1.82 mi to center
10.0Exceptional
(146 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R5,986/Night
7 Nights - R41,908
Cottage
- Florida
- ·
- Islamorada
- 1.15 mi to center
10.0Exceptional
(138 Reviews)
1 Bedroom
1 Bath
2 Guests
1100 ft²
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
R5,496/Night
7 Nights - R38,464
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
R6,476/Night
7 Nights - R45,336
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
R62,310/Night
7 Nights - R436,170
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
R56,911/Night
7 Nights - R398,382
Condo
- Florida
- ·
- Islamorada
- 0.52 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
10 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
R48,537/Night
7 Nights - R339,763
House
- Florida
- ·
- Islamorada
- 0.52 mi to center
4 Bedrooms
4 Baths
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
R46,757/Night
7 Nights - R327,305
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
R45,563/Night
7 Nights - R318,933
House
- Florida
- ·
- Islamorada
- 0.84 mi to center
8 Bedrooms
7 Baths
22 Guests
- Private Pool
- Oceanfront
Hot Tub- Fireplace/Heating
R44,455/Night
7 Nights - R311,187
House
- Florida
- ·
- Islamorada
- 0.52 mi to center
4 Bedrooms
4 Baths
10 Guests
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
R42,976/Night
7 Nights - R300,838
House
- Florida
- ·
- Islamorada
- 4.16 mi to center
7 Bedrooms
7 Baths
16 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
R42,223/Night
7 Nights - R295,565
Top-Rated Holiday Rentals with a Pool in Windley Key
Over 575+ 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
R10,531/Night
7 Nights - R73,714
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
R22,248/Night
7 Nights - R155,734
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
R14,255/Night
7 Nights - R99,785
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
R12,620/Night
7 Nights - R88,348
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
R10,528/Night
7 Nights - R73,698
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
R10,717/Night
7 Nights - R75,016
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
R11,783/Night
7 Nights - R82,481
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
R11,092/Night
7 Nights - R77,653
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
R8,640/Night
7 Nights - R60,481
Pet-Friendly Holiday Rentals in Windley Key
Over 273+ 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
R4,439/Night
7 Nights - R31,081
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
R11,704/Night
7 Nights - R81,921
Hotel
- Florida
- ·
- Islamorada
- 1.61 mi to center
8.2Excellent
(1006 Reviews)
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
R3,663/Night
7 Nights - R25,643
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
R7,657/Night
7 Nights - R53,592
Resort
- Florida
- ·
- Islamorada
- 0.88 mi to center
8.7Fabulous
(83 Reviews)
18 Baths
69 Guests
418.14 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
R10,695/Night
7 Nights - R74,868
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
R5,642/Night
7 Nights - R39,486
House
- Florida
- ·
- Islamorada
- 0.90 mi to center
10.0Exceptional
(25 Reviews)
3 Bedrooms
2 Baths
6 Guests
960 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R8,316/Night
7 Nights - R58,207
Cottage
- Florida
- ·
- Upper Matecumbe Key
- 0.90 mi to center
10.0Exceptional
(19 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R15,900/Night
7 Nights - R111,304
Cottage
- Florida
- ·
- Upper Matecumbe Key
- 0.85 mi to center
10.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R10,375/Night
7 Nights - R72,626
Large Holiday Rentals and Private Villas in Windley Key
Over 121+ Large Holiday Rentals and Private Villas in or Near Windley Key
Villa
- Florida
- ·
- Islamorada
- 1.85 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
3 Baths
6 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
R10,291/Night
7 Nights - R72,033
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
R8,157/Night
7 Nights - R57,102
Villa
- Florida
- ·
- Islamorada
- 0.52 mi to center
9.6Exceptional
(75 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
R12,032/Night
7 Nights - R84,228
Villa
- Florida
- ·
- Islamorada
- 0.90 mi to center
10.0Exceptional
(16 Reviews)
2 Bedrooms
2 Baths
4 Guests
850 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,952/Night
7 Nights - R48,665
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
R2,966/Night
7 Nights - R20,765
Villa
- Florida
- ·
- Islamorada
- 1.82 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1600 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R7,466/Night
7 Nights - R52,257
Villa
- Florida
- ·
- Islamorada
- 0.90 mi to center
9.8Exceptional
(40 Reviews)
2 Bedrooms
2 Baths
4 Guests
750 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R5,642/Night
7 Nights - R39,486
Condo
- Florida
- ·
- Islamorada
- 3.88 mi to center
9.8Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
11 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R3,786/Night
7 Nights - R26,499
House
- Islamorada
- ·
- Venetian Shores
- 0.16 mi to center
2 Bedrooms
2 Baths
10 Guests
1600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R7,500/Night
7 Nights - R52,505
Wheelchair Accessible Holiday Homes in Windley Key
Over 220+ Wheelchair Accessible Holiday Homes in or Near Windley Key
Condo
- Islamorada
- ·
- Plantation by the Sea
- 0.04 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
4 Guests
1300 ft²
- Spa
- Fireplace/Heating
- Pool
- Ocean View
R3,817/Night
7 Nights - R26,714
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
R5,751/Night
7 Nights - R40,260
Resort
- Florida
- ·
- Islamorada
- 1.53 mi to center
9.2Exceptional
(1307 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Ocean View
R7,200/Night
7 Nights - R50,395
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
R5,234/Night
7 Nights - R36,635
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
R5,947/Night
7 Nights - R41,628
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
R3,737/Night
7 Nights - R26,153
Condo
- Islamorada
- ·
- Plantation by the Sea
- 0.04 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
R2,726/Night
7 Nights - R19,084
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R4,042/Night
7 Nights - R28,296
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R3,764/Night
7 Nights - R26,351
Windley Key Private Villas and Holiday Homes Under $200
Over 60+ Windley Key Private Villas and Holiday Homes Under $200
House
- Florida
- ·
- Islamorada
- 3.86 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R2,909/Night
7 Nights - R20,369
Apartment
- Florida
- ·
- Islamorada
- 3.85 mi to center
2 Bedrooms
2 Baths
6 Guests
1345.49 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
R2,175/Night
7 Nights - R15,227
Hotel
- Florida
- ·
- Islamorada
- 0.63 mi to center
7.6Very Good
(1004 Reviews)
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
R3,033/Night
7 Nights - R21,226
House
- Florida
- ·
- Islamorada
- 3.85 mi to center
9.8Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R2,497/Night
7 Nights - R17,469
House
- Florida
- ·
- Islamorada
- 0.16 mi to center
2 Bedrooms
2 Baths
4 Guests
1280.91 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
R3,164/Night
7 Nights - R22,149
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
R2,176/Night
7 Nights - R15,227
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
8.8Fabulous
(8 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R3,206/Night
7 Nights - R22,445
House
- Florida
- ·
- Islamorada
- 3.65 mi to center
8.8Fabulous
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R3,188/Night
7 Nights - R22,314
Apartment
- Florida
- ·
- Islamorada
- 1.61 mi to center
8.6Fabulous
(25 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R3,206/Night
7 Nights - R22,445
Instantly Bookable Holiday Homes in Windley Key
Over 386+ 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
R7,055/Night
7 Nights - R49,390
House
- Florida
- ·
- Islamorada
- 1.79 mi to center
3 Bedrooms
3 Baths
6 Guests
1700 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R12,051/Night
7 Nights - R84,360
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
R8,698/Night
7 Nights - R60,893
House
- Florida
- ·
- Islamorada
- 1.86 mi to center
10.0Exceptional
(57 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R6,555/Night
7 Nights - R45,880
House
- Florida
- ·
- Islamorada
- 1.62 mi to center
10.0Exceptional
(50 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R7,336/Night
7 Nights - R51,351
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
R6,874/Night
7 Nights - R48,121
House
- Florida
- ·
- Islamorada
- 1.83 mi to center
10.0Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R7,126/Night
7 Nights - R49,884
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
R6,304/Night
7 Nights - R44,133
House
- Florida
- ·
- Islamorada
- 1.35 mi to center
10.0Exceptional
(27 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Ocean View
- View
- Kitchen
- Parking
R7,416/Night
7 Nights - R51,911
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 R13,166.
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.
- SEASONAL WATERFRONT RENTAL in Venetian Shores, Islamorada, Pool & New Dock
- Islamorada waterfront villa
- Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!
- Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
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:
- Anglers Reef- Family Friendly Community at a Fraction of the Cost.
- Ragged Edge Resort & Marina
- Treasure Harbor
How many Casai.co.za 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 | 40 |
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