800+ Private Villas and Holiday Rentals in Windley Key |
Windley Key Holiday Rentals
10.0
Exceptional
(192 Reviews)
- Florida
- Islamorada
- 1.83 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,780/Night
For 7 Nights د.إ.12,461
10.0
Exceptional
(2 Reviews)
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
House
- Spa
- Pool
- View
د.إ.3,548/Night
For 7 Nights د.إ.24,833
9.8
Exceptional
(74 Reviews)
- Florida
- Islamorada
- 0.52 mi to center
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Hot Tub
- Spa
- Fireplace/Heating
د.إ.2,991/Night
For 7 Nights د.إ.20,941
10.0
Exceptional
(188 Reviews)
- Florida
- Islamorada
- 1.86 mi to center
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,917/Night
For 7 Nights د.إ.13,419
9.6
Exceptional
(19 Reviews)
1550 ft²
6 Guests
2 Bedrooms
2 Bathrooms
House
- Private Beach
- Oceanfront
- Fireplace/Heating
د.إ.1,469/Night
For 7 Nights د.إ.10,283
10.0
Exceptional
(124 Reviews)
- Florida
- Islamorada
- 1.17 mi to center
2200 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
د.إ.4,958/Night
For 7 Nights د.إ.34,705
10.0
Exceptional
(116 Reviews)
- Florida
- Islamorada
- 1.80 mi to center
1928 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
د.إ.2,375/Night
For 7 Nights د.إ.16,625
10.0
Exceptional
(94 Reviews)
- Florida
- Islamorada
- 0.86 mi to center
980 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Ocean View
د.إ.1,316/Night
For 7 Nights د.إ.9,214
9.6
Exceptional
(8 Reviews)
- Florida
- Islamorada
- 3.85 mi to center
1360 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,423/Night
For 7 Nights د.إ.9,963
Luxury Holiday Rentals in Windley Key
Over 791+ Luxury Holiday Rentals in or Near Windley Key
New
18 Guests
6 Bedrooms
6 Bathrooms
House
- Oceanfront
- Spa
- Fireplace/Heating
Unlock the Best Price
New
- Florida
- Upper Matecumbe Key
- 0.74 mi to center
1 Bathroom
Couples Retreat
Hotel
- Air Conditioner
- Internet
- Child Friendly
د.إ.13,886/Night
For 7 Nights د.إ.97,200
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 0.89 mi to center
5826 ft²
22 Guests
10 Bedrooms
10 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Fireplace/Heating
د.إ.12,683/Night
For 7 Nights د.إ.88,779
New
- Florida
- Islamorada
- 0.84 mi to center
22 Guests
8 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
د.إ.12,154/Night
For 7 Nights د.إ.85,077
New
- Florida
- Islamorada
- 1.18 mi to center
4 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.11,250/Night
For 7 Nights د.إ.78,753
New
- Florida
- Islamorada
- 1.18 mi to center
4 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.11,226/Night
For 7 Nights د.إ.78,580
New
- Florida
- Islamorada
- 1.18 mi to center
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.10,812/Night
For 7 Nights د.إ.75,687
New
- Florida
- Islamorada
- 1.18 mi to center
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.10,804/Night
For 7 Nights د.إ.75,628
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 0.52 mi to center
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Condo
- Ocean View
- Balcony/Terrace
- View
د.إ.10,345/Night
For 7 Nights د.إ.72,418
Top-Rated Holiday Rentals with a Pool in Windley Key
Over 570+ The Best Private Villas and Holiday Rentals in Windley Key with a Pool
10.0
Exceptional
(173 Reviews)
- Florida
- Islamorada
- 1.80 mi to center
1386 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,897/Night
For 7 Nights د.إ.13,276
10.0
Exceptional
(166 Reviews)
- Florida
- Islamorada
- 1.34 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Balcony/Terrace
د.إ.2,347/Night
For 7 Nights د.إ.16,427
10.0
Exceptional
(146 Reviews)
- Florida
- Islamorada
- 1.82 mi to center
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,334/Night
For 7 Nights د.إ.9,339
10.0
Exceptional
(121 Reviews)
- Florida
- Islamorada
- 1.79 mi to center
1380 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,443/Night
For 7 Nights د.إ.10,103
10.0
Exceptional
(118 Reviews)
- Florida
- Islamorada
- 1.84 mi to center
1980 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.2,704/Night
For 7 Nights د.إ.18,928
10.0
Exceptional
(116 Reviews)
- Florida
- Islamorada
- 1.81 mi to center
2200 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
د.إ.2,849/Night
For 7 Nights د.إ.19,945
10.0
Exceptional
(104 Reviews)
- Florida
- Islamorada
- 1.76 mi to center
1600 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.2,528/Night
For 7 Nights د.إ.17,694
10.0
Exceptional
(104 Reviews)
- Florida
- Islamorada
- 1.82 mi to center
1700 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
د.إ.2,512/Night
For 7 Nights د.إ.17,584
10.0
Exceptional
(95 Reviews)
- Florida
- Islamorada
- 1.79 mi to center
1700 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.2,344/Night
For 7 Nights د.إ.16,405
Pet-Friendly Holiday Rentals in Windley Key
Over 275+ Pet-Friendly Holiday Rentals in or Near Windley Key
10.0
Exceptional
(114 Reviews)
- Florida
- Islamorada
- 0.55 mi to center
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
د.إ.989/Night
For 7 Nights د.إ.6,926
8.7
Fabulous
(1439 Reviews)
- Florida
- Islamorada
- 1.23 mi to center
436.91 ft²
68 Guests
22 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
د.إ.2,608/Night
For 7 Nights د.إ.18,256
8.2
Excellent
(1006 Reviews)
- Florida
- Islamorada
- 1.61 mi to center
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- Balcony/Terrace
د.إ.816/Night
For 7 Nights د.إ.5,714
10.0
Exceptional
(101 Reviews)
- Florida
- Islamorada
- 0.56 mi to center
2000 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
د.إ.1,706/Night
For 7 Nights د.إ.11,943
8.6
Fabulous
(862 Reviews)
- Florida
- Islamorada
- 0.31 mi to center
391.64 ft²
75 Guests
19 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
د.إ.1,282/Night
For 7 Nights د.إ.8,972
10.0
Exceptional
(50 Reviews)
- Florida
- Islamorada
- 0.67 mi to center
2000 ft²
8 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
د.إ.5,010/Night
For 7 Nights د.إ.35,069
10.0
Exceptional
(39 Reviews)
- Islamorada
- Venetian Shores
- 0.19 mi to center
1703 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Pool
د.إ.3,584/Night
For 7 Nights د.إ.25,091
10.0
Exceptional
(34 Reviews)
- Florida
- Islamorada
- 1.42 mi to center
1860 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
د.إ.3,660/Night
For 7 Nights د.إ.25,619
10.0
Exceptional
(9 Reviews)
- Florida
- Islamorada
- 1.32 mi to center
1750 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
د.إ.2,121/Night
For 7 Nights د.إ.14,844
Large Holiday Rentals and Private Villas in Windley Key
Over 122+ Large Holiday Rentals and Private Villas in or Near Windley Key
10.0
Exceptional
(72 Reviews)
- Florida
- Islamorada
- 1.05 mi to center
5000 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
د.إ.5,819/Night
For 7 Nights د.إ.40,732
9.5
Exceptional
(2 Reviews)
1302.43 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Villa
- Private Beach
- Oceanfront
- Pool
د.إ.1,818/Night
For 7 Nights د.إ.12,725
10.0
Exceptional
(20 Reviews)
- Florida
- Islamorada
- 1.85 mi to center
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Pool
- Ocean View
- Balcony/Terrace
د.إ.2,293/Night
For 7 Nights د.إ.16,052
8.0
Excellent
(3 Reviews)
- Florida
- Islamorada
- 3.84 mi to center
1582.29 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Beach
- Oceanfront
- Fireplace/Heating
د.إ.661/Night
For 7 Nights د.إ.4,627
10.0
Exceptional
(7 Reviews)
- Florida
- Upper Matecumbe Key
- 0.65 mi to center
1680 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
د.إ.2,179/Night
For 7 Nights د.إ.15,256
10.0
Exceptional
(6 Reviews)
- Florida
- Upper Matecumbe Key
- 0.76 mi to center
1680 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
د.إ.2,345/Night
For 7 Nights د.إ.16,412
10.0
Exceptional
(6 Reviews)
- Florida
- Islamorada
- 0.84 mi to center
1680 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
د.إ.2,312/Night
For 7 Nights د.إ.16,181
10.0
Exceptional
(6 Reviews)
- Islamorada
- Venetian Shores
- 0.21 mi to center
1960 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,790/Night
For 7 Nights د.إ.12,534
10.0
Exceptional
(2 Reviews)
- Florida
- Islamorada
- 1.41 mi to center
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.3,599/Night
For 7 Nights د.إ.25,190
Wheelchair Accessible Holiday Homes in Windley Key
Over 220+ Wheelchair Accessible Holiday Homes in or Near Windley Key
10.0
Exceptional
(2 Reviews)
- Florida
- Islamorada
- 4.46 mi to center
1536 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
د.إ.1,164/Night
For 7 Nights د.إ.8,146
8.6
Fabulous
(77 Reviews)
- Florida
- Islamorada
- 0.88 mi to center
418.14 ft²
69 Guests
18 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
د.إ.2,383/Night
For 7 Nights د.إ.16,684
9.2
Exceptional
(1307 Reviews)
- Florida
- Islamorada
- 1.53 mi to center
1 Bathroom
Ocean View
Resort
- Hot Tub
- Spa
- Pool
د.إ.1,605/Night
For 7 Nights د.إ.11,231
10.0
Exceptional
(2 Reviews)
- Florida
- Upper Matecumbe Key
- 1.33 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
د.إ.833/Night
For 7 Nights د.إ.5,828
7.8
Very Good
(361 Reviews)
- Florida
- Islamorada
- 1.70 mi to center
234.85 ft²
43 Guests
11 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
د.إ.1,325/Night
For 7 Nights د.إ.9,277
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 1.61 mi to center
12 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.2,553/Night
For 7 Nights د.إ.17,874
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 1.61 mi to center
12 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.2,152/Night
For 7 Nights د.إ.15,065
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 1.61 mi to center
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.950/Night
For 7 Nights د.إ.6,655
10.0
Exceptional
(1 Review)
- Florida
- Islamorada
- 1.61 mi to center
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.847/Night
For 7 Nights د.إ.5,931
Windley Key Private Villas and Holiday Homes Under $200
Over 55+ Windley Key Private Villas and Holiday Homes Under $200
9.2
Exceptional
(11 Reviews)
- Florida
- Islamorada
- 3.85 mi to center
1400 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.710/Night
For 7 Nights د.إ.4,973
د.إ.723/Night
For 7 Nights د.إ.5,064
7.6
Very Good
(1005 Reviews)
- Florida
- Islamorada
- 0.63 mi to center
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- Balcony/Terrace
د.إ.676/Night
For 7 Nights د.إ.4,730
9.6
Exceptional
(7 Reviews)
- Islamorada
- Plantation by the Sea
- 0.00 mi to center
1033 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
د.إ.485/Night
For 7 Nights د.إ.3,393
New
1280.91 ft²
4 Guests
2 Bedrooms
2 Bathrooms
House
- Oceanfront
- Hot Tub
- Spa
د.إ.705/Night
For 7 Nights د.إ.4,936
9.4
Exceptional
(17 Reviews)
- Florida
- Islamorada
- 3.86 mi to center
1367 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.489/Night
For 7 Nights د.إ.3,423
New
- Florida
- Islamorada
- 3.84 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
د.إ.702/Night
For 7 Nights د.إ.4,917
د.إ.453/Night
For 7 Nights د.إ.3,169
New
- Florida
- Windley Key
- 0.47 mi to center
405 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.367/Night
For 7 Nights د.إ.2,571
Instantly Bookable Holiday Homes in Windley Key
Over 367+ Instantly Bookable Holiday Homes in or Near Windley Key
10.0
Exceptional
(83 Reviews)
- Florida
- Islamorada
- 1.84 mi to center
1650 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
د.إ.1,713/Night
For 7 Nights د.إ.11,991
New
- Florida
- Islamorada
- 1.79 mi to center
1700 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Pool
- Ocean View
- Balcony/Terrace
د.إ.2,686/Night
For 7 Nights د.إ.18,800
10.0
Exceptional
(72 Reviews)
- Florida
- Islamorada
- 1.76 mi to center
1620 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
د.إ.1,814/Night
For 7 Nights د.إ.12,700
10.0
Exceptional
(62 Reviews)
- Florida
- Islamorada
- 1.15 mi to center
2400 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
د.إ.3,152/Night
For 7 Nights د.إ.22,064
10.0
Exceptional
(56 Reviews)
- Florida
- Islamorada
- 1.86 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,461/Night
For 7 Nights د.إ.10,224
10.0
Exceptional
(47 Reviews)
- Florida
- Islamorada
- 1.62 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,808/Night
For 7 Nights د.إ.12,659
10.0
Exceptional
(44 Reviews)
- Florida
- Islamorada
- 0.90 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
د.إ.2,059/Night
For 7 Nights د.إ.14,415
10.0
Exceptional
(38 Reviews)
- Florida
- Islamorada
- 1.83 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,741/Night
For 7 Nights د.إ.12,189
10.0
Exceptional
(35 Reviews)
- Florida
- Islamorada
- 0.90 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
د.إ.1,379/Night
For 7 Nights د.إ.9,651
Book a Last Minute Place to Stay in Windley Key
About Casai's Private Villas and Holiday Rentals in Windley Key
Discover more than 800 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 661.6 ft², with nightly prices averaging د.إ.2,963.
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 | 78 |
| Villas | 38 |
| 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
- 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 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!
- 3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .
- Oceanfront 4-BR w/private 31' Boat Slip Included, Pool & Beach, gourmet kitchen
- Isla Key Acaí: Waterfront Boutique Resort, FREE Boat Dockage Sep-Oct Only!
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 800 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 | 41 |
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